I Made It to SVP of Product — Then I spiraled (Jake Woodward)

A huge thanks to this episode’s sponsor: Hire Overseas:

Exceptional Talent for Less - https://www.hireoverseas.com

In this episode, Jacob Woodward, a longtime product and tech leader, shares what happens when a strong resume runs into a brutal job market. He reflects on the year and a half after leaving a struggling company, attempting to go independent, applying nonstop, and still feeling invisible.

Jacob talks about how AI has changed hiring on both sides. Candidates can apply at scale with polished, tailored resumes, while hiring teams are overwhelmed by stacks of applications that start to blur together. He opens up about how repeated ghosting shook his confidence and identity, especially under the pressure of providing for his family.

After hitting a breaking point, Jacob shares how a raw LinkedIn plea went viral worldwide, and how support from strangers, including a Business Insider feature, helped restore his self belief. Now, he’s rebuilding through therapy, meditation, and yoga, and betting on himself as he builds what’s next, including a project to teach kids critical thinking in an AI driven world.

In this conversation, you’ll learn:

• How AI and mass applying have changed the job search, and why great candidates can still feel invisible
• What repeated rejection does to confidence, and how to rebuild without waiting for external validation
• Why therapy, meditation, and yoga became key tools in Jacob’s comeback

Things to listen for:

(00:00) Intro

(01:38) Early entrepreneurship and first exit

(07:20) Facing today’s job market realities

(08:50) Thank you to our sponsor, Hire Overseas

(18:27) Moving beyond a professional facade

(20:11) Sharing a raw LinkedIn plea

(22:09) How AI is reshaping hiring

(28:29) Rebuilding confidence after repeated ghosting

(31:47) Therapy, meditation, and yoga practices

(38:42) Betting on one’s self and building next

Resources:

Connect with Jake:

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

Website: https://www.jacobwoodward.dev/

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