What should a newly-hired talent leader focus on in their first 100 days?

Jeff Winter, VP of Talent Acquisition at Grammarly, has spent decades helping companies scale. As the first recruiter at Chime, he helped grow the team from 100 to 1,500 employees—experience that shaped his approach to stepping into leadership roles with impact.

In this conversation with Shannon, Jeff shares how new TA leaders can build trust, assess existing hiring processes, and make meaningful changes without disrupting what works. He explains why listening is the most valuable skill in those first months, how to align with finance and engineering leaders, and why hiring excellence starts with clarity, not speed.

Key Takeaways: 

1. Listening builds trust faster than action: The best leaders don’t walk in with a rigid playbook. They start by learning the history, understanding challenges, and earning credibility.
2. Finance and engineering are key partners in hiring success: Aligning with finance helps ensure responsible headcount planning, while strong engineering partnerships make recruiting more effective.
3. Not every process needs to be rebuilt: Before changing systems or workflows, leaders should assess what’s working and where there are opportunities to improve efficiency.
4. Treating recruiting as a strategic advantage: The best hiring teams don’t just move candidates through a pipeline. They help shape the company’s culture and long-term success.

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