Ex CMO: I Quit After 16 Years of Climbing the Ladder - and Redefined Success (Annie Katrina Lee)

Annie Katrina Lee, Co-Founder and Principal of Penknife Collective, opens up about the moments that challenged her identity and reshaped her perspective on success.

From bold career moves at Microsoft to walking away from high-profile CMO roles, Annie shares how she navigated rejection, imposter syndrome, and the evolving priorities of motherhood.

Annie opens up about:

• Landing her first tech role at Microsoft by taking a bold risk

• Facing rejection and rebuilding confidence

• How becoming a mother at the height of her career reshaped her identity and priorities

• The tough feedback that taught her the importance of balance

Things to listen for:

(00:00) Annie’s first CMO role and feeling incomplete

(08:43) Landing a job at Microsoft through boldness

(13:10) Facing rejection during the 2009 recession

(14:03) Thanks to our sponsor for this episode, Navattic & Appcues

(17:36) The challenges of being a working mom and its impact on identity

(20:44) Reevaluating priorities after losing your love for the craft

(27:49) The impact of tough feedback: “You care too much”

(39:57) Overcoming imposter syndrome in tech

This episode is presented by:

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

Appcues: User Engagement for SaaS - https://appcues.com/value

Connect with Annie:

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

Penknife Collective: https://www.penknifecollective.com/

Connect with Andrew:

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

Substack: https://media.deliveringvalue.co

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