5 Lessons in Scaling Well: How Head of Talent Jeff Winter Built the Hiring Engines Behind Iconic Growth Stories
Lessons from the TA leader who helped Chime grow from a 100-person startup to a 1,500-person public company by 2025.
VC-backed startups are back in hiring mode. Term sheets are flying, teams are scaling fast, and in AI, speed is the key currency. We’ve seen this cycle before: hiring fast, underestimating the importance of quality control, and discovering months later that productivity and product velocity are taking a hit.
To understand how to grow without repeating that cycle we’ve seen before during high growth periods, ModelExpand CEO, Paria Rajai sat down with Jeff Winter, a seasoned TA leader who’s helped scale Thumbtack, Chime, and Grammarly. His approach has built some of the most resilient hiring engines in tech: ones that could scale fast while maintaining high quality teams.
What follows are his lessons for founders and TA leaders navigating this new era of fast growth.
1. Start with Three Simple Questions to See If Your Company is Scaling High-Quality Hiring
When Jeff walks into a company that’s about to scale (think: 100 people trying to hire 40+ in the next 6 months), he doesn’t start with a fancy dashboard.
Jeff starts with three questions that reveal whether a company is ready to scale quality hiring:
a) Are leaders actually committed to the work of hiring?
Not the idea of hiring being a priority — the practice.
Are interviewers showing up prepared?
Are debriefs happening consistently?
Is there a shared rubric, or are decisions based on “vibes and brand names”?
The easiest way to see this in the data:
Are scorecards thoughtful or filled with one-line “great!” comments?
Do teams hold actual debriefs, or is feedback handled via Slack emojis?
b) Is headcount paced to reality… or fantasy?
Most hypergrowth plan sounds like:
“We’ll hire 40 engineers in H1. It’ll be tight, but we’ll make it work.”
Jeff’s response is simple: show me the math.
How many qualified interviewers do you actually have?
How many interviews per week can they run without harming execution?
Who is going to onboard those 40 people, and when?
If the answers are vague, the plan isn’t real.
c) Is the hiring process adopted, and are people using it critically?
One of his first moves at Grammarly was to pull interview data and look at scorecards. What he saw: almost no “no” votes which meant nearly all the candidates were being passed onto the next round.
On paper, that looks like a great close rate. In practice, it means the team is saying yes to B-players because people are afraid to say no.
Jeffuses clear benchmarks:
“For engineering, I like to see close rates around 65%. That tells me we’re being selective.
When you’re closing 90%+ of engineering candidates, it usually means you’re just hiring everyone who makes it to offer.”
For non-technical and G&A roles, he expects higher close rates (think 75–90%), but only after a much smaller, truly filtered set of candidates makes it to offer.
If a company can’t answer these three questions with data and specifics, it is not ready to scale. It is simply opening reqs without enough safeguards to ensure quality control.
2. Capacity Planning is the Unsexy Lever That Can Save Startups from Underperformance or Getting Too Bloated
Once leadership alignment is in place, the next lever is capacity. One pattern is consistent to Jeff: recruiters can only do great work when their load is reasonable.
His general rule of thumb:
A recruiter working ~6 solid roles can be thoughtful, critical, and genuinely partner with hiring managers.
A recruiter working 12+ roles will eventually do whatever it takes to close. Quality drops, shortcuts happen, and the bar drifts.
So instead of pushing recruiters to “do more,” he builds a capacity model in lockstep with Finance, pacing headcount to what the org can realistically absorb. That means aligning headcount plans with interviewer availability, onboarding bandwidth, and ramp timelines.
When done right, it adds discipline to high-speed hiring and keeps startups from sprinting into underperformance or performance management headaches later on.
If the goal is a high-performing team, the hiring engine can’t stay in overdrive year-round. Pacing and discipline are what preserve quality.
3. Pooled Hiring Creates One Shared Bar and Beats “Every Director for Themselves”
After capacity planning is completed, pool hiring comes next. Pooled hiring creates one shared bar instead of ten competing ones. At Chime, Jeff introduced pooled hiring, one of the most overlooked but powerful hiring mechanics in hypergrowth.
Instead of disparate processes that look like:
Each director running their own process
Each team defining its own bar
Recruiters tripping over each other chasing the same candidates
He centralized the engine:
One funnel per track (e.g., all back-end roles through a single pipeline)
Shared rubrics engineers co-created, so everyone believed in the bar
A Slack-based calibration process where directors reviewed and leveled candidates together
The result?
Tense debates at first but what followed was alignment: a unified engineering culture, faster internal moves, and fewer off-the-grid hiring processes that lowered the bar.
As Jeff put it:
“If every engineering leader thinks they hire better than everyone else, you don’t have talent density. You have chaos with good intentions.”
Pooled hiring replaces that chaos with structure and shared accountability. It ensures quality rises together rather than drifting in different directions.
4. Define “Talent Density” as Fewer Hires, Slower Pace, Higher Bar
Founders and TA leaders are talking a lot about talent density these days. The term sounds sharp and modern, but its definition can be a little opaque and sometimes more buzzword than blueprint.
Jeff’s keeps the definition simple:
“Talent density means fewer hires, slower pace, higher bar.”
The challenge isn’t spotting great resumes. The challenge is whether you’re structured enough to assess talent consistently and onboard new talent well.
That looks like:
Rubrics that guide judgment, not gut calls
30/60/90 day onboarding plans that actually get used
Empowering recruiters to say no, even when the business is pushing yes
Without that foundation, “talent density” is just spin: hiring less without the systems to hire smarter.
5. When Recruiting Runs Right, You Compete With the Best and Win
At Chime, Jeff built recruiting into a hiring engine the CEO never had to worry about.
“The only thing I don’t worry about,” the founder would say, “is recruiting.”
That’s the ultimate bar.
While they didn’t always hit their exact headcount goals, the decisions were always intentional.
The engine was predictable.
The bar held firm.
And the team scaled with real quality control.
By the time Chime’s talent team was in rhythm, Chime found itself in a different talent arena. They were competing with big players at the time including Uber, DoorDash, and Robinhood for talent.
That’s how you know your engine’s working: when your company is hiring against the best and winning.
Scaling Well Starts With Asking the Right Questions. Here Are a Few to Gauge Where You Are:
If you’re running or backing a high-growth startup, ask yourself:
Scorecards: Are there actual “no” votes, or is everyone a soft yes?
Debriefs: Are they happening or just skipped to save time?
Capacity: How many roles per recruiter and does that number make great work possible?
Onboarding: Who owns ramp success at 30/60/90 days?
Cohesion: Can people move within internal teams without having to re-prove their level?
If those answers make you uneasy, you’re not behind: you’re just now at the part where discipline needs to start to take more of a front seat than feels natural.
👇 Partner Note from ModelExpand
At ModelExpand, we help high-growth organizations build recruiting engines that scale intentionally: the kind Jeff describes. Our team of senior talent operators partners with leaders to design hiring systems that drive quality, pace, and predictability from Series A through IPO.
If you’re hiring fast and want to make sure your bar rises, not drops, as you scale, connect with our team to build your company’s hiring engine: capacity planning, ATS implementation, interview plans, candidate generation, executive talent acquisition leadership placements, international expansion strategy, data dashboards, and the foundational infrastructure critical for thoughtful hiring at scale.
