Offboarding isn’t just a goodbye—it’s a strategy. Andy Hamilton dives into why this often-overlooked process can make or break employer branding. We explore how When is redefining offboarding to foster strong alumni networks, improve team dynamics, and boost long-term organizational growth.

In this episode, we look at offboarding, employee experience, employer branding, alumni network, career transitions, team dynamics, leadership, and startup challenges in the tech industry. From building transparent teams to balancing salesmanship with technical skills, Andy shares actionable insights that bridge the gap between career growth and business success.

Key Takeaways:

* Offboarding is a critical yet neglected part of the employee lifecycle.

* A positive offboarding process strengthens alumni networks and enhances employer branding.

* Younger employees value respectful transitions and share their experiences widely.

* Financial costs of poor offboarding practices can hurt long-term growth.

* Leadership must assign a dedicated owner to the offboarding process.

* Transparency and communication are essential to team dynamics and retention.

* Founders need to align technical skills with sales credibility for startup success.

* Startups benefit from hiring committed engineers and fostering supportive cultures.

* Career growth in tech requires balancing coding skills and architectural insights.

* Co-founders should prioritize alignment and clear communication to navigate challenges.

* Transitioning business models can open up new revenue streams.

* Entrepreneurs must adapt to market changes and remain flexible to pivot.

Chapters

00:00 Philadelphia Roots and Real Estate Ventures

05:57 The Importance of Offboarding in Employee Lifecycle

11:56 The Financial Implications of Offboarding

17:54 Navigating Career Moves with Intent

23:18 Navigating Career Growth in Tech

30:03 Salesmanship vs. Technical Reality

37:41 Transitioning to Short-Term Rentals with Apartments Jet

44:19 Building and Leading Effective Teams

Connect with Andrew Hamilton is the Co-Founder and CEO of When, an AI-powered offboarding platform and severance solution. https://www.linkedin.com/in/hamiltonac8/

William Tincup LinkedIn: https://www.linkedin.com/in/tincup/

Ryan Leary LinkedIn: https://www.linkedin.com/in/ryanleary/

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