About the speaker

Jacki Leahy is a dedicated Fractional RevOps Advisor and the visionary Founder of Activate the Magic. For over 9 years, Jacki has been immersed in the dynamic world of tech startups. Going from Kindergarten teacher to RevOps Founder in less than a decade, Jacki brings a unique, human-centered approach to Revenue Operations.

Mark Lerner:

Alright, everybody. Welcome to this episode of the Revamp podcast. I’m joined here by Jackie Lehe. I’ve always admired Jackie from a distance. She’s really fun to follow on social media. I’m sure we’ll talk about that a little bit as well. But before we jump into the meat and potatoes here, Jackie, why don’t you introduce yourself to the folks at home, tell a little bit about yourself and your background, and how you got to where you’re at?

Jacki Leahy:

Yeah, so good to be here, Mark. Long time coming. Yeah. Yeah. So I’m Jackie Leahy. I’m actually a former kindergarten teacher, and I pivoted to tech in 2015. I started out as A BDR and went into outbound prospecting. I loved it, and eventually, I was a BDR team lead and then director of business development at my third startup. I was hired as number 10, the first lady at Link Squares, and I got to build the entire outbound prospecting program. So what we did, how we did it, what tools, who we hired, how we onboarded them, and everything. In the course of that, somebody had to figure out the backend of Salesforce, and I was the accidental admin. And over the course of the two years there, I absolutely just fell in love. So, I’ve actually been on the consulting side of revenue operations since 2020, and I started my own fractional Red Ops consortium in September of 2022.

Mark Lerner:

Wow. Consortium. That sounds very,

Jacki Leahy:

Yep, yep.

Mark Lerner:

You were a former kindergarten teacher. I’m a former kindergarten student, so

Jacki Leahy:

The parallels are uncanny. Right.

Mark Lerner:

So that’s really, I mean, obviously a non-traditional route for this role, which is great. I think that I’m a big fan of non-traditional everything. Has there been any crossover between being a kindergarten teacher and being in RevOps? 

Jacki Leahy:

Oh My gosh.

Mark Lerner:

And now in your consortium. Yeah.

Jacki Leahy:

I mean, being a kindergarten teacher, it’s so much. The operations behind classroom management are so intense. So, I heard this from a mentor, and I really took it to heart. It’s that the measurement of, or the degree of, your classroom management isn’t what happens when you’re there. It’s what happens when you’re sick. All of a sudden, you have to call out, and there’s a random sub that you didn’t exactly plan for. What do your kids do in that situation? That’s really changed my world, and it changes how I really think about revenue operations. It’s really tempting to be the all-important person. I love to be needed, Mark, like, oh, a late-night slack about a board deck presentation. Oh yes, that is my love language. But it’s super shortsighted, and it’s tempting to hold all the Legos and really feel important, but the real power of operations is what happens when you’re out sick. God forbid you take a vacation. And I do think that there’s real power in setting up an organization to do things without me. So, really, seeing it activates the magic. That’s my firm; our relationship is really to fire ourselves, to get you in a situation where you don’t need us anymore either because we got you to such a cool position where you’re able to build your own team internally, or we’ve got things moving and great and so well that you can handle it in house. 

Mark Lerner:

Yeah, so take off the training kind of thing.

Jacki Leahy:

Yep.

Mark Lerner:

Okay. Well, that’s really awesome. But I think kind of transitioning into the topic around internal adoption and the challenges around that, and when we talk about internal adoption, we’re talking about, I guess, our internal customers, whoever the people on the team are that are going to be using the solution you’re implementing or the process you want to apply. So, I guess, starting from the beginning, what are the challenges of getting internal adoption? And when you hit that challenge, what were its negative outcomes?

Jacki Leahy:

So, I look at the real reasons that your CRM isn’t being adopted, and there are two realms. The first realm is human dynamics, and the second realm is tactical strategies. And so, in human dynamics, why isn’t it being adopted? And then also the web

Mark Lerner:

Ops person or you being the person on ops, it’s

Jacki Leahy:

You. It’s you. Yeah. And then it’s also it’s family and then the tactical, it’s your process and it’s your rollout. So the sort of four quadrants.

Mark Lerner:

And does that apply specifically for CRM or a new tool? Does it also apply to a new process as well? Is it applicable? Yeah.

Jacki Leahy:

Oh, a hundred percent. Yeah. I mean, when you get into the tactical strategies, there might be specific tools or templates that you can use specifically for a new sales process rollout or something. But the core tenants, it really can be applied to, whether it’s a new medic thing for the sales team or legal ops is now getting tied into Salesforce. Anything.

Mark Lerner:

So, kind of diving a little bit deeper into the topic, we talk about humans, right? We’re talking about you, real people. When you have this kind of top-down approach to things where you don’t really consider the human element that brings complexity to it, it is almost impossible to completely game out all of that without being there. So you talk about the challenge of assuming everyone else is just lazy, and that’s why they’re not doing it. But in reality, it’s other things. So, what are the ways in which you can apply whatever pressure or influence to get better in compliance and adoption?

Jacki Leahy:

So, if you’ve read the book How to Win Friends and Influence People by Dale Carnegie or Carnegie, I’ve heard that it’s actually Carnegie

Mark Lerner:

So I listened to the audiobook, and they pronounced it Carnegie.

Jacki Leahy:

Carnegie mind-blowing. I think one of the coolest concepts there is really putting in terms of why it matters to the other person. So with the framework of a personality matrix, there are lots of different frameworks to apply, whether it’s a disc or predictive index, there are all sorts of MBTI, all the things. There are four core personality styles of communication: promoting, supporting, controlling, and analyzing. The key is really knowing yourself and what’s important to me, what I focus on, what drains me, my go-to strengths, and also my weaknesses. What pisses me off no other? What are the buttons that people are partly pushing that I get to really be responsible for?

Mark Lerner:

Is it like a quadrant where you fall, and do you only have one label?

Jacki Leahy:

Oh no. I mean, everyone’s all four, right? So it’s like to what extreme you are and in what combination you are always, and it’s a simplified model. It’s not exactly; humans are fantastic, complicated, and nuanced, but it’s a helpful framework. So I’m a promoting style. Everything is awesome. I love to be expressive and creative, but my weakness is I can be a little bit insincere. I can lack follow-through. I can sort of appear phony. Are you telling me you’re actually excited about Salesforce screen flows? No, I am, but that’s just not relatable to a lot of people. And then there’s the friction. Now let’s get into it’s you, right? So it, it’s them rather. So your sales team is probably a lot of controlling styles. They’re competitive, and they want it their way; the only way is the fastest way sort of thing. And they can be a little bit of a tyrant. And I feel like a lot of WebOps people were, too. I’m probably a little weird as a promoter, but there are a lot of analyzers and supporters. So, the analyzers are the ones who are all the way deep in the details. And when they’re interacting with a controller, they’re just going to avoid it.

And the only thing that they’ll go to back themselves up and prove their point is more data. Where the last thing a controlling style person will ever, ever pay attention to is more data, especially if it’s more minute than whatever data you brought to them in the first place.

Mark Lerner:

I imagine the jocks and geeks’ interaction

Jacki Leahy:

With Yeah, yeah.

Mark Lerner:

And sales folks tend to, a lot of them kind of type A personalities and

Jacki Leahy:

Yes. Yeah. So, within the four quadrants, there’s informal versus formal. So promoters and supporters tend to be a lot more informal and a little bit more relationship-oriented. We’ll say, oh, it feels blah, blah, blah. On the other hand, the formal style is more about the control learning style and the analyzing style. They come from the head; they’re more tax-oriented. So if you’re a support or promoter, you might feel barked at either from a salesperson who’s telling you what to do or from an analyzer who’s like, no, this is the way, and it’s like you’re hurting my feelings. And it’s like if you’re an analyzer controller, what are you talking about regarding your feelings? That’s not even on the chessboard. What are you talking about? Yeah.

Mark Lerner:

So it’s interesting taking this kind of systematized approach to an element that often is not really considered, at least where it’s like, okay, we have the game plan, this is what we’re going to do, this is the rollout plan. But the part you’re talking about where most people are considering the fields and the process in the technology is where you’re considering the people that are going to be using this and how to align to their operating system and how to connect to their API. Right? In some,

Jacki Leahy:

Yes. I love that, Mark. How do I connect to their API? It’s brilliant. I’m stealing it. It’s mine now.

Mark Lerner:

As long as I get a little citation, it’s fine. It’s all yours. I

Jacki Leahy:

Doubt that you might get an at some point,

Mark Lerner:

But I totally get it. And I think it is often forgotten, mostly because a lot of times in business, feelings are less important. You got to suck it up and be stoic in a lot of ways, whether that’s good or bad. I make no judgments on it, but it’s sometimes ineffective. So obviously, at least in my experience, this approach is not often done as far as I can tell. When you’ve worked and when you work with folks now, is this the focus on this element of it, something that they are happy about or surprised by? Or do you not even mention it, and you just kind of go forward with it?

Jacki Leahy:

That’s a little bit of the magic and activates the magic. Sometimes, I can make things look really easy, but in the background, I’ve got the CPU really going. So, I am trying to log in as a user and see it from their perspective.

Mark Lerner:

You’re really running with these.

Jacki Leahy:

Yeah, yeah. Well, but I’ve got the analyzer in me, right? Yeah. Connect to their API and log in as and like, oh, conceptually, I really have to step into their shoes and like, oh, right. If I’m a controlling slash analyzing salesperson, no amount of you click here, and you click here. It’s never going to satisfy me if I think this whole thing is stupid. If there’s no direct line between these clicks and scrolls and stupid things to my commission, there’s no amount of enablement. God, I hate that word enablement, which is going to traverse that cavern. We really have to step into them and figure out what’s going to make it actually important to them.

Mark Lerner:

Yeah, it is interesting because in our world, in the business world, enablement is a good thing when using that kind of terminology in the psychology world is often

Jacki Leahy:

Not blah, blah, blah. Yeah. Often I submit that it’s equally as stupid unless you’re really keeping, let’s be effing for real with enablement. Are you covering your butt, or are you actually driving adoption? Are you actually making a difference for your end users,

Mark Lerner:

Right? Yeah. And so, assuming end users aren’t lazy, right? They’re motivated by their experience, what their incentives are, and how it helps them do what they are. And they have a healthy dose of hesitancy, probably from previous experience, where they got loaded with these irrelevant new processes that all that did was make things take longer and didn’t have any value. So what is the Rosetta Stone here in terms of how you appeal to these humans on a real level to make that impact? What kind of keystone are you going after?

Jacki Leahy:

So you’re going to want to hit the different love languages. There’s no one-size-fits-all all. So, you’re going to look at who your end users are. They’re probably going to be some sort of controlling, analyzing, or controlling promoting people and just kind of know them and know what’s going to; what radio station would they listen to? What format would that radio station be in? Make your resources, guides, training, onboarding, and enablement a match for what they need. That is so good, God. One of the things I have a hard time with is Salesforce and written documentation. Tell me, give a gift, give for the love of everything is whole. Give me a gift with a little arrow. Thank you. I’ve got it. And so I’m probably speaking for a lot of promoters and controllers when I say that, but also if I’m interfacing with finance, a gift, actually make them very concerned. Have you thought that out? We are actually fiscally responsible for things, lady. It’s like, ah, right. I really get to lean in on what would be scrumptious to an analyzer.

Mark Lerner:

Interesting. And this idea about humans preferring the path to least resistance, can you tell me a little bit about that and how that translates to this whole concept?

Jacki Leahy:

Yeah, I think humans are alive. So we’ve evolved to be here. So obviously, we haven’t been doing things that activists actively get killed, and we’re driven to survive, not necessarily to thrive. So, as long as I can keep my job and make money, why would I do anything beyond that? And if we really relate with that as neutral, that’s not bad. It’s not good. It’s just so how can we dance with whatever is so,

Mark Lerner:

Yeah.

Jacki Leahy:

Yeah.

Mark Lerner:

Awesome. So it’s a really, I think, novel approach to actually getting adoption because adoption, level of adoption of anything new, is often a key metric. But if your only plan is to root force it down people’s throats, you’re probably going to get a lot of resistance. Whereas if you map it out in the way you’re mapping out the system that you’re implementing, you are going to have a much greater likelihood of success. So, from your perspective, and as you approach this, obviously, we’re in a time where everything just seems like everything’s moving so much faster, and everything changes, and there’s a lot of insecurity from humans and businesses in general. How do you think this plays out in terms of the way you approach this as the rest of this year plays out and we move into next year? Obviously, for all we know, there’s going to be a huge paradigm shift, whether or not. Yeah,

Jacki Leahy:

Yeah. It’s basically a feeling of bracing for impact, and everything that I’m talking about is just so much more heightened. So it’s no longer like I might not get my way. I might get fired. We don’t have the runway to do so, and a lot of rev ops people are incredibly talented. Rev ops people are out of a job and looking for a job. And literally a year and a half ago, you, that was unheard of. But it’s the same thing if you step into the shoes of the CMO or the CRO or everyone is threatened, and what actually happens to the brain under threat is the blood withdraws from the neocortex, which is right behind your forehead. That’s the part of advanced reasoning. And it withdraws back to more of the brainstem. And that’s sort of the survival instinct. So the last thing you want is for your end users to be in flight or free fight or freeze when you’re trying to just show them how they can create an opportunity.

So it’s so important to understand my reputation, what is known about Jackie, the Rev ops person, and what is known about our Salesforce. What is the conversation really, no matter whether it is true or not? Whatever, it’s just what’s, so really, just stand in it, take it on, and just be responsible for it. And it’s more important than ever to really make everyone around me feel safe and important. The only thing that brings the blood flow back to the new cortex is that there are some physical things you can tap on, such as your forehead or scratch your head and cross your median lines. So your right is on the left side and the left is on the right to sort of activate that. But the only thing that will bring blood back is when people feel safe and valued.

Mark Lerner:

Wow. Yeah, I mean, I think a lot of people can relate to this idea. You’re in stress,

You often revert to the fight or flight. And I find it frustrating personally that my objective decision-making when it would be most beneficial seems to be less accessible, which is this kind of paradox of Kafkaesque type thing. That’s actually very interesting. But when you’re in a project or a scenario, you’ve rolled it out in this way, you’ve mapped out how people will interact, and you’ve worked out what their incentives are and how to speak their love language. And with all of that done, there still isn’t adoption. This means maybe the tool just wasn’t effective, or maybe it was a failure. How do you kind of make that judgment and say, maybe we roll this back? B. What do you do in those scenarios?

Jacki Leahy:

Yeah, so it’s going to depend. Is it the solution process? Is it how you got to whatever is in front of them that they’re not adopting? Or is the problem truly that it’s a great product? We’ve had user-authorized testing; it’s fantastic. It literally just isn’t being used, and everyone’s confused. So what is it? What’s the problem? So, not only ten times in that case, but it’s probably going to be your process because, believe it or not, some things do adopt themselves. The biggest aha moment was when we were rolling out Gong at link squares, and the reps started downloading that Gong iPhone app and listening to call recordings. They were podcasts on their commute, right? So if whatever it is that you’re building is actually super supportive and helpful and the end user’s like, oh, this is going to help me actually do my job, this is great. It’ll have a buzz about it. It’ll go viral. It will. When it comes to your process, I think the biggest thing is that there are three shifts: mindset shifts. The first one goes from an order taker to an investigative anthropologist.

Usually, when we’re brought into a botched rollout of something, they fire their consultants, and they bring us in. They usually hire a Salesforce consultant who is probably a hundred times more technically competent than I am, right? But they took whatever discovery, whatever business requirements, and they just literally turned that into technical requirements, and they were off to the races. They didn’t validate it with anybody else. There’s no V one; lemme reflect back to you what I heard. That’s usually the biggest thing that we’re overcoming. And so switching from, well, this is what you said you want. Great. That might be what you agreed to contractually, but are they going to refer you or people? No, it’s shortsighted business-wise and really shifting into being an investigative anthropologist. How does this creature currently do this? I am now filming a nature documentary, and I want to know if I want to actually see these people in action and what they’re doing.

Mark Lerner:

With a British guy narrating in your mind.

Jacki Leahy:

Yes.

Mark Lerner:

A sales development representative is needed. Yeah, I love it.

Jacki Leahy:

Yeah,

Mark Lerner:

It’s funny. I’m imagining a skit in my head. That’s

Jacki Leahy:

So good. Yeah, yeah,

Mark Lerner:

Yeah. No, I totally get it. And so I assume that you’ve had those kinds of situations.

Jacki Leahy:

Oh yeah. Oh yeah. Right now, we’re figuring out there’s just a failed Salesforce experience cloud, which is a partner portal. It is just a botched execution from someone, which is based on what the client is telling me they want, and that’s what they got. But it’s obviously not doing the trick. So, pausing, what do you mean by saying they can see my accounts? What does that mean? And yeah, just being super curious, and it’s like you are studying an alien life form,

Mark Lerner:

Right? Yeah. It’s like a forensic approach to this whole thing.

Jacki Leahy:

Yes.

Mark Lerner:

So, as we roll kind of head into the end of this, we have a few minutes left on the clock. Looking forward to your approach, and I don’t know if it’s completely unique to you, but this approach that you’re talking about is quite novel to me. Have you found a greater level of people being open to it recently? Do you get

Jacki Leahy:

Yeah, the times are changing, right? And beyond doing silly things in Salesforce, my mission is to transform how we relate to each other at work. Instead of beating each other up and being competitive, what are we creating? Let’s have some fun. Let’s have some joyful, powerful, sustainable growth.

Mark Lerner:

Yeah, I’m nodding so much. Yeah,

Jacki Leahy:

You’re nodding. Yeah,

Mark Lerner:

Let’s do it. I dunno what it is, but let’s do it. Yeah,

Jacki Leahy:

Let’s do it. Let’s treat each other people. Let’s collectively join forces. Let’s have some fun, man.

Mark Lerner:

Yeah, I love it. I mean, the positivity is a breath of fresh air. Obviously. We often can get sucked into the banality and the,

Jacki Leahy:

It’s seductive complaining. People love to have a problem. We love to have; this is an Alex Ram mosey thing. People love having potential and a problem because it’s a buffer and an excuse for why they’re not living up, right? It’s Oil.

Jacki Leahy:

Yep. It’s a shame protection.

Mark Lerner:

I hear that. Yeah. I’m just, now, everything you’re saying, like

Jacki Leahy:

Goes into a deep, dark spiral, right

Mark Lerner:

When we go sit in front of the mirror and cry and eat some ice cream. So, to the folks at home, if you enjoy this topic and are super fascinated and interested, like I am, Jackie is going to have a session on the agenda for the upcoming Rev ops AF conference in San Diego, which deal hub will be at. We have a really fun time; this is a legitimately fun thing set up for it. It’s a bit of a secret, but it’s going to be, I think, enjoyable. Yeah. And I know Jackie’s going to be there. So

Jacki Leahy:

Yeah, promo code Jackie, J-A-C-K-I for 10% off, and then I get some credit somewhere if I get the most signups. Mark, do you know about this? I might get the high roller suit.

Mark Lerner:

That’s really,

Jacki Leahy:

That’s, yeah.

Mark Lerner:

Alright, so I’m going to edit that out. Use Mark MAR. No, I’m just joking. I know DH has one, but if we win it, I wouldn’t share anyone. So Jackie, before we jump off, why don’t you tell the folks at home other places they can follow you or learn more about you or what you’re doing?

Jacki Leahy:

Thank you. Yeah, so I love LinkedIn. That’s my social network group choice. So Jackie Leahy, J-A-C-K-I-L-E-A-H-Y. I’m also built in two different communities. One is for go-to-market operators who know that their brilliance is made for more than simply exchanging their time for money. So this is called the Cauldron. So we have a Slack org, and we meet once a month. You might see the Cauldron witching hour, so into the cauldron.com with little dashes between the words. And the other one is soul and strategy. It’s for lady entrepreneurs to really connect with some brilliance. We also meet once a month for a monthly coming-home session. The next one is on May 8th.

Mark Lerner:

Sounds wonderful. As a fan of LinkedIn, I can say that following Jackie is well worth it.

Jacki Leahy:

I went viral two weeks ago, Mark.

Mark Lerner:

Yeah,

Jacki Leahy:

Yeah, it’s a Pardot one.

Mark Lerner:

Yeah, right. All right. Well, Jackie, thank you so much. I’m looking forward to getting to meet you in person next month and seeing your session. Thanks again for taking the time to chat.

Jacki Leahy:

You’re the best. Thank you.

Mark Lerner:

Bye-Bye.