194. Mastering Flywheels & OKRs (w/Brendan Fortune)

Product Coffee

In this exciting episode of Product Coffee, host Kevin Gentry sits down with Brendan Fortune, Director of Product at Customer.io. Brendan shares his unique journey from the music industry to product leadership, how Customer.io scaled from 60 to nearly 300 employees, and the key role OKRs play in aligning teams for success. They also explore the concept of flywheels, managing product roadmaps, and the challenges of remote work.

Brendan was nice enough to share his Annual Planning via Product Flywheel Miro board. Check it out here!

📅 Episode Timeline:

• [00:00] – Welcome & introduction to Brendan Fortune

• [00:34] – Brendan’s career journey: From music to product management

• [01:25] – Why Brendan thrives in startup & mid-sized companies

• [02:00] – Life in Minnesota: Remote work, family time, & hobbies

• [03:09] – Music-making with kids & the joys of Kung Fu

• [04:00] – The growth of Customer.io: From 60 to 300 employees

• [05:32] – Brendan’s challenge: Building OKRs that align with real outcomes

• [07:25] – Introducing the concept of a flywheel strategy

• [10:00] – How Customer.io's flywheel aligns data, messaging, & influence

• [14:21] – Structuring product squads & assigning objectives

• [20:00] – Using Prometheus & Mixpanel to track metrics & influence behaviors

• [25:19] – Combining annual & quarterly planning cycles

• [30:00] – Leadership’s strategic pillars & their impact on product teams

• [33:50] – Brendan’s "rock tumbling" ritual: Collaborative product reviews

• [37:00] – Navigating budgeting & resource allocation

• [41:29] – The shift from CapEx to OpEx & its impact on product planning

• [45:20] – Brendan’s advice: Discovering your flywheel & measuring success

• [46:26] – Where to connect with Brendan Fortune

---

📩 Got a question or comment? Send it our way, & we might feature it on a future episode!

➡️ Where to Connect with Brendan:

LinkedIn: https://linkedin.com/in/bfortune34

Resources Mentioned:

• Good to Great by Jim Collins

• Measure What Matters by John Doerr

• Platform Revolution by Geoffrey G. Parker, Marshall W. Van Alstyne, Sangeet Paul Choudary

• Hooked by Nir Eyal

• Reforge resources on growth loops & flywheels

Enjoyed the episode? Don't forget to rate, review, & subscribe to Product Coffee on Apple Podcasts, Spotify, or wherever you listen!

☕ Grab some Product Coffee merch! Visit productcoffeepodcast.com to order your mug or sticker.