Jacki Leahy: Activating B2B SaaS Growth with AI

Kyle James (00:01) Hey, welcome to the AI Chronicles podcast. I'm your host, Kyle James. Today we're going to be discussing how a business consulting company called Activate the Magic was able to scale its business by helping other companies turn revenue operations into a growth engine. They specialize in helping business to business SaaS startups grow from zero to 10 million in annual reoccurring revenue. If you're in the business consulting space or even in the AI space, then you need to listen closely. Have you found that your AI agent is hallucinating or just mishandling basic conversations? Speak to GPT trainer. GPT trainer fully manages your agent for you, eliminating hallucinations for good while drastically improving your AI agents response. Go to gpttrainer.com to learn more. So for our guests today on the show, I have Jacki Leah, who is the founder and head of go to market at Actiq the magic. It's a boutique rev. revenue operations agency based in Boston, Massachusetts, with a journey that began in the classroom and now it thrives in the boardroom. Jacki, she helps business to business SaaS startups grow from zero, literally zero dollars to 10 million in ARR. Jacki brings a great mix of strategy, systems and storytelling, empowering early stage teams to scale smarter with tools like HubSpot, Salesforce and many others. Whether she's matching mapping out the go-to market strategy or untangling tech stacks. Jacki's mission is clear. Make revenue operations a growth engine, not just a roadblock. Hey Jacki, welcome to the show. How are you doing today? Jacki Leahy (01:41) I'm great, thanks for having me, Kyle. Kyle James (01:43) Yeah, super excited to have you on. So, so walk me through like with activate the magic. How did it, how did it come to be? Jacki Leahy (01:50) Well, everything was by accident, Kyle. ⁓ So I've been on the consulting side of RevOps for B2B SaaS since 2020. I joined a Salesforce consulting shop. I was there for two years. And then I took Jaco van der Kurz's ⁓ Growth Revenue Growth Architecture cohort. Jaco van der Kurz, he founded Winning by Design. And I got so obsessed with Kyle James (02:10) Wait, what's his name? Jack who? OK, OK. Jacki Leahy (02:20) operationalizing the bow tie and other sort of like first principles forward applications to VDB SESS. I spent like nine months of just my all of my downtime creating like solutions in Salesforce and Jaco got wind of this and recruited me to build the DevOps practice at Winning by Design. But it was a it was 2022 and everything just kind of went sideways. Kyle James (02:35) Yeah. Jacki Leahy (02:47) So I was laid off and the last thing I wanted to do was interview. So I put up my little shingle and like two months in I was like, oh this is too much work. I brought all the friends and then another friend and then six months later I was like, wait did I accidentally start a business? And yes, yes I did and it's a lot of fun. We're coming up on our third year anniversary this late summer. Thank you. Thank you. Kyle James (03:04) Hahaha Wow. That's awesome. Congratulations on that. So I, with it being, you know, the, the, the spin of it was like the revenue operations, right. As the core of activate the magic. But before we like get into the, to the systems, like, I mean, why, why this space, you know, especially if you're like, it was an accident. But like, why that it was it because of the, the, the Jocko that you mentioned, or is it something different? Jacki Leahy (03:34) Well, everything was by accident. So I pivoted into the tech world. I'm a forward teacher and real estate agent, but I wanted to get into the tech startup world because everything else that I did, I would figure out and then get bored. But I figured with tech startups, there would always be something new. And I was right. So even though I was the tender age of 33, I started as a BDR. That's the entry level sales. Kyle James (03:42) Nice. Jacki Leahy (04:03) rep position in like b2b tech and all of my co-workers were like 12 days out of college which was excellent but then by my third startup i was hiring number 10 at link squares the first lady hire and i was brought on at 350k arr and in two years we got to nine million and yeah zero marketing it was all cold outbound like events word of mouth and Kyle James (04:25) Wow, wow. Jacki Leahy (04:33) I was brought on to build the business development team system and throughout doing that somebody had to figure out the backend of Salesforce. Right? So it's like I had a pain, this is my profession, but then I just stumbled into absolute passion. Salesforce was like business legos. Like what do you need done? I can make it happen. Different Kyle James (04:42) Mm-hmm. Mm-hmm. Jacki Leahy (04:54) tech and systems. was like, I felt like I was in the matrix. I was like, I know what to do. Kyle James (05:01) Yeah, no, that's that's amazing like that's a huge jump what were the numbers that you said again it was three from 350 to 9 million That's that's incredible and I could see why now that you're you're working with the startups because like for you You've you've been in the industry you've been in that space before where it was a startup and you took it What were some of the things outside of like the Salesforce and like the back end? What were some of the things that maybe you? Jacki Leahy (05:06) Yeah. Nine million. Yeah, it was cray cray. Yeah. Yes. Kyle James (05:27) you contributed that you think might have really helped with getting a company from 350 to 9 million in revenue. Jacki Leahy (05:34) Yeah, well like ⁓ probably socially inappropriate levels of curiosity and like grit, right? Like I do not recommend if you want any sort of semblance of what they call work life balance. Like I cried, but like happily, it wasn't even suffering. Like I was just very, very happy. Like it was my hobby, it was my life. ⁓ But I think I brought, you know, a wealth of. Kyle James (05:50) Hmm. You're like, I grinded just cause. Jacki Leahy (06:03) background experiences, right? I was renting apartments in Manhattan during the financial crisis where I figured ⁓ how we got clients was through Craigslist. But I was like, wait, why am I posting all these disparate Craigslist ads? I had a point of view, a tone, a voice. I love comedy. So I'd make people laugh. And then I was like, let me link them all back to a WordPress site. So I was doing in-brow. Kyle James (06:14) nice Jacki Leahy (06:31) Somebody tell Matt and Darmesh that I actually created inbound marketing. Just kidding. But yeah, on my WordPress blog, I would feature the apartment hunt for people in three months after they moved in, apartment tours. So by the time people reached out to me, they were like, Jacki, I cannot wait to find an apartment with you. Because really, that Cuban side. ⁓ Kyle James (06:34) . Jacki Leahy (06:56) I think just being really clear of like, hey, I don't know what I'm doing, but I'm going to build in public. ⁓ Yeah. I think that really helps. Yeah. Kyle James (07:00) Hmm. Yeah, that's amazing. And so like for someone like, you you started kind of pursuing the, ⁓ kind of the startup companies and seeing, cause you, you yourself had been in that space and you've done the grind. I think any startup can relate that like it's, it is a grind and you've got to figure out the code and, crack the nut. Right. ⁓ so walk me through though, like with, with a client, you know, someone who comes and learns more about you. Jacki Leahy (07:17) Yeah. Kyle James (07:28) they want to learn more about the company, become a client. What does that journey look like for them if they were to ⁓ jump on board and... Jacki Leahy (07:37) Oh, yeah. So usually B2B tech startup, you might have Salesforce or HubSpot, but then I ask, okay, but if you're actually gonna run a forecast or like a pipeline meeting, it's like, oh yeah, Google Sheets. It's in a Google Sheet. So it's almost like, I like to call it the Google Sheets empire, right? And that is fine. Like I think a lot of Rev Ops people will be like, don't do that. Do that. I'm definitely like, there's... Kyle James (07:39) Yeah, yeah. Jacki Leahy (08:06) growth and there's efficiency, I am growth. So like, go for it. When all of a sudden it's usually that founder led sales or that early, that first kind of sales leader, there's like an all of a sudden moment where like, my gosh, I can no longer keep all of these deals in my head. Or like, did I update my Google sheet tracker? Like if it happens, is this for real? ⁓ Kyle James (08:09) Hmm. Right, right. Like is this for is this the right data like This person has a similar name. I'm I don't know if that's the same which person was our last name. Yeah Jacki Leahy (08:37) Exactly, exactly. And when it happens, you'll know, like, don't go into self beat up. That's actually a good sign. It's a good sign. And it's almost like if you're a pilot, ⁓ first you learn to fly by like, ⁓ there's the horizon. But at some point you want to level up and you really have to trust your instruments. So that's sort of what we do. Just enough infrastructure, automation, sort of like workflows, just so you can. Kyle James (08:44) Hmm. Hmm Jacki Leahy (09:05) You can do what you do, right? Build your team, be in on the deal making, but also when you go back to your computer, have a sense of what's going on in your pipeline by a dashboard, ⁓ by trackers and stuff like that. Yeah. Kyle James (09:20) Yeah, absolutely. so like, you know, setting up the right CRM HubSpot Salesforce, and I imagine there's a couple other, you know, tech stack that you recommend. Um, and especially when it comes to, like, know a lot of these popular platforms have like AI integrations into them and, know, how, obviously this AI podcast, right? Like how, how have you been integrating AI on your side? And then maybe even like some of the tools that you've seen some of your clients being, you know, using as far as the AI side goes. Jacki Leahy (09:51) Yeah, well, hot off the press, sales engage of a platforms like SalesLoft, Outreach, Apollo, their days are numbered and like Outreach's days are numbered. ⁓ And what's taking its place are tools like Clay for data finding and enrichment, ⁓ tools like Unify, Unify GTM is amazing, Default is amazing. What I've actually found and have Kyle James (10:01) Mm-hmm. Jacki Leahy (10:20) actually implemented for myself because I loved it so much. It's called Ample Market. Their new product is called Duo and it's like all the data you could ever use. ⁓ Also sort of AI filters for your persona and you can set up a couple different triggers like if they viewed your LinkedIn or your website or something, you can have it just automatically populate an entire sequence based on ⁓ who you Kyle James (10:41) Mm-hmm. Jacki Leahy (10:49) you train it on what your value props are and how you like to message. And once it finds someone that matches, boop, they'll, every morning, go in and I have 10 or 11 people to kick off in a sequence. And they're they're custom made little sequences and you can say call heavy or no calls or LinkedIn heavy. You can set up your druthers, if you will. ⁓ And so, Kyle, what... Kyle James (10:50) Mm-hmm Jacki Leahy (11:16) Like I did the job of VDR, right? I did it. Kyle James (11:20) Wow. Yeah. Jacki Leahy (11:20) What used to take me four and a half hours every day is now taking me like eight minutes. Eight minutes, like it's insane. So now I can like, I can do my outbound. I can feel like I'm on top of everything. And it's like, I'm sipping coffee, watching the late show from last night and just boop, boop, boop, boop, boop. And I can probably actually put those on autopilot. Like when I feel like. Kyle James (11:37) Yeah. Yeah. Sure. Yeah. Yeah. Yeah. And so like, you know, especially when you talk about some of your clients or even some of these start, you know, small, small startup companies, tech companies, and they are using a Google sheet and they are using Excel documents and Jacki Leahy (11:46) Ready. Yeah, it's crazy. Kyle James (12:01) There's no CRM, there's no tools outside of maybe using Chad to BT. Like what are some of those, I guess, like transformations that you've seen when they finally start working with you and, activate the magic, when they start working with you and what kind of results are they getting after you've, you've kind of coached them through and help them scale their company to a more appropriate revenue. Jacki Leahy (12:21) Yeah. Yeah, I think the first actual like benefits come from it's more of like the emotional side of like confidence that because ⁓ Like, where's the companies usually like we're selling sort of despite ourselves. We don't really know what's happening. We don't have a sales process. And it's like you do. You just you don't you don't have it articulated or documented. So what we're able to do is just a couple like looking at what's going on in your Google Sheets or in your whatever systems, doing some right alongs with your end users will be able to sort of using those artifacts. ⁓ Kyle James (12:39) Hmm. Jacki Leahy (13:02) document what your sales process is. Right? And then all of a sudden we'll have a good idea of where your biggest constraint is. usually it's in early on, it's usually acquisition. I like to, is it acquisition? Like getting new leads, attracting new leads, do people know who you are? Or are they even aware of the problem that you solve? Which is actually a big problem right now. Kyle James (13:02) Right. Jacki Leahy (13:28) Or conversion like once they're in your pipeline. Are you closing them? and then of course like onboarding and expansion like Do your clients stay do they pay the bills sort of thing? Yeah, yeah expansion and all that stuff. So usually it's in the acquisition. So Just just all of sudden being like oh, I know who who we serve how we serve them How to like talk about our key persona? Kyle James (13:32) Yeah, keeping that retention. Yeah. Jacki Leahy (13:57) ⁓ where they are, how we're going to engage with them. So just some clarity and some, ⁓ now seeing the crazy revenue target at the end of the year that I'm gonna have to stand in front of the board and be like, we did it. You're like finally Kyle James (14:12) Yeah, yeah. Jacki Leahy (14:14) saying like, ⁓ this isn't just a pipe dream. It actually, is, if I just do this, this, this and keep my head on a swivel, we'll get there. Kyle James (14:24) Yeah, yeah, absolutely. think about like, you know, even within our company or in different other companies I've seen, it's like they have this process of, when a lead comes through, this is what I do and this is the results that's happening and they're getting some sort of number, like some sort of revenue from it. But then you come in and it's like, Hey, look, just analyze everything from the beginning to the end. And then let's identify, Hey, what are some bottlenecks or some, some of those, with some of the artifacts that you mentioned? Jacki Leahy (14:52) Yeah. Kyle James (14:52) And then from there, it's like making changes and you know, I don't know how many clients are still you were working with, but like what, what are like maybe one or two that maybe come to mind that you've just seen, like since you started working with them, it's been just a absolute change, whether it's just like a process or it's a change in revenue or change in direction. Like what have you seen so far? Jacki Leahy (15:15) Yeah, one of our biggest, so we have about 12 clients right now. ⁓ We're going through a ghost part, which is really fun. ⁓ But one of them, I mean, they came to us there, they had sort of one go to market motion going fine. They added a second one, like a second product, and it's just very different. And it wasn't really in Salesforce yet. Right, so that whole team was running off of a Google Sheet or 12. Kyle James (15:40) Hmm. Jacki Leahy (15:45) And then they had different, of course it's like the copy, like final, final copy, right? Like, no, this is the one, like trying to put it in the title of a Google sheet, right? So, and everything was hand tabulated, so they didn't really know where things were. So being able to like just lightly document what they're doing, bring it into Salesforce and also be able to like unify both sales teams in one system, because they have the same sales leader. So that sales leader instead of like, Kyle James (15:50) Mm-hmm. Jacki Leahy (16:13) what's going over there and what's going on. It's like, okay, on one dashboard I can see where do I need to coach today? Right? Kyle James (16:21) Yeah. Jacki Leahy (16:23) What team needs the most help today? And based on some gone crackers and some looking at what's happening on the funnel, like, ooh, this is actually, if I spend my time here, it's gonna make the biggest difference. So, because I think sales leaders care so much and they're so like, There's so much to do. You will never be done. So you could either run around like a chicken with your head cut off and like, ⁓ I hope I'm doing the right things. Or right, just a little bit of Kyle James (16:48) All right. Jacki Leahy (16:51) like, hey, start here. ⁓ It looks like the thing that you're worried about, probably because you, a friend was talking about some AI like chatbot or something like, I need that. was like, do you? Let's take a step back. Cause your, your website conversions are not a problem. Actually, if you look. Kyle James (17:04) Hmm. Yeah. Jacki Leahy (17:10) Here though, this little handoff is where you're losing. ⁓ So let's actually tackle that. And it's like, ⁓ right. Kyle James (17:15) Yeah. So it's like taking, taking all that, like almost like the data, clearing it up, getting it all in one, like unified place and then going, okay. You as a sales leader, as an example, like, Hey, looking at this data and these numbers, like I know that you want to spend time on that shiny new object over here, the fish, right? Like, but Hey, actually what we're looking at here is the data says that Jacki Leahy (17:20) Mm-hmm. Yeah. Kyle James (17:36) or even just what you're, what's in front of you is saying, you need to spend time with this part of your team because that's going to get you closest to that next sale or that change in process. So, and, so for, especially those businesses that are listening in, they're in that place. Maybe they're a single, you know, solopreneur or they've got a small team, five, 10 people like, they're under that 10 million, uh, reoccurring revenue. Where would they go to learn more about, you know, Jacki Leahy (17:40) Exactly. Kyle James (18:03) what you do Jacki and then more about activate the magic. Jacki Leahy (18:07) Ooh, well I hang out on LinkedIn, so just find me on LinkedIn, send me a DM, I'm very friendly. And if you would like to kind of look into what your key constraint might be, I do have a little, it's called Fire Focus Tool. You don't even need to give your email. It's completely ungated, completely free. It's activatethemagic.com and just click on Fire Focus Tool and it'll get you some insight. ⁓ Kyle James (18:22) Hmm. Nice. Jacki Leahy (18:35) And it'll lead you to a step-by-step on how to fix that kicking straight that you can literally just hand to your junior person. Go fix that. Yeah. Kyle James (18:43) Nice. Absolutely amazing. Awesome. Well, cool. Thanks for sharing that. Definitely go there. We're going to wrap it up from here. Thank you so much, Jacki, for joining us and sharing more insight on Activate the Magic. And just the impact that you're making for not only your company, but also for many other SaaS startup companies who are just trying to get to that first mountain top, right? It's a bit of a climb, but I'm sure the breeze is nice and refreshing once you get to the top, or closer to the top, I should say. I keep climbing, though. I'm breathing heavier, harder, and every time. Jacki Leahy (19:04) Yep. That's what I'm told. I keep climbing. ⁓ Kyle James (19:18) Anyways, amazing. And remember if you're a startup or business consulting company and your AI agent is hallucinating or just mishandling basic conversations, go to gpdtrainer.com to learn more on how we've helped our clients fine tune their AI agents. Thanks for listening in. Hope you have a wonderful rest of the day. Thanks, Jacki. It's great having you on. I really enjoyed this. I'm looking forward to seeing everyone on the next episode of the AI Chronicles.