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Master Your Up-Market Strategy Like A Unify PMM

Product Marketing Adventures · 2026-07-21 · 1h 5m

0:00--:--

Key moments - from our scoring

Substance score

66 / 100

Five dimensions, 20 points each

Insight Density14 / 20
Originality11 / 20
Guest Caliber16 / 20
Specificity & Evidence13 / 20
Conversational Craft12 / 20

CaptivateIQ, a commission management software company, had early success selling to mid-market SaaS startups but noticed signals that enterprise buyers were seeing outsized value. Quintin Smith, brought in as founding PMM during a Series C fundraise, faced the challenge of determining whether these large deals were anomalies or a pattern worth pursuing strategically. Rather than chasing every shiny object, the team invested heavily in a win-loss program combined with quantitative analysis of deal patterns, tracking customer industries, incumbent solutions, and buying personas across their won and lost deals. This revealed critical insights: enterprise customers weren't concentrated in software alone - medical devices, banking, and financial services showed strong traction - and deals succeeded when senior stakeholders like CFOs and VPs of Finance led evaluation, not just operational users like sales compensation analysts. The breakthrough was recognizing that while commission analysts cared about speed and ease of use, C-suite buyers viewed commissions and incentives as a strategic lever for driving business outcomes: optimizing rep retention, controlling go-to-market spend, and aligning incentives with new product launches. By reshaping the narrative from "operational pain relief" to "strategic business driver," CaptivateIQ doubled enterprise ARR within a year, proving the shift was scalable, not a fluke.

Key takeaways

  • →Win-loss programs combined with quantitative analysis of industry, incumbent solutions, and personas are foundational to identifying and validating up-market expansion patterns before committing resources.
  • →Enterprise deals succeed when you identify and target above-the-line personas (CFOs, VPs of Finance) rather than operational users, and craft messaging around their strategic priorities, not ease-of-use for lower-level champions.
  • →Sub-industry segmentation (medical devices vs. general manufacturing, banking vs. general financial services) enables more precise targeting than broad vertical categories and uncovers higher-value TAM.
  • →Incumbent solutions present both a risk and an opportunity - tracking what systems enterprises currently use reveals pain points and forced migration windows that can accelerate deal velocity.
  • →Intentional focus and dedicated resources for a specific up-market motion prevents dilution of effort and validates whether product-market fit exists at higher price points before scaling the organization.

Guests

Quintin Smith

Topics in this episode

PositioningMessagingWin-loss analysisproduct marketingMedical devicessales performance managementCaptivateIQcommission management softwareup-market expansionpersona analysisincumbent solution trackingsub-industry segmentationbanking and financial services

Questions this episode answers

How do you identify whether large enterprise deals are repeatable patterns or isolated wins?

Invest in a win-loss program paired with quantitative analysis of deal data - track industry, incumbent solutions, and buying personas across won and lost deals. Look for unexpected patterns (sub-industries, specific legacy vendors, above-the-line personas) that differ from your SMB/mid-market playbook; these signal a new repeatable motion.

What personas drive enterprise commission software deals forward?

Above-the-line personas like CFOs, VPs of Finance, and sales leaders lead evaluation and have organizational sway, whereas sales compensation analysts (the primary users) are champions but lack decision-making authority. Enterprise deals close when messaging aligns with executive priorities - strategic incentive alignment and business outcomes - rather than operational ease.

How should messaging change when moving a product up-market to enterprise?

Shift from user-centric narratives (e.g., "we make your job easier") to strategic business narratives that resonate with CFOs and senior leaders (e.g., "optimize incentives to drive new product adoption and control go-to-market spend"). The product value remains the same, but the frame changes from pain relief for operators to strategic advantage for the business.

What role does incumbent solution tracking play in up-market expansion?

Tracking the legacy software enterprises currently use reveals both pain points and forced migration windows - for example, if a major vendor is forcing expensive re-implementation, it creates urgency and open buying windows. Target accounts on specific solutions with campaigns addressing their known frustrations.

How do you balance the risk of chasing enterprise deals while maintaining SMB/mid-market momentum?

Be intentional about resource allocation and focus. Validate that your product delivers value to enterprise buyers before scaling effort. Use win-loss and deal analysis to confirm repeatable patterns; if you don't see clear signals across multiple deals, the risk of churn and misalignment is high.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

14 / 20

The episode delivers a solid case study with actionable frameworks (the 4Rs: Research, Refine, Ready, Report) and specific tactical advice around win-loss analysis, persona segmentation, and messaging hierarchy. However, there is considerable filler - repetitive affirmations, throat-clearing, and conversational padding (

I love that," "I totally agree," "Yeah," etc.) dilute the density. The core insights about identifying executive vs. user personas, sub-industry segmentation, and incumbent displacement are valuable but not particularly novel to experienced B2B operators.
quotes a result, the Commission analysts were bought in on that too, because it makes their function more high value

Originality

11 / 20

The 4Rs framework is a decent mnemonic device but represents a fairly standard approach to go-to-market strategy (research, strategize, enable, measure). The core insight - that moving upmarket requires persona re-targeting and messaging shifts toward executive value - is well-established PMM wisdom, though the specific application to commission software is contextualized. The episode lacks counterintuitive or first-principles arguments; instead it reinforces conventional best practices around win-loss and stakeholder alignment. The Profound messaging critique adds little novel perspective.

I like to think of a lot of like PMM work and like being capsule, encapsulated or at least the approach should be thought, uh, like repeatable in a way that is under like the same framework. And I, I've like coined this with like a four Rs.
moving up market isn't as simple as just selling to bigger companies. Enterprise buyers often care about different things. They have different stakeholders involved, and the messaging that helped you win those earlier customers may not resonate

Guest Caliber

16 / 20

Quintin Smith is a strong guest with directly relevant operational experience: founding PMM at CaptivateIQ during hypergrowth (unicorn raise, Series C), now PMM lead at UniFi (AI-native startup). He has executed the exact playbook discussed at scale and can speak to real outcomes (2x enterprise ARR in one year, named logos like Stripe, Datadog, Stifel). However, he is primarily a PMM practitioner rather than a CEO or revenue leader, limiting his perspective on enterprise sales mechanics beyond the marketing angle. His current role at UniFi suggests active involvement but details are thin.

I was the founding PMM at CaptivateIQ, helping build the product marketing function during a period of hypergrowth
being able to 2X that enterprise and our ARR in that first year with all the campaigns and plays we were running was like really validating. We're starting to see those get knocked down. We had like logos like I think, uh, Stifel, Stripe, Datadog. Um, there was some in the - Oh, Raymond James Canada was another one

Specificity & Evidence

13 / 20

The episode provides some concrete specifics: named enterprise logos (Stripe, Datadog, Stifel, Raymond James Canada), a stated 2x ARR outcome in the first year, and details about CaptivateIQ's Series C raise to $100M at >$1B valuation. However, much of the methodology discussion stays abstract (e.g., "pivot tables," "analyzing patterns") without detailing actual data sizes, conversion rate changes, or campaign performance metrics. The Profound critique mentions tryprofound.com but doesn't cite their actual metrics or results. Many assertions lack supporting numbers or evidence.

being able to 2X that enterprise and our ARR in that first year with all the campaigns and plays we were running was like really validating. We're starting to see those get knocked down. We had like logos like I think, uh, Stifel, Stripe, Datadog.
They were gonna raise 100 million and just over a billion-dollar valuation, so unicorn status. You know, had the, uh, New York Stock Exchange billboard

Conversational Craft

12 / 20

The host asks reasonable setup questions and uses follow-ups, but rarely challenges or probes deeper. When Quintin makes claims (e.g., "throw away everything you know"), the host affirms rather than pushes back. The conversation feels warm and collegial but lacks sharp skepticism. The host does double-click on certain points (e.g., persona messaging), but the questioning is rarely adversarial or designed to expose assumptions. The Profound critique section is notably weak - the host asks Quintin to suggest improvements, but they don't interrogate whether Profound's current approach might be optimal for their stage/audience. No disagreement or productive tension emerges.

I love that insight. That's really helpful.
I love it. You guys leaned into the aspirational kind of tone

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

messaging34market28step28sales25marketing25love24team22success21different21folks19research19enterprise18start16today16product15persona15

Episode notes

Landing your first enterprise deal feels like you cracked the code. Then leadership wants ten more, and suddenly “going upmarket” becomes the plan, even if your motion still looks mid market. This episode is about what actually changes when you move into enterprise, and why it is not just selling to bigger companies. It is a different buyer, a different story, and a different way of proving value. Quintin Smith joins me to break it down. He is a two time founding PMM, currently leading go to market at Unify, and previously helped scale CaptivateIQ during a major growth phase. He shares what it took to turn enterprise from a lucky win into a repeatable motion. We get into the enterprise buyer dynamics that most teams underestimate, including the importance of the full buy team and the narrative shift required to win at that level. Quintin also walks through his Four Rs framework for building an upmarket strategy that can actually run, from research and refinement through enablement and reporting. We also do a messaging critique of Profound, a company helping brands improve visibility inside AI platforms like ChatGPT and Microsoft Copilot.

Full transcript

1h 5m

Transcribed and scored by The B2B Podcast Index.

I have to start today with a brief story. So it was when, back when I was working at Twilio, and our portfolio was one of the newer ones to the business. We operated kind of like a startup within a larger organization. we had this big deal close, right?

And it was one of the first massive enterprise deals that we got. And of course, the sales leadership ex- is excited, and the executive team is excited, and we're all celebrating. And then someone said something like, "We need to get more of these deals, more like this one." I remember that moment so vividly, and I'd bet there are other PMMs out there who have been in similar situations because it always falls on PMMs to help create the strategy and messaging to get there.

All B2B companies out there have been here at some point in time, where they've had success in SMB or mid-market, and then they start looking up market. But moving up market isn't as simple as just selling to bigger companies. Enterprise buyers often care about different things. They have different stakeholders involved, and the messaging that helped you win those earlier customers may not resonate with the people who are signing the larger contracts.

So today's episode is about how to identify those signals and turn them into a repeatable go-to-market motion. And I could not think of a better person to have this conversation with than Quintin Smith. Quintin is a two-time founding PMM who has spent his career helping high-growth startups figure out how to turn those early traction deals into scalable growth. He was the founding PMM at CaptivateIQ, helping build the product marketing function during a period of hypergrowth, and today serves as the product marketing lead at UniFi, where he's helping shape the go-to-market strategy for one of the fastest-growing AI native companies in go-to-market.

Today's case study actually comes from Quintin's time at CaptivateIQ. During a period of rapid growth, the company started seeing signs that enterprise buyers were getting outsized value from the product. So the challenge was figuring out whether those wins were isolated successes or if it was the beginning of something much larger. So Quintin helped uncover those patterns behind those deals, reshape the messaging, all around the executive buyers, and built the playbooks, enablement, and campaigns that ultimately doubled enterprise ARR within a year.

Quintin, it is amazing to have you on the show. thanks so much for having me. Have been following the f- uh, show. You've had some amazing speakers on, so really grateful to be here, Um, and just a little, uh, additional on myself.

So as you kinda mentioned, I've been in, uh, I've been in, uh, product marketing or sales enablement role for almost a decade now. So have seen a lot of different things there, uh, lots of different - all of the ins and outs of it, uh, across multiple different companies, more enterprise-y all the way down to now a, uh, under 100- employee startup, uh, in AI. So have seen it on all fronts, but h- really passionate about PMM, super excited to be here, and really s- like passionate about how PMM plays such a critical, um, middle role in a company between what you're building and how you're selling it.

So really excited to talk about all that today. I love that. So just as a sneak preview for some of our guests, not only will we talk about this awesome case study, but just given, Quentin, your unique background and kind of, you know, places you've served, I'm gonna try to also cover just the experience of being a founding PMM, and then also being a founding PMM at an AI native company where that is such a buzzword in and of itself, and there is such a mixture of hope and excitement and maybe a little bit of distrust with all this AI talk.

So, I wanna try to squeeze all that into this conversation as well. Enfin So without further ado, let's dive right in. Okay. So you are currently at UniFi, and I wanna come back to UniFi and your time there.

But today's case study is actually about another startup you worked at, and that was CaptivateIQ. So give us a quick summary for those who may not know, what is CaptivateIQ? What's kinda the main service offering? Awesome.

Yeah. So when I joined, or at the time I joined, as simple as possible, uh, CaptureIQ was commission software. So what it did was, commissions obviously like often a back office function for like incentives, so paying out your sellers based on how they perform, uh, often run in spreadsheets, but it can be in- highly inaccurate and also can be like a strategic driver for your business. So, uh, it's a really important function that's often overlooked and no great tools for it.

So, uh, CaptureIQ, um, was one of like the fastest growing in that, displacing spreadsheets and really bringing on a lot of, uh, startup early stage brands to their commissions platform. So, now they've even branched further into the sales planning world and into this broader category of sales performance management for folks familiar, uh, with that space. But, um, yeah, that's really what CaptureIQ is, so I love that, and it's, um, it's very helpful as we start to think about what this case study is going to look like, 'cause I imagine we're gonna get into, um, your particular persona and, you know, what things were resonating with, you know, mid-market versus upmarket segments.

So, okay, now thinking more closely on CaptivateIQ, tell us more about what the situation was like, you know, when you started there. obviously we're talking about moving upmarket, but maybe, like, right before that became a priority, what was going on and, and what led to that? so a little bit about my background. So when I joined Catbird IQ, I was hired as the founding PMM.

I believe I was the fourth person on the marketing team, and they were just seeing a ton of success. I came in right before the Series C. They were gonna raise 100 million and just over a billion-dollar valuation, so unicorn status. You know, had the, uh, New York Stock Exchange billboard, like really exciting moment for the company and really that like critical like juncture in growth, right?

Where they'd seen a ton of traction with kind of lookalike hot startups in the SaaS space at the time. I think this was a 2021, I wanna say at the time. Uh, but just a lot of like, they had folks like Gong, who was like a fast-growing up, up-and-coming Sa- SaaS player that they'd had from the beginning, and similar type, like these smaller but really hyper-growth SaaS companies that they'd grown well with, seen success with. of like, like go-to-market darlings, you know?

Like, that s- that space was, like, getting really hot, I feel like, in that time. It's still actually very, and a very attractive space to be in 100%. So they were like one of the hot players at the time who was getting to working with other folks at similar stage and seeing a lot of suc- success as they grew out their go-to-market organization and naturally needed to stand up at scale commissions plans really quickly. So that was proving out really well, selling a lot.

Uh, but as they were maturing into this really, like, established more mid-market and kind of crossed the chasm, like, uh, classically moving to those large scale buyers, um, they were looking to really build out a more robust both marketing function, sales function, and really just across the business. So that was really the point at which I came in and kind of that like strategic juncture for the business Yeah. Okay, so, the company's at this really exciting moment, and it was a, it was both of natural progression for the company, but there were also a lot of market signals that there was appetite that was, that maybe started and just easier to capture in this enterprise, or, um, I'm sorry, in this mid-market and SMB segment.

But you start to see signals that, okay, now enterprises are catching on. It's so funny. I feel like enterprises, while they have the biggest budg- budgets and biggest teams, they're actually sometimes slower to pick up on the innovations, right? So what was actually then going on?

Like, what was the actual business challenge that you personally, became tasked with then? Yeah. So, and it was funny, we'd obviously, uh, in addition with some of the traction we're seeing, like there were a few logos that had come through the door that were like, "Oh wow, we're actually unlocking value for this really large scale company." Like whether that be in SaaS or even some of the like adjacent more like tech forward companies and non-SaaS industries.

And we're just like, uh, as I think you just get like shiny object syndrome in a company when you see like, oh my God, like we've been selling, you know, 30 ARK, ARR deals and we just sold a 200K. What if we just sold 10 of these and we can meet our all of those different things? So the business starts to get really, uh, you know, everyone gets a little bit, not distracted, but the, uh, opportunistic when that shows up naturally. So, uh, when that started happening and we like even identified like early on that that was like there was some, like a key proponent of our product was that we're like highly flexible.

We're almost similar to a spreadsheet where you could really build anything, and that was like highly valuable for enterprises, uh, in the space. So like that was another thing that we're like, okay, there's probably something, like there's probably something here that we could lean into, but it wasn't necessarily like, okay, like intentional move up market. It was more like, okay, how do we replicate these like three 200K deals or like this 600K deal we almost won like last year based on that loved us, but just we didn't have this one feature and really like turn this into like, what if we put intentional dollars, effort, like marketing focus, enablement all towards this thing and sprint at this and what can happen?

So that was really the task at hand is like, hey, can we like make this repeatable and like actually go find more of these? So that was, that's where we're at. I love that, and I wanna, um, double-click on something you said. You mentioned a lot of things, but one of the things in your list that you mentioned, and in addition to obviously, like, resources, but focus on something like this.

And the reason why, I know that sounds really trite, but the reason why I wanna double-click on this is because I have seen, as you pointed out, organizations get really excited about chasing the shiny object, but you're still trying to maintain everything else. And when, e- especially for a startup, when you're spread too thin like that, you lose focus. So it sounds like you were very intentional, very intentional about, "No, no, no, this is the strategy we're going to try to make repeatable, so let's go after that."

So where did you start, I guess, with all that? What's kinda the first thing that you did? Yeah. And that's such a, like, good observation.

I think that's so easy to get, like, distracted, and there needs to be, like, intentionality in that, like, push. It can't be, like, an outlier thing where like, oh, you know, three months later this customer is churning because we realized we weren't cut out for this, right? Like, that was not we were, like, seeing out of the gates, and I think, like, that would've been, like, a full mistake if that had b- had been the case, and, like, that's oftentimes probably what happens.

Like, some companies and just products are really f- well fit and can, like, achieve, like, massive scale selling to SMBs and being this really user-forward, self-serve, like, fast, uh, lower ARR companies. So at the time, like we were looking into a bit of that, but, like, what was, like, those first steps we took? One fortunate thing that we had is like, um, we had already a really st- as our PMM team, we had a strong win-loss motion set up, which if for any of the PMMs listening, like win-loss can be one of the most strategic and valuable programs you can, build out at any company, like the insights you get from them.

I think, like, the pr- challenge with win-loss is like, it feels like, like a nice to have oftentimes, where it's just like this, you know, and it's not on fire, right? It's just like a thing you could add as like, as like a vitamin versus like, yeah, like a painkiller, you know, with the business. But it has such a strategic impact when it's done right, and we really, like, invested in that early. So we're able to, like, use not only that program, which gives you a lot of, like, qualitative insights from, like, these 30-minute interviews that we'd have with a one-off sales, one-off with the close-won and close-loss champions that we talked to.

In addition to that, we were running, like, and this was pre, like, real AI - like strong AI or like s- uh, wide AI adoption. So I was building, like, pivot tables and spreadsheets of like, okay, for all of our close-won and close-loss, like for the deals we won in enterprise, what industry were they in? Which personas were we winning with? Which incumbent solutions were they on?

And kind of looking at these splices of the market and seeing, oh, okay, where are there, like, wedges or, like, things that we're like, "Oh, this is, like, a unique insight. That's surprising." Like, this is, like, very unique, uh, based on, like, goes against what we, like, had previously understood or, like, how we have sold historically. So that really allowed us to, like, really start devising a strategy based on, like, those insights we're in, like, turning over rocks with those, like, qual-quant analysis in advance of this, which can, like, really guide the strategy.

So that's where we really started on that front. I love that. I have to echo the value in a good win-win loss program. That is where we have unlocked so many unique opportunities at multiple organizations that I personally have worked at.

and I know we're gonna talk about AI. I know we're gonna talk about it. But, but I just have to say really quickly, there is some value in not outsourcing everything, o- every part of your analysis to AI, because there are things that you as your human judgment is stronger at discerning than, you know, a bot basically. So, while I'm not discouraging using AI, especially for like synthesizing information and analyzing a lot of stuff really quickly, like I'm not saying don't do that.

I… That's also valuable. But this was all - The way you did was pre-AI, and that's pretty impressive. Yeah, I know. I can't wait to tell that to my kids one day.

Um, Yeah. Kids these that, "Oh, I actually did this stuff before. Like, we used to have this thing called a spreadsheet," you know, and like all these different things. So, um, yeah, it's crazy, crazy to even think about these things.

But, uh, regardless, couldn't agree more. And like the win lo- uh, to the win-loss point, like it's a great way to like, you know, PMM I think struggles oftentimes to like, and I've had the same struggle myself, like earning your seat at the table and like having like the strategic viewpoint in an organization versus like being more of like a marketer or kind of like this no man's land or like enablement. There's all these different things. So win-loss is a great way to like, make that more, like more established, so Absolutely.

It's such a good place to start, too. Like, if you - There - I've heard a lot of PMMs want to do voice of customer research and, you know, maybe they don't know what kind of topic they should choose. Always just start with win-loss. It's the lowest hanging fruit.

It's easiest to get, you know, buy-in from stakeholders on how you're gonna spend your time and how it's gonna be valuable and all that good stuff. So, you know, love to echo that. Okay. So when you started to look at some of the data from some of your win-loss, uh, analysis, what, like, started to emerge in terms of trends and, like, you know, g- Tell me more about the signals you were seeing with some of that data.

Yeah. I think like there were a few things that really came to mind, uh, or like really popped out when we looked at it. I think the first thing is like, and this is like natural as you move up market, but the world isn't just software companies. Like, they, you're not like they're the on- the only companies that you can sell to.

We started seeing like really strong traction in like, and if you look at it at a surface level, it's like, oh, manufacturing and f- financial services, but those like have the largest TAM, so like you're naturally gonna see more traction in deals in those. But when we like double-click, it's like, okay, within those, there's like sub-industries of like medical devices and banking were ones that we actually were knocking down on market customers with. So like by kind of understanding a little further there, like there's more nuance and niche, and you can get a lot more specific in your campaigns for like sub-industries versus like, "Hey, like we are, you know, commissions for manufacturing companies," and like that doesn't change if you're, you know, building tractors versus, you know, man- like plastic, like soap bottles or whatever it is.

So, uh, I think that was a really valuable insight. The second was like incumbent solutions. So like, hey, no matter what, and we should always be trying, and like conversational intelligence makes this so easy today, but like tracking what solutions that companies are on is so valuable to understand like, oh, what are the pains they're seeing? Like how can we replace them?

Why? And like we identified like one specific software that like as legacy was making folks go through a migration, and everyone was hating it and like forced to change anyway and re-implement, and that's was like a really big driver of a lot of like both won deals and just, uh, at least like inbound for us. So that was another one where it's like, okay, we should be like targeting campaigns at all of these customers of that solution today. Um, and then the third one, um, I think the… Oh, the persona piece.

Yeah. Uh, persona looking at like, hey, who's actually leading these evaluations? This just feels like an obvious insight, but like when we had a leader in the r- like a above the line persona, so like more of a senior persona in the room, uh, like whether it was like a head of finance or a VP of FP&A, like accounting or even a sales leader, that allowed us, or even ops like more rarely. But when they were in the room versus having like your sales compensation manager or like your sales commission to analyst who's naturally like was really into like the making this job a lot easier than before, but like what they cared about above the line was just completely different.

Like they didn't mind, like a CFO or a VP of finance didn't mind that like commissions was like difficult. That wasn't really like compelling. So we had to think of a new narrative that didn't just resonate with the persona because they just weren't, didn't have organizational sway, so. Yeah.

Oh, I love that insight. That's really helpful. okay. So there's a collection of signals that you picked up on that were more unique to your enterprise segment as you started to dig in to some of this data.

So now tell me a little bit more about, you know, maybe like the biggest things that you learned about like be- the actual buyers behind some of this. You started to tell me a little bit more with the personas. Is there more to the story there? Yeah.

Um, one of the things like, on that persona front, like we have, you know, sales commission, analyst, sales comp, like they're oftentimes really focused on just like getting this out on time. It's a grueling and brutal role for any of my, any out there, any listening, but, uh, sales comp analysts out there, like it's a really, man, it's a really grueling role where you're having to sprint at the end of the month or right after end of month to get commissions payments out in a very short amount of time, aggregate all the data that's come down, making sure that Salesforce data is, you know, correct, or Salesforce CRM data is in the right place, turn that into your, uh, commission outputs based on your plans and issue those out, make sure they're accurate.

You're always gonna get like clawbacks or like complaints, uh, inquiries from your sellers who don't understand the comps. So they're, you're just like up against it and like you only, Like the only time you're really like organizationally like called out is when something goes wrong, which is a tough position to be in. and what we found is those, again, those personas, like we really like had success with those early on and like they exist in these roles, but they weren't really driving - Were getting a lot of inbound, but they weren't driving the deals forward.

they were gonna be on board no matter what. But how do we convince like the folks above them to say like, "Hey, this is a organizational, strategic, challenge that your business is having of like, 'Hey, your reps aren't getting paid on time,' or like, 'Your reps are like leaving the company because their comp plan, it doesn't stack up with like how others in the industry,' and stuff like that. Like that is really compelling and like your incentive structure could actually be optimized to drive towards the new business initiative that you have, like selling this new product, adding services, like breaking into a new, uh, industry.

Like if you're really thoughtful about commissions and incentives, like you, that can be a strategic advantage for a go-to-market organization. So we wanted to really lead with a narrative that more aligned with that messaging rather than, uh, the messaging that's like, "Oh, like we'll just make your job easier and get these commissions out on time." So Okay. So what I love that it sounds like you did here is you looked at the whole buy team, right?

Through this big analysis that you did. Maybe it started with win, win-loss, but you had all these other, you know, supplemental and additive data sources that you were looking at. But you ultimately got super focused and clear on the full buy team for the enterprise segment and each persona for that buy team. And this is something that I think is so hard to do, is you get really good at, like, the champion, right?

The, the person, the persona for whom the product was built. And for you, you talked about, like, an incentives analyst or something like that, a compensation manager, something. That - something like that, right? But, you know, swap that out with whatever this could be in any business, in any, for any product.

But what I think is the really hard part for a PMM is to take the narrative that was so beautifully crafted for that one persona, and as you pointed out, it means meaningless to the person who actually signs at the end of the day in enterprise. And what gets really hard is crafting the narrative that now will resonate with both or with a full buy team. How do you do that? Like, that's can be so difficult.

so any other insights you can share around how you thought about that? Or, or did, did you find, like, a commonality maybe between those two personas and landed on a narrative that kind of fit both? Like, you know, tell me more about that. Yeah.

I think like one of the things as we like devised the messaging, and a lot of this, like we, uh, you know, uh, I was not going at this alone. We had other PMMs and just like an organization who has really bought into this at least. But like we had really, like we're talking to folks like across the buyer team, like you have this like user obsession with like these primary champions, and that's who we work with, but also like getting curious about like those folks higher up in the organization.

What we found is that like this, um, narrative in which there's really like commissions or incentives as a strategic lever for your business, like, like starting to like rethink of like, oh, this is just back office, like getting payment out similar to like a pay stub versus like, no, incentives are a strategic driver for whatever business objectives you're going up against. That's a C-suite level like value prop. At the end of the day, like the commission analysts were bought in on that too, because it makes their function more high value, right?

Like they don't wanna see themselves as just like, you know, trying to get those commissions payments out. They wanna view it as like, oh, I wanna see like the trends of like, oh, we're only hitting, you know, 70% of quota, or everyone's hitting 110% of quota. That's actually a bad commission plan. Like, I need to like advise my team that like I wanna be like looking at like the reporting and analytics and say, "Oh, this is actually, these outliers are not good for us, or this trend is not good for us.

We should revise our comp plans to support like what makes more sense for the business." And then they become more strategic as well. So I think really everyone organizationally was like bought with this aspirational view of what it should be. How tangible that actually is adapted, adopted in organizations is a different story.

But I do think that really like was a narrative that we could tell had bite and was gonna like be able to like allow us to convince folks to move that way. I love it. You guys leaned into the aspirational kind of tone, but also reframed, I guess, like the jobs to be done of your primary champion from, you know, basically being like, not, rather than saying like, not that you said this 'cause you didn't, but like cog in the machine. You know, you've heard of that phrase or similar phrase before, reshaping it to, no, you, uh, your role can be a strategic asset to the business, and this is how that translates.

And that also worked really well with your executive buyer as well. so once you built out this new messaging for the upmarket enterprise segment, w- how did this start to actually show up for you in like a go-to-market motion? Yeah. Uh, like the way I see like this is like once you actually have that like messaging in place and have done that work, now it's like the fun part, right?

Of like how do you turn this into like readying your both marketing team, like across the board of like demand gen, social content, and then wrangle your sales team too with like, uh, speaking the same language, pitching discovery on this new persona, uh, demoing to them, like all making sure that both of these streams and like your enterprise playbook across the board is like humming. So we did a lot across the board. Like this persona insight was one, and we had this message around like return on incentives or ROI, right?

Like you wanna get more return out of this, so that was like kind of the catchy, punchy version of it, of thinking like this is a strategic thing. You need to get more return, which is obviously more revenue that you're getting out of the incentives that you're putting forward. And this is done through like really rigorous, like looking into your commissioned plans and structures and analyzing it and not spending time running the ca- all your time running the actual calculations.

So that was what we leaned to as like a kind of a headline message, but we ran a lot of like mini plays and campaigns out of this too, right? Like we were doing those sub-industry campaigns that I messaged - m-me-mentioned around medical device, the medical device space and banking. So like adding landing pages for those, like interviewing customers, getting specific case studies for those, and starting to like stand up like a full go-to-market bill of materials for that specific space and like slides.

Then like working with our sales engineers to make sure like the demo talk track w-woven, like we had like an org for that specific type of industry, and like it was built out with plans that reflected their business. So just starting to like build like empathy into your, uh, go-to-market motion into small things that can make such a huge difference. And it's not like one particular thing, but really shifting across the board and really setting them up to have more conversations that's gonna show up in a way that's gonna reflect the audience you're going after, um, really like kinda throwing out the old playbook and not just trying to like throw the same thing you've been doing over and over again and had success with yesterday to - and to run an entirely new different audience.

Yeah. So it sounds like it was a both a mix of internal readiness and, um, I don't wanna say external readiness, but maybe like external like asset building. so once you launched with all of this, like this was, it sounds like a, a large volume of work, both in terms of deliverables and the enablement. Like you launched it.

What happened in the end? What were the results? Yeah. Um, the - I think you mentioned the big one earlier on, but like being able to 2X that enterprise and our ARR in that first year with all the campaigns and plays we were running was like really validating.

We're starting to see those get knocked down. We had like logos like I think, uh, Stifel, Stripe, Datadog. Um, there was some in the - Oh, Raymond James Canada was another one. Um, BD, like these really big like Fortune 500 type of companies, uh, that were really strong and like, uh, great ones for us to you know, hang our hat on and like also continue to like break into those spaces that we'd already seen success in.

So that was really exciting and a great way to kind of validate, uh, like the hypotheses and like the analysis that we did early on. So that was great to see there. I love that. Yeah, it's so impressive.

Well done. and here's the biggest takeaway for me is your super valuable insight was hiding inside your existing customer base. Like, you didn't have to go do some massive, you know, third party research or, um, you know, you didn't have to spend thousands of dollars with an analyst to try to figure out what do, what do enterprises want, you know? You knew, and you c- because you followed the signal, and then you built a repeatable system around it.

so now what I would like to do is turn this into a playbook, uh, 'cause I'm sure, as we pointed out in the beginning, like, I personally have my own move up market story, and I bet hundreds to thousands of PMMs out there are in the thick of it right now. And, um, this would be a very helpful playbook for them. So coach me on this one. What's the first step in this playbook if I wanted to try to mimic your success?

Yeah. I like to think of a lot of like PMM work and like being capsule, encapsulated or at least the approach should be thought, uh, like repeatable in a way that is under like the same framework. And I, I've like coined this with like a four Rs. I need to put like a LinkedIn article or a blog or Substack out there eventually.

But, uh, my, my four Rs framework, which is, uh, you're starting with your research, uh, so really understanding the market. Uh, then you're refining that research. So like, okay, of all my findings, what are the insights? And then like what is my messaging positioning strategy, right?

You're taking those inputs and refining them. Then readying. So, um, I mentioned this like obviously you think about like enablement as like the classic, uh, form of this, but I also think like readying your marketing team to go out and like push top of funnel around this. So like what type of like webinars or events should we attend or like content should we run?

Like that's still like readying that team with the insights, messaging, positioning to do that. And then even your post-sale adoption or CX, whatever, however you're framing that organization, making sure they're ready to take on new customers that reflect that new strategy and thing that you're pushing towards. And lastly, report. So like how, how did we succeed?

Where are there room for optimization? Where are there maybe like, um, you know, hints and, uh, signals of success that we can, can double down on? So really like having that analytical like look back where you can start to predict where you're headed next. So, uh, that's really just that research, refine, ready, report is how I like to think about it.

I love this as a marketer. I love a good alliterative framework. So good. Okay.

So basically, these are your, this is your playbook, right? These are your four steps. Step one, research. Step two, refine.

Step three, ready, and step four, report. So, I wanna put a little bit more, you kind of, you summarized already, but I wanna put a little bit more action, um, into some of these for the PMMs out there, or maybe, or just like a quick, like, definition. So if your step one is research, like, just give a good, like, definition of that for me or maybe, like, bullet point list out, like some must-haves for the, for the research phase. Yeah.

Um, I always think like research is like best done like qua - it's like a symbol everyone knows, but like qual and I-quant is so both so important. Like everyone, like a lot of firm folks are like, "Oh, like we could just go like, you know, run like analysis of like our Salesforce data." And like now it's easier than ever with AI, you can do that. But to your point earlier, like there's so much value that can be derived from qualitative conversations like ha- going out and speaking to a champion, like asking them what's working, what's not, and like really like double-clicking into the questions or hypotheses that you have, testing what you have.

I think that's so critical today, especially in like this over AI world. Like the more you can get in real life and like IRL and just like start to like talk and understand where someone's at, like that is so impactful. Um, also another like hack, like I love conversational intelligence tools like Gong that we use Attention like now at UniFi. Like they are so ins- valuable for me to just be like, uh, I can query an agent and say like, uh, "Tell me like, you know, of calls with enterprise companies, like what are the most common like 10 pain points that have come up, like aggregated across calls?"

And like that used to be like us just like going out there and like l- combing through like calls or like asking a, a, an experienced salesperson and like the fact that you can be so much faster and actually so much more like precise is like really helpful. So It's, it's unbelievable. So, uh, I actually like can't even imagine like the world like, like it's Kids these days don't know. don't know how hard it was, but I think it's a good thing long term that we'll have like, oh, like we've s- seen it done and we know how we got there, so we have the ability to… Like I think that's why I'm like, I'm like, I'm busier than I ever have been, but like I'm also like, I'm more productive than I've ever been, but I also am like working more than I never ha- I ever have.

And it's because I think it's because I'm like, oh wow, I can go do all this stuff that used to take me like a month in like a week or a couple days. So a very interesting time we're in, but super Oh, 100%, absolutely. It's not, it's not slowing down either. Um, okay so I love this for the step one for research, and I just wanna throw out there one more time that the win-loss program is such a good, like, just always on.

It should be an always-on program, you know? I mean, that's something you shouldn't stop doing. so okay. All right, so then step two was refine.

So if I've done step one, I've done my research, I have both qualitative and quantitative, um, so what do I do with the step two with refine? Yeah. Uh, like usually like when like I've like run an analysis here, like turning that into like some sort of like a readout, even if just like to like aggregate the information or like consolidate the information in a way that makes sense of like, okay, like here's what I went out and did, and here's like the key insights across these different like some of the findings, of course.

Yeah. So what did you find in this analysis? What are those critical things? And then like starting to piece that together.

If like, okay, if we know XYZ about like our enterprise buyers, like we know they value flexibility, we know that like the executive - like they've been, like they're in like long-term contracts with like these tools that they hate or whatever it is, and like, oh, like, you know, the executives are the only ones who are actually going to like move the needle here. Like how does that inform how we message and position? Like, and really, okay, well, then we know like this is the splice of the market that like our positioning, like this is like the perfect competitor, like incumbent or like profile of organization that we wanna go after, like your ICP in that sense, the personas that make that up and like really start to like, uh, you know, really like sharpen how you view the market and who you're going after.

And then like turn that into, okay, like we believe this is who we're going after, here's what is about them, and here's what we can offer them. Okay, like now let's like do kind of like the more fun part of like how do we message to them in a way that's compelling and like start to like, both in a way that's like really clear, but also like that's punchy and grabby and like grabs you and like really res- will resonate with that persona. And then like also taking that to make sure you put it in front of some folks, which is the critical step that's easy to skip, but like not only just like, you know, sharing it with the executive team and getting nods, but like really g- and this makes it easier to go to the executive team too and say like, "Hey, I had 10 conversations with like leading, like VPs of finance and like this, they all agreed that this is the most compelling narrative and thing for us to do."

It gives you so much more gravitas 'cause like messaging as you, I'm sure you know, b- better than anyone, Al, like it's like so hard 'cause everyone has an opinion and no one's right, right? Like it's just like a very difficult thing that is so apparent, it's so known and out there and like, so wrangling, like the more you can like back it up with like, "Hey, I've actually gone out and got feedback on this," adapt, adapted and learned and like apply that back, it can be really helpful, so.

I love it. I love it. I'm gonna l- um, I'm gonna call out a few, a few things because the refine step is loaded. There are there's a lot to do in your step two of refine because now you've done all the research, but you're turning it into a kind of like a findings readout report for your stakeholders.

But then as part of that, you're kind of building the strategy along with it because you're matchmaking your findings with the opportunity and, um, what y- basically your product's capabilities and, how that's going to show up in terms of messaging. and you're also saying, "And by the way, we've already done this message testing for this new messaging. Here are the findings of that too." so it, it's, it's a lot to do in the refine, um, step.

But I think it's, it's, uh, it's good that it all happens together in the same step because it's a very, it's a very natural way to do all of that activity. Yeah. Yeah. Such a critical one too, right?

Like that is like PMM's like opportunity to shine is in that refine pillar, right? Like everything is like, you know, other functions are doing, but like PMM's ability to like shape and sculpt and like carve out and actually turn that into something that's gonna resonate is like, I think can be a superpower for PMMs if you can get it right, so Totally, totally. Um, I wanna g- I'm gonna shamelessly plug a couple of my other podcast episodes here that I think will be super helpful for a PMM.

So one is, uh, uh, is Kevin from Fleetio. Um, he, his case study is actually he worked at a company called Hims for a little bit, um, the big, the healthcare, you know, conference everyone's familiar with. Yeah. So he, in his, like, case study, he talked about how he did this, like, message testing kind of like, uh, workshop with executives and stakeholders, and just his method for that was really helpful.

So I just wanna, like, shout out to anyone who may be like, you know, wanting to, as part of their refine step, do like a little, like, messaging workshop with your stakeholders. That was a really good one. Another one is earlier on in our conversation, you mentioned doing like some competitive… You mentioned alternatives, competitive alternatives, and I don't know if that would be part of your step one or step two. Like, I don't know if that'd be part of your, um, research step.

I think maybe it would be. So I should, maybe I should, this should be a plug for, like, the step one in the research. I have another podcast episode with, her name's Mindy from Klaviyo. She l- built a repeatable system for exactly what you described, Quinten, as like looking at the pains of your competitors and building, like, a system around how you speak to those pains from a competitive, um, uh, objection handling, basically.

So I think, like, maybe the research bit obviously happens in your step one, but maybe as part of your refine when you're starting to build out some of that messaging and you're, you're considering those alternatives, those competitive alternatives, like as you already pointed out, and I'm validating what you said with, um, another professional in the business, she, she does it the same way. So plug for Mindy from Klaviyo. That's another really good episode Yeah, Kevin and Mindy.

I'll have to check both of those out. That sounds really helpful. The messaging workshops are awesome. I think like that's such a good way, like again, the messaging thing, like the hardest part of messaging is getting buy-in.

Like that's like always It really is so true. That's how it gets watered down, and you can build out this perfect messaging that's so good for your buyers and the buy team, and then you get some executive coming in, Yeah. And those workshops, like, which I don't do enough of, and I think they're so, like, I - they obviously, like, you have to get everyone on the calendar and take their ti- like, very val- very expensive, like, meetings just from like a time standpoint. But the fact that you can get everyone agreeing and, like, also just be part of the journey of like, "Hey, we started here.

This is what we said. Based on what we said, here's where we ended up." Like, that allows it to, like, all connect and, like, have less room to, like, continue to like, you know, spur, like, you know, uh, iterate or just, like, provide feedback throughout that process, so Yeah. I think what's really beneficial for you is that just as a founding PMM, I'm making a little bit, a few assumptions here.

Maybe this is all wrong, and maybe it's more like varies from situation to situation. But you probably already had a lot of more trust and, um, I guess like not necessarily autonomy is not what I'm trying to say, but that trust and faith from your executive leadership that maybe some of - You don't have to do quite as much hand-holding with like some of those messaging workshops, because you guys are probably already so tight that you're working together so, um, frequently anyway.

Um, and they're probably also just by nature of being at a startup very close to some of the work too. So I'm guessing that it's not quite as difficult to get some of the messaging buy-in. Maybe I'm wrong, Yeah. I agree.

Like, it's always like a difficult task. I sit next to my C- uh, CEO right now, so like I like, that is my desk mate, so, uh, so that's exactly where, where we're at. But I totally agree, and like, I think like, obviously like bigger organizations will like bring in a big expensive like agency, and then they're like, "Tell us about your business." And like they go through these like long, expensive cycles.

And so like having someone ingrained and who's seen it and like also just like has a good feel for like how like your founders and your leadership team see your business and how you sell and all those different things, and also just like leaning into your sharpest like field folks too, like whether that's a CSM who sees like our most successful customers or like a sales rep who just like really has it and like gets it and their message lands way better than everyone else, like that continues to validate your work, so.

100%, absolutely. Um, okay, I don't wanna get too far off s- off track. So your step one was research, your step two was to refine, and now step three is to ready. And they'll, like, some of this is, like, enablement.

Like, what are the other, like, co- just quick out- actions that I should take for the step three ready? Yeah. I think you should just view these as like three different, like, layers, right? So you have your, like, marketing lens that you're taking for this.

So, like, it depends on whatever initiative you're running, but, like, in this enterprise push, right, we're gonna, like, w- wanna run full-scale campaigns in, like a - I'm, like, been fortunate I'll work with, like, a demand gen leader, a growth, uh, leader on, like, as a partner on that front of like, "Okay, here's our persona messaging, ICP. Like, here's what we wanna do. Here's some ideas. Like, let's get together.

Like, you can come, uh, take that and, like, come back with, like, campaign ideas we can work together on. I'll sh- work on what the messaging is and, like, you're gonna actually think about what are the channels this is gonna be most successful in, what are the tactics we're gonna execute on, and then go out and execute those." So that's like a pairing, like you do that across, you know, social, paid, like, uh, webinars, content events, like all those different things. Like, you're working with them to, like, take what you're doing and translate it into something marketing facing that's gonna help you drive the right leads and, like, really, uh, build a reputation in that new segment, audience, vertical seg- whatever you're going after.

So that's the piece on the marketing side. Then you have your sales, right? Of like, okay, what does the new playbook look like? And you have to have a salesperson come with you on this journey.

Like, I've done a lot of sales enablement and, like, making sure that you have, like, one of your best sellers or a sales manager who's trusted, like, working with you to build these things so you're not just like the mark PMM who comes in and tells, like, a sales team how to sell when they go and take it on the chin every day. It's never gonna resonate, and it's never gonna, like, move the group. So you need, like, a champion in the room with you who's actually gonna, like, train on the demo, and you're gonna be like, I'm color commentary about like, "Hey, this is the industry we're going after."

Like, now they're, you know, gonna work, you know, Al, my sale- like enterprise AE who's had a ton of success, is gonna show you how you would demo to a medical device company, like, and, like the nuanced change in the messaging that, like, happened. So that's, yeah, like that's really the key piece with, uh, sales. And then, like, obv- you have your like, I say it's like pitch, disco, demo, like all those pieces, getting that right is super critical. Lastly, on your like post-sale side, just making sure that they have everything they need that, like, speak the same language, know the type of companies that are gonna be coming in, and they are ready to support them, implement, like, uh, continue to, like, what are they trying to achieve as success, and, like, how does that change from, like, historically how you've talked to folks.

Terminology is super key if it's gonna be, like, new styles of businesses and making sure it doesn't feel like, "Oh, like this person knows nothing about how my business works and isn't a trusted consultant for us." So yeah, making sure all three of those teams, like, feel equipped and ready to take on the strategy you've done, because if any of it falls off, like you're really like, it's a lot of that work is gonna be for nothing. So super Totally. Totally.

Okay, so the three layers for the ready step are, um, marketing, sales, and customer success or/support teams. Makes perfect sense. Okay, so bring us home with step four of report Yes, report. This is, I mean, this one's obvious, but you're really just looking back at how performance did, and I think those three channels are the same way I like to look at this.

So like, okay, because if, for example, if you're having success, which is like our goal was like to close, you know, a million dollars in revenue in this new vertical as an example. Like, if you didn't achieve that, like you can't just point at sales, you can't just point at mark- like, you have to really like uncover like what went wrong or what went right, honestly. So like were the campaigns we were running successful? Did the goals we set out to achieve get achieved?

So on like the content piece of the mar- webinar, like the event, like what was like well engaged and what should we continue to double down on versus what isn't working? Or is none of it working and we need to like go back to the drawing board and figure that out? Same with the sales side of like, oh, our win rate is just way lower than it's been. Like maybe sale, oh, I'm seeing in sales calls they're not adopting the new talk track.

Like, oh, we need to make sure like we retrain or like enforce this in like a really positive way. Or like they're actually not seeing success and they're churning out and like maybe there's a product problem we need to feed back to the product team, or like we need to like help them like equip better our CSMs to like handle these conversations. So really like, um, I - that's more of like a qualitative way of like, okay, what's happening? But really starting to like look at what your goals were across all those different channels, seeing how you stood up, and then like double-clicking based on like either where you're really seeing success or really not seeing success can really be is the way like I've approached this, so.

So good. I like all the different, like, angles that you're looking at for reporting, too. So one thing that I've noticed is that AI is, like, obviously incredibly good at, like, finding patterns, and, um, but deciding which patterns still feels, like, superhuman, right? And I'm curious how much you agree with that, and then also how you think AI could be changing part of your… changing or enhancing part of your playbook Yeah.

Um, this, like the pattern thing is so interesting of like being able to like analyze data is such a… One, like it's a skill like I like had to learn of like for like these like segmentation analysis and like probably not my like historical skill set. You know, I didn't go in and get like a finance degree and like be on all my time in spreadsheets, so it was a learning curve to get there. But like learned a lot of that. But the fact that now I can like say like, "Okay, I wanna look at like based on the deals we've won, what were the leading persona?"

And like I can like get that data right away is like so invaluable and so fast as like an insight and like one that you wanna continually build like systems to like have that always on of like surfacing trends in your closed loss data as an ex- closed won, closed lost data like over time. Not to be ignored is like continue to do those win-loss interviews. But, uh, regardless, you should still be identifying those like with AI, like quant- having a system set up is super critical there.

I do agree though, like that's where like there, the shift is of like, okay, like they're gonna show me the trends of like, oh, like, you know, 20% - like we only win like 5% of deals when like the champion is like a sales com-compensation manager. Like they're not gonna be like, "Oh, like we need to like move, like we need to change our strategy to go after these personas." Let like connect the dots of like, oh, we need like the executive buyer in the room. And that's something that PMM from your context, from your like experience that you can say like, "Oh wow, this trend, that to me tells me this.

Let me go out and quickly just like double click and do a few things and understand a bit more and like be curious." And like we can still use AI for some of that, like follow on analyses, but like you're the one that's like making hypotheses and like, oh, like connecting the dots on these things that like AI naturally isn't going to do. And like you're gonna read out like, oh, this like insight without like direction is just like, it's like kind of useless. So like you're the one that like takes that and points it where it needs to go, so.

Yeah, totally. Your judgment, your opinion, your discernment, your empathy, those are things that you can't rely on AI for. Um, okay, so you're now at Unify, and this is basically your kind of second time being this founding PMM at a startup. What parts of this playbook are you using for Unify, and anything you'd, like, change or swap out?

Yeah. Um, I still would say I use most of this, of like that approach. I think like being like research forward and then like taking time to like refine those insights into something compelling and like writing the teams and reporting on success. Um, the things I will call out is that the timeline of those has di - like just being in a startup has like gone from like months-longs or quarter-long projects to like weeks-long or days-long, you've got AI now.

Yeah, exactly. So now it's so much easier. So, um, I do think that's been like the biggest shift rather than the process itself of like, okay, like we're - let's go look at trends to see like where there's opportunity that we're missing out on. Like, okay, great, like we've looked at this.

Like, okay, let's like, you know, h- what is our positioning for that, like going after it. So, uh, we're even working on like a big launch now of like, okay, understanding our buyers and like how we're refining it, and then how are we gonna like, uh, we have like a bunch of enablement sessions next week. So a lot of this stays the same, but like the biggest change is the time- your capabilities and the timelines. But yeah, we'll just continue to like be the human in like the room and like, don't let yourself get lazy.

Like, I find myself doing this a lot, where you're just like, it would be easy just to like take what I'm found and like put it in a doc and kind of keep going. But like the more you c- like with AI, right? Like, that just makes every- it easy, like there's like a laziness epidemic that's gonna be created out of this, that like your opportunity to be like, I'm not only like AI, but I'm also just like, I'm like almost like its own like manager, where I'm like taking everything that it's showing me and being like, "Oh," like, "Here's my feedback," or, "Here's like my insight," and like, "Let's turn that into a plan."

And like really like being like a partner that way rather than just like, oh, letting it do the work for me and like let it - 'cause it's not gonna have that like intellect that you have from being a PMM for years, and like that's the advantage like you still have in your career, like against AI, if you wanna keep your job, is like your experience and your context and those different pieces. So, um, that's what I, love that. yeah. So that's kind of love that so much.

Yeah, your experience and your context. I love this. Um, okay, last question for you, Quintin, on this topic. Um, what's one piece of advice you have for a PMM who is currently trying to move upmarket working at a startup?

Yeah. Um, I think the big thing for me, like throw away everything you know. Uh, which I think is an important thing of like, uh, in the way we just said how important experience and context is. I don't mean it in that sense.

Um, but what I mean is like, hey, your old playbooks aren't going to work. Like, just because you succeeded with this here and had a ton of success doesn't mean it's gonna work like over here. And like that is like a really hard thing to like accept sometimes of like, oh, we're like, oh, but like this is like a track record. Like I'm a really successful rep, and like I'm not gonna change my ways 'cause I've seen success.

So like not only yourself, but also just like getting folks to buy into that shift is like super crucial to having success with these things. So I think like that's one of the first pieces, like both like yourself of like, hey, like if you were starting from scratch and like joining as a PMM to like, with that specific initiative almost as like a contractor or hired gun, take that lens so that you don't get like caught up in like, oh, like my biases or like I, I'm like what like the best reps are saying, and like start, start anew and see kind of how that treats you.

I think that's really, uh, really important thing and like it's easy to like bias towards what's worked versus like, okay, I'm gonna need to do things entirely different. So that's definitely what I would advise on that front. Love it. Thank you so much.

This is such a helpful playbook and perspective, and I am definitely going to use your four R framework of research, refine, ready, and report. So helpful. Okay. Yes.

Um, all right, so now it's time for the next segment of our show. This is the messaging critique. This is where we as product marketing expert- experts get to analyze real world messaging, and the fun part is, Quintin, you as the guest of my show get to pick the company that we look at. Some quick ground rules.

Um, you're gonna pick a company, ideally one that you feel like you know the c- uh, target audience really well. Um, you're gonna tell me what stands out to you as really, uh, working really well with messaging, something you wish the PMM would've considered differently, and then we're gonna iterate on how they can take it to the next level. So without further ado, please reveal the company that we'll be looking at today Yeah, we're gonna be looking at Profound. Um, so, um, for folks who aren't Is it profound.

ai? That's a good question. Um, I'm looking at it. I think it's tryprofound.

com Oh, try profound.com. Okay, try… Okay, just for folks who want to follow along. Um, yes.

So Profound, um, is an AEO GEO, which is a new co - answer engine optimization, uh, is like the new hot phrase in like the AI world. So basically how to think about it is like how do you optimize for people who are searching in Chat or Claude or, uh, Perplexity, wherever they're, wherever they're going to do what they would usually do in Google. How do you make yourself one of the vendors when they ask, "Oh, I need a new, uh, privacy tool for my business," or, "I need, uh, I need a new like tractor for my farm."

Like whatever that you're going in there to look for, like they are a company that helps you show up, uh, within those LLMs, which is really powerful and obviously powerful. Okay, so tell me, walk us through their, who their target audience is and, like, what stood out to you about their messaging Yeah. And, uh, the reason I bring them up, we use them at, uh, Unify. Um, they're, um, we're, uh, we - So we've been, um, I'm actually not, I maybe I- I've gotten access and gone in once or twice, but we actually have a, uh, like a growth engineer on our team, which is interesting, who owns the platform, uh, who's really smart.

Uh, real- like, um, I would consider him like more almost like a go-to-market engineer who's, uh, running and building, building these kind of things. So definitely a new world role, role and like skill set. Um, but, um, what the… Um, sorry, I forget the, where I was going Yeah. So who, um, walk us through their, like, target audience.

It sounds like maybe, like, growth marketer maybe could be the actual, um, you know, target audience. But then, like, tell, talk us through the actual messaging and, like, what's, what's working really well with it? yeah, so who Profound sells to is, um, and partially they're like creating their own new roles, but really I think the focus, like, as you, like, look more, um, like classically an organization like content teams, um, PR, brand, like folks that are like h- helping you, like show up with your content in those, like any sort of SEO analysts probably will be moving, like having this under their, uh, under their purview going forward.

Uh, growth marketers is another one that's definitely, uh, like search optimization, any of those types of roles, digital marketer even could kind of fall into that, in that world Yeah. And then, um, if we look at their messaging, so I'm on their website right now, tryprofound.com, and I see kind of like a, um, maybe like a rotating. They have marketing agents to win, and then it rotates out the different LLMs, or I guess like, at least like the top most popular ones.

Um, and then it says, "Reach millions of consumers who are using AI to discover new products and brands." Yeah you - what's standing out to you about their Yeah. And honestly, it's funny, this is like the same thing that stood out to me about like in - So like, you know, I'm in SF, I'm walking by like tech billboards every single day, and like as a PMM, I'm like, like I'm actually like interested in these things and like I'm like entertained by critiquing, right? them.

I'm like always trying to be into speaking. Of course, I like wanna start a LinkedIn series about this eventually, but people hate them and like it's a whole, that's a whole nother like can of worms of like people hate the AI billboards. But regardless, um, what I like about, they have stood out to me around like this key point of clarity. Like I think their messaging is some of like the clearest, like they aren't trying to do too much.

Uh, I think like there's like a spectrum in messaging of like, like punchiness and like creativity and like clarity, and I really think they do an excellent job of just being explicitly clear about something that's really, really new, really com- like complex, new, like you have to like educate the entire market on what this concept is. They are doing that in a way that's very just like, "Hey, this is explicitly what we do. We help marketing agents to win in Microsoft Copilot."

Like, okay, like yeah, that like piques my interest of like, okay, you are going to help me show up in or like help me win in those LLMs or specific tools. So that like is something that's consistently in some of their just ads and stuff have just like impressed me on those fronts. I l- yes, absolutely. okay, so what's working now, what do you think is then maybe room for improvement on some of this?

Yeah. Um, I would just say like to that point of like that spectrum of like creativity and like clarity, like there's probably a room to be like more like punchy potentially on some of their branding of like, um, we - like even just like a strong like manifesto POV of like the future of like, you know, for example, like I think, and I'm just going through the page, they might have some of this, but like so much of search today is naturally just shifting from Google and historical sources to LLMs, and there's probably like a, uh, arbitrage opportunity to like be showing up in LLMs right now in a way that like will probably will not exist in five years.

Like everyone will probably have this figured out. It'll be part of like the generic marketing approach. So this is like a new channel that you can go out and like be kind of like this sneaky lever for you to like have success in the market. So I, I would say like leaning more into like that of like this like, oh, whoa, like they're changing like the way like - they're like on the forefront of like how marketing is going to shift.

I think there's probably an opportunity for that, but they might be doing that in other channels and like maybe like founder-led marketing and stuff like that. But yeah, but I think there's probably an opportunity to continue to do that here too. And then how would you take it to the next level? Like, if you were kind of on the ground floor and, like, taking the, taking the good parts of their messaging and, like, maybe iterating or bringing it to the next level, maybe even implementing some of your playbook, how would you, you know, how would you coach them on this to, to really, uh, take it up a notch?

Yeah. I think like, uh, a thing that would probably be interesting to understand, I'm just like curious about that, like just as a marketer, I'm very curious, uh, about like how they're thinking about this role doesn't exist, and I think they introduced like a similar to like, uh, Clay, like the, they have like a marketing engineer or content engineer title that they're like leaning into right now. But naturally, like not a lot of those exist in the world like today. So like how are you thinking about is obviously as you're thinking about enter- growing an enterprise, you're gonna have to sell to existing people who haven't done this before and aren't doing this today.

So how do you convince like those folks to go out and use a tool and do a practice that they've never thought about or done before, and that you're the one to do it with them, like, and take them on this journey? So it takes, I think it takes a lot of like, it'll probably take a lot of education and I'm sure they're doing a lot of, uh, really good work of this. I know like two of our team attended like a conference that they had a while back and said it was really awesome. Uh, but yeah, on that specific point, like g- as they, I imagine would be going up market, I would like go out and have like conversations with like established digital content, like marketing, SEO, like whatever, like niche of the marketing organization, like a, like I would wanna say legacy, but like maybe current state marketing organization, how might view this, who they think should own it, who's really best fit for it, what skill sets do they need, what about their product like resonates today versus doesn't, and like how do you make like, 'cause you continue to evolve both your messaging and your prod- and positioning to serve not, not only this like new audience that you're creating, but also this like aspirational, like, hey, this is where our business is going and like we need a, like a message that's gonna resonate with those folks too.

Yeah, I really like the aspirational angle, and I think that mirrors to, you know, what you were thinking when you guys were kind of moving upmarket and, um, you know, re- um, rethinking your narrative. So okay, Profound, very cool. Uh, shout out to any Profound PMMs. You've got some fans, and also Quentin has some really good ideas for you, so check it out.

Yeah. Very impressive stuff over there. So they're doing a great job Absolutely. Yeah, we love it.

Um, okay. So Quintin, one thing I like to make space for in this podcast is a moment of gratitude, um, 'cause in product marketing or marketing in general, none of us get to where we are in our careers without learning from each other. So just a big genuine thank you so much for taking the time to come on and share your expertise on the show. Um, I really appreciate it.

And then I'd also love to turn it around, um, to you and give you an opportunity to shout out some PMMs who have made a really big impact on your career and brought you to this moment to where you are in your career today Awesome. Um, yeah, and thank you for that. Like, thank you for having me. This has been so much fun.

It's been fun to go through this process with you. I love what you're doing for PMMs out there. Like we - I think it's gonna be like a, it's kind of like a niche role and sometimes isolated role in an organization, so creating community around this I think is super important, and so I love the work you're doing, so keep Oh, of course. Thank you.

Yeah. Let's hear those PMMs yeah, gosh, so let's get them together. But, uh, the one I'll give a shout-out to, there's so many great ones in my… So shout out to all of the, all of the PMMs in my world. But, um, one who actually has recent- uh, departed the PMM world, actually, uh, entire- is now, um, entirely departed to a different industry.

But regardless, um, uh, Ani Golovko is her name. She was our director of PMM for a while at Ketridge IQ, and she has, uh, brought this really like strategic, methodical, like data-driven approach. She came from the biz ops world and like really like brought on that like research side of like The quantitative, had historically, but I was more focused on that readying world for so long, and she really like, uh, was really a big proponent of like, in order to like establish PMM and like make like yourself a strategic player and, and a team, like you really have to be like data-driven and curious and, uh, uncovering rocks and analyzing and like doing these things without AI.

So, um, I've like learned so much from her. It was really - Uh, she was a really great, uh, manager, leader and like, um, yeah, we had, uh, so have so much appreciation for that. So shout out to Ani. Oh, I love that.

It's so good to have those mentors and coaches who are, like, in the data with you and, like, kind of coaching you on how to, how to look at it and view it. So good. Okay, last question for you. Where else is it best to access your expertise?

Is it just best to find you on LinkedIn? Yeah, feel free to connect with me on LinkedIn. I don't have a source for my, uh, knowledge or expertise yet. Feel free to connect with whatever knowledge and expertise I can offer.

But yeah, happy to connect with folks, chats. I'm always interested in talking, uh, product marketing. So yeah, feel free to connect with me on LinkedIn Awesome. Sounds good.

Again, thank you so much, Quentin. This was so, so good. And hey, PMM listeners, if you liked this episode, please share it with a PMM friend, and I would be so grateful if you would leave a review. It helps tremendously with our reach.

Thank you so much for coming on this adventure with us today. I hope this episode leaves you with inspiration to take in the next step of your own journey.

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