Executives from large companies often fail at startups. Lindsey Scrase succeeded in her move from Google to Checkr because her experience at Google Cloud was akin to a resource-constrained startup, building from scratch without established systems like Rev Ops or enablement.
Checkr's CEO was specifically looking for a data-driven, operational leader to build a multi-segment sales motion. Lindsey Scrase's skills were a direct match for this need, creating a "product-market fit" for the hire that ensured success beyond just a general culture fit.
Successfully challenging an incumbent in the enterprise market is not just a sales initiative. Checkr required a literal "handshake around the table" from engineering, product, legal, and GTM teams to ensure universal commitment and resource allocation for the strategic shift.
To remain agile against incumbents, challengers need rapid feedback. At Checkr, the Chief Product Officer and product managers meet with customers daily, joining sales calls to create a tight, fast learning loop that informs the product roadmap directly from user needs.
A common failure mode when moving upmarket is committing to build every unique feature a prospect requests. This creates a "snowflake" roadmap that is not scalable. Successful companies learn to differentiate between true deal-blockers and nice-to-haves, maintaining strategic focus.
When Checkr's enterprise outbound motion wasn't working, it wasn't a single issue. It took 1.5 years of tinkering with people, processes, and strategy to diagnose and fix all the underlying problems, highlighting that there are no silver bullets for complex go-to-market challenges.
Instead of a "spray and pray" approach to enterprise, companies should first conduct a deep vertical analysis of their existing mid-market customers. Identify the "rich niches" where NRR and GRR are highest, and use those as the focused starting point for the upmarket push.
When starting an enterprise motion, don't embed it fully in existing processes or isolate it completely. Create a dedicated "tiger team" with named individuals from sales, marketing, and one dedicated product manager who becomes the embedded leader and coordination point, accelerating learning and execution.
When hiring enterprise sales reps, especially for a challenger brand, the most critical trait is a demonstrated hunger for generating their own pipeline. Lindsey Scrase's team won't hire reps who have only had leads passed to them, as the grind of outbound prospecting is a mindset, not just a trainable skill.
The hardest part of moving to COO is intervening in peers' domains. To avoid defensiveness, Lindsey Scrase found she had to get out of her own way, explicitly tell people her job was to partner with them on their challenges, and build trust through established communication cadences.
To combat the natural tendency for decisions to flow up in a founder-led company, the CEO and COO must explicitly document which high-stakes decisions they alone will make (e.g., major brand campaigns, M&A). This clarifies what can and should be pushed down to the rest of the organization.
In a world of imperfect information, a good decision can lead to a bad outcome, and a bad decision can get a lucky good outcome. Lindsey Scrase focuses on developing a good process for making decisions, recognizing that this is what is controllable and builds trust, even when individual results vary.
Checkr moved its sales compensation from bookings (estimated spend) to actual revenue realized from customer usage. This was a "game-changer" that eliminated overpayment for non-activated deals and aligned the entire sales motion with true customer value and long-term success.
Checkr's executive team meets every morning for 30 minutes with no set agenda. This ritual fosters deep trust, enables real-time alignment on urgent issues, and reinforces that the leadership group's primary allegiance is to the company's overall success, not their individual functions.
Instead of waiting for quarterly business reviews, Checkr uses AI to analyze all customer interactions (support tickets, sales calls) to surface real-time signals. This allows them to identify growth opportunities (e.g., product feature requests) or churn risks proactively, enabling immediate action.