Learn why chief operating officers need hands-on sales experience to succeed. Insights from Checkr's COO on building enterprise teams and scaling operations.
Why Future COOs Need Sales Experience | Lindsey Scrase
Key Insights
- Sales experience builds operational rigor: Direct revenue ownership teaches decision-making discipline and resource allocation that translates across functions
- Enterprise sales differs fundamentally: Selling to Fortune 500 companies requires different tactics, longer cycles, and cross-functional alignment than mid-market sales
- Trust and data drive executive leadership: Combining data-driven decision-making with empathetic, hands-on management accelerates organizational growth
- Decision velocity matters: Clearly defining who owns what (DRI framework) prevents bottlenecks and keeps organizations agile
- Customer connection is non-negotiable: Even as COO, staying close to customer calls and feedback provides intuition that dashboards alone cannot
The Sales-to-COO Pipeline
Lindsey Scrase, COO at Checkr, spent over a decade in revenue-focused roles before transitioning to operations. Her journey illustrates why hands-on sales experience is critical for future chief operating officers.
When executives move from large, established companies to startups, the transition often fails. Scrase succeeded because her background at Google Cloud taught her to build with limited resources and no playbook. At Google, her team had no sales enablement, no revenue operations, and no formal systems—just scrappy, data-driven execution at scale. That mentality transferred directly to Checkr, where she joined to transform a successful mid-market business into an enterprise player.
What made the fit work wasn't generic leadership skills. It was understanding what Checkr's founder Daniel needed: someone laser-focused on multi-segment growth, operationally rigorous, and obsessed with data-driven velocity. Scrase knew exactly what she was selling because she'd lived it.
Building Enterprise Sales from Scratch
The hardest transition in B2B growth is moving from mid-market to enterprise. Deals are larger and target lists smaller, but decision cycles stretch 12+ months. Enterprise buyers rarely switch providers; they evaluate new vendors only every few years, and switching costs—in engineering time, regulatory compliance, and strategic alignment—are immense.
When Checkr decided to enter enterprise, they quickly learned that the playbook for selling to 200-person companies doesn't work for 25,000-person organizations. Enterprise requires entirely different talent: sellers who've navigated complex org charts, built trust with C-suite stakeholders, and managed multi-threaded deal progression.
Scrase's approach was intentional. Rather than assuming mid-market success would translate, she hired a sales leader with proven enterprise scaling experience in gritty environments. She embedded a dedicated product manager directly with the sales team to gather daily customer feedback. She insisted that engineering, product, legal, and HR all commit resources—this wasn't a side project or pilot.
The focus was ruthless. Instead of chasing every enterprise opportunity, Checkr identified specific verticals where they already had strong mid-market traction: staffing, gig economy, retail, hospitality, manufacturing. Those industries needed Checkr's technology and understood its value against entrenched competitors.
The Role of Sales Compensation in Alignment
One of Scrase's biggest operational wins was fixing how Checkr paid its sales team. When she arrived, reps were compensated on bookings—the estimated annual value customers would spend. In reality, Checkr's revenue model was consumptive: customers paid per background check run. This created a massive misalignment. Reps got credit for deals that might never fully activate, inflating expectations and destroying trust.
She redesigned compensation to tie payouts to actual revenue realized, not projected spending. This single change ensured sales incentives matched customer success and company revenue, eliminating the shadow compensation culture where internal arguments over "what should have counted" undermined leadership credibility.
The broader principle: compensation design flows directly from business model. Get it wrong, and your entire organization optimizes for the wrong outcome.
Events Still Work (Yes, in 2026)
Post-COVID, many companies abandoned events as outdated. Checkr doubled down. Why? Enterprise sales is built on trust, and trust requires human connection. A buyer's career is on the line when they recommend a major vendor switch. No email sequence or LinkedIn message replaces the credibility built through in-person connection.
Scrase emphasized that events must deliver genuine value—not generic sponsorships or stadium skyboxes, but curated experiences or thought leadership. Checkr hosts everything from Houston Rodeos to product premieres, always targeting the right buyer personas at the right seniority level. The ROI remains strong because attendees rarely get external context away from daily work pressures, and peer-to-peer connection remains invaluable.
From CRO to COO: The Mental Shift
Becoming COO required Scrase to step outside her core competency. She was exceptionally good at go-to-market; she had to learn to push supply chain improvements, hiring velocity, and cross-functional strategy with the same rigor.
This required explicit trust-building with peer leaders. Scrase and Daniel, Checkr's founder, invested intentional time in one-on-one feedback and relationship development. When Scrase questioned another function's approach, it wasn't empire-building—it was genuine problem-solving on behalf of the company.
She established C-staff cadences: daily 30-minute standup meetings with no rigid agenda, bi-weekly business reviews with the top 20 leaders using a "document-first" culture, and twice-yearly in-person offsites with the top 80 leaders. These rhythms built muscle memory for cross-functional alignment and early problem-catching.
Pushing Decisions Down (and Knowing Which to Keep)
A critical operational principle: executives should only own decisions where their ROI exceeds what someone deeper in the organization could achieve. Everything else should be pushed down.
Scrase and Daniel documented which decisions truly needed CEO involvement: major product roadmap trade-offs, M&A, VP-level hiring, large deals above a threshold, major brand campaigns, and product monetization changes. Everything else gets a DRI (Directly Responsible Individual) assignment and decision authority.
This prevents the common failure mode: decisions naturally flowing upward until executives become bottlenecks. By explicitly asking "where can we push this down?" every quarter, Checkr keeps velocity high and ensures people deep in the org have the autonomy to act.
Staying Close Without Micromanaging
Even with strong delegation, Scrase stays deeply connected to the business. She sits on the sales floor, listens to deal discussions via Slack channels (Checkr has a channel per customer), and regularly participates in customer calls. This isn't surveillance—it's osmosis.
Data dashboards tell you what happened. Customer conversations and team osmosis tell you what's about to happen. Scrase relies heavily on intuition layered over data, and staying close is how intuition stays calibrated.
What Makes a Top-Performing Sales Rep
Across every sales team Scrase has led, the best performers aren't necessarily the most outgoing. Many are introverts who turn it on strategically. What separates elite reps is:
Trust-building: The ability to establish credibility and psychological safety with customers—a gift that becomes a skill through deliberate practice.
Strategic thinking and tenacity: Top reps think like team captains, mapping all moves in advance, rallying resources, and executing relentlessly. They're not improvising deal-to-deal; they're executing a coordinated strategy.
The worst mistake is hiring people who've only ever worked in established market-leading positions where leads came warm and quotas were easy. Those reps rarely succeed in scrappy, outbound-heavy environments where pipeline building matters most.
Strategic Metrics and Ambitious Goals
Checkr tracks roughly ten core metrics instead of hundreds. The framework: start with revenue, then decompose into drivers—new logo acquisition, deal size, upsell and retention (Net Revenue Retention), churn.
For a consumption-based business with strong NRR, there's a subtle trap: hitting annual targets while under-planting new customer seeds. By mid-year, this becomes obvious, but by then momentum is hard to rebuild.
Scrase separates explicit new-logo goals from expansion goals, with different owners for each. This forces clarity on growth sources and prevents the false confidence of "we're winning overall" masking specific weakness.
For quota-based, core financial metrics, the target is a hit within ±5%. For strategic stretch goals, Checkr labels them explicitly as "10x goals"—ambitious bets that require fundamentally rethinking operations, often by leveraging AI. This prevents the demoralizing experience of constantly missing overly aggressive targets while still pushing innovation.
AI as an Operational Multiplier
Checkr has deeply embedded AI across operations, supply chain, customer support, and dispute resolution—eliminating manual work. An entire operations team is building toward a 90%+ AI resolution rate for customer issues using generative AI, not just chatbots.
On the sales side, Checkr built an AI orchestration layer for outbound activities, consolidating 20 different tools into a single agentic interface that personalizes outreach based on real-time signals. Six months in, outbound pipeline as a percentage of total pipeline is growing measurably.
Engineering is generating over 8% of production code with AI. The key learning: avoid building AI for its own sake. Focus on customer-facing impact—like a customer 360 view that automatically triggers support escalations when a customer shows distress signals.
Advice for Future COOs
For leaders aspiring to become COO—especially those without sales backgrounds—Scrase emphasizes: directly own a number. Running revenue teaches you decision-making discipline, resource allocation under constraint, and customer obsession that are foundational to operations.
If you transition from sales leadership to COO, invest intentional time in understanding company financials, RevOps mechanics, and board-level priorities. Many sales leaders stay narrowly focused on quota and miss the broader business picture, which becomes a blocker to COO success.
The combination of sales rigor + operational discipline + genuine care for people is what allows Scrase to lead cross-functionally without ego. She's not building an empire; she's removing obstacles for the company to win.
Conclusion
The path from sales leader to COO works because sales teaches you to own outcomes, make decisions with incomplete information, and build trust under pressure. Those skills transfer directly to operations—but only if you approach the COO role with the same customer obsession and hands-on rigor that made you successful in revenue. The future COOs who will lead exceptional companies are those who earned their stripes in sales first.
Original source: Why future COOs need sales experience | Lindsey Scrase (COO, Checkr)
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