In this episode, Gav sits down with Karren Jensen, co-founder and CEO of Conductor Software, to unpack the misunderstood world of psychological safety and why it might be the biggest lever for performance most organisations are missing.

Expect a candid, behind-the-scenes look at what it really takes to launch a B2B SaaS company from scratch - completely bootstrapped.

Got questions or topics you want us to cover? Email us at journey@sixsides.co

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In this episode, we cover:

• What psychological safety really is - and what it isn’t
• The biggest misconceptions leaders have about “soft stuff” at work
• How fear, stress and silence quietly destroy performance
• Why organisations struggle with values, trust and accountability
• Karren’s career before Conductor and her grounding in neuroscience
• The personal experiences that shaped her obsession with psych safety
• The moment Conductor’s founders validated their hypothesis with a first client
• Bootstrapping the business and landing early wins
• How psychological safety translated into millions in revenue impact
• Leading through COVID, AI disruption, and constant uncertainty
• How Karren’s definition of success has evolved over time
• Why protecting our humanity matters more than ever
• Advice for founders standing on the edge of taking the leap
• Why community and champions matter, especially for female founders

Chapters:
00:00 Intro and what The Leap is really about
02:00 What Conductor does and why psych safety is misunderstood
05:30 Why psychological safety isn’t about being “nice”
11:00 What happens when teams don’t feel safe
16:00 Leadership pressure, COVID, and decision fatigue
18:30 Karren’s career before founding Conductor
21:00 Experiencing psychological safety first-hand
26:00 Values, boundaries, and accountability at work
30:40 Feeling unfulfilled and early signals of change
34:00 The moment Conductor took shape
37:00 Bootstrapping and early wins
39:10 Surprises and challenges in the early days
41:10 How founding changed Karren as a leader
44:00 Redefining success and protecting humanity
47:40 What Karren is most proud of
50:10 What keeps her going during tough moments
53:00 Habits that keep her grounded
56:00 What she wishes she knew before taking the leap
58:20 Advice for founders on the edge
01:02:30 Pride, resilience, and legacy
01:04:00 How to connect with Karren

Roman Galikov is a co-founder of Create Financial...they help founders and business owners take control of their money with smart, personalised financial advice. They specialise in wealth strategy, risk protection, and long-term planning - without the jargon. Think of them as the team that helps you build a financial engine strong enough to support your ambitions, not just your expenses.

Gavin Tye is a sales strategist and the creator of DealBuddi and co-founder of SixSides. With over 20 years of experience in high-value SaaS sales, Gavin has cracked the code on why businesses struggle to close deals and how they can transform their approach. Sales Market Fit aligns positioning, go-to-market strategies, and sales execution into a repeatable process that wins more clients with less friction. Learn how to stop relying on hope and start winning with a deliberate, proven sales strategy at salesmarketfit.co.

Links:
Founder Collective: https://founderscollective.com.au/founders-collective
FC's Newsletter: https://founderscollectivecommunity.substack.com/
Book a call with Gavin:
Conductor Software: https://www.conductorsoftware.com/

Connect with us:
Karren Jensen on LinkedIn: https://www.linkedin.com/in/karren-jensen-ceo/
Gavin on LinkedIn: https://www.linkedin.com/in/gavintye/