Former CMO shares her inner game secrets (used by the Top 1%) (Kelly Gillease)

In this episode, Kelly Gillease, two-time CMO, daily meditator, and former search marketer turned executive leader, talks candidly about the inner game behind durable leadership. She traces her path from debating podiums to performance marketing at Hotwire, through scale-up chaos at NerdWallet and post-acquisition life at TripAdvisor/Viator—sharing how mindfulness, therapy, and a “true, kind, necessary” feedback filter helped her steady teams when everything felt on fire.

Kelly opens up about a tough DEI misstep, how she took the feedback without getting defensive, and why she chose to “run toward” hard conversations instead of retreat. She gets tactical about cross-functional influence (and why debate training still matters), building reputations through appreciation rituals, and choosing environments that actually fit you, even when the shinier title says otherwise.

In this conversation, you’ll learn:

- How to use “true, kind, necessary” to deliver (and receive) feedback that lands, and what to do when it doesn’t

- Practical rituals for team resilience: appreciations, mindful pacing, and calmly problem-solving without losing speed

- How to pick the right work environment for your wiring. and navigate the politics, pacing, and trade-offs of big-co vs. startup life

Things to listen for:

(00:00) Intro

(01:47) Kelly’s roots, early influences, and formative values

(03:51) Where creativity meets ROI: loving both art and math

(09:05) Thank you to our sponsor, Navattic

(13:50) Scripts and mindsets for hard feedback and conflict

(24:23) Owning a DEI misstep, pausing, and moving forward

(29:22) Gratitude rituals at work and at home that build morale

(39:58) Why big-company bureaucracy wasn’t the right fit

(44:20) Radical honesty, necessary conversations, real growth

A huge thanks to this episode’s sponsor:

Navattic: Interactive Product Demo Software - https://navattic.com/value

Resources:

Connect with Kelly: https://www.linkedin.com/in/kellythepea/

Connect with Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcapland/

Substack: https://media.deliveringvalue.co

Hire Andrew as your coach: https://deliveringvalue.co/coaching

Join Growth OS: https://deliveringvalue.co/growth-operating-system