From Sales Rep to CRO: An interview with Cliff Simon

Although we unequivocally disagree with this action, companies dialing back compensation plans because their reps “earned too much” is not uncommon. 

It’s something that Cliff Simon, Chief Revenue Officer at Carabiner Group, experienced first-hand during his early career in sales.

Cliff, who sold wireless and Internet of Things (IoT) services for one of the major wireless carriers, earned six figures a year in 2013 while overperforming against his sales compensation plan. 

That’s when his employer switched that portion of his comp plan to a measly $5,000 quarterly bonus. 

What followed? You guessed it.  An exodus of sales talent — Cliff included. 

As frustrating as it was for Cliff at the time, this move sparked his transition to SaaS and ultimately led him to the startup space, where he remains today as a CRO and supports other startups in advisor and fractional executive roles. 

“I went from a 90,000-person company to 30,000,  3000, 300, 35, and employee No. 3 in 2020 at Carabiner Group, where I now lead our go-to-market function,” Cliff said. “It was this downward progression of finding more responsibility, having a stronger impact on the business strategy, and getting closer to the data.” 

We sat down with Cliff to gain insights into his career transition. The revenue leader shared a bit about his journey from rep to C-Suite and offered advice for others interested in climbing the sales ladder from IC to CRO. 

Check out our Q&A below. 

Q&A

Once you worked at smaller organizations, how did the shift begin from sales toward RevOps?

Cliff: Everywhere I went, the smaller the company, the more I got my hands dirty, whether it was comp plan design, territory design, driving metrics and conversion rates, improving the handoff between sales, implementation, and customer success, or managing the sales and marketing relationship.

Also, I lived in Excel spreadsheets more than any sales rep had the right to.

I didn’t realize all those pieces were the connective tissue within RevOps. They happened to be what I enjoyed the most, in addition to signing contracts, which is always fun.

When did you begin gaining more RevOps responsibilities? 

Cliff: I spent a lot of time between 2016 and 2018 doing what would be considered RevOps. I worked closely with my Salesforce admin team and the architect, conducted quality and assurance tests, and helped debug. I constantly ran through the system and tried to figure out what would happen if I clicked this and then that.

Then I started overssing comp plans and was still running sales. And when my boss went out on extended medical leave in 2018, the responsibility to run everything on the GTM side fell to me. 

What other RevOps-related things were you in charge of while leading a sales team?

Cliff: During this period, we were also going through a Salesforce Classic to Lightning migration, and all sorts of stuff was breaking. My team was small enough to guinea pig it, and I’ve always created documentation. So, as we first went through this process, I built essentially our sales playbook. And without realizing it, I acted as an admin while generating anywhere from 54 to 65% of my team’s number. 

As CRO, what teams do you oversee, and how are you improving as a leader? 

Cliff: I’m responsible for our GTM motions: sales, marketing, customer success, partnerships, and RevOps on the GTM side of the business. I also have a hand in financial planning and analysis. 

As far as learning and improving, you need to become unconsciously competent within areas of your role to perform at a high level. Some come from experience and natural ability. Others require a bit more digging in. I was weakest from a marketing aspect, so I spent the first 18 months at Carabiner meeting with one to two marketing VPs or CMOs weekly to put myself through a make-shift marketing school. 

How has your affinity for data-inspired your path to CRO?

Cliff: I like being data-driven, and as CRO, sitting over the entire business, I won’t be successful if I can’t touch all the data points and understand how the entire customer journey works. I would feel significantly hindered if I couldn’t understand why customers choose us, how we address their problems, and how we deliver recurring impact to them long-term. All of that has to correlate to the customer buyer journey. What is the value that they’re hypothesizing that they will receive from us? How do we get into the weeds and solidify that on a later-stage call?

Then, once onboarded, what’s the time to first impact? How do we continue to drive recurring impact and value to their business so they stay with us long-term?

Taking that together, alongside a desire to change the way people perceive B2B sales and using tools to adapt how we sell, it scratches an itch for me. 

What will it take for CROs to be successful this year?

Cliff: The new breed of CRO will have to be far more data-driven than the person who was just really good at sales. You’ll have to understand the “whys.” 

You’ll have to get good at servicing your existing customers and understand how to drive an upsell and cross-sell motion to improve net dollar retention, gross retention, and net promoter scores. 

Lastly, what advice do you have for reps looking to make it to CRO one day? 

Cliff: Take on the things that your boss wants to get done. Don’t wait until they ask. Show initiative, drive impact and value, and find things that interest you. The other is to do the same with new company initiatives. Grab them by the horns and do your best to help the company achieve those aims.

I like numbers and playing with spreadsheets. And because of that, I naturally desired to go toward a RevOps, data-driven world. 

So if something like that interests you, lean into it. 

Thanks for sharing your thoughts and experiences with us, Cliff!

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