Enterprise Monetization Podcast – Episode 22

Host: Sandeep Jain
Guest: Cliff Simon (CRO, Carabiner Group)

Sandeep Jain: Welcome to the 22nd episode of the Enterprise Monetization Podcast. I'm your host, Sandeep Jain. In this podcast, we invite thought leaders from the monetization space—CPQ, billing, and usage billing—so you can learn about challenges, opportunities, and best practices in enterprise monetization.

Today, I’m thrilled to have Cliff Simon with us. Cliff has extensive experience in revenue operations and sales. He is currently the CRO of Carabiner Group, part of the SPI growth firm that offers RevOps as a service. He is also actively involved in RevOps communities like RevOps Co-op, Pavilion, and GTM Fund.

Cliff, welcome to the show!

Cliff Simon: Thanks for having me, Sandeep. Really appreciate it.

Sandeep Jain: Before we dive into the complexities of quote-to-cash, would you like to share a fun fact about yourself?

Cliff Simon: Sure! Since I spend so much time in strategic thinking and ideation, I enjoy woodworking. I believe if you use your mind all day, you should balance it by doing something with your hands. Right now, I’m working on a large piece made of black walnut—a hall tree with drawers for my family.

Sandeep Jain: That sounds great! Is this a hobby, or do you sell your work?

Cliff Simon: Just a hobby. I’m not into making and selling charcuterie boards on Facebook Marketplace. But this current project has been going on for a year and a half—my wife is eager for me to finish it!

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Background & Carabiner Group

Sandeep Jain: Cliff, you have a deep background in sales and revenue operations. Can you share a quick summary for our listeners?

Cliff Simon: Absolutely. I’ve been in the go-to-market space for about two decades. I started in a Fortune 20 company and learned how departments like finance, legal, and implementation interact. Over time, I moved into progressively smaller companies—90,000 employees, then 30,000, then 3,000, and so on. At Carabiner, I was the third employee and the first executive hire.

As I moved into smaller organizations, I took on more strategic leadership and operational responsibilities, aligning sales, customer success, and marketing.

Sandeep Jain: Tell us more about Carabiner Group. What does your company do?

Cliff Simon: Carabiner Group is part of SBI Growth, and we help CROs become more effective by providing RevOps as a service. We focus on aligning ICP strategy with customer journeys, developing robust processes, and implementing the right technology to enable go-to-market success. We currently support hundreds of companies.

Sandeep Jain: Do you specialize in any particular types of businesses?

Cliff Simon: Most of our clients are B2B, though we do work with some B2C and B2B2C companies. Our focus areas include technology, media, telecom, large national nonprofits, financial services, healthcare, life sciences, and manufacturing.

Sandeep Jain: And what about company size?

Cliff Simon: We work with companies of all sizes—from $1M ARR startups to $28B public enterprises. Our sweet spot tends to be companies in the $25M–$75M and $350M–$3B ranges.

Challenges in Lead-to-Cash

Sandeep Jain: Having worked with companies across their lifecycle, what are the top three challenges you see in lead-to-cash?

Cliff Simon: Surprisingly, the same issues appear across company sizes:

1. Lack of Internal Alignment – Many companies struggle with inconsistent definitions for key metrics like ARR, discounting rules, and product structures. Without clear definitions, execution becomes chaotic.
2. Misaligned Go-to-Market Motions – Companies often apply the same sales playbook across SMB, mid-market, and enterprise segments, despite differing customer needs.
3. Overloaded Tech Stacks – Many businesses accumulate redundant tools without a clear strategy, leading to inefficiencies. While CFOs have cut back on excess spending, many companies are now reevaluating their technology choices.

Sandeep Jain: That makes sense. Companies must define their metrics clearly, tailor their sales strategies, and optimize their tech stacks.

Self-Serve, Usage-Based Billing & PLG Challenges

Sandeep Jain: Many CROs and CFOs are prioritizing self-serve and usage-based billing. Some struggle with where to store thousands of PLG customers in their CRM, while others find it difficult to manage self-service and sales-led pricing within the same quoting system. What’s your take?

Cliff Simon: Most CRMs like Salesforce and HubSpot were designed for sales-led motions, not PLG or consumption-based pricing. Businesses must think strategically about their architecture. For example, a customer of ours faced a challenge with Stripe accounts—they had separate accounts for PLG and SLG motions, making reconciliation difficult.

Additionally, revenue reporting for usage-based models is tricky. Some companies only review ARR on a quarterly basis, which doesn’t align with fluctuating usage patterns. This can create misleading financial reports for investors.

Future of CPQ & Revenue Architecture

Sandeep Jain: How should companies structure their CPQ and billing systems to support different revenue motions?

Cliff Simon: Ideally, a single system should handle all motions, but that’s rarely the case. Many companies have patched together systems designed for different models, creating inefficiencies.

More businesses are shifting toward value-based pricing. Companies like Zapier have operated successfully with a usage-driven model, and we’re seeing others move in that direction. AI and automation will accelerate this shift.

Sandeep Jain: What advice would you give to vendors building RevOps solutions?

Cliff Simon: Focus on simple, intuitive UX/UI and ease of implementation. Salesforce CPQ, for example, is powerful but cumbersome—many businesses struggle with its complexity. The future belongs to solutions that enable self-serve configuration without requiring extensive consulting support.

Final Thoughts

Sandeep Jain: Cliff, this has been an insightful conversation. Before we wrap up, can you recommend a book, podcast, or resource that has influenced you?

Cliff Simon: I’m more of a conversational learner, but one book I read and enjoyed was The One Thing. It emphasizes focusing on what truly matters instead of multitasking.

Sandeep Jain: Great recommendation! Cliff, thanks for joining us today. This has been a fantastic discussion.

Cliff Simon: My pleasure. Thanks for having me!

End of transcript.

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