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

Summary

What looks like a warm, boutique onboarding experience on the outside is often powered by something much less glamorous on the inside: a person copy-pasting LinkedIn headshots into slides at midnight.

In this episode of the WorkOps Podcast, host Jeet sits down with Amie Taylor, Senior Director of People Operations, Rewards and Technology, for a refreshingly honest conversation about the hidden cost of "human API" processes.

Amie walks through a three-year saga at a previous hyper-growth tech consulting company where the entire day-zero-to-day-one new hire experience ran on Google Forms, manual IT tickets, and one very overworked TA coordinator hunting down headshots for the CMO's town hall slides. She shares how she eventually built the business case, the internal politics she had to navigate, why it took a team member filing overtime to finally break through, and the bittersweet twist at the end when she left right after getting the project approved.

She and Jeet also get into how she's applying those lessons today—consolidating HR systems at her current company, using critical thought as the test for what to automate, and why some processes (like leave for someone facing a serious diagnosis) should stay stubbornly human. If you've ever inherited a process held together by goodwill and overtime, this one will hit close to home.

Timestamps

• 00:23 Amie's path from psychology to global payroll
• 04:46 Inheriting a high-touch onboarding process powered by "human APIs"
• 06:12 Google Forms, missed steps, and a candidate experience built on anxiety
• 08:23 Hours spent hunting down headshots for town hall slides
• 11:00 The three-year fight to get buy-in to automate
• 13:00 Getting the project approved, then resigning right after
• 15:13 Rebuilding similar processes today with full stakeholder buy-in
• 19:47 The "critical thought vs. machine work" test for what to automate

Takeaways

• Audit the hidden labor inside "high-touch" processes before you call them culture
• Quantify manual work in overtime and bottom-line impact, not just employee experience
• Build stakeholder buy-in by making the decision feel like theirs, not yours
• Use "critical thought vs. machine work" as your test for what AI and automation should touch
• Protect the human moments—leave processes, serious diagnoses, tough conversations—no matter how advanced your tooling gets
• Remember: if the process doesn't scale, it's not your culture, it's tech debt

Guest LinkedIn: https://www.linkedin.com/in/amie-taylor-5b99b810/

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

See more at kinfolkhq.com

Summary

What if the most honest feedback about why people leave your company isn't in the exit survey at all—it's in the Slack threads, Zoom transcripts, and emails already happening every day?

In this episode of the WorkOps Podcast, host Jeet sits down with David Hanrahan, SVP of People Success at SolarWinds, for a candid conversation about one of the most broken processes in HR: the exit survey.

David walks through his years-long love-hate relationship with exit surveys, including a moment at Zendesk where he got so frustrated with the bad signal that he actually told the team to stop running them altogether. He and Jeet get into why exit data is so unreliable, how bias from both departing employees and their managers rewrites the real story, and why he believes the future is in predictive signals from real conversations rather than post-hoc questionnaires.

David also shares a contractor agent pilot that SolarWinds recently shelved, what it taught them about where AI belongs and where it doesn't, and how he's coaching his business partner team through the shift from tactical request-handling to strategic HR. And he closes with a line that stuck with me: in this era, people leaders need to think of themselves a little more as technologists and a little less as psychologists. If you lead people ops, build HR systems, or are just trying to figure out where AI fits, this one's worth an hour.

Timestamps

• 00:33 From accidental psychology major to SVP of People Success
• 02:13 Why SolarWinds calls it "People Success" instead of HR
• 03:02 The exit survey problem at Zendesk and why David shut them down
• 06:16 How bias from both employees and managers corrupts exit data
• 12:34 Why employees are more comfortable asking AI sensitive questions
• 16:16 The contractor agent pilot SolarWinds shelved and what it taught them
• 21:05 Freeing up business partners for strategic HR through automation
• 23:33 Flipping exit surveys on their head with predictive signals

Takeaways

• Interrogate the data you're treating as gospel; exit surveys carry more bias than most HR teams admit
• Start with one high-impact area when adopting AI instead of trying to flip everything at once
• Understand where a human needs to stay in the loop before building an agent—narrow scope without judgment design usually fails
• Be explicit with your team about why you're automating; relinquishing work requires trust in what comes next
• Look for retention signals in the conversations already happening, not in surveys you have to force people to fill out
• Think of yourself a little more as a technologist and a little less as a psychologist in this era of HR

Guest LinkedIn: https://www.linkedin.com/in/davidhanrahan/

Company website: https://www.solarwinds.com

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

See more at kinfolkhq.com