Episode 43

Building Lasting Trust in Your First 100 Days as a TA Leader

About this Episode

Jeff Winter has more than 25 years of experience in talent acquisition and has helped scale high-growth companies across industries. As the first recruiter at Chime, he grew the team from 100 to over 1,500 employees before stepping into VP-level leadership. Now at Grammarly, Jeff is focused on aligning talent strategy with long-term business outcomes while leading an established team through its next stage of growth.

In this episode, Jeff shares the mindset and tactical approach every new TA leader should bring into their first 100 days. We explore how to build credibility through listening, evaluate what needs to change without disrupting what works, and partner with finance and engineering to make smart, scalable decisions. If you’re looking to set the right foundation in a new role, this conversation is essential listening.

Topics

Recruiting

This Episode's Guest

Jeff Winter

VP of Talent Acquisition @ Grammarly

Jeff Winter is the Vice President of Talent Acquisition at Grammarly. Over his 25+ year career, he has helped companies like Chime scale from early-stage to hypergrowth, including growing their team from 100 to over 1,500 employees. Jeff also founded and led Gravity People, a recruiting firm operating since 1998, giving him deep experience across both agency and in-house talent leadership.

Takeaway 1

Start with a listening tour 👂


When Jeff starts a new role, he doesn’t come in with a rigid playbook. He focuses on learning the history, meeting people across the business, and understanding how the team operates before making any changes.

Why It Matters: Leaders build trust faster by listening than by acting. A thoughtful listening tour helps uncover what the team values and what needs to evolve without disrupting what’s already working.

Quick Tips:

  • Prioritize conversations with long-tenured team members. Jeff meets with people who’ve been through different company stages, including growth, layoffs, and change. They provide context on what worked, what didn’t, and why.
  • Balance feedback with your own observations. Jeff listens closely to how people describe the culture and pays attention to the energy they bring to the conversation. Enthusiasm or hesitation can reveal just as much as their words.
  • Approach each conversation with curiosity and optimism. Jeff notes that how you show up matters. Coming in with energy, a smile, and a learning mindset helps others open up and feel safe sharing real feedback.

Takeaway 2

Partner early with Finance and Engineering 🤝

Jeff suggests that every new TA leader should build strong relationships with three people early on: a well-respected engineer, a key finance partner, and a senior team member who understands how work really gets done.

Why It Matters: Recruiting doesn’t happen in a vacuum. Partnering with finance helps surface overlooked tools, budget issues, and planning gaps. A strong engineering contact can help move quickly when technical support is needed.

Quick Tips:

  • Ask finance for vendor and tooling data. In Jeff’s experience, finance often has visibility into contracts and spending that the talent team may not. Reviewing these early can reveal where tools are underused or overlapping.
  • Find your most influential engineering partner. Build trust with someone who can unblock issues like SSO approvals or tool access. Jeff notes that these relationships are essential when something urgent comes up.
  • Be proactive about financial responsibility. Jeff explains that being financially responsible makes it easier to do your job. When you’re not constantly defending costs or managing tool sprawl, you can focus on building real recruiting impact.

Takeaway 3

Not everything needs to be rebuilt 🧱

One of the most common missteps Jeff sees from new leaders is the instinct to replace existing systems without understanding how they work. Instead, he takes time to learn what’s in place and why before making changes.

Why It Matters: Unnecessary change can erode trust and slow momentum. The goal isn’t to rework everything. It’s to elevate what’s working and thoughtfully improve what’s not.

Quick Tips:

  • Start with how systems are actually used. Jeff recommends digging into how tools and workflows are functioning today, not just what’s listed in documentation. Are they delivering real value?
  • Review spend and usage patterns. Jeff pays attention to where workflows slow down. Reviewing contract terms, unused tools, or manual steps in the process can highlight where the biggest inefficiencies are hiding.
  • Leave efficient processes alone. If something’s working well, protect it. Jeff says walking into a system that doesn’t need major change is a good thing and a sign to double down on what’s already successful.

What Hiring Excellence Means to Jeff

For Jeff, hiring excellence  is about alignment. It’s ensuring recruiters and hiring managers are telling the same story and creating a candidate experience rooted in clarity and care.

“We’re not just here to fill roles,” he shared. “We’re pitching culture. We’re pitching the work. And we’ve got to feel good about the story we’re telling because, for the candidate, this is a life-changing decision.”

Excellence isn’t about speed. It’s about building trust and doing things the right way, consistently.

>> Watch the Clip

Jeff's Recruiting Hot Take 🔥

Jeff challenges the idea that interview processes still work just because they’ve been used for years. After so much workplace change, especially post-pandemic, many companies haven’t evolved how they define excellence. He encourages talent leaders to reexamine their rubrics and ensure they reflect today’s culture, not just legacy expectations.

>> Watch the Clip

Timestamps

(00:00) Introduction

(02:20) The importance of a listening tour in leadership transitions

(03:52) Why new TA leaders need a 100-day plan

(07:42) Building trust and credibility across an organization

(12:18) Evaluating existing recruiting systems and tools

(15:08) The hidden costs of unused hiring tools

(24:08) How hiring processes need to evolve with changing workforces

Hosted By

Shannon Ogborn

RecOps Consultant & Community Lead @ Ashby

Shannon Ogborn is a Recruiting Ops expert with nearly ten years of experience at companies from Google to Hired Inc and more. She’s shining a spotlight onto what makes a recruiting strategy one of a kind.

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