From lobbying to leadership: How Josh Pudnos built his RevOps career from the ground up

James Geyer: All right. It is time once again for our latest boardroom RevOps episode where we are bringing you valuable tips from RevOps experts so you can make to the C-Suite James co-founder of AccountAim. Here we are the RevOps BI platform. Super excited to be joined by Josh Pudnos today, the head of RevOps at Nava Benefits.

Uh, great to have you on Josh.

Josh Pudnos: Yeah, thanks for having me.

James Geyer: Today we’re gonna talk about a few things, uh, primarily, you know, Josh’s experience becoming a VP of RevOps, stepping into that role, also assessing kind of leadership roles in RevOps and how to interview well on them. And then we’ll also cover some tactical questions at the end given Josh has some experience around exit readiness for, for multiple companies.

But before we dive into everything at once, Josh, do you wanna share your background for folks?

Josh Pudnos: Sure.

So currently, uh, and, and pretty recently head of RevOps at Nava Benefits, we are a tech forward, tech enabled. Healthcare benefits brokerage company. And, uh, yeah, just a few months into the role here. Before that I was at a enterprise SaaS company called Exiger, where I was the founding head of RevOps, building out that program for a, a quickly scaling company, talk about it later, you know, exited, uh, for a, a large figure to, to pe And before that, uh, RevOps at a company called falcon.io that was acquired, uh, and, and merged together with a company called Brand Wash.

Taking over the name there. So I, uh, that’s really where I, I, uh, you know, cut my teeth and, and learned the ropes, um, of the game. Before that, I actually really started in lobbying, and so I made a, an interesting transition. To tech from lobbying was first exposed there to go to market and different go to market roles, more analysis, more strategy.

Few bumped around a few different roles, uh, before landing at, uh, Falcon. And, uh, slowly evolved into looking at analysis and, uh, how to use that to leverage that and, and acceler our, our go to market motions.

James Geyer: That’s great. There’ll be a lot to unpack in here, but a few things, uh, I already love off the bat as we come full circle.

Jan was one of our first guests on the podcast, and I think he was your RevOps leader back at Falcon and Brandwatch. That’s right. The, the protege has become the mentor here, and then you’re definitely our first ex lobbyist, uh, as well as remaining to do a whole other episode on the, the deep dives at dc.

But we’ll say that maybe for a spinoff podcast. So at Exiger is kind of when you became VP head of RevOps for the first time. I wanted to cover from just like a career perspective and maybe on my quick reflection, like what do you attribute to your success making it to vp. I think a lot of RevOps folks tell me that they kind of feel stuck in the director role.

And so yeah. Tell me, how do you think you make made that jump?

Josh Pudnos: Yeah, so I think there’s some core attributes about somebody who’s ready to make that that jump. Um. And those are, I think, just a overwhelming sense of curiosity around constantly wanting to inspect why certain things are working or not working the way they are.

Um, and then what really sets people apart is the ability to develop a point of view, a perspective, having high agency around that and, and doing that sort of self-driven. Um, and then coming with an agenda and, you know, you’re seeking, seeking buy-in from your various stakeholders on what needs to happen next.

That’s sort of the differentiation between somebody who’s maybe at a, a more of a director level and going to a VP level. You need to have a platform develop a per perspective and, and drive forward the agenda together with your stakeholders. Um, but I think also what’s really important, and, you know, if we’re gonna talk about hiring or, or interviewing.

Is developing. I know people talk about it all the time, but I think it’s, it’s really relevant in, in RevOps is your brand. I had just come off of a few years of working through a major merger of, of two equally sized companies. Falcon with about a hundred million in revenue, brand watches is about a hundred million in revenue.

And overnight bringing them together, um, and a one plus one equals three type of scenario. But going through those pains and the challenges of that was a great learning experience. Also a really great launchpad. For me, it was, it was something I could anchor myself on and be able to, to talk about a scaling journey that a lot of companies found really valuable and interesting.

And when I was speaking with Exiger, this is a company at a major inflection point, as I think a lot of companies are, when they’re ready to hire their first head of RevOps. They were really pivoting from a tech enabled company into a SaaS company. I built some tech and Boston Tech and kinda merged it together and said, Hey, we want, this is the, this is the path forward.

We need a modern SaaS motion. And there I was able to talk about what good looks like. Shout out to Jan. Jan Meyer over my, uh, boss and, and mentor over at Brandwatch at the time really taught me a lot and I was able to use that as a great talking point, a great brand for myself as the, there I was, the scale up guy.

And I’ve been through that motion and I can bring that to you. And so I think, you know, when I talk to, I talk to a lot of different folks who are looking maybe at, at new roles, wanna make that night’s sleep and how they get that job, how they get even their foot in the door. And I think determine what it is that sets you apart from the other candidates, the other folks out there.

And, you know, it’s not, it’s not gonna resonate with every company, but there are several that have. That vision for themselves going forward. And if you pair that well, it’s, it’s gonna resonate really well.

James Geyer: Yeah, that’s super interesting and I want to maybe just jump right into that before I do. I think your answer was fantastic to, what does it take to make vp and there are a lot of kind of sub components in it, but I would sum up what you described.

It’s really like pro proactivity and that’s kind of what I counsel folks as well. Based on how many VPs of RevOps I’ve spoken to now is like to make it to C-suite or just short of the C-suite, you really have to have that opinion. You have to drive the business forward. And so just being an order taker, just working on systems won’t cut it.

And so I think you have to self-identify what’s going wrong, what can be an improved, and that’s where like bias, I think AccountAim or other data platforms really come into play. You have to have control of the data so that you can see what’s happening and make those recommendations that are grounded in fact, because that’s what folks are looking for at their RevOps hire.

Let’s dive deep into like the personal branding, uh, bit though, I think like you talked really well about your experience, specifically taking your past experience, you know, branding yourself, what you could bring to a company, going into scale, maybe generalized a little bit, like, how can folks do this themselves?

Like how would you counsel someone to kind of look in the mirror and understand what their personal brand should be?

Josh Pudnos: I think it’s, a lot of times it’s thrust upon you. Um, in my case, you know, I, I didn’t. I didn’t go out seeking Falcon ’cause I was like, this is a great acquisition. I wanna, I wanna learn how to operationalize a merger.

It was thrust upon me. And, and so those were my circumstances and, and obviously I was able to leverage it from there. I think there are a lot of people who go through, you know, they’re, they’re in a RevOps role where the company’s downsizing or going through a major, major shift. Maybe they’re going through a huge, uh, scale up phase.

Maybe they’re going through a divestment, like there’s a number of different scenarios here where you’re going through something. Maybe it’s just like maybe staying flat is a win, and maybe it’s being. Taken on by, uh, PE and just changing the entire motion, adding a new product, a new, a new product, a major, a new major motion.

There’s something that you’re going through where you are learning yourself for the first time, but you can then apply that lesson elsewhere. And there are others going through similar challenges themselves.

James Geyer: Yeah, totally. And I think this is where like interviewers put on your discovery hat, like you guys have probably watched a lot of sales calls, understand what a good discovery looks like.

You kind of need to do that in a job interview. Right. So what I’m hearing from you, Josh, is like. Figure out what the hiring manager is actually looking for. What stage of company or what stage of growth is the company you’re interviewing within? And look back and see like do you have any relevant experiences or attributes to that?

And if so, really focus on branding yourself as like the expert in that thing. Because I think so often folks are afraid to call themselves an expert, but most people are just winging it, right? So if you have even one good experience doing something that’s relevant, like you probably know more than a lot of people.

And so don’t be shy to kind of like brand yourself as such. Is that a fair encapsulation of kinda what you’re describing? A hundred percent?

Josh Pudnos: Yeah.

James Geyer: Absolutely. That’s great. So, okay. That’s kind of like branding yourself, figuring out what the hiring manager is looking for as we think about stepping into a new role.

Like how can you assess if a role is a good fit? I, I hear a lot of horror stories, uh, especially in RevOps of like, you know, the job that was sold to me is not the job I stepped into. So how do you think about assessing roles that you’re interviewing for?

Josh Pudnos: Yeah, I think, I mean, to the last point, like, the ground is always shifting.

You know, you might take a job, say you’re gonna start in two weeks and, and then get a call from. An executive there saying, oh, actually, like there was an org change last night. Wanna give you a heads up. Like, so you never really know what you’re getting yourself into. But there are some really good indicators I think, you know, you wanna look back and say, what did I like about previous experiences and what didn’t I like?

What circumstances were holding me back and what would the inverse be if I had the opposite of that, would I excelled there? And so, you know, maybe you had a bad experience with a certain type of person. Or, or somebody who had a certain perspective. You know, so much of RevOps and sales is almost philosophical and how you like, where you wanna focus and what the motion is.

So, you know, for me in particular, what I was looking for was a high growth environment. I, I like that could be more mature. Uh, my previous company I, I joined at, we were around 60 million in revenue, could be less mature. I’ve been at a series A company, so I, I was looking for the sweet spot for me, but I wanted a high growth environment.

One where. I would be bringing a lot to the table where they didn’t, where I knew I could have a major impact. I was also looking for an environment where you had executives with a lot of experience who had done this before. I would say this before, who would be a partner in, in the growth and not somebody I’d be having to maybe educate along the way.

Those, those were important factors for me. And then, you know. Just obviously like the, the, the personal dynamic, the, their perspective of RevOps, their vision of how, if, you know, if the role’s gonna report to the CRO, what does that CRO head of RevOps dynamic look like? What does that look like? But the CMO, what’s their interaction finding?

James Geyer: This I, that one Josh, that’s kind of a, it’s hard one to dive into, like personal dynamics. Right. Do you have any tips on, on that one?

Josh Pudnos: Um. I dunno if it’s a great answer, but it’s, you know, I, i, i in every one of my interviews, like, tell me about your relationship with the CRO. Tell me about your relationship with the CMO.

Uh, depending on who you’re at, who you’re talking to, they’ll be telling, you know, that it, it’s, it’s hard for people to hold back and, and say, you know, if, if, if there are fractures, if there are different philosophies on what’s to prioritize over others. But it’s an important question to ask. Um, and, and also tell me about a great experience you had with.

You know, with a former head of RevOps that you would wanna, you know, replicate and tell me about some elements of where things that you don’t wanna replicate, things you don’t wanna experience. Again, that, that’s also another line of questioning that I always went into.

James Geyer: I think that’s helpful and I’m now wondering if, uh, your lobbying DNA is feeding into some of this, this straight shooting.

I, I think it’s great though, Josh, let’s come back. We jumped right to understanding new jobs, interviewing for ’em. I wanna come back to becoming a vp, how to be successful there. You mentioned some attributes, uh, that you kind of attribute to your success to making VP super, super great. You and I spoke a couple weeks ago and you had kind of mentioned.

That you felt like you were pretty good at knowing like what is or isn’t scalable as you think about like RevOps processes and that’s taken you a long way. Like can you expand on that? What did you mean by that? Why is that so important as someone steps into like the VP role?

Josh Pudnos: Yeah. You know, I, it’s kind of to the old startup, uh, mantra.

Like, do, do what doesn’t scale and then like build process around it. I’ve spent time building the reports and the dashboards and being like, ah, this is like really laborious. If we had this one field, we could, we could, uh, streamline it a whole lot. That’s a really, maybe an obvious one, but it’s really exemplifies exactly what I’m talking about when I think about managing quotas or territories.

I’ve done the things I’ve, I’ve poured over spreadsheets in a way where I realize like, this doesn’t make sense. This does not, you know, it, it’s time consuming for myself and. There are inefficiencies built in for the business as well. And so like in order to scale, you need to do these things differently.

So really just think back to where have you spent time, uh, unnecessarily, and what can you do to build processes to identify weaknesses in your, your overall business? And either automate it away or put structure in place to help eradicate some of that.

James Geyer: Yeah, so I’m hearing just awareness first of all, which sounds simple and obvious, but it’s not necessarily, it’s really easy to get kind of caught up in just like in the weeds, in the spreadsheets.

So awareness on where you’re spending your time, uh, what’s taking a lot of time isn’t going well. How do you analyze this from the sales team perspective? Is this just conversations with them? Is it as simple as that to hear where their pain is or is, or is it something else?

Josh Pudnos: Yeah, I think that’s a starting point.

And, and it’s, you know, we, we interact a lot with sales leaders or, or, or other go-to-market leaders, and I always try to remind myself, maybe not as good as I always want to be, but taking the time to have one-on-ones with the reps or when they ping you for a, you know, a 10 minute question, always trying to carve out just a little time at the end to ask, Hey, what’s, where are you spending too much time?

Or What’s creating drag for you? What’s creating friction and. Maybe it’ll open up an entirely different area, you know, a, a new priority to focus on. Maybe it’ll be nothing but collecting those one by one. You know, you help build trust between the two of you, which is always important. Mm-hmm. And also identify new areas that to potentially explore to, to streamline things.

James Geyer: Great. More sales 1 0 1, rapport, building trust, empathy. It’s good stuff. Yeah.

Josh Pudnos: Exactly.

James Geyer: Let’s talk about stepping into kind of VP head of RevOps role for the first time. Uh, proactivity was my big takeaway from the attributes for success that you talked about. But how about expectations from leadership for a vp, VP of RevOps versus a director?

I’m sure proactivity is one of them. Is there anything else there that is kind of newly expected of you once you step into that kind of top seat?

Josh Pudnos: Yeah, I think, um, really being able to develop your own perspective. You know, I, I had a former boss of mine, the CFO told me about. An earlier role where he came in, um, to a new company and was reporting to his CFO and they said, I want you to tell me something about the business that I don’t know.

Mm-hmm. And so I think, you know, you, you’re, you’re gonna be stepping into roles of various levels of complexity or maturity. Maybe it’s the first set of RevOps and there’s a lot the business doesn’t know about itself. Maybe it, you know, maybe you step stepping into a role where the previous incumbent was really.

Solid and mature and built a great program, but seeking out that information really early on, having those conversations with the people on the front lines, but also digging into the data and, and trying to identify new learnings and pulling on those threads. I think is a good way to start.

James Geyer: Yeah. That’s really powerful.

How about, it’s kind of similar to expectations, but a little bit different. How about when you stepped into this role for the first time? What were the new challenges unique to the VP level role? Anything stick out to you that was kind of a surprising challenge?

Josh Pudnos: I think, again, it’s gonna, it’s gonna differ depending on the level of maturity of the organization that you’re stepping into.

When, when, when I was an Exiger. I was surprised, you know, this, this was an organization that had no RevOps program and was really building a, a, a modern go-to market team for the first time. There was a lot of education about fundamental, uh, processes from just pipe, you know, keeping your opportunities up to date and your pipeline clean.

Uh, like just the concept of forecasting is new for a lot of organizations, surprisingly. Number of organizations, that one, and just the amount of time I, you know, I, I took to. Uh, enable folks on really basic, uh, basic sales, one-on-one type type of operations. Conversely, you know, at Nava, just, it’s a very lean team right now, and I stepped into, you know, I was fortunate to have a pretty solid CRM set up.

It was, you know, pretty sophisticated. Hygiene wasn’t so great and we’re working on that, but. It’s a lean shop. I’m not the most technical person, as you can hear from what I’m talking about. It’s more strategic level things and analysis, but having to dive into and take over and just constantly reverse engineer how the CRM works to fix this one little nagging bug and, and really teach myself how, how to revamp everything.

It’s a challenge. It’s not my favorite thing to do, to be honest. I don’t, I don’t wanna be caught in, bogged down in the systems. It’s important too. It’s important for how they work. ’cause I, I wanna be able to trust the data so I can provide those insights to my, my leadership team.

James Geyer: Totally. The sales 1 0 1, sales 1 0 1 piece at Exiger is so interesting because that is a huge blocker for many new RevOps functions of like, it’s kinda like evangelizing.

What is RevOps like? Why is data important? Why is doing this extra? Uh, kind of admin work as a rep important. It’s a tough one to overcome, especially when you step into a place with long tenured reps or if you’re an enterprise sales motion, um, that maybe isn’t quite as data driven. How did you overcome that?

Josh Pudnos: I don’t know if I ever did, to be honest, but I think I always try to, when I’m presenting new processes to folks, it’s really easy for me to put on the lens of why are we doing this for the business? And I, I usually try to bring that home, but what’s in it for them? Why are we having you go through this process to record your activities?

Why, why do we have you input this data and what can I, you know, if you do this, it’s tit for tat. What am I gonna provide you? And so always bringing that home for them. And, you know, it’s not necessarily gonna get it over the line, but you’re gonna get a half step closer to them actually following things properly and, and, and follow through on those things.

Give them that extra data, give them that report that’s gonna allow them to prospect in a different way at at a higher rate. Um. That is a direct result of them doing the work and putting that data in. So make it valuable for them.

James Geyer: Yeah, makes sense. I think that’s great. Generalized advice for a lot of things in RevOps.

Josh, let’s switch gears here. We’re coming up on time here shortly, sadly. Uh, but I wanna switch into something a little bit more tactical. And so I think the Exiger example is actually a great point. A lot of companies, especially PE-backed or a little bit more mature companies are bringing in RevOps for the first time as RevOps gets a little bit more developed, more known.

And I think for that reason, um, more and more RevOps folks are going to be. Focused on what I call like exit readiness. So if they’re in a world of more investment, getting acquired, going public, PE owned, there’s a different level of scrutiny to allow the exit process to work. And so, um, let’s actually maybe start with like the extra example.

So I think there, you guys went through an exit, you said earlier. Like, explain a little bit of just like the due diligence process. Maybe even start at a high level for folks that might not be super familiar with what that is. Like, what is it and where, how, how was, uh, RevOps involved and, you know, what’s your advice for kind of being ready for things like this?

Josh Pudnos: Yeah. So, uh, we went through a process. We, we partnered with an investment bank, uh, a and a, a team there to help sell the business. And that’s through that due due diligence process. You’re effectively preparing a book to present to potential buyers. To help them understand the business. You know, you, you hear about investment bankers, uh, spending.

You know, 120 hours a week, uh, in work, they really do work that way. Uh,

James Geyer: I’m a recovering investment making analyst, by the way, to serve my career. Yeah. So my ptsd as I, as I hear this

Josh Pudnos: exactly, so there’s a really intense period where they’re trying to finalize that book, and maybe they’re in, you might go through multiple cuts of this.

Actually, no. You will go through multiple cuts of this, this book, especially as you get down to a few final buyers, they’re gonna be asking additional follow up questions. And so you’re in this constant feedback loop of cut the data this way. Present it this way. Dig deeper. Dig deeper, show us this information for de depending, you know, my experience, it was for about two, three months of really, really long hours.

And fundamentally what you’re doing is it’s, it’s really pretty basic analysis stuff that you’re, you’re, you’re trying to help them understand historically how you’ve done and projecting forward based on your pipeline, what you might, you know, what the business may be looking for over the next year or so.

And I think. One of the challenges, at least in our case, and I would be, I’d be surprised if it wasn’t the case for others, is you’re often presenting the data in a way that doesn’t make sense for your business or may not be consistent with how you’ve classified, you know, or, or segmented your, your business and how you’re doing your reporting.

And you now need to transform it into a different way because that is how the buyer potential buyers are thinking about it. So that was, that was one, uh, challenge and, and just why it took so many different cuts and you always have to make sure that the. The data ties from, from this report to that report, um, where you’re, you’re having to reclassify things in different ways than you’re typically used to.

The other one, the, the advice that I’ve given a lot of folks is, um, they wanna look at historically how you’ve done so they can use that to project forward. And so if you don’t have a way of snapshotting, uh, you know, on a daily basis or a weekly basis, you know, your, your CRM data. You want to do that as soon as you can, because what that allows you to do is show the progression from day to day or week to week or month to month in a way that you probably can’t do with your outta the box Salesforce reporting.

Yeah. So, you know, whatever that looks like, whether it is an outside tool or setting up snap, you know, I, there you can set up snap some level of snapshots within Salesforce as it is, but, um, the more granular you can get, the better. So, but you can only, it only works going forward, so you can’t set up snapshots and, and, and.

Look backward. Three years. It’s, um, only as good as it is today. So set it up today. Invest in it now and, uh, have fun with it. Hopefully you have a nice payoff. Um, and you’re, hopefully you’re part of the, the exit policy and you can continue on, but, and you get a nice little payday for yourself.

James Geyer: Yeah, definitely so much to unpack though, but I think you’re spot on.

Um, and this s residency with my time in investment banking, they’re like. Cutting the data a million ways. So I think having snapshoting across the entire go to market data set is really important because you might not know that someone wanted to look at trended data for this data point or that data point.

Um, and so hopefully you have a, you know, data warehouse set, a bio internal team supporting go to market, or you bring something like AccountAim to kind snapshot over time, and you get that going quickly and it’ll save you like a world of pain, as we both know. That’s really interesting and helpful. One other piece on m and a is.

And exits. And so you also mentioned that you worked out, I think you started at Falcon, is that right? Which then merged? That’s right. Merged with Brandwatch and Yes, the Brandwatch brand. I wanna talk, so we just kinda talked diligence and prep. I wanna talk post acquisition here. Like, uh, a merger of equals is basically like change management on steroids, right?

You have two existing organizations, two different sales processes, two different CRMs, data sets. Two different everything, and you gotta like mash it together and give these people who had success typically in their own business change to some middle ground process. So like, I’ll leave this broad in this example.

How did you manage change? Like any specific examples that come to mind to do this effectively?

Josh Pudnos: Yeah. And, and this is gonna happen a million different ways depending on the circumstances of your, of your merger. We had the, I think the, the fortune of, you know, we were really, really bringing the two organizations together and they were gonna operate as one.

But pretty much in their legacy capacity. My legacy company was more SMB and mid-market. The others was more mid-market and and enterprise. So headcount more or less stayed the same. Leadership pretty much stayed the same. That’s gonna be different for I think a lot. I think that’s probably atypical.

Mm-hmm. But where we needed to bring things together and where the challenges were, and then that’s not so much tension, but the challenges were aligning on sales processes, on philosophy, on what we’re prioritizing, just learning their business. And, and identifying the opportunities to bring them together, I think very quickly, you know, your, your owners are going to want to find synergies, and so finding and setting up processes where the two organizations, the two legacy organizations can sell together.

Quicker. Quicker to, to, you know, more quickly bring up the ACV or bring about new revenue. Find ways of working together to, to come back to recently closed, lost opportunities where now this new feature or, or um, or ability. Is able to, you know, re win that opportunity. Upsells. Like, that’s, that’s where you’re gonna get some good traction, good quick wins, and, and show off a lot of what you can do.

And then to the extent possible, like every organization’s gonna deal with this work. I, I, you know, if you can fight the, the organization’s urges to debate indefinitely how you merge your sales forces or work out of them separately. Like it’s, it’s a really challenging endeavor. Mm-hmm. Do not let it be too, you know, if, if you can mitigate it, like don’t have two separate instances for indefinitely, try to bring either one organization to the other or build a brand new one.

But you need a decision. Ultimately, it’s, a decision is better than no decision or kicking the can down the road forever. That’s a big challenge, but really working, being the glue and, and we’re often in this role in RevOps being the glue between different leaders and, and helping them understand each other in their businesses, finding a way forward.

For the new business is, is a really great place for, uh, RevOps to be.

James Geyer: Yeah, I think that’s great advice and we could unpack all of that with an entire other episode. Maybe we will in the future. Sadly, we’re out of time today. Josh, I thought this was great. I really appreciate you coming on. I’m excited to get this out.

Josh Pudnos: Thank you so much for

James Geyer: your time. This was, this was fun.