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Inside Sales Compensation Planning with Canva's VP of RevOps

The RevOps Hero Podcast · 2026-03-12 · 38 min

0:00--:--

Key moments - from our scoring

Substance score

54 / 100

Five dimensions, 20 points each

Insight Density11 / 20
Originality9 / 20
Guest Caliber15 / 20
Specificity & Evidence12 / 20
Conversational Craft7 / 20

James Jackson brings deep experience from Microsoft, Cisco Meraki, DocuSign, and Snowflake to discuss the foundational principles of sales compensation planning. The core insight is that compensation should express a company's strategic intent - whether hypergrowth, steady state, or protect-and-grow - rather than define it. For hypergrowth companies pursuing net new ARR, Jackson recommends 50/50 base-to-variable splits with aggressive comp mechanics; for mature, stable companies, 70/30 or 60/40 plans with lower leverage work better. He addresses the persistent misconception that all reps should hit quota (he targets 50-60% quota attainment with 90% mean attainment across the team). BDRs and SDRs should be compensated on qualified opportunities rather than meetings or leads to avoid garbage-in-garbage-out pipeline problems and create joint accountability with AEs. Jackson emphasizes that RevOps leaders often underestimate the importance of change management: roadshows, back-channeling with influential sales leaders, and ensuring stakeholders feel heard drives adoption far more effectively than top-down decree. He also stresses the critical role of clean definitions, pipeline governance, and pipeline councils in making comp plans work at scale.

Key takeaways

  • →Sales compensation should express company strategy (hypergrowth vs. protect-and-grow), not define it, with structure and leverage changing based on strategic intent.
  • →Design for 50-60% quota attainment with top 10% of reps reaching 250%+ to drive healthy tension, rather than aiming for universal quota achievement.
  • →Compensate BDRs on qualified opportunities with secondary incentives for closed deals, not just meeting volume, to ensure accountability and prevent pipeline quality problems.
  • →Change management and stakeholder buy-in - via roadshows, back-channeling, and making people feel heard - matters as much as the technical design of the comp plan.
  • →Clean data, clear definitions, and strong governance models (like pipeline councils) are foundational; forecasting and comp plans cannot work without them.

Guests

James Jackson

Topics in this episode

Account-Based Marketing (ABM)Sales compensation philosophyAccount executive (AE) comp structureBusiness development representative (BDR) compensationSales development representative (SDR) compensationTerritory and quota settingPipeline governance and pipeline councilsAttainment distribution and quota setting principlesConsumption sales modelsSales forecasting and data integrity

Questions this episode answers

What percentage of sales reps should actually hit their quota?

James recommends targeting 50-60% of reps hitting quota, with top performers reaching 250%+ attainment and a mean team attainment around 90%; universal quota achievement signals quotas are set too low and money was left on the table.

Should customer success and partner teams be on commission-based compensation?

It depends on company strategy: if the focus is top-line hypergrowth and bookings accountability, then yes - comp should reflect that accountability across all go-to-market roles to drive consistency.

Why should BDRs be compensated on qualified opportunities instead of meetings booked?

Compensating on meetings or leads alone creates garbage-in-garbage-out problems where BDRs have no incentive to qualify, AEs reject bad leads, and you get finger-pointing between teams; qualified opportunities create joint accountability.

How often should a company revisit and adjust compensation plans?

Mature companies typically plan annually with few mid-year adjustments, while hypergrowth companies may need six-month planning cycles to adapt to changing growth trajectories and maintain conviction in quotas.

Who should own compensation design versus commission execution?

Ownership varies by company, but ideally RevOps or sales strategy owns comp design and enablement while finance may handle execution; the key is collaboration between RevOps, sales leadership, and finance throughout the process.

What our scoring noted

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

Insight Density

11 / 20

The episode contains a handful of genuinely useful operating rules - specific attainment distribution targets, the SPIFF-vs-replan decision framework, and the BDR qualified-opportunity argument - but large stretches are padded with pipeline housekeeping tangents, EQ platitudes, and the lengthy career bio. Insight-per-minute is moderate, not dense.

Comp philosophy to me is typically 50 to 60% of reps should hit quota. I want my top achievers to make a lot of money. I want my top 10% of reps to be 250% plus attainment and I typically want around 90% mean attainment.
If you have a pipe gen pacing model or you have a pipeline model, I've seen this at multiple firms where BDRs are 150% attainment, they're crushing it. Thales is not crushing it.

Originality

9 / 20

The framing that comp should 'express' not 'define' strategy is a clean articulation, and the SPIFF-as-surgical-alternative argument is practical, but the rest recycles widely circulated compensation orthodoxy - hunter/farmer splits, leverage ratios, change management via stakeholder inclusion - without a genuinely contrarian or first-principles angle.

sales comp should be the expression of the company's strategy. It shouldn't define the strategy, it should express the strategy.
you can be technically right. And whenever you have a split issue, you have some type of field friction. You can be technically right, but that doesn't mean from a leadership perspective, how you show up is just as important.

Guest Caliber

15 / 20

James Jackson is a genuine senior practitioner with direct RevOps ownership across Snowflake (2,700 reps, $3.5 - 4B), DocuSign enterprise build-out, and Cisco Meraki ($1.5B - $4B scale), plus real quota-carrying experience at Microsoft - this is credible depth, not a career podcast guest.

I was at Snowflake where I ran Revops and owned all of our planning, compensation and systems...2700 reps, they all have a custom quota, completely different model
we scaled the business 1.5 to 4 billion over three years

Specificity & Evidence

12 / 20

The guest provides concrete attainment distribution targets, explicit OTE split examples ($250k OTE, 50/50), scale figures from named companies, and two vivid anecdotes with real numbers; however, most company-level stories are anonymised ('prior company') and causal data - what changes actually drove which outcomes - is largely absent.

you're looking more towards a 5050 plan where if a rep makes 250k OTE 125 is base 125 is the variable
we calculated. It was like tens of dollars of commissions to the global account manager. And we probably spent like 20 hours like running this analysis

Conversational Craft

7 / 20

The host primarily restates or confirms the guest's points rather than probing them, never challenges an assertion, and several questions are simple definitions-checks or scene-setters; there is no productive friction or follow-up that extracts deeper specificity.

When you say leverage you mean uh, base versus commission. So higher leverage is more commission based for their total comp. Lower leverage is higher base percent and a lower relative commission amount.
And specifically making sure you're spending probably more time than you naturally feel like you would, specifically over indexing on the communication time

Conversation analysis

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

Share of words spoken

  • Speaker B89%
  • Speaker A11%

Most-used words

sales44comp34plan20drive19revops18important18strategy16different16market13growth13leaders12team12sure12course12back11compensation11

Episode notes

In this episode, Chris Strom sits down with James Jackson, VP of Revenue Operations at Canva, to discuss how companies should approach sales compensation planning. James shares lessons from his experience leading RevOps and go-to-market strategy at companies like Microsoft, Cisco Meraki, DocuSign, Snowflake, and now Canva. The conversation covers how compensation plans should reflect company strategy, how different sales roles' comp plans should be structured, and how RevOps leaders can manage comp planning across sales, finance, and leadership. They also discuss common comp plan mistakes, when to make mid-year adjustments, and how to align incentives across account executives, BDRs, and customer success teams. If you work in RevOps, sales operations, or go-to-market leadership, this episode provides a practical look at how compensation planning works inside high-growth companies. Topics covered: How sales compensation should reflect company strategy Structuring comp plans for AEs, BDRs, and CSMs Quota design and attainment expectations Aligning sales, finance, and RevOps on comp planning What to do if you need to adjust comp plans mid-year Using SPIFFs vs.

Full transcript

38 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: This is the RevOps Hero podcast where we talk to real life revenue operations leaders to learn what it takes to turn you into a RevOps hero at your company. Hey everyone. Welcome back to another episode of the RevOps Hero podcast. I'm super excited. For today's guest we have James Jackson. He's the VP of RevOps at Canva. And today we'll be talking through sales compensation. This will be our first episode in our podcast on this particular area of RevOps and it's such a crucial part of a, uh, company's go to market motion. So I'm super excited to get into this topic. James, welcome to the episode here. I'd love to hear a little bit of your background and how you got into Revops to start with.

Speaker B: Thanks Chris. I appreciate you having me. I think like a lot of Revops professionals, it's not something as a kid you wake up and imagine yourself doing 20 years from. From now. Right. And so it's something I feel all of us stumble into in our own way. And so my story is I actually engineer. Very fortunate to be first to college in the family. I fell in love with go to Market and so my first job at a school I was in Phil Markin, so, so I built out new vertical markets. I was presenting in front of customers with sellers and I just fell in love with go to market. Got my MBA at Harvard Business School with a focus on B2B sales and corporate strategy. And unlike a lot of my peers that went to consulting and venture capital, I wanted to carry the bag. So I went to Microsoft, I sold Azure in the enterprise space. You can imagine this person with no prior sales experience selling to the likes of an Oracle, a VMware, all these very large accounts like Tesla. And I was on the company's first consumption sales plan. It was a brand new model back in 2016 and I was very fortunate, had very good success. But I knew I didn't want to stay in sales for my whole career and so I transitioned into sales strategy go to market strategy. At Cisco Meraki, we scaled the business 1.5 to 4 billion over three years. I had a global team that aligned closely with our sales leaders. Some companies might call this like a business partner role or like a field operations or field strategy role, but we had a lot of great growth. We designed our drive to 5 billion plan and it was a great experience learning management skills as well as building out that kind of strategy lever. I wanted to then go into more of a detailed ops, like a true ops role and so an opportunity presented itself at DocuSign so I joined there to build out their enterprise sales ops organization and the CRO we know very closely, we're still very good friends. It came up through the ranks from SMB and they said James we want you to build out our enterprise, go to marketing. So I built out a verticalized sales team, I built out account based marketing and uh, our industry experts team. So the folks that want to speak the language of the customer for your financial services or government or healthcare life sciences. And so I built out capacity model, I built out pipeline, pipe, gem model. All of that was built out and all the structure and rigor that goes around building a high performing sales team. And so a lot of fun, great experience working closely with our CRO and executive team. Also a unique time I joined 2021. This was at the height of COVID We had just seen over 100% growth and then there was a bit of a decline at DocuSign following. We called it the COVID hangover. And so managing a lot of very difficult change from a hyper growth stage to a more measured growth stage was an exciting time. And then more recently I was at Snowflake where I ran Revops and owned all of our planning, compensation and systems. And also hyper group company grew 3.5 to 4 plus billion. And basically if you could imagine consumption company, 2700 reps, they all have a custom quota, completely different model and a really difficult at scale model. We did a lot of transformation on how we run territory quota, how we build out proper SPM tool and governance. And also how do you transform compensation plans to drive top line growth. Sridhar was very intent on if I make an investment, how do we drive the right system structure and people to drive very high growth and re accelerate the company. And so was a key role in driving that strategy. And then currently at Canva and I was joking with you before, my joke with Canva is a uh, unicorn pregnant with a unicorn and so very large PLG company. I own, um, all the B2B operations and everything from compensation to strategy ops fall under that role. And it's just been a fun journey and so super excited to be here. And it's something where in my career I've found a passion for sales and for go to market and I've pursued it both sides of the aisle. Right. I've carried the bag and I've also been on the other side setting the quotas and territories.

Speaker A: Yeah, there's a lot of different topics around comp planning and maybe uh, great starting point might be to talk about ways of approaching comp planning for different job roles like account executive versus like the sales development rep versus sometimes customer service teams or customer success teams have some success based compensation there too. Can you talk to us a little bit about how companies oftentimes approach comp planning for different roles like that?

Speaker B: Absolutely. Look, there's a lot of companies that have an maybe, um, not a holistic view of compensation and I mentioned this frequently with others which is people get sales comp mixed around. They think sales comp is going to be that is the strategy of the company and it's the opposite. The company has a strategy, it's going to be either top line hypergrowth, it's steady growth, it's maybe more of a defend and protect retention motion. But the company has, the CEO and the CRO have a strategy on what they want to see in the company. And sales comp should be the expression of the company's strategy. It shouldn't define the strategy, it should express the strategy. And so all of the metrics, all the measures, our comp philosophy, everything anchors on around that core truth of expressing that strategy. And so when you think about how you compensate, for instance, you mentioned an account executive. Right. If I am in a protect and grow element which I've been at companies that have been more on that protect and grow stage, the measures I'm looking at are total contract value, I'm looking at retention, I'm looking at things that will create drive more even handed growth. And that attainment profile is very balanced. You don't see people massively overperforming and you don't see a lot of people massively underperforming. And typically these are very mature, stable companies that might not have hyper growth but they want 10 year talents that know what they're doing. And so that is one strategy and that's how you express it. Those sellers might have a uh, lower variable. They might be 60, 40 or they might be 70, 30, so 70% base, 30% variable. If I'm in a hypergrowth it's going to be the opposite. I'm going to be focused off incremental ARR or gross new monthly recurring revenue. I'm going to be focused on only what you produced over what you already have as a rep and I'm going to be flexing a higher variable rate. And so you're looking more towards a 5050 plan where if a rep makes 250k OTE 125 is base 125 is the variable. So those measures, that structure is very different. The other thing that's often overlooked is, is how what's my customer base of life? There are a lot of companies that are focused on net new logo acquisition. And so you'll specialize a hunter versus a farmer motion. And those roles might have different comp mechanics, they have different rate tables. And so the more aggressive your comp plan, the more acquisition heavy the comp plan. It's going to be more feaster Fanon, you're going to have refs that might have sub 30, sub 40% attainment and that's okay. And so the attainment distribution profile for a hypergrowth company, it's way different. And the number one complaint everyone in RevOps will understand the number one complaint is the myth is that everyone should be able to achieve their quota. And that's not how you design complaints. Comp philosophy to me is typically 50 to 60% of reps should hit quota. I want my top achievers to make a lot of money. I want my top 10% of reps to be 250% plus attainment and I typically want around 90% mean attainment. I don't want to see drastically higher or lower than that.

Speaker A: The mean a little bit lower than a hundred percent.

Speaker B: Yes, exactly. You have oversign baked into your plan and so you want to have healthy tension in your go to market function. It shouldn't be a shoe in. If you set the quotas too low where everyone achieves, you may have left money on the table.

Speaker A: Right.

Speaker B: If you set them too high and you stretch the refs too much, you might lose good refs. And so there's a very healthy tension that goes into how you set the quotas and the comp philosophy. It's a difficult conversation. Depends on the maturity of your sales team. Leadership should be aware. This is our comp philosophy. This is our North Star as a go to market organization. And that's how we design the comp planes. And so typically account executive will be the most leveraged. If I'm a bdr, if I'm a csm, if I'm a sales engineer, I'm typically going to have a less leverage plan. So higher base but lower variable. It's the proximity to customer that should dictate how that comp plan is structured.

Speaker A: When you say leverage you mean uh, base versus commission. So higher leverage is more commission based for their total comp. Lower leverage is higher base percent and a lower relative commission amount.

Speaker B: Yes, that's spot on. Yeah, exactly. Hyper growth Typically higher leverage, slower growth, more stable, more mature, maybe a little bit lower leverage. And the number one question I get is, is it's the edge cases. Do I want customer success on a comp plan? Do I want my partner team? If you have a partner account manager or channel account manager, do we want them on an account plan? And to me the question always goes back to what is the strategy of the company? If the focus is top line hypergrowth, if it's on bookings accountability, then your comp plan should reflect that and that that means driving accountability in all of your go to market roles as much as possible. And so I'm always a fan of tying to those principles and making sure we're consistent in how we drive as a RevOps leader, how do we drive consistency and discipline in our approach? It's a difficult job and it requires lots of alignment between sales and finance and HR and making sure everyone's on the same page.

Speaker A: And oftentimes you will do for the sales development reps, you'll do a less leveraged comp plan for them. Can you tell me a little bit about that, why you approach it that way?

Speaker B: BDRs and SDRs, it's defined differently at different companies. The definition I typically use is SDR might be an inbound person that is managing and qualifying leads to pass on to reps. A BDR is kind of a broad term. It could be inbound or outbound. Right. They might be doing some outbound prospecting but typically less leverage. These are relatively junior roles and what you want to do there is you want to make sure as much as possible. In my perspective, you tie them to revenue and it's a difficult thing. And it's still a debate in the RevOps community on how you compensate a BDR. Some like to compensate on number of meetings booked, some like to compensate on sales qualified opportunities or squos or or leads. To me, I love qualified opportunities. If it is something where the BDR is comped on meetings or just number of leads and they're not qualified, then it's going to be. You have the chance that it's going to be garbage in, garbage out. And so reps Tiffany don't have a slow target, they don't have the same targets as a bdr. And so there's not a disincentive for them not to accept the lead from a bdr. And so you run into this kind of difficult situation where if you have a pipe gen pacing model or you have a pipeline model, I've seen this at multiple firms where BDRs are 150% attainment, they're crushing it. Thales is not crushing it. The ARR is not showing up in a green way and it can become a finger pointing match. Oh, the numbers are wrong. Sales isn't doing their job. And so having joint accountability as much as possible is to me very important. And so I like qualified opportunities, I like incentives that promote. If a BDR passes on an opportunity that closes, there's some type of commercial incentives, either a bonus or some type of positive secondary incentives for bdr. I like to see that. I like to see. And uh, I think bdrs really like to see that ah, they're on the hook and they enjoy the rewards of like things that drive and push the business forward. So I'm a big believer in making sure roles are interdependent on one another and they're all connected to those first order principles of how we want to run compensation at the company.

Speaker A: Yeah. And then also the job of communicating and establishing common definitions of success along the way so that it doesn't turn into finger pointing and you're not closing the leads. Well that's because the leads are bad. I point at you, you point at me. That's what can happen if you don't have those common definitions between all the teams. Right?

Speaker B: Absolutely. And that's why a lot of companies, if you ever hear the term like pipeline council or plc, that's why pipeline council is so important. There is art and science to our roles. And so getting the data right, getting the right metrics right does matter. It's a lot of work. But then what follows is you need to drive the right behavior and the right culture at scale. And that is a journey every company has to come to terms with. If we don't have the right definitions, we don't even know what the scope of the problem is. We don't know the magnitude of uh, if we're off force, if we're not pacing on pipeline generation, we need to understand the baseline of like where we are and how big is the issue. Right. And so it's all foundational to one another. It's the same thing with forecasting. Some companies that don't have clean sales stages, they don't have clean exit criteria, the pipeline becomes undefined and not dispositioned and it becomes unclean. And if the pipeline's not clean, then I can't forecast. Right. And so all connects together. Pipeline forecasting. The data has to be right, the definitions have to be right. But then you need the governance model on top of it. How am I driving accountability as a sales leader and how am I running my organization that there's a culture of excellence and that it's not okay to have a surprise raised in week 11 of the quarter. Right. We need to be dialed in and we need to incentivize an award behavior and culture that incentivizes making sure we're accurate on forecasting and we're not sandbagging and we're not doing funny things with pipeline. And those governance mechanisms are as important as getting the metrics right. And that involves influence. That involves working with sales and different personalities and egos and peculiarities about how sales leaders run their business and meeting them where they are. Every sales leader is different. There are sales leaders that are very number certain. There are sales leaders that are more kind of vibes and personality driven and uh, on that side and one's not right and one's not wrong. You have to meet the sales leader where they're at and you have to drive influence to make sure we drive durable change in the company. And I think that is what's really important as important as getting those numbers right. And so having closed loop feedback is important. Building trust is important. I've been on pipeline councils where the finger pointing between bdr, you could do the same thing with marketing. The foundational issue is do I trust the numbers? And if I do trust the numbers then where is the gap? And if I understand where the gap is, what are we going to go do about it? It's not what is sales going to do or what is marketing going to do, what are we going to collectively do as a go to market leadership board to fix the gap and push the business forward. And I think those are constructive conversations but they have to be built on trust and they have to be built on the data being right in order to facilitate that trust getting built.

Speaker A: That leads to one of the other questions I wanted to hear from you on is which job roles are are involved slash responsible for the COP plan. Is it more revops? Is it more sales leaders? Is it both? How do they work together?

Speaker B: Yeah, the answer is every way. It's interesting. Companies have different philosophies on ownership and what that racing model looks like. In some companies compensation and M commissions roll into rev ops. In some companies they roll into finance and in some companies we bifurcate comp design and enablement and policy from commissions which is actually executing commission payments. In some orgs finance might own the commission side and then SOPs or RevOps might own the comp design, enablement and policy side. And to me it is a very difficult role because you're leading with data, uh, you're leading with looking at very complex information. You're looking at historical attainment pipeline coverage, you're looking at the end value, you're looking at the richness of the territory which also ties into that model. I had a rep at a company that, uh, prior company that was the first in their market and they had 300% attainment and we were adding the second rep to that segment and I had a pretty junior analyst said, okay, we gotta raise the quota of 3x. I said no, we're not gonna raise a quota 3x. Like it doesn't linearly follow attainment just because you're having high attainment. Right. There's peculiarities. There's a primarily inbound role, very fixed tam. And we were diluting that book by in half essentially. And that person was also like a machine, like a complete rock star. And so there's always an art and a science to these roles. Right. Uh, the most common thing I've seen break down is sales comp goes into an iBreach. They may have gotten some feedback of uh, what worked, what didn't work. They come back in six months and they put a proposal top down. And these are the new comp plans. This is what we're doing and that's it. And um, that is a huge failure. You need to bring in sales, you need to bring in finance along for the ride and all parties need to feel heard. It doesn't mean I'm going to agree or do what sales or finance wants me to do, but I'm going to listen, I'm um, going to be principled and I'm going to make sure they feel heard. And so I've done roadshows at uh, prior companies where I sit down with sale leaders and I have a very, very, um, and very canned conversation on what work within the work. I hear them out and I did a road show and I actually played back. This is what I heard, this is what we're going to do about it. And they were part of my tiger team. I had their pictures on a slide that said comp tiger team. These are the sales leaders, these are the finance folks that are on this tiger team. This is what I heard. Here are the themes. Let's go fix it. And I brought them in on the journey and as I iterated I would back channel with a couple of influential leaders. This is what I'm thinking about. What do you think? Where could this break? Where could this not break? And you iterate, you bring a couple people in and I'll never forget this. I was presenting out our final comp plans and uh, the first slide I had, it said these are our comp principles. And then the second slide said, here's the feedback we heard, there's a left, right slide, here's the feedback we heard, here's the four or five thieves on the right. Here's what we're doing to fix it. And the sellers largely felt heard and they understood we were part of the process. We weren't included in the process of prior years. And I was very proud of that moment. And I think that's the thing a lot of Revops folks sometimes miss is the human element. They're scared to talk with the CRO, with the sales VPs, with the sales leaders, with the ICs on the ground and feedback, stripping out the noise and diplomatically driving buy in by bringing them into the process and making them feel heard. I think it's very important. It doesn't mean we're going to agree with them. Right. Do everything that they ask for, but it does mean we drive more change management, we drive more support out the comp plan and we're in it together. And so I think that's the dynamic that I really stress when it comes to driving, partnership with sales and finance

Speaker A: and specifically making sure you're spending probably more time than you naturally feel like you would, specifically over indexing on the communication time and uh, just aligning with the different teams and their perspectives on it. When a lot of, a lot of people's natural inclination is I, I would just rather just be working over here on my spreadsheets and my dashboards.

Speaker B: Yeah, a hundred percent. My alpen metaphor for it is traffic. Right. I can be in traffic and someone could be doing something illegal that I don't like and I can cross the crossing path on my bike or walk across a path and the car doesn't slow down. For me, I could technically be right, go walk in front of the car. But you're hit by a car, right? So Right. And you're going to not have a great experience. It's the same thing in life, it's the same thing in companies. To be an effective leader, the higher you go up in leadership, it is less about the pure technical skill, it's less about always being the smartest person and always being right. But it is about driving more influence and Bringing people along for the ride and making sure people feel heard. In my experience, executives, uh, they have personalities, right? They have unique personalities, they have unique peculiarities. They may or may not always be right. And so working closely and being collaborative and bringing people along for the ride, it's so important. It's actually like one of the most important skills. I think growing your career is driving that influence. And it's just so overlooked. People think it's only about the raw talent and being always right and being fast and efficient. Very important things still. But that is what I think separates good from great, is that bringing people along for the journey and that EQ of driving influence across a complex organization.

Speaker A: So we've been talking a lot about doing the comp plan. I'd also like to hear from you about course corrections. And if the plan isn't on track, what do you do at that point? How do you do course correction? How do you go about it?

Speaker B: Yeah, it's a great question. And how a company approaches planning tells me a lot about the maturity of the company. If a company is very mature, planning is an annual process and there are uh, not so many course corrections required. If it's a hyper growth company where I'm either accelerating or decelerating quickly, there's some uncertainty and maybe lack of conviction on what that growth might be. I might have a six month planning process. I may actually bake in to my DNA as an organization that I'm going to plan every six months instead of every 12 months. And so there's a couple of red flags that we need to look at on driving the course correction. The bar for a course correction should be very hot, right when you are announcing a structural change, if it's the quota, if it's a change in compensation, that is a huge signal you're a go to market org. I wouldn't say it's credibility loss, but it is acknowledgment that the plan that we made at the beginning of the fiscal year needs to be adjusted. Like either something changed extrinsically in a market or something changed internally. Uh, whether it's a new product launch or a product launch that maybe didn't land as expected where we needed to course correct. And so being open and transparent and acknowledging these are the reasons why we're making the change should be communicated to some extent. Leadership. The intensity of the issue drives how I respond to it. I was at a company where bookings were slowing down. We had great consumption, doing a good job on consumption, but free cash flow was hurting. And it was the end of Q2 when we started to observe a pretty sizable gap in free cash flow. And so we needed to drive more bookings. To me it would be inappropriate to redesign the comp plan mid year because this is something that needed to be course corrected but not to the intensity to where we needed to drive like a major replan. And I think that disruption bar is so high. So more tactical solve is to drive a spiff. You can incentivize total contract value or ACV any type of bookings component to drive that. Letting a uh, bad plan ride. That is an option. But like I said there needs to be a uh, analysis on what that threshold is appropriate to do that and when it is inappropriate. And what I observe is in a younger company, everyone different sales personalities. Some people immediately think that they need a replan, they need a quota reduction. People have different personalities. You have to manage those personalities. There has to be a data driven structure on when and when it is appropriate. When it is not appropriate, is it an isolated issue with one segment or one geography or is it a global issue? And to me that drives the blast radius on how I respond to it with either a formal course correction mid year or a more tactical spiff structure redesign. I've only driven mid year course correction twice. One was at a company that had hypergrowth and was essentially slowing down so significantly to where ELT CEO CRO got involved, CFO got involved and we built a proposal on what that right sizing would look like and what the uh, risk, what's the plus and minus of running this looks like. And so I think being that balance neutral party to lead with data, uh, and to look around corners is what's important. That is probably where I built the most Trust as a RevOps leader is looking around corners and anticipating what that executive is thinking and how I would respond to it and having that prepared in one shot as opposed to doing only what was exactly requested and not thinking a couple steps ahead.

Speaker A: Uh, oh, that's an interesting. I hadn't thought of that as an option. If you need to do a mid year course correction to maybe consider something less disruptive like adding in a new spiff as an alternative to just redrawing everyone's quotas and commission rates and something very dramatic like that.

Speaker B: Yeah, absolutely. There's different levers you can pull depending on how dramatic of a course correction you need. And I think that's what's important. On that free cashflow issue, we did a ton of scenario analysis to look at what would it take to fix this? If I were to redesign comp plans, what's the plus and minus? If I were to do a spiff, what's the plus and minus? Finance wants to know how is it impacting my cost of sale? Is it cheaper or more expensive to do a structural spiff versus changing comp plans? Legal is concerned about making changes. Getting everything processed and signed off mid year is very disruptive and the signaling to the field, it's very dramatic. You're telling your field that essentially we either made a mistake or things changed. And once you open that up, um, in the back of the rep's mind, they'll never admit it. In the back of their mind they're thinking, if things continue to not do well, will I get another quota relief? So that's why I say it's a very high bar and it's not something I reflexively go to unless that that bar is hit. And so it's typically a global issue where we are significantly off course and we need to do something pretty dramatic to fix it.

Speaker A: We're coming up on probably the last question here and I'd like to hear something a little more fun and that is, what are one or two of the craziest comp payout stories that you've seen over your career so far? Yeah.

Speaker B: I don't know if it's fun or not, but I will say from a red OTS perspective, a lot of times, depending on culture and the personalities, you are the good guy or the bad guy.

Speaker A: Right.

Speaker B: And so I've owned the escalation committee. Escalation committee is not a fun thing to own. Um, where if someone feels that their comp is not fair or there's an issue with comp, they want to escalate. Right. And so a lot of time you're the team that has to sometimes say no. And had a wreck company that was on maternity leave and she had a suit. It was like an eight figure renewal that was coming in and it would have been a very large, deep in the six figures commission check to drive this renewal. Her boss and her, she was just really stressed out that the company's leave policy was to pay out 80% OTE. When you're on leave, you don't get commissions, you don't worry about commission. And so this person was just.

Speaker A: But her ote, this one deal was so large that was going to be a huge factor in her ote. Right.

Speaker B: Would have made over like hundreds and hundreds of thousands of dollars on the one deal. So way above ote very sensitive topic, very concerned. The policy is a policy. But at the end of the day, we're human beings, right? People think rev ops. It's just about the numbers. It's just about data. It's also about being a good human being. Right. What I learned and what happened is obviously this person did all the work leading up to the renewal. She should not be penalized for going on maternity. That's not acceptable. And so you work with legal and we made sure that person had confidence that person be made whole who would not be penalized. That person should not have to leave maternity. Close won the deal and then go back on maternity. That's silly, right? I think it's a crazy story in just that sales has a right to sometimes be. There's a little bit of maybe distrust of uh, finance or revops because we're the folks that sometimes say no. But I do think like balancing. I think about that story a lot. I think at the end of the day, it's about being a good human being. On the opposite side, I had a sales leader screaming, swearing at me. They had a customer that is in like the tractor heavy agricultural machinery space that had thousands and thousands of locations across the world. And we had agreed that all revenue will flow up to that global account manager. And I, uh, like, all right, I hear you, like, let's do the analysis. And as you know, every CRM, the data is not clean, and tracking thousands of subsidiaries that may or may not have an account ID in your CRM, it's not an easy task. So we, we ran the analysis. It was a pittance, I think we calculated. It was like tens of dollars of commissions to the global account manager. And we probably spent like 20 hours like running this analysis and analyzing and making sure we captured every single account. So we did like quite a bit of work. But I'll never forget the, the sales leader was so worked up and swearing and just angry. And we showed the analysis and it was a lot of work. And the person was f your analysis. Like, I don't care about what your numbers say. It's about the principles. And in the back of my mind, in my revoff's hat thinking, this is silly, this is very immaterial. But on the opposite side, I realized you're also a human being and they believe they're entitled to this. They drove a global deal structure and they don't care about complexity. That's my job is to worry about complexity. Their job is they want to drive the right motivation and the right motions with the field, and that's what their primary concern is. So for me, that was a great lesson where, you know, the person was very passionate about what they believed. I had the data, and we still have to compromise and do the right thing to also manage the qualitative side of sales, which I think is an important lesson. So I always counsel and advise, go to market leaders. You can be technically right. And whenever you have a split issue, you have some type of field friction. You can be technically right, but that doesn't mean from a leadership perspective, how you show up is just as important. And so being quantitatively always accurate and right, it's important. But also managing the emotion side of people you work with and building trust, even as important, Honestly, it's as important. And so, uh, I always think of that in the back of my mind. Pick compensation is like, one of the most sensitive topics in our field. It's always an emotional aspect to compensation. And so I always take a lot of gravitas. And these stories are crazy. It's always these edge cases that come up. But I always try to take it with respect. I was a rep. My wife was pregnant in San Francisco. My base salary didn't cover all my expenses. I had to make sure I had commissions to, uh, survive moving out to the Bay Area. And so I feel a lot of empathy with the sales leaders and executives that I work with. I try to carry that insight with me in how I express my role.

Speaker A: I think that's a great note to wrap up on here. Thanks for taking the time to talk, uh, through all these things with us here, James. I was learning a lot my, myself. I think a lot of the people who watch or listen to it are going to learn a lot themselves, too.

Speaker B: I appreciate Chris. It's something I'm passionate about. I genuinely enjoy. And so it's such a pleasure speaking with you and thank you for having me on.

Speaker A: You've been listening to the Revops hero podcast from ClearPivot. To learn more about how our team of revenue, operations and HubSpot experts can help you become a Revops Hero at your company. Me, visit our website at www.clearpivot.com.

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