Summary

In this episode of The WorkOps Podcast, Jeet sits down with Weston Fillman, Director of People Operations and Employee Relations at 1Password, to unpack what it actually takes to get an HR transformation funded, and what changes when AI enters the room. Wes describes the months of pre-work that won him more executive budget than he asked for at a 10,000-person enterprise tech company, the reframe he'd apply to the same project today (people systems as infrastructure, not engagement), and the role-redesign conversations he's having on his team at 1Password as AI starts to automate the operational layer of HR ops. A field guide for any People leader heading into their next budget cycle.

Timestamps

00:00 Welcome and Wes's career path (TFA kindergarten to 1Password)

02:45 Inheriting a broken hiring process at a 10,000-person company

07:00 "You can build a new house, but the floor plan's wrong"

08:00 The structured plan, executive buy-in, and a budget bigger than expected

11:00 Sideways socialization: leading without authority across HR peers

13:30 1Password rolls out org-wide agent-building, and modeling AI as a leader

17:30 Build vs. buy in 2026 (and why it's really build AND buy)

22:30 The role redesign conversation: AI rewrites the JD, doesn't cut the role

26:00 The reframe Wes would apply today: people systems as infrastructure

30:00 Where People leaders should start their own AI journey

Takeaways

- HR transformation budgets are won in the months of pre-work before the e-staff ask, not in the room itself.

- The reframe from "employee experience" to "business infrastructure" is the single change that turns the same HR project from nice-to-have into board-level fundable.

- AI lands well when leaders treat it as a role-redesign conversation, not a layoff conversation. Most operational work was never on the JD anyway.

- Cross-functional buy-in (sideways across peer HR leaders) matters as much as executive sponsorship for any large People transformation.

- The best AI on-ramp for an individual contributor is to start with the work they're not great at, not the work they already excel at.

Connect with the Guest
Weston Fillman on LinkedIn: https://www.linkedin.com/in/westonfillman/
1Password: https://1password.com/

Sponsor
This episode is brought to you by Kinfolk, the AI service desk built for HR.

See more at kinfolkhq.com