Katie Stratton, Chief Growth & Strategy Officer at Shipt, Real Leadership

Episode Description

What happens when a leader who spent a decade inside one of the most influential technology companies in history decides to bring that playbook to the world of same-day delivery?

Katie Stratton is the Chief Growth and Strategy Officer at Shipt, the Target-owned retail technology company that specializes in same-day and next-day delivery. Before joining Shipt in 2023, Katie spent nearly 12 years at Meta, joining as the 90th employee in the New York office before the IPO and rising to lead U.S. sales for dining and delivery. Earlier in her career, she honed her craft in the agency world, working with brands like Toyota, Cadillac, and Unilever.

But Katie's path wasn't a straight line. A pivotal moment early in her career, a courageous conversation in a toxic work environment, sparked by her mother's advice, opened the door to Facebook and set the trajectory for everything that followed. That same willingness to speak up, take risks, and lead with clarity defines how she operates today.

In this episode, we cover:

• How a toxic early-career experience and her mother's advice became the catalyst for Katie's entire leadership journey
• What it was like to join Facebook pre-IPO as the 90th employee in the New York office — and what she learned from leaders like Sheryl Sandberg and Carolyn Everson
• How Shipt is evolving from a startup into a mature growth company — and why grocery and human connection are at the center of the strategy
• The story behind Target Circle 360 and Shipt's no-markup pricing model
• Why Katie compares AI to How to Train Your Dragon — and how she's training her own "dragon" personally and professionally
• Why "clarity is kindness" and "I got that wrong" are the leadership phrases she lives by
• How the "threshold" principle and intentional presence help her lead a national business while raising three kids
• What it means to be a "tip of the spear" leader — and why people only follow when the path is clear

This is a conversation about the moments that shape a leader — the courageous conversations, the career-defining leaps, and the daily discipline of showing up with honesty and humanity.

Key Moments

01:47 - What Shipt does and how the preferred shopper relationship works

05:23 - Shipt's inflection point: pivoting from startup to mature growth company

09:07 - Building Target Circle 360 and the no-markup strategy

11:54 - How AI will shape the future of Shipt — and why human connection is the edge

14:44 - The "How to Train Your Dragon" analogy for AI

18:00 - Lessons from nearly 12 years at Meta and leading through COVID

21:40 - Vulnerability as a leadership strength: "We didn't hire you to know everything"

32:32 - The toxic agency experience and her mother's career-changing advice

37:19 - How one conversation led to Facebook — and a career-defining 12 years

41:23 - Leading with kindness: why clarity is kindness

43:23 - The "tip of the spear" leader and machete through the sugar cane

45:15 - Staying energized: thresholds, presence, and intentional balance

Show Notes

Katie Stratton — LinkedIn: https://www.google.com/search?q=https://www.linkedin.com/in/katie-stratton-a1b4154/

Shipt: shipt.com

Shipt — LinkedIn: https://www.linkedin.com/company/shipt/

Target Circle 360: target.com/circle/360

Wait Until 8th: waituntil8th.org

Jim Weaver — LinkedIn: linkedin.com/in/jim-weaver-36457418

Real Leadership Podcast: realleadership.oningroup.com

Real Leadership — LinkedIn: linkedin.com/company/104897916

The Ōnin Group: oningroup.com/clients