In this episode, Diego von Söhsten, immigrant operator, product leader, and Director of Product Growth at Jobber, opens up about the “after you’ve already proven yourself” flavor of imposter syndrome. He recounts a moment when a senior executive publicly tore down his work (and blamed his accent), and how he rebuilt confidence, created alignment without air cover, and ultimately earned a promotion while shipping a freemium foundation that mattered when COVID hit.
Diego talks about learning to over-communicate up and across, turning anti-role-models into fuel for the leader he wanted to become, and building a growth org that prized clarity, storytelling, and psychological safety. He also shares practical ways underrepresented builders can find mentors, ask for help without shame, and protect their inner game when the ground keeps moving.
In this conversation, you’ll learn:
- How to turn painful feedback and bias into long-term fuel for resilience and credibility as a leader.
- How to use storytelling and structured communication to create alignment and influence without authority.
- How to build a support network of mentors, peers, and self-awareness to stay grounded under pressure.
Things to listen for:
(00:00) Intro
(01:53) Diego's career beginnings
(06:01) Diego’s experience being criticized for his accent
(10:43) Thank you to our sponsor, Navattic
(15:05) Overcoming and growing from adversity
(24:04) Understanding user drop-off and alignment
(24:46) The power of storytelling in product management
(26:38) Building and leading effective teams
(29:31) Diego’s advice to those struggling to find their place
(33:13) Working with a good team member who just couldn’t fit
(44:58) Balancing passion for work and professional boundaries
A huge thanks to this episode’s sponsor:
Navattic: Interactive Product Demo Software - https://navattic.com/value
Resources:
Connect with Diego: www.linkedin.com/in/diego-vs
Diego’s official website: https://www.vonsohsten.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
Join Growth OS: https://deliveringvalue.co/growth-operating-system
