In this episode, Kraig Swensrud—3x founder, CEO of Qualified, and former CMO of Salesforce, reflects on the people and pivotal moments that shaped his career. From early bets placed on him as a rookie sales engineer, to mentors who opened doors, to colleagues who pushed him to take bold risks, Kraig shares how relationships powered his path from Oracle to founding three companies.

He opens up about the leaders who invested in him, why he now pays it forward by spotting future superstars inside his own company, and the simple practices that build lifelong bonds. Kraig also offers grounded advice for early-career professionals: take more risks than you feel comfortable with, lean into emerging technology, never burn bridges, and remember that today’s peers will be tomorrow’s industry leaders.

A candid, inspiring look at how great careers are never built alone, but together.

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Time Stamps:

* 01:33 - Introduction to Kraig’s Journey

* 01:47 - The Salesforce Acquisition Story

* 05:04 - Taking Risks and Building Relationships

* 06:19 - Breaking into Tech and Early Mentorship

* 08:18 - Paying It Forward: Mentorship Today

* 10:26 - Forging Relationships Through Work

* 11:45 - The Tech Industry Is Smaller Than You Think

* 13:56 - Networking Strategies and Building Connections

* 18:46 - Leveraging AI and Technology in Networking

* 19:50 - Cold Emails and Standing Out

* 23:10 - Lessons from Marc Benioff

* 25:40 - Final Reflections and Career Advice

People That Helped Kraig Along The Way:

* 06:19 - Norman Gennaro – One of Kraig’s First Bosses, CRO of Miro

* 02:14 - Sean Whiteley – 3x Co-Founder with Kraig, How They Got Their Start

* 7:06 - Phillip Merrick – It Started With a Cold Email

* 13:59 - Alex Bard – Thanksgiving Ritual That Builds Lifelong Relationships

* 15:50 - Dan Darcy – Surround Yourself With a Superconnector

* 18:46 Rich Campbell – Grab Onto a Technology To Grow Your Career

* 23:10 Marc Benioff – Master Networker and Someone Who Truly Cares