Talking RevOps Strategy for Effective Sales Comp with Cliff Simon
While executives obsess over territories, tools, and training, there's a fundamental crisis happening right under their noses.
Less than 40% of salespeople hit quota.
Meanwhile, 17% of sellers drive 84% of the revenue.
Let those numbers sink in for a moment.
Sales compensation plans are driving behaviors that benefit individual reps but destroy company outcomes.
Cliff Simon knows this crisis intimately.
As CRO of Carabiner Group and a HubSpot-recognized 2024 Modern Sales Leader, he's seen compensation dysfunction destroy teams from both sides of the equation.
"Comp is meant to drive the behaviors and outcomes that you want to see," Simon explains.
This isn't just a sales problem. It's a RevOps crisis that demands immediate attention.
The Personal Cost of Broken Compensation
Simon experienced compensation dysfunction firsthand early in his career at a Fortune 20 company.
"I was blowing it out and they turned something that was making me six figures a year in commission into a $5,000 quarterly bonus," he recalls. "It's incredibly deflating, and you saw a mass exodus of talent."
This scenario repeats across thousands of organizations daily.
Sales teams get incentivized to chase deals that look impressive on individual scorecards but terrible for business health.
Reps prioritize existing customers over new logos.
They focus on short-term wins instead of sustainable growth. They bring in customers who churn within 12 months.
"You get really interesting comp plans where salespeople are being incentivized to do things that are really good for them but not great for the company," Simon notes.
The math is brutal.
When less than 40% of reps hit quota while a tiny minority drives most revenue, your compensation structure is fundamentally broken.
Why RevOps Must Own Compensation Strategy
RevOps teams sit at the perfect intersection to solve this crisis.
"RevOps ends up tying back to the overall go-to-market strategy," Simon explains.
This strategic positioning gives RevOps teams unique advantages over traditional HR or finance functions.
They have access to the complete customer data.
They understand the entire revenue journey.
They can model different scenarios before implementation.
They see where compensation plans fail and where targeted incentives can drive specific outcomes.
"RevOps is typically at the tip of the spear," Simon emphasizes.
Organizations with formal RevOps functions see 36% more revenue growth and 28% higher profitability compared to companies without this strategic alignment. The ROI case is clear.
Yet many RevOps teams still operate without dedicated budgets, forcing them to prove value while solving fundamental business problems.
The AI Revolution in Compensation Design
Simon's team leverages AI strategically to solve compensation challenges that manual processes can't handle.
"We're big Gong users, recording all customer interactions and training sessions," he shares. "It helps drive enablement, documentation, and ensures we don't miss things while holding both ourselves and customers accountable to timelines."
Beyond conversation intelligence, his team uses emerging tools like Sweep.io for automated documentation and process mapping.
"We don't have to manually create all those flows in Miro or Lucid Chart anymore, saving tons of time."
The productivity gains are measurable.
Teams using AI tools report shorter deal cycles, larger average deal sizes, and higher win rates. They save an average of 12 hours per week on administrative tasks.
However, adoption remains uneven.
While 45% of sales professionals use AI weekly, the gap between early adopters and laggards is widening rapidly.
Organizations that lag in AI adoption for RevOps will lose credibility as data-driven decision makers.
The Five Fatal Compensation Mistakes RevOps Teams Make
Despite having access to better data and tools than ever before, Simon identifies critical errors that plague compensation planning:
1. Formula Fixation Without Foundation
"They don't think it through all the way. They just do their normal 50/50, slap on 10% or 6-10% accelerator, but never actually think about what that means."
The math might look clean on spreadsheets, but the underlying assumptions often crumble under scrutiny.
RevOps teams must ask harder questions.
Is the quota even attainable given market conditions?
Does the total addressable market support these revenue targets?
Have you provided adequate enablement for teams to succeed?
2. Ignoring Cohorted Customer Data
Simon tracks "cohorted data around customers actually coming through the door.”
Most organizations obsess over acquisition metrics while ignoring whether compensation drives quality customer acquisition.
If your sales team consistently brings in customers who churn within 12 months, your compensation plan is broken regardless of how many deals close. The lifetime value math doesn't work.
3. Underestimating Enablement Requirements
When less than 40% of reps hit quota, the enablement gap becomes massive.
You cannot compensate your way out of poor training, unclear success patterns, and inadequate support systems. Compensation amplifies existing capabilities rather than creating them.
4. Missing the Business Context
Technical competence without business understanding leads to compensation plans that optimize for metrics instead of outcomes.
Understanding unit economics, customer lifetime value, market dynamics, and financial modeling becomes essential for strategic compensation design.
5. Failing to Experiment with SPIFFs
Simon emphasizes using special performance incentive funds for experimentation in "new opening markets or new product lines" rather than treating compensation as static.
Smart RevOps teams use targeted incentives to test assumptions and drive specific behaviors. They gather data before making permanent compensation changes.
This experimental approach reduces risk while providing insights that inform broader strategy decisions.
Building the Business Acumen RevOps Needs
The technical skills that brought most RevOps professionals into the field won't drive their next-level success.
Simon recommends specific development paths:
"Join a community like Pavilion where you get access to really smart people and courses. Winning by Design's YouTube channel has hours of videos with strong content. I made most of my team take their actual courses."
The business acumen gap represents both challenge and opportunity.
RevOps professionals who understand financial modeling, customer economics, and market dynamics become invaluable strategic partners rather than tactical executors.
This evolution aligns with broader market trends.
As AI handles more tactical work, human professionals must focus on strategic thinking, relationship building, and complex problem-solving that machines cannot replicate.
The Compensation Tracking Framework That Works
Rather than vanity metrics, Simon focuses on leading indicators that predict long-term success:
Customer Quality Metrics:
- Ideal customer profile alignment rates track whether sales teams target the right prospects.
- Customer renewal rates by acquisition source reveal which compensation strategies drive quality customers.
- Time-to-value measurements show how quickly new customers achieve success.
- Expansion revenue from new customers indicates long-term relationship potential.
Sales Performance Indicators:
- Deal quality scores beyond just size measure strategic value and fit.
- Sales cycle efficiency by rep and territory identifies best practices and problem areas.
- Pipeline conversion rates at each stage reveal where compensation incentives create bottlenecks.
- Customer satisfaction scores tied to rep performance ensure quality doesn't suffer for quantity.
Compensation Effectiveness Measures:
- Correlation between incentive payouts and desired outcomes validates plan design.
- Rep retention rates by compensation tier show whether plans attract and keep talent.
- Goal achievement distribution across the team identifies systemic issues versus individual performance gaps.
- ROI on compensation spend versus business results measures true effectiveness.
"It's a longer-tail exercise that takes time to analyze properly," Simon acknowledges.
"But those indicators tell you whether you're incentivizing teams to bring in the right types of customers."
Why RevOps Professionals Must Act Now
The window for RevOps teams to establish themselves as strategic compensation architects is narrowing rapidly.
Three converging forces make immediate action critical:
The AI Disruption Reality: While AI adoption accelerates, the productivity gap between early adopters and laggards becomes insurmountable. RevOps teams that don't leverage AI for compensation analysis and performance prediction will lose credibility as data-driven decision makers.
The Talent Crisis Acceleration: With high sales turnover rates driven largely by compensation dissatisfaction, the cost of inaction compounds daily. Every quarter RevOps teams delay compensation optimization, they lose high-performers while retaining underperformers.
The Strategic Positioning Opportunity: As traditional HR and finance functions struggle with compensation complexity, RevOps teams have a unique window to claim ownership of this strategic lever. The organizations that act first will establish competitive advantages that are difficult to replicate.
The question isn't whether RevOps should own compensation strategy.
It's whether your team will seize this opportunity before your competitors do.
The Future Belongs to Strategic RevOps
Simon's insights reveal what's possible when RevOps professionals combine technical excellence with business acumen and strategic thinking.
They transform from order-takers to revenue architects by mastering the intersection of data, technology, and human performance.
The companies winning this challenge share common characteristics:
- RevOps teams develop both technical skills and business understanding.
- Compensation plans focus on customer outcomes rather than just sales activities.
- AI-powered insights drive continuous optimization rather than annual planning cycles.
- Strong enablement programs support quota achievement instead of hoping for individual heroics.
- Data-driven experimentation replaces assumption-based planning.
Watch the Full Conversation
Want to dive deeper into Cliff Simon's insights on RevOps and sales compensation strategy?
Watch our complete interview where he shares additional perspectives on AI adoption, enablement frameworks, and the evolving role of RevOps professionals in modern organizations.
In the full conversation, you'll discover:
- How to evaluate your current compensation structure against market realities
- Specific AI tools and implementation strategies that drive measurable results
- Advanced frameworks for building business acumen within RevOps teams
- Real-world examples of compensation experiments that transformed team performance
Taking Action: Your Strategic Next Steps
The data is clear. Traditional approaches to sales compensation are failing at unprecedented rates.
The solution requires RevOps teams to step into strategic leadership roles, armed with better data, clearer business understanding, and technology that amplifies human insight.
Immediate Actions:
- Audit your current compensation plan against actual customer outcomes rather than just sales metrics. Focus on retention, expansion, and lifetime value rather than just acquisition numbers.
- Invest in business acumen development for your RevOps team through communities and structured learning. Technical skills alone won't drive strategic influence.
- Implement AI tools for conversation intelligence and process documentation. Start with proven platforms that deliver measurable productivity gains.
- Design experiments using targeted incentives to test new approaches before making permanent changes. Use SPIFFs to gather data and validate assumptions.
- Track cohorted customer data to understand the long-term impact of sales incentives. Measure what matters for business outcomes, not just individual performance.
The organizations that master this intersection of RevOps strategy and compensation design will build sustainable competitive advantages.
Those that don't will continue watching their best talent walk out the door while their sales teams miss quota year after year.
Ready to Transform Your RevOps Strategy?
Leaders like Cliff Simon demonstrate what's possible when RevOps professionals become strategic architects rather than tactical executors.
At Visdum, we're building a sales compensation management platform that empowers RevOps teams to make this transformation.
Our tools help you analyze compensation effectiveness, track cohorted customer data, and design experiments that drive real business outcomes.
Whether you're struggling with quota attainment, sales turnover, or misaligned incentives, the solution starts with treating compensation as the strategic lever it truly is.
Connect with industry leaders, access actionable insights, and discover how RevOps professionals are solving the compensation crisis at organizations just like yours.
Explore how Visdum can transform your RevOps strategy and drive measurable revenue growth.
.avif)
