RevOps Squared
Ray brought three decades of experience in subscription software to the founding of RevOps Squared. With two CEO tenures, five exits (three strategic, two private equity, and one IPO), and multiple leadership roles across marketing, sales, services, and customer success, he had accumulated what he calls "a lot of scars of what I did wrong." The insight was simple but powerful: existing SaaS benchmarks were too generic. A $5 million ARR company with a $25k ACV selling to enterprises needs different metric targets than a $5M company selling $1k seats to SMBs, yet all were being measured against the same standards. Ray created RevOps Squared to bridge this gap—using external benchmarks coupled with internal metrics to drive better decision-making.
Ray developed a comprehensive SaaS performance metrics framework centered on five enterprise value pillars: capital efficiency, operational efficiency, customer acquisition, customer retention, and customer expansion. He identified six core metrics that matter most: Rule of 40, CAC payback period, CAC ratio (blended, new, and expansion variants), gross dollar retention, net dollar retention, and CLTV to CAC. Each metric was segmented by business attributes—ACV, ARR size, pricing model (subscription vs. usage-based vs. hybrid)—rather than lumped into broad categories. The platform also included benchmarks calculated from actual company data, with the latest benchmarks published every six months to stay current with market conditions.
Ray launched the product through speaking engagements, including a keynote at SaaSOpen.com, a high-bar conference with over 100 speakers from SaaS companies. This positioning as a thought leader on metrics and enterprise value became the primary customer acquisition channel. He also directed users to RevOpsSquare.com and emphasized the interactive portal where companies could see their metrics against cohorts.
The segmentation by company profile proved to be the core differentiator. By breaking down benchmarks by ACV (1-5k, 5-25k, 25-100k, 100k+), revenue stage (5M, 10M, 15M+), and pricing model, Ray showed founders why their CAC payback might be 22 months (enterprise) versus 12 months (SMB)—and why that's okay. He also introduced the CAC ratio metric (especially expansion CAC ratio at 69 cents median) to show founders they should invest more in upsell and cross-sell motions. The correlation analysis was striking: Rule of 40 jumped from #5 to #1 as a predictor of enterprise value in 2022-2023, with an R-squared of 0.44, while revenue growth remained close behind at 0.38. This real-time data shifted how investors and founders thought about growth-at-all-costs versus balanced growth with profitability.
RevOps Squared had just kicked off its industry's largest benchmarking program in partnership with 12 companies including Sage, TAC, Maxio, and SaaS Optics. Participation was 100% anonymous, and participating companies received free access to the interactive portal to benchmark against cohorts. The 2023 benchmarking cycle was underway, with updated benchmarks planned for publication in late April to reflect Q4 2022 and Q1 2023 trends. Ray noted that CAC payback period had already decreased about 15% in the first two months of 2023 due to reduced sales and marketing spending, though the sample size was still too small to confirm a trend.
- •Ray solved a real problem he experienced across five exits by recognizing that generic benchmarks fail founders because a $5M company with $25k ACV operates under completely different constraints than one with $1k ACV, making his segmented approach immediately valuable to a broad audience.
- •The framework's predictive power—Rule of 40 showing R-squared of 0.44 as an enterprise value predictor and the discovery that expansion CAC ratio should drive investment strategy—gave founders actionable, data-backed insights rather than vanity metrics, justifying their adoption of the platform.
- •Positioning himself as a thought leader through high-bar speaking engagements like SaaSOpen.com keynotes created inbound demand from founders and operators who already trusted his credibility, bypassing the need for traditional sales and marketing spend.
- •Publishing benchmarks every six months with real company data kept the insights current and relevant, preventing the platform from becoming stale while continuously attracting new cohorts of users wanting the latest market standards.
- 1.If you have deep domain expertise from multiple exits or leadership roles, identify a specific problem where existing generic solutions fail a material segment of your target market, then build segmentation logic (by company size, business model, or ACV tier) that makes your solution meaningfully different.
- 2.Develop a core framework of 4–6 metrics that directly correlate to enterprise value or business outcomes, then back each recommendation with correlation analysis or predictive modeling to give users data-driven confidence in your guidance.
- 3.Establish yourself as a credible thought leader by speaking at high-quality, curated conferences and industry events where your target audience congregates, and always direct attendees to an interactive tool or portal they can use immediately to see their own metrics.
- 4.Commit to a regular update cadence (e.g., every six months) of benchmarks or insights based on actual customer or market data, and make this refresh cycle visible to users so they view your platform as a living resource rather than a static tool.
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