With two decades of mid-market and enterprise sales experience chalked up, Cliff Simon’s move towards revops was fuelled by his enthusiasm for all things GTM. He’s currently CRO for Carabiner Group, offering RevOps-as-a-Service to financial services firms, high-growth technology startups, non-profits and educational institutions.

We caught up with Cliff to get his perspective on current challenges in the revenue industry, what sales people should be doing more of, and how he sees AI changing up the revops game. As you’ll find out, Cliff is big community player and we highly recommend following him on LinkedIn for his latest content contributions!

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1. What was your path to working in revenue operations?

I started with a sales background and have been working in the mid-market enterprise sphere for close to two decades. 

Everywhere I went, as I gained more responsibility as either a manager, director, whatever, I started having to do more revops-y things: territory planning, comp design, running comp calculations, and then helping to manage the handoff processes between departments, building those processes, enabling them, executing them, iterating on them. Tying together sales, marketing, implementation, customer success.

So I got to see a lot of the nitty gritty and got pulled into doing all kinds of QA work in Salesforce; all the different things that end up happening as you're at a myriad of startups trying to grow. 

Then I had a really interesting opportunity come up to hop in with Carabiner in its super early days, and I’ve love it so far!

2. From your experience, how do sellers typically view revops? What advice would you give salespeople to be smarter in their approach to revenue operations?

I think salespeople tend to get a little too caught up - let's call it tunnel vision - around their specific role and tasks. And it's like, “oh man, I'm killing it. I'm bringing all these deals in,” or whatever that feeling might be. 

They want to go and win, but the way in which they may be winning may not be best for the company at heart; those deals that they're bringing in might not be the types of customers that actually renew.

But something I’ve noticed it that many of the best salespeople all tend to go off playbook quite a bit. They go after the deals that everyone else thinks are lost, or they may adopt some additional processes that they see as necessary that others don't, and it causes them to do a little bit more experimentation. 

There's definitely an opportunity there to learn from those folks, but they all have to be mindful of how the things that they're doing play into the overall business.

3. As a CRO, how do you encourage marketing, sales, and customer success to collaborate effectively?

It's a team sport. Revenue is a team sport. And I'm in a bootstrap business. So for us, it all has to work together. 

We think deeply about things like gross margin and C-level buy-in - it’s really important you get all that to click. We all have to be focused on educating and attracting the people that are in market, and we need to be able to do that in an effective way, get them through their buying journey, and make sure that the way that we're communicating with them aligns with the way that they are trying to purchase from us.

And then on the back end, we have to make sure that we're delivering the appropriate amount of impact. We've promised them something, so we have to be good to that promise and do what we said we're going to do. I think if you do those things, you're going to set yourself up for having the best chance of success.

4. What advice do you have for others building revops in a bootstrapped environment?

Keep things very vanilla. I learned you have to make sure that you’re not over-engineering things so that you don't have to unwind a whole bunch of stuff later. I definitely try to take my own advice! 

We've kept our system simple while capturing all the data points that we thought we may need five, six, seven years down the line. That’s another thing I’d recommend: collecting as much of the appropriate metadata early on so that you can have more historical data to look back on it and work through. 

5. You’ve touched on how sellers get tunnel vision and foget about the bigger picture. What other common misconceptions to you run into when it comes to revops?

A common one is that every revops person is the same. Or that an admin is enough or that they're gonna be able to figure everything out. Everything's figureout-able, but the list of things that revops is asked to do on a regular basis usually far outpaces the ability of the people that are in seat to do those things!

But then, I think that’s something that almost comes by design. Technically speaking, revops is not a revenue generating function; it's a cost center. But when utilized appropriately, it can be an accelerator for growth.

It's one of those growth levers that you get to pull because your data is in order and you're able to give the right information to the right people at the right time. All of that's well and good and it does work, but it takes intentionality and it takes consistency. 

Too many companies are willing to put in some time and effort for a small period of time, but not willing to see it all the way through. They have stakeholders that are influencing things and expecting quick results, so there's a level of pressure there to make things happen fast. Sometimes taking the long view isn’t prioritized, and I can understand that.

6. You’ve spoken recently about seeing a rise of community-led growth in 2024. Would you elaborate a little more on that and how teams should look to build that muscle?

To be honest it started even pre-pandemic; being successful meant going to conferences and becoming a thought leader in the places where your customers were, helping them become educated. 

Post-pandemic, I think that became even more important as everyone was craving community and human connection. Now we've all sort of lived in these online communities for a bit and people are excited to get back in person networking. What I think is difficult for many is that they expect to show up and see instant success, or “I'm going to go to this place or that place and all of a sudden the deals are going to fall out of the sky,” and that's not how it works.

Being a salesperson, selling for a company, growing your career - it’s all a long game. It's those long term relationships that make a difference because they're your advocates when you're not there.

Our friends over at SalesIntel.io are running a new series, B2B Pipeline Pioneers, that touches on this; at the end they always ask, “you've got 100 pennies, where are you putting your 100 pennies in these different go to market motions?” It’s been really cool to see that the majority of the folks that are considered to be these pioneers in go to market are putting their time, money, and effort into things like community, events and partnerships.

Whereas the old playbook was marketing spend to drive inbound leads or spending a ton of money on SDRs to do an outbound campaign. Those things don't always work in the way in which they used to anymore. There's too much noise. 

But the funny thing is like, we're all just discovering this right inside of tech. Enterprise has been doing in-person events for decades, right? Everything becomes cyclical.

7. From your experience of heading up RevOps teams, are there any specific traits you look for in RevOps hires or that you value in your team?

Curiosity and adaptability are really important; just because something's been done one way before and it's worked that way before doesn't mean it's going to work that way again this time. There's a good likelihood that it could, but you need to understand all the variabilities that exist. 

And I think that's like one of the big difficulties of like revops. People expect, “oh, I bring in this person who's VP of revops at such and such a company. They know how to build this thing.” Maybe they do, but maybe they weren't the person that actually built it in the first place and they were brought in to manage it.

You want people with skills that are going to complement the team you already have in place, both from a revops perspective, but also within the executive leadership team, being able to see problems that you may not be able to.

8. What's your take on AI? Are you using it and how do you see it influencing revops?

We use it in a variety of ways. Obviously, the whole content generation is the low-hanging fruit. We also have some tools for forecasting to help figure out how much pipeline we're going to generate before the quarters even start. 

I don't see AI as a people killer. I think it's going to allow those of us out there who are looking to work smarter to do so. And it's going to eliminate the jobs that shouldn't exist in the first place - no one should be an SDR! 

Let's find better ways to engage with potential buyers than just spamming the hell out of them on email and phone. I want LinkedIn to be fun again!

9. So what are the dangers you see in revenue teams becoming overly reliant on AI?

Take email writing; I think as more people start using tools like Lavender, the overall bar of email is going to be higher, which means over time, our minds are going to learn to sort of filter out the things that we don't think are valuable. And the bar for what's going to be valuable is going to have to get that much better every time. Because we can't keep going through 200, 300 emails a day!

So AI can feed into the digital noise, but that’s going to keep pushing us back to craving that face-to-face human connection.

10. Finally, how would you describe revops to a five-year-old?

I would tell my four-year-old son that revops is sort of that connective tissue. We do woodworking together, so I would tell him that revops is the screws and the dowels and the nuts and bolts that sort of hold all these different pieces together. 

For instance, we're building a bunch of cabinets right now; we take the time to carefully measure them and cut them so that everything is the right size, and then we have to hold it all together. And then ultimately you still need someone with the strategy to design it, architect it, and then you need a team to execute and put it together.

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Be sure to follow Cliff on LinkedIn for more revops insights!

‍If you're looking for more revops inspiration, check out our list of 20 must-follow revops leaders.