In this episode of the Chirp Podcast, Lee-Anne Scott welcomes Dennis Daigle, founder of Sidecar CTO Coaching.

The conversation revolves around the highs and lows of running startups, the evolution of the CTO role, and the significance of personal branding.

Dennis, a former startup founder and current CTO coach, shares his journey, lessons learned, and how he pivoted towards CTO coaching post-startup to guide other CTOs and tech leaders.

He emphasizes the need for CTOs to cultivate a strong vision, improve communication with their teams and CEOs, and establish a strategic approach to increase their brand visibility.

Lee-Anne & Denis also discusses the necessity of obtaining external coaching to foster progress, ensuring a smooth transformation path for different clients, and building a sustainable future with employees vested in the company's goals.

00:04 Introduction and Guest Presentation

00:38 Dennis's Journey as a Startup CTO

02:03 The Importance of a Coach in Startup Journey

02:55 Dennis's Current Role and Responsibilities

03:53 The Transformation Path for Startup CTOs

04:42 Dealing with Startup Failure and Lessons Learned

07:17 The Role of CTOs in Startups and the Need for Support

10:58 The Importance of Connecting CEO and CTO Roles

18:55 Challenges and Misconceptions for First Time CTOs

22:19 Overcoming Communication Barriers in Teams

22:40 The Power of Inclusion and Participation in Decision Making

24:20 The Importance of Team Alignment and Shared Vision

24:38 Connecting Team Efforts to Financial Outcomes

25:19 The Role of Feature Flags in Product Development

26:58 The Importance of Team Awareness in Business Sustainability

27:31 Innovative Approaches to Team Motivation

31:00 The Value of Personal Branding for CTOs

32:47 The Importance of Delegation and External Facing Roles

35:49 The Role of Coaching in Leadership Development

36:22 The Power of Personal Branding and Social Media Presence

38:03 The Importance of Servant Leadership and Transformational Coaching

38:49 Closing Remarks and Future Conversations

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Connect with Denis here: linkedin.com/in/daigledenis