Rob Levey: From Rolodex to AI: The Evolution of Revenue Operations

Welcome to Go to Market, a podcast for RevOps, sales, and marketing leaders to dive deep into industry insights and best practices. Go to Market is sponsored by Fulcast, the go-to-market cloud. My name is Amy Cook and I am so excited to introduce Rob Levy, SVP of RevOps for Rob Leverage. Rob, how are you doing today?

Doing great. Thank you for inviting me, Amy. Great to be here.

Oh my gosh, I'm so excited. When we chatted before this meeting, before our podcast, I just got to know you a little bit and I'm just super excited not only for all of the expertise you're going to share, But also I find your background to be completely so interesting and very diverse. So can you just tell me a little bit about your background?

Yeah, well, I'm, I, I truly am a global warrior. I was born and raised in, in Zimbabwe in Africa and, uh, moved, moved to the UK in my early 20s and then to the States in my 30s and married a Brit. And we were gonna be in the US for a 3 years, she told me, and 24 years later, we're still here. But, you know, one of the things I did growing up was play field hockey because there's not a lot of ice in Zimbabwe. So it was a big men's sport out in the Southern Hemisphere countries. And, you know, to give back a little bit, I decided to start officiating, umpiring the sport in the US about 12 years ago. Where, as you probably know, it's a women's sport. So this week I just wrapped up another season of 4 seasons of field hockey. I still officiate Division 1 women's collegiate stuff. So it's a pretty interesting side hobby that, put it this way, keeps me grounded because you certainly get shouted at a lot by the coaches and the players. So, you know, not dissimilar to, you know, the life of a RevOps leader.

So I imagine that just as you are officiating, you know, between teams in hockey, I'm assuming like as a RevOps leader, you probably have to do your fair share of officiating. Is that right? Between—

yeah, I mean, it's collaboration and I think that dual respect of coaches and officials, both respecting each other and what they see really does help. And that does apply to business, whether it's RevOps or across any department, finance, marketing, sales, product, production, whatever.

Well, I really love the metaphor of team for business. I feel like, don't you think that, you know, that metaphor is so, so well suited? You know, sometimes people think of a company as a family, but that's not really true. A company is a very performance-based group of people, very much like a sports team, right? Yeah. And so when you talk about, you know, RevOps and, and that collaboration and that group of individuals coming together, you know, in a high performance scenario, have you seen RevOps evolve over time?

Yeah, I mean, I've been in it since the very early days when it was probably started as SalesOps in the early 2000s. I was with a company and we were one of the early adopters of Salesforce. And, you know, I think over the last 25 years it's definitely evolved and I've seen a couple of generational changes happening over those years for sure. Really?

Oh, interesting. I've never heard anyone talk about generational changes before because I think partially because it's such a new industry, but it, that's so interesting. So what was Generation 1 like?

Yeah, I mean, in the early days it was the adoption of Salesforce. There was no HubSpot, there was nobody else. They were pioneers in the CRM space. Gosh, I don't even remember Marketo, you know, marketing automation tools that definitely weren't around. And sales was a very close-knit community. You know, I really date myself here as the old white guy, but salespeople had Rolodexes. And they had contacts and you'd go to a show and you'd get a business card. And that was the gold and, you know, the livelihood of salespeople. So along came this CRM where we now had to tell salespeople, actually, you gotta put all those contacts into a company database and, you know, all hell broke loose, literally, you know, salespeople were saying, no ways, why would I do that? you know, then I give away my prized asset, which is my contacts, which is what you employed me for. And it truly was the gold of sales, you know, because, you know, people would go through the Yellow Pages, which was a big thick telephone book to get telephone numbers of people. And if you had it, you know, in your Rolodex, you were golden. I think that was the early stages of sales ops. It became quote, planning sales comp plans as we know it, but the real management of that CRM and its seismic change to get salespeople to say, okay, hang on, we are gonna start to record an opportunity in a database and track how it flows and goes, and convincing them that that may actually be helpful to them as opposed to just a company mandate.

Yeah, that to me, that is so fascinating because I feel like Salesforce had to sell this to be used by salespeople and the salespeople didn't want to use it. Yeah. How did they, how did they get around that? Was it just forced on them by sales leaders or how did that happen?

It was amazing how quickly they got market share and became known.

Mm-hmm.

You know, they've always been, and this isn't a promotion for Salesforce, but they've always been good with community. And I think they did get to people like me, it wasn't a fully fledged function, but there was always somebody doing sales ops or admin type stuff. And I think they got to that community very quickly, educated them, and everything flew very quickly from there. And I, I just think it was, yeah, a little bit of brute force, but mostly getting to the person that kind of was in the weeds. And I always had a good relationship with my VP of sales. And once you started to do comp plans for them and then, you know, early days of territory planning, you know, which tended to be zip code based in the US in those days, the value started to become kind of a duh moment. You know, it was like, yeah, of course. It took the salespeople a little while longer and I think there was a lot of training involved. I remember traveling around the globe convincing salespeople that this was a good thing. Wow.

That's fascinating.

And I really think coming from more junior person, a little bit of a finance background, but not the VP of sales saying you have to do this. It was an easier way to change and get people on board than just that forced down your throat. VP of sales says you gotta start entering data and helping them understand the why. You know, that's always been my mantra is why. Well, if you haven't got leads, if you haven't got opportunities, if you haven't got food on the table, this is gonna tell us, and then everybody's gonna rally around you from sales, you know, customer success, those types of organizations. We're gonna start putting lead gen programs together for you. That was the why of we're trying to help you not be a police force.

That totally makes sense. Very interesting. So you would call that generation one. Just get everybody onto Salesforce or a CRM. Yeah. Okay. Interesting. So then how did things start to change? How did you move into Generation 2?

Yeah, I think Gen 2, 2A was the emergence of the sales intelligence tools. I think starting to become more scientific with the pipeline in particular and starting to forecast what's gonna close, what isn't. And I think tools like You know, Clary coming in, those types of tools really, really help to connect the bridge between sales and finance to say, hey, we can use this as an accurate way of forecasting what the business is gonna be. Because prior to that, it would be a lot of anecdotes, a very strong VP of sales saying, yeah, well, yeah, I'm convinced this deal's gonna close. And that's where I found my niche was kind of speaking a language between finance and sales. I'd often joke, I said, I can speak finance and I can also speak sales because the CFO and the CRO typically are at loggerheads with a more charismatic personality in sales saying it's gonna close and a CFO saying, you know, show me the data. And I think that kind of scientific evolution of data-based intelligence that moved into financial modeling making forecasting a little bit more scientific and a little less artistic.

That's so interesting. And that's really where you found your sweet spot, was that nexus point between finance and sales.

Yeah.

Yeah. Very interesting.

Yeah. And then sort of 2B was, you know, I think marketing and CS to some extent, customer success has always been a little bit separated from the sort of sales ops machine, which is where most of the effort was put. You know, this is the current pipeline. How are the salespeople doing? Are they closing? You know, what's the productivity of sales, sales, sales? It was always sales. And that to-be became go-to-market where no, and the introduction of revenue operations, which was bringing those 3 groups together and saying as much analysis and analytics and diagnostics that we've done of Understanding the current pipeline, what can we do up funnel with marketing to really understand lead conversion? And are we generating the right type of pipeline and leads as well as the backend of customer success in a B2B environment, SaaS environment where it's all upsell? What's the net retention of those customers and how are we minimizing downsell and churn and, and, and optimizing upsell.

Very interesting. Yes. So I'm part of that to-be generation where I'm calling up the sales leader going, hey, what are your target lists? Because I need to understand where we're going to be putting more focus and emphasis. And the sales leader coming back to me and saying, why do you need the target list? It wasn't that long ago that that separation was very distinct. And I love the way that even in the past few years, things are coming together and we're instead of the sales funnel, we're getting more of a flywheel type of model.

Yeah. And it's not just a forecasting tool. Some of the platforms out there like Gong or Chorus, really getting into the customer intelligence of understanding what the customer's saying, you know, what words are they using? Of course, that's absolutely essential to building your demand gen programs from a marketing perspective. But I see now that in itself evolving much more towards product, getting the product teams, product development incorporated and saying, this is where the product can go based on what our customers are telling us. And I think all of that where we started with field hockey and teamwork, that's bringing that whole team back together and it's all company, you know, it's not just sales and marketing working together. It's not just sales and CS handovers. It truly is all company bringing together revenue. Obviously revenue is mainstream output, but bringing those parts together with a lot of intelligence from customer conversation tools and stuff like that.

That makes sense. So, you know, you've lived and breathed this for years. What is— do you think if people were to lean in on one thing in particular What would you say that people should do?

I think it's customer intelligence and I see that as the next gen. This is where we're going. And with AI in the last year and a half, 2 years, like RevOps, AI can mean everything, you know, lots of things to lots of different people. But I think if we focus on customer intelligence and that's what I did at my last company, you know, we had a big call it a BDR team, but that was more research-driven BDR where we did our territory mapping, territory planning through accounts, and then we did a lot of account intelligence. So before the rep even picked up a phone or tried to get into an account, we would give them a detailed book on all of the aspects of that company that they would need. To help penetrate new business or upsell and, and drive a bigger renewal. That business happened to be fonts, and, and there was a lot of information around font use from the web, from applications. So there was a lot of data to draw on, but we've never been short of data. What we've been short of is the intelligence behind that and what's going on in that company that's going to help the sales rep sell their product into that company. You know, that's where I think the next generation goes. It's far more customer-centric, but it's far more intelligent-based. So you're not just making up cold calls with personalization of Rob Levy's LinkedIn account, but you're actually understanding the company that Rob Levy works for, what their key priorities are. And how you can tailor your product or solution into solving their problems.

That is so well said. And that really is kind of this next generation of becoming customer obsessed.

Yeah.

Could you tell me a little bit more about how this all is evolving around territories? You mentioned that everything used to kind of be zip code based. How, how are people working with territories now with all of this new focus on accounts and intelligence?

Well, I mean, it's one of the things that drew me to Fulcast, to be honest, was the depth of variety, the way you could build territories. You know, I think we got pretty stale with zip code based. It was an easy way to do it. You know, company starts, they do well in New York, they hire a rep, do exceptionally well. So then, oh, we need 3 reps in New York, and then they break New York City into zip codes.

Right.

And that really doesn't speak to your language, the ICP. Who is the customer? Are, are you splitting a, a geographic region where it absolutely makes no sense?

Yeah.

And it all drives back to the Generation 1 sales macho approach of, well, just give a guy a sales territory and he'll be fine. He'll figure it out. No, make it easy for the sales rep, for him or her. And so I think the flexibility of look at your business where you're having successes, it could be account-based, but it could be even more deep than that. It could be very vertical market-based where you go in after and you've had some success in healthcare or as a security company, you've had some success in financial services. We'll double down on that where you've had your successes, go back to your choruses or your gongs, find out what the customer's actually using the product for and build your territories around that intelligence. And the more finite and the sharper the knife you can apply to it, the better the territory is gonna be because then you can do that intelligence. You can provide the rep with everything, arm them with everything they need to go into that account and know you're gonna have much higher success rate because you've got good testimonials from other financial services companies that have bought from you, use cases that where they've used it, it all fits, those pieces fit together. As opposed to just, I give them Illinois because they happen to live in Chicago. And in this day and age, especially since COVID you don't have to be in territory, in geographic territory to be successful. In fact, it's almost become the opposite. I can't remember the last time I heard of a sales rep having to fly in to close a big deal with a CEO flying on a helicopter, like the old days of, I think the Cisco CEO was renowned for that. You know, that doesn't happen anymore. You can close million-dollar deals over the phone. Now. I just think it gives you a lot more flexibility to get really good with understanding your ICP.

I love that. Really appreciate you saying that because obviously that's important to us at Fulcast. And what we think the secret sauce is, is exactly what you said, which is combining the territory policies and management and performance to plan with the customer intelligence so we can get deeper insights and really support the sales team in ways that they've never been ported before. So we're very excited about it. So you're obviously at the top of your game. You have been doing this for a long time and I know it's a grind. So how do you stay at the top of your game? And it could be anything. It could be maybe you meditate or do cold plunges in the morning. Like, what is your secret?

I think I sort of gave it away at the start. I love to get shouted at by coaches on a field hockey court. That does keep me young and it keeps me fit. But I think to stay on top, for me, I've become a bit of a scholar on the tech because I think there's been a huge amount of tech innovation in the last, particularly 5 years. I do think there's a bit of overkill right now. I think there's probably too much out there and there is consolidation going on, but for me to stay on top of what can really help drive and impact sales, marketing, and customer success helps me stay with the game, but it's also fun, especially the AI side. It's just automation, you know, stuff that used to take you or me hours and hours going over those customer lists and understanding them on an Excel sheet. It can be done in minutes. And that's exciting when you can convert the laborious to almost instant and focus on the stuff you really enjoy, which is how do we actually drive business? Isn't that the mantra of RevOps anyway? We get stuck in the CRM, we get stuck adding fields, we get stuck in Excel sheets, and we never get to do or don't spend anywhere near enough time on the strategic important stuff of where we grow in the business. And if you can move to that, that's what keeps me excited and invigorated is the more these tools can help us declutter all the boring stuff. Yeah, that leaves us more time for the exciting stuff, which is growth.

I absolutely love what you said just now. From my perspective, RevOps leaders are the wizards because they have the tactical knowledge, the operational knowledge, and also the strategic knowledge. And that's very hard to find. And I feel like if businesses can fully utilize The RevOps leader in a strategic position, which is now available through these RevOps tools, that's the secret sauce. That is how they're going to elevate their growth in ways that they've, they've never thought possible in an efficient way. So thank you for saying that much more eloquently than I did.

No, I think what you said in an efficient way is that's the key is there's always a thousand things the RevOps team can do. What we've, as RevOps leaders, what we've got to get better at is that prioritization. Work on the stuff that's truly important. I've said it many times and maybe I'm a bit grumpy when I say it, but learn to say no. You can learn to say no in a really nice way, which is like, no, not now. We might consider it later, but you can't just say yes to everything because then you will be in the weeds.

That's absolutely right. Well, thank you so much, Rob, for your time. It is such a pleasure to be able to chat with you and very much appreciate all of your expertise and your insights.

Oh no, thank you, Amy Cook. It's been a pleasure. I really enjoyed it.

Thank you.

Thanks.

Business, yes, that's business.

Business, yes, that's business.