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First Round CapitalWhy future COOs need sales experience | Lindsey Scrase (COO, Checkr)
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At a glance
WHAT IT’S REALLY ABOUT
Why COOs need revenue ownership: enterprise growth, incentives, cadence, AI
- Lindsey Scrase describes why executives from large companies often struggle in startups and explains how her approach to learning new contexts, plus her scrappy scaling experience, helped her succeed at Checkr.
- She outlines what it takes to challenge entrenched market leaders, emphasizing humility about gaps, a focused vertical strategy, and full-company commitment when shifting into enterprise.
- She explains why moving from mid-market to enterprise is harder than it looks, citing long buying cycles, complex stakeholder maps, brand-awareness hurdles, and extensive product “last-mile” requirements.
- She shares operating mechanisms she uses to keep alignment and speed, including naming a single decision-maker (DRI), pushing decisions down the org, and running a daily 30-minute executive meeting with no agenda.
- She details how Checkr changed sales compensation and how the company is applying AI in operations and go-to-market, while shifting from many individual experiments toward more centralized, scalable workflows.
IDEAS WORTH REMEMBERING
5 ideasAdapting from big-company roles to startups requires a learning mindset and comfort with scrappiness.
She says she adapted well by enjoying unfamiliar contexts, learning from first principles instead of “foisting” prior views, and because her earlier work at Google Cloud involved scrappy building with limited enablement and ops support—conditions she found comparable to her startup environment.
Taking share from an incumbent starts with humility and sharp focus on winnable niches.
She argues challengers often underestimate gaps versus incumbents (especially in marketing and go-to-market investment) and emphasizes choosing focused verticals where you can win, rather than trying to “capture everything overnight.”
Enterprise expansion is hard because it changes sales motion, product demands, and timing dynamics all at once.
She describes enterprise as fundamentally different: long decision cycles, infrequent switching windows, multi-stakeholder decision-making, brand-awareness gaps, and product “last-mile” requirements that force hard trade-offs about what to build.
The enterprise roadmap lives or dies on correctly classifying customer requests.
She says success hinges on separating true deal-blockers from nice-to-haves; otherwise teams either build one-off “snowflakes” for every prospect or refuse necessary changes and can’t close deals.
Early enterprise efforts work best as a dedicated pod that’s connected—not siloed.
She emphasizes starting enterprise with dedicated, tightly connected people (including a dedicated product manager embedded with the effort) while avoiding isolating the initiative from the rest of the company.
WORDS WORTH SAVING
5 quotesPeople think, you know, Google had a ton of resources. Obviously, we do, like, unlimited funding in some ways for, like, the startup that was Google Cloud, but it was very hands-on, scrappy, building and scaling with, with very little resources and, and scale.
— Lindsey Scrase
I think it requires a lot of humility to understand, like, where, where are you gapped versus, you know, an, an incumbent.
— Lindsey Scrase
Enterprise is the same, and it's absolutely not.
— Lindsey Scrase
The sales acumen is incredibly important. You're not order taking.
— Lindsey Scrase
I think that what I've learned over the years is that you're, you could make a really good decision and still have a bad outcome, or you could make a really poor decision and have a good outcome.
— Lindsey Scrase
SPEAKERS
Brett Berson
hostHost/interviewer from First Round Capital who guides the conversation with structured questions and framing.
Lindsey Scrase
guestCOO at Checkr, previously CRO, speaking about go-to-market, operations, and scaling frameworks.
High quality AI-generated summary created from speaker-labeled transcript.
