The prevailing narrative right now is that AI isn’t really working in GTM. Cool demos, shiny tools, but nothing moving the needle. That’s a fair read for most — ChatGPT launched in 2023, and expecting broad ROI this quickly was always unrealistic. We’re still learning how to use this stuff.

But “most” isn’t “all.” A handful of GTM teams are getting exceptional results from AI, and it’s showing up where it matters. On the SMB side, it’s Kyle Norton’s Owner.com. On the mid-market and enterprise side, it’s Matt Braley’s EliseAI.

Fewer than 40 sales reps, well above $100M in ARR, quotas above market, and 80% of reps are crushing them. Something’s working, and we need to figure out what.

Then there’s Matt himself. He joined his last company, InvoiceCloud, as an AE when they were at $400K in ARR. He left as CRO at $200M after taking them public as the youngest CRO of a public company, culminating in a $4B exit. He could have called it a career. Instead, he stepped away, worked on himself, and came back to do it all over again in AI. That kind of arc is worth clicking into.

In today’s Q&A, we dig into what’s actually working at EliseAI, how Matt thinks about building a sales org in the age of AI (he’s hiring btw!), and the work he did on himself between InvoiceCloud and EliseAI that’s making him even better this time around. Enjoy!

Asad Zaman: You had this beautiful journey at InvoiceCloud. You joined at $400K in ARR as an AE, became CRO at $30M ’til $200M, and took them public. Now, you’re back in the CRO seat with EliseAI — one of the few AI companies above $100M in ARR. How does it feel being back? 

Matt Braley: When I left InvoiceCloud, they were at $200M in ARR, and EliseAI is heading that way. So in a way this feels like I’m picking up where I left off, but in the AI world, which is really exciting.

Asad Zaman: What do you think is going to be the same as last time, and what’s different? 

Matt Braley: I think that as you grow and get bigger and bigger, the thing that stays the same is that there are different phases of growth and business maturity that require different systems, processes and strategies. Every time you double, you have to think about it almost as an entirely new business from first principles.

You have to keep rethinking everything you’re doing, challenging what you’re doing now that’s working, and asking: “Is it going to work in a year, a year-and-a-half, two years?”

The difference is that InvoiceCloud was a 40–50% grower YoY. There, you’re rethinking everything you’re doing maybe every two years. But because of the speed that EliseAI is growing — 100% YoY, which we expect to continue — it’s magnified. You’re rethinking it on an annual basis or even every six months. Also, it’s a completely new and different industry for me so I’m just really digging into the customers and industry, and tailoring my approach and thinking to fit the market.

Asad Zaman: Does the importance of systems increase as you scale? 

Matt Braley: Yeah, I think that’s a big difference when you’re trying to get to $1B. You can have some okay systems and a few star reps running through walls and doing heroics to get to $100M. Even maybe $150M, $200M. But to get to $1B, you need a product so strong that a mediocre sales team could sell it, and a sales team so strong they could sell a mediocre product. And the only way you get to that level on the sales side is through relentlessly building and refining your systems for hiring, training, and upskilling.

Asad Zaman: I love that! So much of it is going to come down to teaching sales, which I know you love. Does that stay the same?

Matt Braley: I don’t think it’s much different from the core principles of what you’re trying to teach. I’m trying to teach sales fundamentals, multi-threading in an enterprise sales cycle, how to build effective business cases, how to build champions. The fundamentals are all the same. 

What has changed is the AI tooling, which is making the ability to put a robust training system in place and upskill people faster. The things that used to be very manual are becoming automated. It’s adding fuel to that fire.

Asad Zaman: When you were young, you were an athlete. A really good one. How much of that early experience shaped the type of professional you became? 

Matt Braley: I’ve always been focused on achievement and just been extremely competitive. And I think that it’s not just about being competitive with other people — which I absolutely am — but it’s being competitive with yourself. Asking yourself: “How do you beat the person you were yesterday, or last week? How can you be 1% better?” and iterating on everything you’re doing. That’s always been my mentality. 

One thing that’s evolved over the last four or five years is where that drive comes from. Early in my career, it was fueled by self-criticism — and to be honest, it worked. The inner critic kept me accountable, prepared, and constantly pushing. But over time, I realized it has a ceiling. When fear of failure becomes the primary fuel, you get more risk-averse and less creative, and you burn energy on anxiety instead of execution. I’ve since shifted toward a drive rooted in mastery — wanting to prove to myself what I’m capable of with each new challenge. The intensity is still there, but the thinking is clearer, the energy is better spent, and the results are stronger.

Asad Zaman: I still struggle with that, and it makes one miserable in the long term. I’m sure many readers do, too. So, I appreciate you being open about it. What led to the change? 

Matt Braley: I think it was after InvoiceCloud had its IPO. I’d worked my whole life to have this outcome, and we celebrated for a week, but then I was questioning, “Wait, is this it?” 

There was something missing at the end of the process. I’d assumed the outcome itself would feel like the reward, but what became clear is that the real value was in the years of leveling up — building new capabilities, navigating genuinely hard situations, and figuring things out as the problems got more complex. That’s what I find rewarding, and that’s what I’m looking to do again in a new environment with a different set of challenges.

I realized I love seeing something with a lot of potential and figuring out how to make it better, to reach that potential. Whether it’s someone early in leadership, or someone like a sales rep who has a lot of grit, coachability, curiosity, and a really high ceiling. Or a company with business problems that I’m positioned to solve. That’s where I draw my motivation and my inspiration from now versus the constant inner critic from before.

Asad Zaman: We’re all going to have to deal with some friction in life and business. When those tough moments hit and the natural momentum is negative, are you naturally programmed to not get negative or have you had to figure out how to get out of that mind frame?

Matt Braley: No, that would be disingenuous. I definitely get into negative mind frames. I think whether it’s macro or whether it’s self-inflicted, there are two moments: the first is the mistake, and the second is how you show up in response to it. I can’t control the thing that’s happened in the past, but I can control how I respond to it. 

The question is: How do you put those things in perspective — tune out the mental noise about the things in the past that have been mistakes or caused you pain — and just focus on the thing that’s in front of you.

Asad Zaman: Right now we’re at this really interesting moment in sales, where we’re leaving the SaaS era and entering the AI era. Sales went through profound change in the SaaS era, and in many ways, improved. What are some problems you see that we need to address in this era? 

Matt Braley: The challenge right now is that it’s almost like the art and the craft of sales was lost in the SaaS era. There were so many people that were able to have a lot of success in selling without good selling fundamentals.

The tech world is littered with AEs who were never taught the basics. Now they’re mid-career and they don’t want to spend the time learning the fundamentals.

Something that’s taken me really far in my whole career is that I was so focused on the craft of sales. And because of that, I know that if I’m building a team of leaders and reps, I’m able to impart that craft. 

Asad Zaman: What are some of the biggest fundamental gaps you see in mid-market and enterprise sales?

Matt Braley: Discovery!

Asad Zaman: Yeah, every time I buy a product, the interaction quickly goes to the deck, and it’s all about them and their business. I’m very quickly getting bored, disengaged, frustrated. 

Matt Braley: Gap Selling is my favorite book on sales in an enterprise context. One of the principles is that no one gives a f*** about you, but everyone starts their sales presentations with how much money they raised and how many logos they have.

People want to know if you understand them, and can you help them to solve a problem.

A question that we ask in our recruiter screen is: “What methodology do you use for deal health?” And I still get 20% of people say “BANT,” which blows me away.

Asad Zaman: Really?

Matt Braley: It fundamentally doesn’t make any sense. You’re going to talk to a lot of people early in a deal that don’t have authority, and most of them probably don’t have budget yet. Billions and billions of dollars of software get bought every single year by people who didn’t have that software in their budget.

If you actually do effective discovery and understand their business, find pain, and then, tie that to a top-three business priority, they’ll find the budget. 

Asad Zaman: Yeah, how am I supposed to know what to have budget for, especially now with AI? So, come, knock on my door. Tell me what’s possible. If it’s really good, I’ll create some budget for it.

Okay, discovery is one fundamental. What else are you noticing later in the funnel that’s a pretty big gap for people these days?

Matt Braley: Reps have trouble pivoting. They’ve talked to a mid-level person, maybe a VP; they understand their process and their pain, and they understand how their product solves that pain. But pivoting to having an executive-level conversation with an economic buyer is completely different in an enterprise context.

I see a lot of reps struggle in executive conversations, which is a signal that they don’t have executive presence. They use the same talk tracks with execs as they do the front line.

Asad Zaman: How much of this is inherent, or can be developed?

Matt Braley: Oh, it can all be taught.  

Asad Zaman: What’s the prerequisite?

Matt Braley: Curiosity, coachability, grit.

I want to be clear: I keep saying “enterprise selling,” and it’s important to define what I mean. To me, enterprise selling is multi-stakeholder, multi-department, long sales — 4+ month cycles — in contrast to the kind of enterprise sales where they’re doing million-dollar deals in a month, just talking to the CFO. The latter lacks the complexity and the difficulty of traditional enterprise sales.

In terms of training enterprise sellers, you have to have a really high level of curiosity. You have to actually be interested in learning about the business and the people you’re speaking with.

Asad Zaman: A focused curiosity.

Matt Braley: Yeah, if you’re showing up to prospect meetings and your focus is just trying to get to the point where you can show them a demo, that’s a problem. Maybe you can win in a hot market or with a really strong product-market fit, but you’re going to do poorly if waters get rough at any time in the future.

To be really great at discovery, you have to have an actual interest in the person and their business and their day-to-day. You have to consider what’s causing them pain and frustration, and where the broken processes are, and how that impacts their objectives.

I think most people treat discovery like it’s a list of questions to get through, because it’s a stage and an opportunity that they’ve been told they have to do rather than being genuinely curious in the conversation. That lack of curiosity shows up, and then those people don’t end up doing discovery well, and the rest of the deal suffers.

The majority of reps do that, which is why you can go really far getting the fundamentals right.

Asad Zaman: To have the sort of journey like you had at InvoiceCloud, to even have the opportunity to do what you’re doing at EliseAI — what’s the give that one legitimately has to be willing to make?

Matt Braley: Most of your free time. Look, it’s mentally taxing. It’s tiring. I’m putting in 13, 14 hours a day right now. A lot of times it’s six to seven days a week. It’s almost like you have to think about yourself as an athlete who’s getting ready to go run a marathon. You have to be mentally prepared.

Asad Zaman: Do you think you would have been able to do it as effectively if you went straight from InvoiceCloud to EliseAI? Like, if you didn’t have a stint in advising in between.

Matt Braley: Hell no. I was burnt out.

Asad Zaman: You need a break, right? I think it’s underappreciated after a run, to take a break.

Matt Braley: Yes, absolutely. I think that everyone should take multiple career breaks throughout their journey. You need that time to reset.

Asad Zaman: How important is it — especially early on — to work with people who see the talent in you and give you room to run?

Matt Braley: A lot! Throughout I’ve had people who were betting on me. At every step of my journey at InvoiceCloud, people believed that I could take on more, that I was capable of doing more. The CEO at InvoiceCloud, Bob Bennett, was a great mentor — he really believed in me and kept trusting me with more, even though I was learning as I went.

If you’re in a good company, all of the really high performers are typically given that trust, opportunity, and responsibility by leadership. To experiment and learn from your own mistakes. I had that experience at InvoiceCloud and I will give that to my team at EliseAI.

Asad Zaman: This is my last one — what’s the most under-appreciated input for being able to do what you are doing?

Matt Braley: I can’t overstate how important it is to have a life partner or spouse who’s in it with you and understands all the things you’re doing. I don’t know how I would have done this without my wife Avery.

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