Fixing the Constraint Holding Back Your Startup Growth

# Transcript

> It's about acquisition, getting a message out to the right people at the right time, getting them excited enough to hop on a call with you.

> What's the very first thing that you look at an audit when you're stepping into a new revenue engine?

> It's just so necessary to take a step back and say, "Okay, what is actually my constraint here?"

Welcome back to another episode of the Bridge the Gap podcast powered by Revenue Reimagined. Today's guest is the amazing, the incredible, the fantastic Jackie Ley and Little Freddy. Jackie is the founder of Activate the Magic where she helps CROs bring certainty to their revenue engine. She works with scaling SaaS companies to uncover hidden bottlenecks, fix misalignment across go-to-market, and build systems that actually support predictable growth. This episode is going to be about why most revenue problems aren't visible in dashboards, what's really breaking inside GTM systems, how to fix the engine, not just the reporting, and a few sneak peeks from Freddy. Jackie, welcome to the show.

> Thanks for having me. And Freddy.

Special guest. Freddy is on the show. Awesome. Super Freddy in the artwork. Freddy might be part of the program. Let's be real here.

> Clicks. If you want clicks, this little guy, man.

I love that. Super pumped to have you on the show because I think RevOps is like one of the fastest growing departments and places people need, and it's starting to go lower and lower from a revenue perspective. But one of the things you talk about a lot is that you can't fix what you can't see. And so you say most CROs are flying blind. What are they missing?

> Okay, so it's not so much that they're missing. It's that they're hyperfocused, right? CROs become CROs because they're really good at closing deals. And so naturally they're just so passionate and so competent, overcompetent, at the mid to bottom of the funnel. If you're a hammer, everything looks like a nail. So they're looking at a number and they're like, "Let's close more deals." Very rarely though, I say it's like up to 60 million, right? Above that, I have no idea what's going on. But up—

> I love that honesty.

> Yeah, that's for somebody else. But rarely is that going to be the constraint, right? So I like to simplify the learning by design customer journey bowtie, which has seven segments. I like to just bring it down to three for early stage: acquisition, conversion, and expansion. And so CROs love to hang out in the conversion, right? Like, what turns whatever I get into cold hard cash. That's what they do. They're really good at that. That's not the constraint only because they're really good at it. That's just not the hardest part about early stage. Early stage is about acquisition, getting a message out to the right people at the right time, getting them excited enough to hop on a call with you, right? And so it's just so necessary to take a step back and say, "Okay, what is actually my constraint here?" It's like a hose. If I've got a hose that's kinked in half, there might be little kinks over there or over there, but until you fix this, it doesn't matter.

And so one of the things that I'm seeing a lot because we went through this growth-at-all-cost world and they were so worried about MRR, ARR, bringing things in, that GRR is suffering a lot. And I don't think a lot of founders, CROs, CEOs are really understanding. Because they also have this NRR number, so NRR is masking the churn ratio that's happening. And I think the CROs and CEOs of these companies have a better handle on the front end. As you were just saying, bring as many people in as possible, get them in the funnel, close them—acquisition, acquisition, acquisition. And then all of a sudden they go to get funding and the investors are like, "Well, what's your GRR look like?" And like, they're under 85 percent. And then the investors are like, "Well, you're not investable."

> Right?

> So, where's that shift from the NRR, the ARR, MRR world into the GRR world? Because you do need top-of-funnel, but you also need to make sure you're retaining.

> Yeah, exactly. This is why I like to, on a quarterly basis, we always step back and see what the key constraint is, right? And so if we've been fixing conversion a whole lot—I mean, acquisition—conversion usually takes care of itself. But if we've been focusing on acquisition all of a sudden that's no longer the constraint. What might start becoming the glaring constraint is you're not getting people onboarded properly, or you've got an accounts payable problem. That's a turn problem. That's a retention expansion problem. One of the reasons I'm loving this new era of go-to-market is it's much less siloed. I'm finding GTM becoming much less siloed. And our biggest impasse is usually with the finance. So connecting the finance—now that we're not siloed, we have a better grasp around finishing that loop between, "Okay, is who we're onboarding working? Are those people happy? Are they getting a ton of value?" And using that to inform acquisition again. So completing that loop.

So yeah, exactly. If I'm looking at 85 percent, I'm going to dig into what is going on. Are we not doing a good job of onboarding? Can we just get quicker to that first impact? Maybe it's literally just getting them to use it successfully. Because there's so much vying for our attention. So like one of our clients, she bought something months ago and she's like, "I can't believe we haven't even gotten this implemented." It's like, I bet right there's a hundred million things going on. So is it first impact? Is it onboarding? Is it just doing a better job about renewals? My suspicion though right now is because everyone is very like, "I'll sample this, I'll try this, I'll test it out." So they sign up with a credit card, forget about it, and then all of a sudden the credit card expires or what have you.

> Or they just use a one-time use card and then it doesn't even matter.

> Okay, Adam, with the pro tips here. Yeah, exactly. And so if you were just to look at the metrics, you'd be like, "Oh, we need to do two or three more deals."

So you just said a lot of things, right? And I agree with all of them. But you got to start somewhere. And as someone who's in the fractional RevOps space, like you don't have the benefit of working full-time for a company and getting exposure to everything over years. Like no one's calling you to say, "Hey, Jackie, everything's going great. I'd love to use Activate the Magic." It's usually the opposite. It's usually like, "We have a problem. Someone left. We're brand new. We don't need full-time RevOps." Whatever it happens to be. What's the very first thing that you look at an audit when you're stepping into a new revenue engine? Like, where do you start?

> Yeah, so we're going to do a tech stack audit and just general assessment of what's happening with acquisition, conversion, expansion. What's the level of broken? What's the level of dumpster fires? Because chaos is the glitter of growth. And so if there's not dumpster fires everywhere, I'm more suspicious, right? And so our job is to figure out where all they are. Also, listen to the reps and the people who are squawking. Okay, I want to gather all of those inputs and then both hard cold facts, but also the human input. And I want to take a step back and look at all those initiatives. And I want to rank them by the impact that it'll have if we focus on it. How much revenue will this unblock? How confident are we that if we do this, it's going to happen? And then ease—how simple is it to make it happen, right? So link on all those and then pick what is telling you to pick.

> But can't I just put that in a fancy cloud prompt? Like, why do I need people for that?

> You kind of don't. I actually just published a GitHub skill.

> I was trying to give you a layup to be like, "No, you can't just put this in a cloud prompt."

> You can. No, you probably can, but people don't.

> I mean, touché.

> Yeah. I actually published a skill. You can grab it to see whether your constraint is acquisition or conversion. Via MCP enter HubSpot or any old CSV, it'll kind of take you through. But yeah, it might be hard to do if you don't have technical experience. Or like, it's hard for me to say because I've seen like hundreds.

> Yeah, I mean, listen, I think there's good and bad with AI, right? Full disclosure. So Dale and I spent an hour before this call literally knee-deep in coding. We're rebuilding our website. Dale is rebuilding our website. And like, I think he did a really good job. Super impressed. But I think what's happening with AI right now, and listen, we're huge proponents of AI.

I think everyone should be using it responsibly, but what I'm seeing is I think people think, "Oh, I could just put a prompt in Cloud and fix all of my problems because AI is going to do it." And rather than whether it be Revenue Reimagined or Activate the Magic or hiring a full-time RevOps person or demand, whatever it is, there are places for AI to replace, there are places for AI to accelerate. How are you guiding your clients on how to use AI properly versus, "Oh well, you don't need RevOps. You just need to plug into Cloud and Cloud will be your RevOps." Because I'll tell you, if you're going to do that, pardon my French, you're going to screw your business.

But I do want to say, if you're just starting out, if you're in the zero-to-one world, go for it, right? When other people's money, other people's careers, job security start being on the line, it's time to be less cavalier about it. I would call that cavalier.

Yeah, that's a nicer way than mine. And I think the CEOs that I see that are winning and just building momentum and actually joyful when I talk to them, they really respect the revenue engine as our overlord, right? It's process over heroics, all the things that RevOps have been screaming about on LinkedIn for a decade.

So when does someone need RevOps? We've run across this a lot, right? We work with companies from five to 100 plus. And it amazes me the size of companies that don't have RevOps. Like a $50 million ARR company that we're working with, zero RevOps. I don't understand. When is the right time to stand up a RevOps function?

Here's something I keep seeing with sales teams I work with. Generic sequences don't work anymore. We've all gotten so good at turning out the noise that even your own buyers are ignoring you. The problem isn't your reps. It's that your sequences are static and your signals are somewhere else entirely. That's why our clients use Nooks. And the thing that stuck with me is that their sequences actually stay fresh because the signals update them automatically. Right buyer, right moment with no manual babysitting. If your outbound feels like it's shouting into a void, go check them out at nooks.ai/bridgeridge the gap.

Again, this is for early stage. I encourage people to just use Airtable or Google Sheets. Have your Google Sheets empire until you're actually experiencing the pain of systems and process not being there, right? Then it's time. It's time.

Yeah. I mean, hopefully you're getting RevOps looking at stuff before that, but let's be real. It's not, yeah.

Can't hear you, Dale.

Yeah. I think people are, it's funny because we're working with another client and there was a conversation like, "Do we hire RevOps or do we hire another AE, right?" And it's like, because once again back to the initial conversation we're having, let's just put more people, more volume, more top of funnel. We'll fix the rest of it. But then you open up their HubSpot, nothing's in HubSpot. There's no process, there's no renewal pipeline, and then there's a conversation of like, "Why is this happening?" It's like, well, and I think there's a mentality of like, "That's just busy work and there are other things that need to get done." But like, doing a visual chart, doing a process flow, doing like you are missing so many parts of what is actually happening in your overall process, and then you can actually decide whether you should be using AI or not because not everything is AI enabled.

And so if you break it down into fundamentals, like go-to-market, if you want solid go-to-market execution strategy, do the fundamentals really, really good. I know it's super boring. It's like, "Oh, put it in HubSpot. Oh, create a dashboard. Oh, trust your data." If you do those three things, the rest of it you can build on top of. But if you can't do those three things, you're just wasting money.

That's a take.

That sounded like I disagree with you, Dale.

I agree with you, right? But we're not in academia.

Sure.

So I think I'm just so much of a realist that it's not going to happen.

Why can we not stop for a minute and be like, "Okay, let's document the process. Let's understand what that looks like. Let's agree on what the stages are between everything. Let's agree on what the entrance and exit criteria are" because GRR is important to us, because getting the right ICP clients into our process, the back end of the bowtie is important to us.

Yeah, yeah. I think it starts at the top. If you have that sales leader who is responsible and has been through it before, then yes, they're going to approach it like you do. Who I'm seeing as the sales leader at earlier stage is not that person yet.

Okay.

And so honestly, I just want them to. And maybe it's not the CRO by the way. Maybe it's starting even further at the top and it's the CEO. That's not me, CEO.

Yeah. I encounter a lot of product-oriented or engineering CEOs, and it is just, um, even if they do, they're like, "Okay, we do need it and we'll do this huge thing." It's amazing what we do, and it's just like, "Okay, so what?"

Who's harder to work with, Jackie? An engineering CEO or a sales CEO?

Harder to work with? Yeah, from a RevOps person, an engineering CEO. Harder. Yeah, unless it's not, usually a 22-year-old who just graduated from MIT.

I mean, touché, right? So if it's who founded their company and they know everything? A minute ago they're not anything. They're just a small child.

We work with both very product-focused CEOs and very sales-focused CEOs. I personally find the sales CEOs to be harder to work with because they're more resistant in my opinion to advice, because they're sales CEOs and they know how to sell, and like, you're telling me what? Like, I'm a sales CEO. I know how to sell. Where the product ones, I feel like, are like, "Listen, I pay you to tell me how to build go-to-market. Tell me how to build go-to-market." Rare exceptions, but I remember one very, very, very vividly, and Dale will know who I'm talking about, where I feel like every single piece of advice it was like, "No, that's not going to work" or "No, I want to do this" or like...

Yeah.

Dude, then what? Why am I here?

Yes.

Well, that's the thing. And I think that's on us to sort of pressure test and be like, "Listen, you're not in enough pain to listen to me. So go against that brick wall a couple more times and come back when you're crying, and then we'll talk."

Well, it's like we tell a lot of our, like, even the product CEOs. I was just talking to somebody the other day, and I was saying I never wanted to be the first CRO in the door because I knew you're going to run into all sorts of issues. In fact, I didn't want to be the second, maybe even not the third, because by the time you're getting to that place of hitting your head against the wall like you're saying, you're like, "Okay, now I'm going to listen to somebody," and it's not that they don't understand go-to-market. The challenge is go-to-market is changing so quickly, and you just cannot have, you don't have enough bandwidth or time to understand the products that are coming out, the changes that are happening. Like, am I using Claude? Am I using GPT? Am I using this wrapper that's on top of Cloud? It's just creating so much churn in the world that I think you would have to do it full-time all the time.

Yeah.

To be successful. And if you don't have a GTM engineer or a RevOps person that kind of understands this, it's very difficult to comprehend because what worked 12 months ago is not working anymore.

Dude, what worked 12 days ago doesn't work anymore. It changes so fast.

Yeah. Well, first principles stay the same though, right? Go interrupt people's days and start a conversation, right? That's...

Yeah, but it's harder and harder to do that. That's the problem is like, yeah. Listen, we all, you know, have titles on our LinkedIn that make us nonimmune to the outreach of having our days interrupted to have conversations started. And how often does something break through the noise that you're, and I will tell you, we've bought lots of things from cold calls over the past three years. But how often does something really break through the noise that it's like, "Oh, I'm willing to read this or listen to this?" And now with Gmail's new filters, like you're lucky if it even gets to you.

No, yeah, exactly. But what I will counter with is we have this whole crop of AI-native companies that are growing 20% month over month.

Yeah, so yeah. I'm seeing them.

# Transcript

Fastest growing companies are actually via some sort of marketplace or partner resell, which is what I'm seeing, because they can really get to—yeah, they're stacking the big Legos rather than the tiny little one, one little piece Lego. They got the big—yeah.

And that's how you win.

That's how you win. And so it's happening. And like it used to be triple, triple, double, double, double. Now it's like 10x or go away for funding. It's real. It's real. And like as a consultant, as someone who has 10 people relying on who we bring in, right, I kind of have to have a bias for who we partner with as well.

We have to as well. And I'll tell you, the AI native thing sounds super cool and super interesting, but we've worked with AI native companies and it's difficult to get support. Things don't work. "Oh, just ask the bot." It's like, okay, that works to a certain point. But at scale with clients, it works with the early adopters. They want to tinker, they want to play, they're okay with things failing. But when you're getting into organizations that are 10 million ARR, they don't want to be tinkering and playing around with things. They want things to work. And what I've noticed in 2025 is a lot of tinkering. 2026, people are like, "AI is a thing, it's going to stay here, it's here to happen. But if you don't have a real story around how you're going to execute, yeah, I may try your product, but I'm not going to be in it for the long term."

And they're all overlapping. The amount of technology in the AI native world is such that these simpler things are becoming very easy to replicate, so they're making it—I don't know. I find similar products coming out to the market all the time and I'm like, "Okay, this is the same thing with a bit of a different twist to it."

Yeah. So are you biased towards companies and orgs that aren't trying to just be the cheaper or easier replacement for X, but using that as—what was your entry fee, right? Of course, we're doing that, but we're actually going to go further, further than you could before, right? So even in internal processes and stuff, if I'm just replacing something with AI but doing the same thing, I'm doing a disservice. How about one here?

Yeah.

Who's doing it really well?

What am I in love with right now?

Oh, text-wise?

Yeah.

Oh my God. I love Common Room, big time. They do a really good job at identity resolution. And it had—you put into it your ICP and your personas and everything like that. So it's got that. The biggest problem with AI right now is containering and organizing the data and aiming certain things at different things. Did that make sense? Anyway, but they do a really good job of having all those things, and they already pre-trained for those specific things that you need in sales. So I love that. Another one that I am absolutely loving is Sibil. S-Y-B-I-L. It's sort of like—it's everything—

Conversational intelligence. It's everything you wanted Gong to be.

Yeah. That—I won't rain on your parade. That's a space that's near and dear to my heart. I think Sibil does some things I agree with you on—everything you wanted Gong to be. I used to be the biggest Gong fan. I want to be careful here. I used to be the biggest Gong fanboy on the planet. It was my dream company. I wanted to work for them more than anything else. And I think they are the OGs of what great marketing looks like, and no one could ever take that away from them. Devin Reed built an incredible brand. I think the product—

I'm sorry.

Chris Orilla. Got to get—

Yeah, Chris Orilla, Udy, all of them. The product was the best thing ever. I think there are so many better alternatives out there right now. And I will take a lot of heat for this from the Gong haters. I don't care. I've said it publicly for a long time. Spending money on Gong is a fool's game right now in my opinion, and I will die on that hill.

Yeah.

Sorry, Dale. It might cost us a sponsor or two here or there, but—

Yeah, I'm not owned, so I will say Gong is absolutely cooked. Zoom Info's days are numbered.

Ooh, that's a hot take. That's a very hot take. Interesting. So Zoom Info's days are numbered. I go back and forth on this. I think data is a commodity. I think data is a dime a dozen. I think there are so many places to get it cheaper and better, and we do. I'm in love with Freckle right now. I'm in love with Orange Slice right now. Neither of which use Zoom. I think Zoom Info is trying to do better. They brought over Molly Bowdensteiner to lead their RevOps, and she is one of my favorite human beings on the planet. But the product itself, I think what they're trying to do, sadly, might be too late. I think had they done it a year ago, fantastic, but what they're trying to do now, I don't know. And they're really expensive.

Exactly. And even Clay is outdated at this point.

Now that's a really hot take. Tell me more about that. My issue with Clay—why I went Freckle versus Clay—is I just feel you need a master's degree to understand Clay, and you have to be so dedicated to it. Where Freckle does arguably the same, and I was able to pick it up in 27 minutes.

Oh man, I think you're going to have to show me Freckle after this because—

Yeah, would love to.

Not a sponsor, not paid. I genuinely like the product.

Yeah, like I actually am sort of sponsored by Clay, but—

Oops.

Oops. I haven't heard from them in a while, but sometimes $900 ends up in my PayPal.

Not really.

I would like $900 in my PayPal.

So I'm not really sure what that is, but no, it's like you said, it's really difficult. The learning curve is really high. The costs are outrageous. And it's just slow. Like I don't have to try to update things. It's like, "Hello, I'll come back later," and it's like, "Oh yeah, we were doing that."

Wake up.

But this is the problem with technology. Let's go back to what we just spoke about—how quickly AI is changing and which tools to use. Six months ago, and listen, I still think Clay is a great product, but it has its place. But six months ago, Clay, Clay, Clay, Clay. Now we're sitting here talking about alternatives. And this is why I think number one, certainly us at RevOps and everyone I know, is hesitant to sign a one-, two-, God forbid three-year contract with anyone.

Number two: why seat-based pricing is getting trumped by usage-based pricing. While I think it's very hard to implement—Dale and I were just talking about this this morning with Digital Ocean—like, I'll pay for consumption. If I'm using it, it's absolutely cheaper than going and hiring a person. But what I don't want to do is say, "Well, we have three seats, so I have to pay for three seats." I just got a renewal for Lucidchart this morning. Dale doesn't even know this yet. And they want to raise our price. And my question to myself is, "What's our alternative?" Because I'm not willing to give them the price increase they want.

No. Lucid guys, oh no. Not you guys, but Lucid, if—

No, no, no, I hear you. There are so many things, and technology is moving so fast, and they all tie directly into RevOps and tech stack.

And look at it. You have Cloud Design. You have Google coming out with design stuff. You know that ClickUp, like these project management tools, you can literally code a project management tool that can do exactly what you want because the challenge with some of these bigger products is they try to be everything to everybody because they have investors and you have to keep going and building them out. However, here's a hot take: I actually even think CRM is going to go away. I think people are going to start building their own CRM and they're going to build it to spec for what they need it for, and then they're going to move. Like when you get a real good RevOps GPM engineer who's going to be paying HubSpot and Salesforce and all these people $150 a user? That's scary to people when you are going to start growing stuff, and then you're like, "Now I got to configure it and I got to hire a consultant to build it out," and blah blah blah.

Yeah, yeah. I don't know. I think um—

Can only speak for like three month increments at this point, but eventually, yeah.

I'm with you. Yeah, eventually, yeah, CRMs will be disrupted. But not yet. Not yet. I think, and I'm still telling people to go with either Salesforce or HubSpot.

Fantastic to play with, but like, if you're actually building an organization, it's not ready for prime time. And yeah, yeah, and like, but you can, but should you is the question.

I don't know. I am wondering why is Salesforce cost so much and why I can configure every single little button that I and then I got to buy other technology to do what Salesforce is supposed to do.

Listen, listen, I Mark Benioff is making Salesforce very hard to defend or even like at this point. My name is Jackie. Techstack is my love language. I get emotionally attached to technology. Like some of the heat I have for ZoomInfo is because of who they are as a company.

So I'm going to pause here. Here's what I'd love to do because sadly we're running up on time. I would love to do a whole 45 to 60 minute tech stack teardown with you. Honestly, hands to God, because this is my love language too. Dale could join. I'm very curious Dale's opinion, but he's going to be like, "Adam does that. Adam does that. Adam does that." Although there are certain things he has very strong opinions on. I think that would be a fantastic episode. No direct, but like very real because I agree with you. A lot of it isn't just what you build. It's who the you are as a company.

Yeah.

So I'm totally game for this.

Look at us over the last 20 years. I mean, like, if you think renewal or compliance is loyalty, no, no. We're, I'm actually counting down the days.

What? What do you mean? If you don't renew, you have to delete all of our data from your system unless you were smart enough to know that you had to exclude that clause.

One of my clients—

And we'll sue you for it.

Yeah. She was sued. She was, the company was sued. They do that. Like people say, "Oh, it's just a—" No.

Oh, no.

I know. I know fractional people who have worked for them who have been sued. Okay, we've got to go to rapid fire, otherwise we are going to go on a total tangent. We will schedule a 45 to 60 minute techstack podcast only. I love it. All right, let's move to rapid fire.

What is the most misleading go-to-market metric that people obsess about?

MQLs.

Yeah.

What do you mean is an MQL?

I hate that term.

Harder problem: visibility or execution?

Wait, say that again.

Harder of problem: visibility or execution?

Visibility.

What's one tool companies rely on too much, or type of tool if we don't want to name a specific—

Oh, like a sales engagement platform.

Cool. Agree.

One thing you'd fix in most B2B companies: the SDR to AE handoff.

And AE to CS. Like, same, same.

No, they don't let us do that. Like, CS is just ignored.

Jackie, what's one habit that builds go-to-market clarity?

Shamelessness. Like, own the up. Like, own it. Be like, "Oh, that was me. That did not work. What are we trying to do now?" I see people like 10 toes down digging graves because they made some weird decision a year ago and it's like, "Buddy—"

I just broke something at a client the other day and like it really broke something and I was like, "Listen, I did it. I'll fix it, but stop searching. It was me."

Yeah, yeah. I will fully own my ups because it makes us better.

Yeah.

Well, it makes you human as well.

Last one as we wrap this up: dream vacation destination.

I don't go to Fiji.

Fiji. My daughter keeps telling me to go to the Maldives because they're going to be underwater soon. Should they?

Oh, it's the other place. The Seychelles.

Yeah.

Yep.

Yeah. Maybe we should do an off-site team retreat and talk about tech stack.

Yeah, yeah.

Do a pteranodon in the Maldives.

I'm game. I love it.

Jackie Leahy, activate the magic. Where can people learn more about GTM?

I am very fun on LinkedIn. It's Jackie Leahy. LinkedIn.com. It's just Jackie Leahy. J-A-C-I-L-E-A-H-Y. And if you're in Pavilion or Women in Revenue or Operators Guild, I am in those Slacks. I live and breathe in those Slack orgs. So you can find me there too.

Awesome. Thanks for joining the show.

Thank you.