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First Round Capital

Why future COOs need sales experience | Lindsey Scrase (COO, Checkr)

In the latest episode of Executive Function, Brett sits down with Lindsey Scrase, COO of Checkr.

Brett BersonhostLindsey Scraseguest

Jul 30, 20261h 8mWatch on YouTube ↗

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.

CHAPTERS

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Chapter summaries

Adapting from big-company operator to startup executive at Checkr
Brett Berson asks why many big-company executives struggle in startups, and Lindsey Scrase explains why her transition worked. She attributes it to personal comfort with new contexts, relevant prior experience building scrappy go-to-market systems, and strong fit between what Checkr needed and what she offered as CRO.
- •Lindsey says startup transitions often fail, and frames her success as a mix of personal traits, prior experience, and company fit
- •She describes enjoying new contexts and learning from first principles rather than imposing a fixed playbook
- •She points to her time in Google Cloud as scrappy, resource-constrained building at a scale similar to Checkr at the time
- •She explains Checkr’s CEO wanted a data-driven, operational CRO to scale multi-segment, high-velocity sales
- •She emphasizes vetting mutual expectations in the interview process to ensure fit
Competing against an incumbent: humility, focus, and company-wide commitment
The conversation shifts to strategy when there’s already a category leader. Lindsey explains the need to understand gaps versus incumbents, pick focused verticals where you can win, and ensure the entire company commits to the investment—especially when pushing into enterprise.
- •Lindsey says challengers need humility to recognize where they’re behind incumbents
- •She notes underinvestment in marketing and go-to-market is a common early mistake when challenging leaders
- •She argues enterprise is not the same as earlier-market selling, and requires sharp focus rather than trying to win everything at once
- •She lists vertical focus areas where Checkr sees strong value (e.g., staffing, retail, hospitality, manufacturing)
- •She stresses enterprise expansion requires whole-company buy-in across engineering, product, legal, people, and go-to-market
Why the enterprise leap is harder than it looks
Brett probes why moving from mid-market to enterprise can destabilize companies. Lindsey details long sales cycles, complex decision-making, low switching frequency, brand awareness gaps, and the heavier product “last mile” required to satisfy enterprise needs.
- •Lindsey says enterprise deal cycles can be year-plus and opportunities arise infrequently due to long contracts
- •She explains internal decision-making is slow because switching vendors consumes major internal resources
- •She describes enterprise selling as complex trust-building and multi-threading to find the true decider
- •She notes brand awareness often doesn’t translate to enterprise buyers in different geographies
- •She highlights enterprise customers often require specific product, regulatory, or feature requests beyond “off the shelf”
Deal-blocker vs. nice-to-have: avoiding snowflake roadmaps while still closing
Lindsey explains one of the hardest enterprise muscles is distinguishing true deal-blockers from customer wish lists. She outlines the failure modes of over-committing to every request (creating one-off “snowflakes”) or being too rigid and losing deals—often leading to sales/product finger-pointing.
- •Lindsey calls separating deal-blockers from nice-to-haves a key determinant of enterprise success
- •She warns that saying “yes” to every request fractures the roadmap into customer-specific one-offs
- •She also warns that refusing needed changes prevents closing, triggering sales/product blame cycles
- •She reiterates that focus and hands-on account strategy matter, not just running a repeatable sales motion
- •She shares that fixing enterprise outbound at Checkr took significant time to uncover people, process, and strategy issues
Getting enterprise started: right talent, rich niches, and dedicated cross-functional support
Brett asks how companies should begin building enterprise. Lindsey emphasizes table-stakes capabilities (enterprise sellers, account-based marketing, product/engineering investment), then recommends starting with narrow “rich niches,” using deep RevOps analysis, and assigning dedicated individuals (including a dedicated product manager) without isolating the effort.
- •Lindsey says enterprise requires different talent: enterprise sellers and enterprise marketing (ABM, events)
- •She says product/engineering must be able to handle enterprise “last mile” needs
- •She recommends a focused start, avoiding “spray and pray,” and expanding from strong mid-market vertical performance
- •She describes using granular RevOps analysis to identify “rich niches” and then rapidly iterating campaigns
- •She advocates a small, dedicated enterprise pod including a dedicated product manager who joins customer calls
Hiring for enterprise grit: prioritizing scar tissue and outbound hunger
Brett asks whether the revenue leader must have enterprise experience. Lindsey says a leader can succeed without deep enterprise roots, but she found it critical to hire an enterprise sales leader who had built in gritty, challenging environments—and to screen for outbound pipeline creation ability rather than reliance on inbound leads or market-leading advantages.
- •Lindsey says she wasn’t a deep enterprise expert initially, so she hired a leader who had built enterprise motions multiple times
- •She distinguishes “market leader org” experience from experience building enterprise while challenged
- •She describes internal mobility from SMB/commercial into enterprise at Checkr
- •She says outbound demand-generation hunger is hard to teach if someone hasn’t done it
- •She notes Checkr avoids hiring enterprise reps who only worked with leads handed to them
Why events keep working: trust, differentiation, and peer value
Brett asks why events remain high-ROI despite changes in selling. Lindsey explains enterprise buying is a leap of trust, and in-person human connection matters; events must offer high value (unique experiences or strong thought leadership) and provide peer networking benefits that justify the opportunity cost.
- •Lindsey says post-COVID events initially dropped off, but pilots showed strong returns and led to renewed investment
- •She frames enterprise purchase decisions as trust-based and career-relevant for buyers
- •She argues events must be compelling enough to outweigh personal and work opportunity costs
- •She describes focusing on unique experiences or meaningful thought leadership rather than generic invitations
- •She says peer networking is a major draw and events aren’t “dying anytime soon”
The CRO-to-COO shift: cross-functional influence, peer dynamics, and CEO partnership
Lindsey describes the hardest parts of moving from CRO to COO as the mental shift into peers’ domains and learning how to drive change without direct authority. She also discusses building trust with the CEO, maintaining the right balance of involvement, and ensuring alignment while the CEO steps back from day-to-day operations.
- •Lindsey says the biggest shift was leaning into areas outside her direct org and partnering with peers
- •She gives examples: improving supply chain, recruiting velocity, and rethinking metrics with the CFO
- •She describes intentionally continuing to build trust and give feedback with the CEO
- •She notes the COO role included running company business reviews while keeping the CEO informed on what he cares about
- •She emphasizes finding the ongoing balance between operational ownership and founder awareness
Process without bureaucracy: decision rights, DRIs, and pushing decisions down
Brett raises the tension between process and agility. Lindsey explains Checkr’s work to stop decisions from automatically flowing upward by documenting which decisions the CEO owns, assigning a single decision-maker (DRI) for initiatives, and using “ROI of executive time” as a lens for delegation.
- •Lindsey says in founder-led companies decisions often flow up by default, increasing internal overhead
- •She describes documenting which decisions the CEO must make (e.g., big deals, major brand campaigns, major monetization shifts)
- •She explains Checkr’s use of a DRI model to reduce “swirl” and clarify ownership
- •She argues executives should make only decisions where their time yields high ROI versus lower levels
- •She notes continued effort to push decision-making down layers over time
Hard decisions: hiring, negotiations, and building decision-making skill
The discussion turns to what’s consistently difficult even with strong judgment. Lindsey highlights executive hiring and high-stakes negotiations, and explains her view that good processes can still produce bad outcomes—so teams must focus on decision quality, timeliness, and learning rather than perfection.
- •Lindsey names executive hiring as especially hard because candidates can be great interviewers and stakes are high
- •She shares she has made bad calls by over-indexing on relevant experience or on “intrinsics” that didn’t translate at exec level
- •She describes negotiations as hard due to imperfect information and no perfect answers
- •She emphasizes you can make a good decision and still get a bad outcome (and vice versa)
- •She says making no decision is worse than making an imperfect one, and she works on building trust in others’ decision processes
Staying close to the business: customer proximity, Slack visibility, and intuition with data
Brett asks how to avoid becoming detached as a leader. Lindsey describes deliberately staying close via physical proximity in the office, structured Slack channels per customer/deal, and ongoing customer conversations—because qualitative context and frontline insight are essential complements to dashboards.
- •Lindsey says leaders must stay close to avoid operating without context
- •She describes sitting with teams to absorb what’s happening and talking in hallways
- •She notes Checkr’s structured Slack approach (channels per customer and deal) helps keep pulse
- •She describes her style as intuitive decision-making layered with data
- •She believes the best decisions come from getting close to customers and frontline teams, not executive “pontificating”
Rebuilding sales incentives for a consumptive revenue model
Brett asks about incentive design, and Lindsey explains how Checkr changed sales compensation from bookings-based to revenue-based to match a consumptive model. She argues comp must reflect what the company is trying to achieve, align to what individuals can influence, and avoid misaligned payouts that drive overselling or poor go-live outcomes.
- •Lindsey contrasts SaaS-style booking credit with consumptive models where revenue depends on usage ramp
- •She says Checkr’s prior bookings-based comp led to overpayment and misalignment when customers didn’t go live or ramp as expected
- •She describes shifting to being comped on revenue to align rep pay with customer value and company results
- •She notes they also consider leading indicators (e.g., some credit at close) while staying aligned to revenue realization
- •She emphasizes right incentive design makes downstream decisions (like headcount) easier and warns against blindly accepting a sales leader’s default comp playbook
What top sellers do differently: trust-building plus strategic execution
Brett asks what separates the best seller from everyone else. Lindsey challenges stereotypes about extroversion and says standout reps combine customer trust-building with diligent strategic planning, resource orchestration, and tenacious execution over long cycles.
- •Lindsey says great sellers aren’t necessarily the most outgoing; many can be introverted but “turn it on”
- •She highlights trust-building with customers as a core differentiator
- •She says top reps excel at strategic thinking and planning the “moves” needed to win
- •She emphasizes sales is a team sport and the best reps orchestrate internal resources effectively
- •She describes top sellers as disciplined executors and strong project managers rather than improvisers
Operating cadence: daily no-agenda exec syncs and document-driven business reviews
Lindsey outlines Checkr’s leadership rhythms, including a daily 30-minute C-staff meeting with no agenda, biweekly business reviews with top leaders, and periodic deep dives. She explains how these rituals build trust, increase real-time alignment on fires, and enable rigorous tracking of strategic goals and metrics.
- •Lindsey describes the daily 30-minute C-staff meeting with no structured agenda and how it builds trust and alignment
- •She says it enables fast coordination on urgent issues (customer, engineering, employee) and reinforces “first team” mentality
- •She describes a biweekly review with top leaders using document culture (silent read, comments, then discussion)
- •She explains meetings focus on discussing flagged topics, addressing red/off-track goals, and assigning a DRI for follow-up
- •She details semiannual in-person alignment with broader leaders and VP+ offsites focused on strategy, trust, and execution speed
When data misleads: customer insights, strategic bets, and setting the right goals
Brett asks where dashboards can lead teams astray. Lindsey explains that strategy and product direction often require qualitative customer input, gives an example of repeated customer concerns shaping investment priorities, and discusses metric design—especially the difference between financial targets that should be hit and stretch goals intended to force new thinking.
- •Lindsey says some strategic/product insights won’t show up in dashboards and require direct customer conversations
- •She describes connecting patterns across customer conversations that weren’t visible in data and using that to guide strategic investment
- •She notes leaders must force themselves into customer interactions because teams may default to “we’ve got this”
- •She says companies often have too many metrics; she prefers starting with revenue and breaking it into drivers with clear owners
- •She argues financial goals should be hit tightly, while explicitly labeled stretch goals can push teams to rethink how they operate
AI in day-to-day operations: scaling support, improving signals, and centralizing impact
Lindsey describes where AI has had real production impact at Checkr: operations (support and resolution), sales outbound orchestration, and engineering productivity. She also explains the evolution from broad AI access and experimentation toward centralized, shared agents and workflow integration that drive measurable business outcomes.
- •Lindsey says operations uses AI to resolve support issues, improve customer satisfaction, and scale without proportional headcount growth
- •She explains AI-generated signals can highlight growth opportunities or distress based on support patterns and call themes
- •She describes an agentic outbound orchestration layer that reduces tool switching and triggers customized outreach based on signals
- •She notes strong adoption in engineering, with much code being written with generative AI
- •She says they’re moving from distributed tinkering to more centralized, shared agents and workflow-based systems to avoid “AI for AI’s sake”
What aspiring COOs should build: sales ownership, metrics fluency, and low-ego leadership
To close, Brett asks what earlier-career people should do if they want to become a COO. Lindsey emphasizes that future COOs who will own revenue should have sales leadership experience, deep comfort with numbers and company-level metrics, and a leadership style combining rigor with care for people, trust-building, and low ego.
- •Lindsey says aspiring COOs outside revenue should run sales teams at some point if they’ll own revenue later
- •She emphasizes the importance of customer interaction and understanding what it’s like to “own the number”
- •She says sales leaders who want to become COOs must intentionally build financial and metrics fluency beyond quota focus
- •She highlights her own blend of operational rigor and people/culture focus as key to her COO success
- •She says low ego and prioritizing company success over empire-building is important to how Checkr operates

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