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The Self-Made AI Champion: How She Built Her Career by Saying Yes to the Scary Stuff | Ashley Gross

Unlocked Professional: AI and Future of Work · 2026-06-03 · 45 min

0:00--:--

Key moments - from our scoring

Substance score

60 / 100

Five dimensions, 20 points each

Insight Density12 / 20
Originality11 / 20
Guest Caliber14 / 20
Specificity & Evidence13 / 20
Conversational Craft10 / 20

Ashley Gross's journey challenges the "work harder" paradigm that most professionals are taught. After being denied maternity leave despite her relentless availability - including taking client calls on the way to the hospital - she realized that pure effort wasn't a sustainable security strategy. She turned to AI not as a trend, but as a survival mechanism, starting with Jasper AI to triage her inbox in 2020. This sparked a broader realization: the tools didn't threaten her job; they freed her to focus on what only humans could do. She later became an AI Champion at an enterprise company, where instead of using AI to shrink payroll, she deployed it strategically to solve cross-functional friction. By automating low-value reporting tasks and building trust across marketing, sales, and product through anonymized customer webinar experiments, she helped drive revenue from a $90M goal to $115M - a $25M overage. Her AI Impact Alignment framework emphasizes that successful transformation requires aligned leadership on clear business problems, small proofs of concept tied to metrics, and clean data paired with redesigned workflows. She identifies a critical gap: while many professionals learn AI tools independently, they fail to articulate strategic value to C-suite audiences. Her book, "The AI Work Week," expands on this philosophy of working smarter, not harder.

Key takeaways

  • →Successful AI adoption at enterprise scale requires aligning leadership on the business problem first - vetting tools with IT, building stakeholder trust, and treating transformation as a 6-9 month crawl-walk-run process, not a quick fix.
  • →The real competitive advantage comes from articulating how AI-driven work connects to strategy and revenue, not just learning tools; being able to communicate value to VPs and directors in 10-15 minutes is the differentiator.
  • →Using AI to solve unglamorous but high-impact cross-functional problems - like automating repetitive reporting or building trust through data transparency - creates compounding wins faster than pursuing flashy initiatives.
  • →Companies still have a massive gap between employee curiosity about AI tools and actual organizational enablement; fear-based security policies and lack of clear direction prevent experimentation, but early adopters who become internal SMEs position themselves as irreplaceable.
  • →The hard work trap is real: overAvailability and grinding longer don't guarantee job security, but building walls of security through strategic tool use, reestablishing control, and documenting your impact does.

In this episode

  1. 1From Control Freak to AI Adopter: Ashley's Early Journey
  2. 2The Maternity Leave Moment: Rethinking the Hard Work Trap
  3. 3AI Impact Alignment: A Framework for Strategic Implementation
  4. 4Bridging the AI Skills Gap: From Learning to Communication
  5. 5From $90M to $115M: Using AI to Drive Revenue Growth
  6. 6Building Trust Across Teams: CRM Dashboards and Customer Webinars

Mentioned

Ashley GrossJasper AIPerplexityClaudeGPT

Guests

Ashley Gross

Topics in this episode

Jasper AIAI Impact Alignment frameworkCRM automation and dashboardsCross-functional team alignment (marketing, sales, product)Anonymized customer webinar strategyCrawl-walk-run digital transformation methodologyAI security governance and risk mitigationData governance and workflow redesignInternal SME positioningStrategic communication to C-suite

Questions this episode answers

How did Ashley Gross drive a $90M revenue goal to $115M using AI instead of cutting costs?

She strategically aligned marketing, sales, and product teams using AI to solve their biggest friction point: trust in shared data. She automated a repetitive reporting task that was straining a small analytics team, built dashboards in an isolated CRM environment, and then created anonymized customer webinars to educate prospects and accelerate the sales cycle - all without reducing headcount.

What was the first AI task Ashley automated as a working mom in 2020?

She used Jasper AI to triage her inbox, which was scary for someone who didn't like losing control. That freed up time, but more importantly, it sparked her curiosity about what else the tool could do and led her to explore broader applications across the company.

What is AI Impact Alignment and how does it work?

It's a framework that starts during discovery calls to assess company culture, tech stack, and motivation before implementing any tools. It aligns leadership on the specific business problem to solve, runs small proofs of concept tied to metrics, cleans data, and redesigns workflows - treating transformation as a documented, metrics-driven process rather than a tool-first approach.

Why do most employees with AI knowledge still fail to advance their careers with it?

They can research and learn tools independently but can't articulate how their AI work connects to strategy or revenue - the communication language that C-suite and directors actually value. Success requires translating technical learning into business impact and getting into the room where leaders ask questions.

What major gap still exists in enterprise AI adoption today?

Despite growing awareness, companies are still frustrating employees by either restricting access to AI tools or imposing fear-based security policies without clear enablement and direction. This environment of fear prevents safe experimentation and quiet quitting, rather than driving the curiosity needed for real adoption.

What our scoring noted

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

Insight Density

12 / 20

The episode contains several practical insights about AI implementation strategy, change management, and career positioning (aligning stakeholders before tool selection, using AI to build trust across teams, creating proof-of-concept frameworks), but also substantial padding including repeated anecdotes, throat-clearing, and moderator affirmations that don't add informational value. The core ideas about 'becoming an SME through communication' and 'building use cases around your 5-year career goal' are useful but not deeply novel or elaborated.

I still see this gap between humans being really good at researching, being really excited about digging into a tool. They'll spend their own money, they'll spend hours learning how to use it. But then they can articulate what they are doing and how it relates to a strategy or a bigger picture.
no amount of good technology can be applied to a company that has poor company culture or a poor handle on their tech stack or just no motivation to change or make their processes better.

Originality

11 / 20

While the guest offers some authentic tactical examples (building dashboards to resolve marketing-sales tension, using CRM automation), the overarching frameworks are familiar: change management as prerequisite, proof-of-concept methodology, aligning leadership before execution. The 'say yes to scary things' positioning and 'become an SME in your company' advice are common career tropes. The hallucination normalization analogy ('humans forget too, we don't call it hallucination') is a mild reframe but not genuinely contrarian.

Most people never hear working harder is not the same as winning. We have been taught that if you just put in more hours, grind longer, and sacrifice more, the rewards will come. But what if that exact belief, it's what's making you replaceable?
How many times do you forget something a day? Do you call it a hallucination though? No. You just forget something, you say sorry, I screwed up, and then you move on.

Guest Caliber

14 / 20

Ashley Gross is a credible practitioner with a demonstrated track record: she drove a $90M goal to $115M using AI strategically, has direct enterprise implementation experience, and has vetted 700+ AI tools over six years. She has authored a book and built a consulting practice. However, she is not a C-suite executive or founder at a major company, and some of her commentary ventures into thought-leadership mode rather than strict operator reporting. Her experience is real but somewhat consultant-focused rather than pure operator.

She took ninety million dollar revenue goal and turned it into $115 million. She didn't just hit that number, she crushed it by 25 million.
I have vetted well over 700 AI tools at this point in time.

Specificity & Evidence

13 / 20

The episode includes concrete examples (Jasper AI spaces with brand guidelines, CRM dashboard automation costing $50 in usage, 30-60-90 day implementation timeline, five-step Salesforce automation) and some named tools (Jasper, ChatGPT, Salesforce, HubSpot, Sauna). However, many claims lack supporting numbers: the $115M outcome is stated but not broken down by initiative; the 'time saved per employee' metric is mentioned but not quantified; the 700 tools claim is broad without examples. Several anecdotes lack specifics (the dashboard that 'freed up' time for the data team has no actual hours saved cited).

So within the first 30 days, they're going to see immediate productivity gains in the form of less hours per employee per week on busy work.
CRMs. Nobody likes updating their CRMs. So the number one use case I get asked for is for sales reps to be able to get on a call. And as soon as that call ends, that transcript and that recording automatically populate into Salesforce's CRM... It cost fifty dollars in terms of usage.

Conversational Craft

10 / 20

The host asks reasonable setup questions but rarely pushes back or probe deeper. When Ashley makes claims ('humans are way more prone to risk than agents'), the host affirms rather than challenges. Follow-ups are often soft ('sounds like very curious') or rhetorical ('do you guys also do the implementation too?'). The host doesn't dig into the specifics of the $115M claim, the actual ROI of her implementations, or potential failure cases. The conversation reads more as a showcase interview than a rigorous business discussion.

Love, love that perspective, Ashley. Appreciate that.
Absolutely. I'm wondering like through the progression of time as you've provided this service, have you seen that employees now or companies, are you seeing a dramatic increase in their capabilities and or experience with AI?

Conversation analysis

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

Most-used words

already29tools29tool20start17different16didn14back13better13sales13call12team12first12change12tech11point11control10

Episode notes

In this conversation, Ashley Gross shares her journey from being a self-described workaholic to becoming a leading AI advocate. She breaks down how she leveraged artificial intelligence to help scale business revenue from $90 million to $115 million while simultaneously reclaiming her time. The discussion covers her proprietary AI Impact Alignment system, practical sourcing tools for LinkedIn, and how solopreneurs and small teams can utilize automation to boost efficiency without losing the essential human element.

Full transcript

45 min

Transcribed and scored by The B2B Podcast Index.

Unlocked Professional: AI and Future of Work: I mean, I quite literally remember taking a phone call from a client on the way to the hospital when I was going to like go into labor. So I was very much that person where I was like, I am there. And I wasn't just saying it. I was I was physically available all the time.

I've seen that play out personally many times as well. And congratulate you for taking that that step because sometimes you ha you're so in a bubble essentially and stepping outside of that is risky. And you mentioned you're risk adverse and you like control. So I guess I understand the control piece, definitely, right?

You you re-established the control, which is great. But again, it is risky. And so a lot of people aren't ready to make that move and don't. But congratulations on doing it.

I still see this gap between humans being really good at researching, being really excited about digging into a tool. They'll spend their own money, they'll they'll spend hours learning how to use it. But then they can articulate what they are doing and how it relates to a strategy or a bigger picture. And that's really like when you get 10 to 15 minutes of.

A C suite, a director of VP's time, that's what they're looking for. Like that's their communication language. And that's helpful tip too, because a lot of times people don't have that opportunity to have those types of conversations or haven't had that experience before or or don't even necessarily know that that that type of, you know, value exists within them that they should promote. I agree a hundred percent.

Here's the truth. Most people never hear working harder is not the same as winning. We have been taught that if you just put in more hours, grind longer, and sacrifice more, the rewards will come. But what if that exact belief, it's what's making you replaceable?

My guest today did not win by working more. She won by working smarter. Ashley Gross was a mom trying to get her time back, so she started using AI, not as a tech experiment, but as a survival tool. The result?

She took ninety million dollar revenue goal and turned it into $115 million. She didn't just hit that number, she crushed it by 25 million. She's the author of the AI Work Week, a book which discusses how to cut hours, automate the busy work, and focus on what actually matters. The book is available for pre-order.

Today, we're cutting through all the noise. We're going to talk about why the hard work trap is a real thing, which jobs are actually at risk, and the exact mindset shift that turns any regular person on a team into someone a company can't afford to lose. I'm personally a huge fan of her work. Very excited to have her join us today.

Ashley, welcome to the show. Thanks for having me. What a nice intro. I'm never leaving.

Awesome. You studied computer science when you were a kid. Were you the type who loved figuring out how things worked? Tell us a little bit about how you grew up and what projects young Ashley liked to work on.

Young Ashley was very creative. So I was working before I had a legal workers permit. So I was a hostess, I think, starting at the age of thirteen or fourteen. I scooped ice cream, I bust tables, and I was a server.

At one point I was a tour guide for a wild horse adventure company where you like took people on a 13 seater open air Humvee and explained the ecosystem and how to keep it safe and clean and the history of the horses. So all that to say, I was lots of things. I was definitely not honed in on one specific topic or task. I was fascinated by all of it.

And if you had a book in front of me, it doesn't matter what the topic was, like I would dive into it and I would read. So I think it was A little bit more about like why things are the way they are and challenging pre-existing ideas because I'm just I'm the oldest of four. So I naturally have that level of spice already. And then figuring out how to take it apart, I think would be the next thing I was really good at.

So sounds like very curious and always looking to jump into new projects, try different things, take on different jobs. I think of even when I think of AI and How it works, that type of that level of creativity wearing multiple hats is something that's critical for the future. May I always talk about this like things maybe were a little bit more niche focused, but I think we're moving back to a space where that type of ingenuity and interest in a lot of different things is very beneficial, which brings you to what you do today.

So that complements it very well. Thank you. You were using AI as a working mom before it was a trend. What was the very first task that you handed off to an AI tool?

And what did you do with the time that you got back? Triaging my inbox. And with the time I got back, I dove into Jasper AI. And it was the year 2020.

And I that was the scariest thing I think I've ever let go of control over. Not good at letting go of control. Not spontaneous. I don't like to let you know, let anything take over.

I'm a very big control freak. So As soon as I did it, I remember feeling, ⁓ wow, that's crazy. And then I was like, ⁓ my God, what does that mean for me and my job? And so then I kind of almost looked at it as a challenge of what can this tool do?

Like what else can it do that I can do? And that was honestly like my motivation to to dig in was that time back, but then almost simultaneously that how good is this thing? What can I do better than it can do? What were some of the things that like the practical things that you did with Jasper?

Especially back in twenty twenty when there wasn't not a lot of other tools on the scene, especially ones that were made for marketers too, because like I was their target audience. The number one way I was using Jasper was their spaces. So you could have spaces with different groups, different rules, kind of like you can now with like perplexity spaces, clawed projects. But add on top of that, there was like a brand guideline sheet and ways of talking and communication and definitions.

So it was able to be localized, you were able to ideate, get feedback, and then also make those changes on whatever feedback was coming in on a global scale. So a lot of the blockers that I was facing was just from working at a global company. So if I wanted anything approved, I was sending somebody a word doc, waiting for them to go in the word doc, tear it apart, then waiting until it was Australia's time zone for that someone else to go in and tear it apart. So doing that in Jasper, specifically in those spaces, was a huge time saver because everybody was in it at once.

And then you were able to just take copy out of it. You didn't have to rework anything in a Word doc. What was the moment when you realized that your old way of working wasn't the best way anymore? Probably when I was told I'm not going to have a maternity leave.

And I realized up until that point, I was just blissfully unaware of how that world works because I was just always taught that if you work hard, If you always are keeping your team's dot on green, even if it's the middle of the night, that translates into how valuable you are. I quite literally remember taking a phone call from a client on the way to the hospital when I was going to labor. So I was very much that person where I was like, I am there. And I wasn't just saying it.

I was physically available all the time because that was just what I was taught. It was just outwork everyone in the room. And that's still something that I believe in. But just having that ripped away from me and realizing I gave way too much power away.

And there's a a world where I can still feel really good about the work I do and the quality of it and love what I do because I am a workaholic. That's just who I am. Like when I love something I go all in. But I can also look at the technology around me and the knowledge around me and make sure that I am creating this wall of security where I'm not just relying on good feelings and morale to to make sure that I'm set up and my family is set up.

It's humbling whenever something like that happens to you. Absolutely. And I've seen that play out personally many times as well. And congratulate you for taking that step, right?

Because sometimes you're so in a bubble essentially and stepping outside of that is risky. And you mentioned You're risk adverse and you like controls. I guess I understand the control piece, definitely, right? You re-established the control, which is great.

But again, it is risky. And so a lot of people aren't ready to make that move and don't. But congratulations on doing it. Thank you.

Thank you. It's well worth it. Appreciate you sharing that, Ashley. You built something called AI Impact Alignment, a system that helps real people on Teams use AI in a way that fits how they already work.

Walk us through what that looks like on a day when you start. that system with the new company. Yeah. So it starts even before that first day.

It actually starts during the discovery call because no amount of good technology can be applied to a company that has poor company culture or a poor handle on their tech stack or just no motivation to change or make their processes better. So my idea really was what should we already be doing on a day to day basis, especially as leaders We should be challenging our quality at all times. If it's amazing, how do we make it better? And just always going forward with this idea of we don't need to have something perfect before we can start to believe in it, before we can start to experiment.

This whole entire idea of we're gonna wait until we reach this milestone or we we raise this amount amount of money or we have this many employees is so ridiculous. So it really just started with thinking about. when people are looking for solutions, when they are looking for someone to come in and be a transformation manager, it's already too late most of the time. So like how can we proactively get companies aligned on what is the business goal that they need to solve for?

And then how are their people going to solve for that? And how are they going to know that their value And their the way that you treat them is going to actually change if they get you to to that point where you wanna be in. So really just looking at it from a framework of let's align leaders on the problem. If you don't all agree, do not expect your people to go out and be able to solve that problem for you because you're the ones giving them guidance.

So we're gonna start there. And then if you have the problem and you've actually defined it well, great, let's move on to the next step. That next step looks like actually tying experimentation. And metrics to little tiny proofs of concept that ultimately all go up to solving that problem.

So, like we're experimenting with that end goal in mind, we're building capabilities with that end goal in mind. We're aligning leadership the whole entire way. And then because we're putting in the work to do this the right way, we're then also able to clean the data, which everyone talks about. But then align the processes and the workflows.

And that's really when you get to the point of company culture, that's what's burning people out. Like company culture doesn't just one day wake up and wreak havoc. It's the workflows that aren't interrogated, aren't changed, the silent burnouts that happen, the quiet quitting that happens, and nobody tries to look under the hood and try to figure out like when did this start to go bad? And it's because there was no clear.

vision and documentation of what they were supposed to be doing and how their impact was actually tied to the company. So it's really just a framework of what should we be doing, what should we have always been doing, and how can we use this AI technology that makes everything a lot faster to help us solve these problems now? Because they need solved for either way. Absolutely.

I'm wondering like through the progression of time as you've provided this service, have you seen that employees now or companies, are you seeing a dramatic increase in their ⁓ capabilities and or experience with AI? So I like AI keeps advancing and but the adoption of AI in particular, are you are like have you noticed that when you come into a company now there's a larger number of SMEs or those executives that you're talking to, do they seem to still have a or do they understand the tools a little bit better now or is there still pretty significant gap in between skill skill set and like when you bring somebody on.

Yeah. So I'd say when I bring somebody on, there's very much an understanding of here's the process. It's not going to be we plug in an AI tool and everything's magical. So I'm showing them this roadmap and I'm showing them this crawl, walk, run method and they're already resetting their expectations for, okay, this is gonna be six months, nine months, because at an enterprise, that that's pretty realistic.

If anything, a digital transformation in under a year is like pretty radical, right? So I think with my clients, they're very much under that same expectation because I get them there before we start to do anything. But I would say across the board with companies, I am still seeing a staggering amount of frustrated employees that are not being being given access to these tools or not being given directions and enablement on how to use them. They get these company policies, they get these really scary security assessments that they have to sign and quizzes.

But that doesn't drive that curiosity. Like fear is not the environment that they need to feel safe enough to actually experiment if they think that anything they put into any AI tool is gonna get them fired. Like that that just doesn't go hand in hand. So there's still, I would say, largely a gap if we take my clients out of it and look at like the broader picture on the enterprise space.

Yeah. And to the audience, right? That gap is also an opportunity. So Since that gap does exist, this is your chance to hop in and start learning some of these tools.

I obviously we always say make sure we're not putting company data into those tools if you're using them yourselves, but start practicing on your own. Try to become that SME within your company in particular that understands how these maybe bring new ideas to the table that your company hasn't considered before. And I think those are all just good positive actions to help your company prepare. I I was in a conversation the other day, but I think this facts fact remains is that we talked about how you being this the SME and AI at your company is never going to be a bad thing, right?

So trying to position yourself in that way is definitely a good way to level yourself up in your career and towards the future. Absolutely. I would also say to that point, knowing is half the battle, but also being able to communicate it. And I see that as being a huge gap as well.

If we're just looking at society as a whole, I still see this gap between humans being really good at researching, being really excited about digging into a tool, they'll spend their own money, they'll spend hours learning how to use it. But then they can articulate what they are doing and how it relates to a strategy or a bigger picture. And that's really like when you get 10 to 15 minutes of a C-suite, a director, a VP's time, that's what they're looking for. That's their communication language.

So I would say to anyone listening. Use AI to help yourself articulate your thoughts and communicate these ideas that you are learning because you're already doing the work. You're just not getting the credit for it because you're not communicating it well. So work on that so that you can actually use this opportunity and all the work you're doing to get into an elevated position and get a little bit more exposure and be in the room when these people have questions that you already know the answer to.

And that's a helpful tip too, because a lot of times people don't have that opportunity to have those types of conversations or haven't had that experience before, or don't even necessarily know that type of value exists within them that they should promote. So I I agree a hundred percent. So you took a ninety million dollar goal and drove it to 115 million dollars. A lot of leaders hear AI and think cut costs, cut people.

How did you flip that script and use AI to grow revenue instead of just shrinking the payroll? I aligned the only department in between marketing and sales that could make marketing and sales work better together, which is product. So it was a good time of there weren't too many AI tools back then. So it was a lot easier to vet them because there was really only two to three that made sense for what we were trying to accomplish at the time at that company.

So I would say the first thing that I did was I actually worked with IT to vet those tools with them because the big hairy, scary, audacious moment in 2020 was it's an AI tool. So is it do we have the same governance standpoint? Do we have a different security assessment of how we're looking at these things? Nobody ultimately wanted to be responsible for if this happens, this is the person that you go to and say this happened.

So I became that person. And I did that because my idea was if I if I was able to implement AI and drive it to time saved, which I had at the time, then I should be comfortable enough to take on that risk because I've had that experience. And I didn't think it was fair to ask anyone else in the company that didn't have as many reps, didn't have as many hours with these tools to put their name on the list, especially not IT, when they're getting hounded on a day-to-day basis already.

So what I did was I rolled up to two managers that were under the CMO at the time. And so her name ultimately was the one that was on the budget line. So she was financially responsible for the tools we rolled out. I was the AI champion in the organization.

So I was quite literally put into a Word document. I'll never forget it. It's never happened again. But I was put into a Word document with everybody from IT from like all the different regions.

And they went through the privacy policy of all of these AI tools that I wanted to bring on. And they wrote down every possible scenario that could go wrong. And they said, if you want these tools to go out and you really want to help us, create plans for if this happens, here's what you're gonna do about it. And then we will use those plans and within 90 days, you can have your proof of concepts with these tools.

If there's nothing bad that happens, if we don't need to rewrite these structures, this can be like our framework that we're using for AI tools that fall into these categories. So one, I worked with IT, which is like not something that a lot of people would go like rah-rah for because it doesn't sound that glamorous. But ultimately, their view was risk, right? And the CMO's view was very much, we need to make sure that everything that we're doing is contributing to sales.

And ultimately product needed to be a little bit closer to both marketing and sales. So I already knew because of the stakeholders going into these like bi-weekly calls that were happening, right? Obviously we're not hitting our numbers. Our sales cycles are a lot longer.

So the friction points are already built up. People already have like their talks ready to go. So when they come into these calls, they're already like prepped for battle and like they're not listening to listen, right? And so what I did was I took the three like crappiest tasks that no one wanted to do that I knew would give me some type of an idea on where we were missing the mark when it came to this battle that exists, I think, everywhere of marketing saying, We're bringing in this many leads, and sales saying, No, you're not.

And then products like, What is everyone saying? You're not even selling the actual product that we just built. So I used AI to dig through the CRM and create a report so that our marketing analytics team didn't have to every two weeks because it got to the point where there was so much tension that this one team of three people had to build every report for every meeting that we were having every two weeks because nobody else was trusting of the data. And so I built A dashboard that we were using over and over and over again by plugging an AI tool into our CRM.

And it was in a very mitigated, isolated environment of it. But immediately by showing them that they could do that, that gave them that trust back because then they didn't feel like they had to wait on this marketing team who shouldn't have even been doing this in the first place for them every two weeks. They're just really sweet. They felt like they had a little bit more control, a little bit more ownership.

So I did this for them, I showed them, we compared it to the marketing team's dashboard and report. It was apples to apples, immediately went and everyone started implementing it. So it freed up that data team's time. It also gave a little bit of control back to everyone because then they felt like they could prepare.

They weren't gonna walk into this meeting blind and then attentions flew. So that was the first thing I did. The second thing I did was I built the trust of multiple stakeholders and different teams. And I looked at our product data in terms of who was using what aspects of our data, when were they using it, what were those teams, like how many employees did those companies have?

When did we win them? What did we win them with? I basically just created like my own little racy, if you will, of every company that we had won within the last six months to a year and how much of our product they were using. And again, I went to marketing and I said, there's a huge education gap.

We could be. speaking to because out of all of our clients that we won, only this many enterprises are actually using this much of our tool. And the other half are small businesses, but they're using every single piece of our tool. So why don't we marry the two and do a customer webinar where every single month we've got two different companies coming in, but it's like a it's like a blind audition, right?

So it was fun. We gamified it, but it was like you'd go into a webinar And I would have an avatar face on so you wouldn't know who I was, but I would be talking to you about how I use your product, right? And if you're a prospect of said company, you're also attending this call so you could hear from customers in real time. We're anonymized, so we don't have to run to comms and get it approved.

We're just giving her honest feedback. And it ended up being like that trust building exercise, took way less time than writing blogs and use cases. And ultimately it was that authenticity that started that conversation and started expediting the sales cycle. So that was the second use case I did.

But not glamorous things, right? Not not glamorous. But imp but important. And obviously those are challenges that enterprise companies run into and being able to uncover and or resolve some of the bottlenecks and up the finger pointing, obviously, that happens.

Those are definitely huge wins. I'm curious, was that a a catalyst for More AI to come with the company after that. Was like that just the beginning and then they noticed the value and then all of a sudden they want that it w they wanted to go all in after that or was there. Yes.

Yeah. GPT, I believe, hit the scene in I wanna say like March of twenty twenty two. So we were wrapping up our numbers and already knew about our pipeline in January or February, because I know I know that we got our bonuses. That's the only reason I remember that because like we overached our pipeline.

And I remember getting a check, and I was like, I'm going to frame this. I feel ownership in this. So yeah, and then ChatGPT came on the scene in March of that year. So it was like immediately afterwards, we invested in ChatGPT tools.

We were onboarding sales reps, like new sales reps, using GPTs, using chats and teaching them like how to access them, use them, ask questions. Essentially get those funny flutters out of their system and then save the good questions and the shadowing for the senior strategic sales leaders because they have to go sell and that's what they're best at. They can't do so much onboarding even though they are the subject matter experts in sales. Did your role evolve after that at all?

Throughout my career, I've seen this happen too, where somebody just starts digging into a space that there's a gap within the company that they don't have a SME within AI or something, and now all of a sudden this person Built their own job. Was it was that your experience too? Yes. I was a global campaigns manager.

And then my role evolved to being a global marketing manager that was integrated, but the AI lead as well. So cross-functional. And I think that was really the moment where I thought, okay, this problem exists everywhere. Like everywhere I've ever worked, those problems existed, but it didn't have anyone that was willing to like sound silly and be a part of these conversations that.

really I shouldn't have even been in in the first place and just say, Hey, I don't know the history here. I don't know I don't know who's right, who's wrong, but here's this tool and I did this thing. Do you want to see it? Because it might make you feel better.

It might teach us something new. I don't know. It just feels like having the same conversation over and over again every two weeks isn't leading us somewhere. So let's try something different.

I think it was just like a little bit of a a boldness and honestly a lot of inexperience of not knowing how office politics work and it it turned out for the best. And that's just as we discussed before, a practical example of taking that initiative, digging into something, and then seeing the payoff for it. Think about the person who's not in tech. Maybe they run a small team.

Maybe they answer emails all day. What does your work actually do for that person on a normal workday? So the smaller your team is, the faster you can actually apply these tools because there's less silos, there's less approvals, there's less ⁓ differences in strategy and approach. So if you are a solopreneur, small business, you run a small team, this is everything that I talk about is truly like you can take what I talk about and then go action on it tomorrow and then come back to me two days later and say, This worked and this didn't.

What should I do now? Or like what should I try now? So I think the scrappier you can be, and even if you're at an enterprise or a mid market company, the scrappier you can mentally be of just challenging yourself to ⁓ look around and actually ask, is this the best we can do? Is this workflow, is this way of working, are these tools actually impacting me on a day-to-day basis?

Or is there a better way of working? And as long as you can say yes to that and you can lean into not knowing and not being the expert for a minute just to test that idea, you're going to be able to go so far and do anything that you want. It's just wild to me the opportunity we have. I keep telling people, you know, in 2020, if you would have told me that I would refer to myself as an AI consultant, I would have laughed in your face.

Because that sounds like a made-up job. And it is. Like it didn't exist a couple of years ago. We're creating the job titles right now just by utilizing our years of experience with our domain expertise and learning how to use AI tools.

Those job titles we're creating. So why shouldn't we be the ones that take ownership of what we should be paid and what the descriptions are for the ones actually doing the work right now? So each company has different sizes, scales, challenges. I'm just curious.

Do you have a common like maybe the top three low-hanging fruit situations that you're you're you're able to implement or recommend that generally most companies see a lot of value in within that first 90 days? Absolutely. I would say it depends on the team, but the problems are still the same. It's where's the admin work?

Where is it necessarily at? And where is it unnecessarily at? Is the admin work going towards creating safer guardrails, eliminating risk? Or is it just there because nobody had ever challenged that process?

And the person that bought that tool left the company 12 years ago and nobody ever thought, should we switch this out? Cause this kind of sucks and we all hate it and it makes our life miserable. So that would be like my call out there is just in terms of the opportunity everyone has right now, the use cases that you can apply are a mix of asking yourself where you want to be in five years from a career perspective. And then creating a list of those experiences that you need in order to get yourself there.

And then using AI, the knowledge, the ability to pick up a phone and learn anything in two minutes, using these tools and using them to get different experiences to make you get that goal a lot faster. That's really, in my mind, the only way to create good use cases because there's amazing use cases that save you millions of dollars and a ton of time. But if you're somebody that's already burnt out and you hate what you do, And you've never challenged, do I wanna be in this industry?

Do I wanna be in this department anymore? Like what do I want for myself? If you've never done that, then no amount of ROI is going to motivate you. So I would say build your use cases around what you need to be the goal of yourself you have in five years, because there's so many of them.

What what kind of timeline do you see? And this is dynamic as well, but what kind of timeline would you say you see where p the point of where you start? working with a customer and where they're seeing immediate value. Okay, so I do it I set this up so that they're seeing value immediately because as a society we've gotten used to instant gratification.

So it's really hard to wait anymore for anything. So I like to have this done in in certain spaces and phases. So within the first 30 days, they're going to see immediate productivity gains in the form of less hours per employee per week on busy work. They will also see a standardization of their documentation, which they may or may not have had.

Either way, they're going to have two things that they really wanted and needed. Emotionally and psychologically, they're going to feel like, okay, what else can we accomplish? What else can we tie into these things? They need to feel really good about it.

And that's when they actually start to experiment. They're not going to experiment when they bring you in. They're going to experiment when you show them the progress that they've already made or you have made for them, or a combination of the two. And that's what's going to get them motivated.

largely to start experimenting. So then at that point you get this mass adoption kind of cliff where you have to continue to propel the momentum, but not so fast that you get change management fatigue, which is a very hard thing to avoid because 90% of the work that I'm doing and every other consulting and automation company is doing is change management. That's it. That's a little technical, but it's change management and the fatigue that they already had before you came in.

So And everybody loves change, Ashley. Exactly, right? So then from thirty to sixty days, that's when I'll throw in more quantitative metrics. So that's when I'll throw in the revenue.

I'll throw in the time saved. I'll throw in what is the goal that leadership has for it's not an if. We're gonna get you that time. We're gonna get you that money.

When we do, right now, before we kick this off and we move from a proof of concept to a pilot. I want you to tell me what you want done with those extra hours, with that extra money. Like we need to have a plan for it. Otherwise, when we accomplish that in the next 30 days, everyone's gonna go find something else to keep busy and that time's gonna be reabsorbed back.

So this is usually where we get to the road mapping phase, and companies will lay out over the next year like what they want to accomplish, what they want their capabilities to look like. Do they want to experiment with new channels, right? Do they want to push a new product out to market because they've got a little extra time and they feel confident that they can take on a new product? This is where the strategic pillars really start to come in.

And then between 60 and 90 days, this is a new product went to market. This is a new channel was incubated, right? Like they're able to try things that they were not able to do before. So we just showed a whole entire life cycle saved.

And at different moments, I dropped in some nuggets of gold in the form of metrics, just when they needed it certain times, not all at once, not all at the end. I mean, making making that much impact in a quarter. is not typical, I would say, r with other tools that people are implementing. So that's a dramatic shift.

I think that's yeah, that's really exciting. I'm curious, do the companies that you work with, do they generally already have LLMs in place? If they do, do you work with their specific LLMs or do you recommend different ones that, you know, you guys are more familiar with or have feel work better? Yeah, so I never introduce a new tool unless they're asking me or saying we audit our tech stack.

We don't like this tool. What do you recommend? So I always work with the tools that they have access to. Within the first 15 days, I'm doing deep dives, I'm resharing my own resources and content.

I'm looking at their whole entire tech stack because almost every part of our tech stack has an AI feature today and it's not an AI tool. So I'm looking at every piece of their tech stack and I'm looking at the wins. That on a day-to-day basis, their employees can absorb, right? The ability to take a call transcript and a call recording and drop it into a sauna, and then it pre-populates a whole entire to-do list in like sections, assigns it out, tags the work.

That could save them, I don't know, four hours a week per person, depending on how long they're taking to write down everything that they need to do in a sauna. So these little wins are what really start this experimentation mindset because it's things that they hate doing. They don't love to do them anyways, but it's in tools that they are used to using. So I'm not introducing a ton of change yet.

I'm just showing them how to use that same comfortable tool in a different way. So it's this mix and match of I'm getting to know personalities, I'm building that trust. They're not changing the tools that they're already using. I'm just showing them how to use it better.

And then I'm automating and connecting their workflows because if they can optimize the AI features, they can automate parts of their tech stack to talk. And then we can talk about agentic capabilities. Is it hard to be more of a generalist than a specialist? Does that ever get into a situation where you're like, this is just too much for we have to niche down?

Is that so I'm an first and foremost, you have to have an architect mindset. So it's not even if I'm coming into marketing or I'm coming into sales, I'm still I'm looking at their tech stack, but I'm also having conversations with the org on what is your future cloud provider look like. What is your future CRM? What are the long term roadmap items for your whole entire company?

Because what we decide here is going to have to make sure that like it fits in really nicely. I don't want to provide them with this amazing setup and then leave and then they have to change everything and be rerouted because these conversations don't happen quickly. So I don't actually see myself, I don't think I see myself as a generalist only because within the last six years, I have vetted. Well over 700 AI tools at this point in time.

So I can confidently say like around year 2023, 2024, a lot of them started being being duplicative. So it didn't phase me as much because everyone else, I was a child at a candy store when they first started coming out, and I was like, I'm gonna try you and then you. And then it got to this point where I could start to open up a a new AI tool. And it'd be like, ⁓ you're a you're an open AI rapper, the Salesforce front end or whatever it is.

So I think that. From my perspective, I'm looking at what tools are they already using that they're comfortable with, because there's probably an agent or an automation company that those builders, those founders, those engineers that worked for those companies that they are used to using migrated into. So they're gonna have a similar user experience, a similar way of working, first party integrations. So I'm looking at it more from a I would just say like an architect connector perspective of what's the least amount of change fatigue, but also what is the best situation for where they're at now and how can we create like a unified strategy so that each team isn't operating out of their own tech stack.

But do you guys also do the implementation too? I don't try to get all the deals. Like at an enterprise, it it's almost like its own marketplace, right? Like you're working with one department and then naturally as that success grows, like other departments are like, We wanna work with too.

We wanna work with too. Yeah. But you can't say yes to everything. And I'm not a big company.

And that's what makes me work. So I'm happy to not put a proposal in all the time. And if anything, I'm pretty risk averse when it comes to work. If I already have a company and they're out getting bids for XYZ work, even if I know them and I have great relationships with them, I'm less likely to actually say, Hey, why don't I just do it since I'm already in here?

Because I've already gained their trust. I want to be the person that when something bad happens, they're coming to me to ask the questions. And before something bad happens, they're coming to me and saying, What do you think the strategy should be? I'd rather be amazing with the experience I have and the solutions I've built already, give or take a few newbies, than say yes to solutions and say yes to solving for problems.

And then not being able to deliver on them because it wasn't the right solution and I just got really excited about the money. And also the change management. Like I have yet to when I do compete and when I do bid with others that are much bigger than I am, I usually win, honestly, because I guarantee the change management. And not a lot of other companies are able to do that.

They want to come in, build the solution, leave, not train anyone on how to use it. And would you say like the volume of opportunities that you have exceeds your capability to like cover those that's an awesome place to be in, Ashley. I I what that's that trajectory. It's super exciting.

It's like you're probably just you have zero time, but it's fun. Ride that bowl. Like it is it is that's what I say. I say ride the wave until it goes, right?

And then decide what else you're doing. So yes. And you said this before. I am a tinker at heart.

So like there is a certain portion of my work week where I need to be building. I need to. It it honestly eats at me if I can't just spend eight hours trying to build something new. Like I, if I can't do something and I can't, if I'm like running into hiccup with an automation or like an agent did something I didn't expect, it will bother me until I figure it out.

Because at this point I'm like, no, no, no. Like we did this with no technical experience and we learned how to code and do all of these cool things. No, this is not going to hit us today. Actually, we talk a lot about use cases today.

What's the number one use case that you get asked for? CRMs. Nobody likes updating their CRMs. So the number one use case I get asked for is for sales reps to be able to get on a call.

And as soon as that call ends, that transcript and that recording automatically populate into Salesforce's CRM, but really any CRM would work as well. And not only that, but it will convert leads to contacts if it meets certain Vant requirements or whatever your company put together. So that essentially you just have to prep really well for the call. You get off that call.

Your CRM's already auto-populated for you. You just check it and then you send a message to your manager saying, here's the results of today. And then you can continue to get back to work. So there's no downtime.

And you don't have to rely on third-party integration tools. That was really where I think a lot of the frustration was coming from when people were asking me. They're like, this tool's supposed to do this. It's supposed to talk to Salesforce.

It's supposed to talk to HubSpot and it doesn't. And we paid for it. Now what do we do? So I think if you can own this by building it in-house as an automation.

It's five steps. It cost fifty dollars in terms of usage. And then you don't have to worry about like buying a tool just for the sake of it updating your CRM because like that should be a given anyways. Yeah.

And I know just from a personal perspective, like the cost of moving up to that next level within those CRMs are can be extremely high. So I can see that being definitely a powerful addition in a and some cost savings too, which nobody hates. Okay. We talk a lot on this show about being an architect, not just a worker, someone who builds systems and not just completes tasks.

Looking at where we are right now, what do you think the future of work actually looks like in the next three, five, and even ten years? Great question. All of our tools are within one application, maybe two applications. So all of the monotonous work that was eating up a lot of our time does not exist.

Therefore, if you are not creating that outcome that is correlating with that workload now, that these tools are actually alleviating that problem, you're going to have some explaining to do. So I I think that's probably the biggest change that I see coming is there will come a day and there already is a day for a lot of companies, like I said, solopreneurs, small businesses, that the tech stacks play nice together. So you can't actually say anymore, ⁓ this didn't work or I had to debug this.

Or this workflow didn't work, guess what? You're gonna have an AI agent that you can ask questions to that knows your workflow. So if you don't know it and the AI agent knows it, that's that there's a gap there. So be comfortable getting uncomfortable in terms of being able to speak more on what you're doing, what you're driving, what that impact looks like, and also just having an opinion about where.

your workflow should go. Because if you don't have that opinion and you're not contributing to that conversation and you're not thinking about how your role is going to evolve, somebody else will. So you better be the one that drives that conversation and is sitting in the driver's seat because you know your work better than anyone else. And so if anyone's going to drive this strategic initiative of implementing agents and automations as employees, just like we look at, you know, full-time hires, part-time hires, contract workers, it better be you.

So get really good at figuring out what you thrive in and all the tasks that you don't thrive in, unless they are draining your battery or they're monotonous, get good at them. Public speaking, being on social media, being able to stand in a boardroom and have an idea and pitch it and be okay with it not landing, but the fact that you've got the experience to do it anyway is just start thinking about what those different opportunities look like and don't wait because if you wait, everyone else that's already diving into these tools and learning how to enhance their communication, their thought processes and remove barriers, they're gonna surpass you very quickly.

Do you just what you know about how things work, I'm curious if you have any perspective on I look at it and I think some of the your talks before that I've heard where you're talking about employing agents as employees within your company. And I think of that future where yeah, we're likely managing agents or subsets of agents. ⁓ do you think my question really has more to do with the hallucination component of that? And right now, you absolutely have to have a heavy hand and keep that human in the loop.

Do you see that? Do you see that situation getting better? Or do you think that there's always going to be a high level of need for a person to really keep their eyes on what this agent is doing? We've already evolved that conversation, honestly.

A lot of companies have, but we have definitely evolved that conversation in terms of. The hallucinations, I think that we try to simplify what we don't know. And so when people were trying to figure out like what's it, what's an agent, what's an automation, what is AI, what does this version of AI look like? Hallucinations were a part of that conversation.

So they got lumped into every single specific category of AI. How many times do you forget something a day? Do you call it a hallucination though? No.

You just forget something, you say sorry, I screwed up, and then you move on. So once we start to normalize these tools. I think that we're already there personally, but like even another six months to a year down the road, we're going to start to realize very quickly as a whole society that humans are actually way more prone to risk, to error than these agents are. And our two options are to either become more robotic, which nobody needs, go to LinkedIn today, you'll see that.

We don't need any more of it. Or to be the ones that are actually dictating where in the org chart these agents and automations land because they need to be doing the work that is repetitive over and over again. That they're learning how to do very well so that the humans don't ever have to go back to thinking about that work and they can evolve their thinking and their roles. Love, love that perspective, Ashley.

Appreciate that. Where can people go to follow you and find out more about your work, Ashley? LinkedIn. It's my favorite social media channel by far.

I'm the most active on it, second to YouTube. Great. I'm already connected to you on LinkedIn, so we're good there. Everything else we talked about today is in the show notes, Ashley.

So Thanks again for helping us stay unlocked. Don't be a stranger. Thanks so much for having me.

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