From Founder to Acquired Exec: Four Lessons from 14 Years

Midnight struck and my SSO token was invalidated, ending my first journey as a Founder turned Executive. 

I feel a mix of sadness from leaving talented colleagues and friends at iCIMS and excitement for the possibilities that come from founding a new company. Spending 10 years as Founder/CEO of Jibe and then four years as an executive at iCIMS proved to be both equally valuable experiences, and I wanted to share some of my lessons learned as a way to show appreciation for the experience.

Relationships are king

Building relationships and helping customers, partners, and co-workers fulfill their missions and advance in their careers has been the most meaningful part of my experience.

A top personal and professional highlight was officiating the wedding of two colleagues. 

Companies: simplicity and authenticity attracts better talent

If you want to attract the best talent, be easy to work for. Make your hiring process simple and aligned with your culture. This provides significant returns versus the effort required to do it.

Candidates: use the early bird advantage

As a candidate, try to apply for a job as soon as it opens. Being early doesn't guarantee you'll move on in the process but it is a benefit worth striving for.

Choose your GTM strategy: “restaurant” or “country club” - not both. Startups thrive with a "restaurant" approach

Focus on solving the problems of your ideal customers and rapidly growing your base. 

Mature, slower-growing companies do better as country clubs

When your focus shifts to stable revenue and profit targets, pivot to a "country club" model by increasing your prices, providing exceptional service, and fostering a tight-knit community of loyal customers. 

Avoid the trap:

Never try to be both, and ensure your team aligns with your chosen approach. I've learned this lesson the hard way. Early focus on a product-driven customer experience means you can focus on top-line growth and product innovation for longer. Ideally, you don't pivot to the country club-like experience until you have 9 to 10 figures of revenue.

Understanding hype vs. substance is more important than ever. Shrinking window of opportunity

These shorter and more intense cycles mean opportunistic windows are getting smaller, giving leaders with a superior understanding of their company's hype vs. substance a growing edge.

Competitive advantage from insight

Discerning this balance better than anyone else in your industry enhances your company’s growth and outcomes in the most strategic areas, like M&A and equity and debt financing.

Communication is key

Transparently share this understanding with your team and Board. I have seen exceptional leaders multiply their success by doing this well. I continually refine this skill due to its nuanced importance.