In a recent YouTube interview hosted by Monetizely, Cliff Simon, Chief Revenue Officer of Carabiner Group, shared valuable insights on building a successful RevOps-as-a-Service business. The conversation explored how Carabiner Group grew from a bootstrapped startup to a seven-figure acquisition in just three and a half years, landing six-figure deals with one-call closes, and how they're adapting to the AI revolution.
From Fortune 20 to Startup: Cliff's Journey to Carabiner Group
Cliff Simon joined Carabiner Group as the third hire and first executive approximately three months after the company's inception. With nearly two decades of experience in go-to-market functions, Cliff was attracted to smaller companies where he could see the direct impact of his work:
"I started my career at a Fortune 20, right? And kept going downstream to find access to more strategic thought process and decision-making and love the smaller companies because you can actually see the impact that you have with the work that you're doing day-to-day," he explained.
Originally brought on as a fractional VP of Sales to build out an SDR team, Cliff's role quickly evolved. Within two months, the SDR strategy was scrapped in favor of a direct full-cycle sales approach.
The Original Business Model: Leading with Value
Carabiner's initial thesis focused on providing US-based, high-quality Salesforce admin resources that clients could retain long-term. Their go-to-market approach was refreshingly unconventional for a services business:
"The way that we sold most of our business was through cold LinkedIn outreach," Cliff revealed. But there was a key difference in their approach: "Always with a hook… not just, 'Hey, I saw you do this.' It was, 'Hey, we know this about businesses like yours. We've done this type of transformation work before. Is this something your business might be interested in looking at?'"
What's particularly fascinating is that they would recommend products they didn't even sell. Cliff notes: "We're not selling that product, but we think that product could be really beneficial for you." This value-first approach led to remarkable results: "We were landing six-figure contracts on one-call closes in the financial services space."
The Pivot to SaaS Clients and RevOps-as-a-Service
With Cliff's SaaS background, the company quickly expanded beyond financial services to solve similar problems for SaaS companies.
"The first really ones to come out there as the fractional RevOps resource at Series B, Series C," Cliff explained. "It's really hard to get all the right pieces because I don't need a CPQ person all time. I need that CPQ person for an implementation and then maybe I need them five hours a week."
This insight led to the development of their RevOps-as-a-Service model. The realization came after a challenging experience with a cyber firm customer:
"We were going to help them with Salesforce but all the problems that we needed to fix first were in HubSpot," Cliff recalled. After outsourcing to a HubSpot agency that underperformed, he decided: "Never again. We have to own all of this end to end because we need to make sure that the client experience and the output of the product always meets the expectation."
Shortly after, Carabiner trademarked "RevOps-as-a-Service" in mid-2021, establishing their ownership of that market segment.
Building Pipeline Through Community Engagement
As a bootstrapped company, Carabiner couldn't afford traditional marketing channels. Instead, Cliff focused on community-based lead generation:
"Being a bootstrapped company, we had no revenues to go and spend on SEO, paid. So, how do you go about actually driving revenue?" he asked rhetorically.
His approach was to engage directly with potential clients where they sought answers:
"In my previous lives, it was always going to the places where your buyers went for their answers. Usually, it was trade shows, conferences. If your company didn't pay for you to go there, you showed up in the restaurant or the bar and looked for name tags."
During the pandemic, these communities shifted online:
"In the pandemic, a lot of that shifted to online communities, Slack rooms, chat rooms. So, we started living in those places," he shared. Cliff emphasized the importance of adding value rather than selling: "Showing up, asking good questions or being able to give thoughtful insights to the questions that others have and doing so in a way that's not salesy."
The W2 Model and Long-Term Retainers
Carabiner's operating model was built on W2 employees rather than contractors:
"Originally our thesis was US-based resources, W2 not 1099, and we carried that pretty heavily until maybe 6 months before the acquisition," Cliff explained.
This approach, combined with their value proposition, enabled them to secure lengthy retainers:
"All of our original customers were year-long retainers in the SaaS space," with some nonprofit customers on "three, four-year retainers, five-year retainers in some cases."
When asked how they achieved such commitment from clients, Cliff emphasized the importance of trust and transparent problem-solving:
"I think the brand helped and we had shown people that we could. So there's a lot of trust. I'm a huge believer in the fact that you only get to build a reputation once and it takes years to do that. You destroy in seconds."
The Impact of AI on RevOps
The conversation shifted to how AI is transforming RevOps. Cliff highlighted increased expectations placed on RevOps teams:
"The biggest change is just how much RevOps is being asked to know. You still have your day job, but it feels like every other department expects RevOps to be an AI genius, a prompt engineer to have their finger on the pulse of what's going on inside of the ecosystem. And I think that's really unrealistic."
For Carabiner, AI has become a force multiplier:
"We've got really smart people that we've spent a lot of time vetting and training and they've gotten to see so much. How can we make sure that we're using technology to leverage the most with our team?"
One standout use case is documentation, which has traditionally been a weak point for many organizations:
"Most teams fail at that, right? And you've got RevOps people that are really transient. They're in and out. Having a tool that can actually do all the documentation for you, what's been built, why it was built, I think that's really valuable."
The New Services Business Opportunity
Looking ahead, Cliff believes AI creates unique opportunities for services businesses:
"If you're starting fresh now, just like in software, you have that innovator's dilemma. You don't have to unlearn bad habits and you can build it in from the ground up."
When asked if AI could enable services businesses to achieve SaaS-level margins, Cliff was optimistic:
"Can I create the type of company using AI with really smart resources in this day and age and drive SaaS level margin because of AI? I think the answer is yes. I wouldn't be surprised if we start seeing it within the next year or so."
The Future of SaaS and Micro-Niches
For SaaS companies concerned about AI commoditizing their offerings, Cliff suggests focusing on highly specialized niches:
"I think the future is finding a very niche market, 100 to maybe a thousand people in your TAM. And building a product that is so integral to them doing their job, they never leave. And you go and rinse and repeat. And you do that two, three, four, five, 10 times with a small team of two or three people."
This approach aligns with emerging trends among younger founders who prioritize lifestyle and impact alongside business success:
"If they can build something that sort of checks a box for them and lets them live the lifestyle that they want to. You can build a couple companies like that and clear quarter million plus a year. That's a great living for most people."
Lessons for Services Businesses
For services companies looking to replicate Carabiner's success, Cliff's journey offers several key takeaways:
- Lead with value, not with selling
- Develop deep expertise in your clients' problems
- Be willing to own the entire solution end-to-end
- Engage authentically in communities where your buyers seek answers
- Build trust through consistent delivery and transparent communication
- Leverage AI as a force multiplier for your team, not a replacement
- Consider how changing market conditions affect your staffing model
As Carabiner Group continues to evolve following their acquisition by SBI a year ago, Cliff remains focused on solving the full spectrum of challenges facing the office of the CRO, now with even greater resources and reach.