From Layoff to Launch: An Entrepreneur's Journey to Creating a Startup in the HR Tech Space

 

In this episode of Value Drivers, Peter Ho sits down with Andy Hamilton, a serial entrepreneur and the CEO and co-Founder of When, a company revolutionizing the employee offboarding experience. Andy shares his journey from real estate tech to founding When after personally experiencing the challenges of navigating health insurance and limited support during a layoff from Expedia.

The conversation explores When's approach to offboarding, highlighting the company's use of AI and concierge support to help exiting employees find affordable alternatives to COBRA and access essential resources like outplacement services and 401k rollover guidance. Andy discusses the financial benefits for employers, including reduced claims and improved brand reputation through a positive offboarding experience.

He also delves into his experiences as a serial entrepreneur, offering insights on fundraising, building a market for a novel solution, and the importance of finding the right investor partners who provide more than just capital.

Key Takeaways

Offboarding is a crucial stage of the employee lifecycle that is often overlooked. Andy's personal experience with a subpar offboarding process after his layoff from Expedia ignited the idea for When, a company dedicated to improving the employee exit experience.

When's B2B model focuses on providing employers with a technology-driven offboarding solution that benefits both the company and the exiting employee. The platform seamlessly integrates with existing HR systems to offer personalized support, including health insurance guidance, access to outplacement services, and financial planning assistance.

COBRA is often the most expensive health insurance option for both employers and employees. When helps employees explore alternative and more affordable health insurance plans through the ACA marketplace and private options, leveraging AI and a concierge team to guide them through the decision-making process.

When's ROI model demonstrates significant cost savings for employers by mitigating claims and reducing dependence on COBRA. The company conducts upfront ROI analysis for potential clients and tracks claims data year over year to showcase the financial benefits of their solution.

A positive offboarding experience can protect an employer's brand reputation and foster goodwill with departing employees. When prioritizes employee satisfaction through exit surveys and strives to make the transition as smooth as possible, recognizing that former employees can become brand ambassadors, future clients, or even boomerang employees.

Building a market for a novel solution requires patience and persistence. Andy acknowledges the challenges of creating awareness for the importance of offboarding and convincing companies to adopt a new approach. He emphasizes the need to be patient with sales cycles and tailor the message to resonate with decision-makers.

Finding the right investor partners is crucial for startup success. Andy values partners who offer guidance, support, and network connections beyond financial investment. He highlights the role of VCs as mentors and advisors who can help navigate the challenges of building and scaling a business.

Chapter Summary

(00:00:53) Chapter 1: Introduction

(00:01:45) Chapter 2: Entrepreneurial Journey and the Birth of "When"

(00:03:60) Chapter 3: When's Business Model and Value Proposition

(00:07:28) Chapter 4: Partnerships and the Competitive Landscape

(00:13:28) Chapter 5: Leveraging AI to Simplify Healthcare Decisions

(00:16:47) Chapter 6: Funding, Growth, and Key Performance Indicators

(00:23:17) Chapter 7: Overcoming the Sales Challenge

(00:37:06) Chapter 8: The Future of Offboarding and When's Vision

Book/Podcast Recommendations

Grant by Ron Chernow

https://www.amazon.com/Grant-Ron-Chernow/dp/159420487X

How I Built This with Guy Raz

https://podcasts.apple.com/us/podcast/how-i-built-this-with-guy-raz/id1150510297

 

Resources:

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