Featuring: Jennifer Spire, Preston Spire

In episode 137, I sit down with Jennifer Spire, Partner and CEO of Preston Spire — a 75-year-old agency that’s somehow still pushing boundaries while many newer shops flame out. Jennifer shares how she modernized a legacy company without losing the cultural DNA that kept it alive for three-quarters of a century. We get into leadership transitions, building a values-driven agency, navigating generational shifts in talent, and how she’s shaping the next era of a Midwest powerhouse.

Key Bytes

• The hidden advantages legacy agencies have but often ignore

• Why values act as a competitive moat — but only if they’re enforced

• How Jennifer leads change without blowing up culture

• The reality of modernizing 75-year-old processes

• Where agencies underestimate the work of staying relevant

Chapters

00:00 Intro

01:20 What it means to run a 75-year-old agency today

05:05 How Jennifer modernized Preston Spier without breaking it

09:40 The cultural DNA that actually drives retention

13:55 Why “values” only matter when leaders enforce them

17:48 Leadership evolution: from partner to CEO

21:30 What younger talent expects from an established shop

25:18 Staying relevant in a fast-changing industry

29:55 How Preston Spire balances legacy and innovation

33:42 Advice Jennifer wishes she had earlier

38:10 Closing thoughts

Jennifer Spire is partner and CEO at Preston Spire, an Ad Age Best Place to Work and Midwest Small Agency of the Year. She is an accomplished agency leader with over 25 years of experience in both consumer and B2B marketing for just about every industry out there. At Preston Spire, Jennifer has played the leading role in reshaping the framework that defines the agency, focused on a strong vision, values and purpose. She has been a speaker at dozens of local and national conferences, has authored articles and thought pieces on various marketing subjects, and has been a board member of several nonprofit organizations. Jennifer was an east coast native before calling Minneapolis home. She was an NCGA gymnast and a gymnastics coach, who also had advertising in her blood, thanks to her grandfather being one of the founding fathers of Madison Avenue.

Contact Jennifer on LinkedIn or the Preston Spire website.