#333 - Caitlin MacGregor, CEO of Plum- on successfully navigating market change

Tech Entrepreneur on a Mission Podcast

This podcast interview focuses on the entrepreneurial journey from the last 5 years to turn Plum into the best Talent Intelligence solution on the market. My guest is Caitlin MacGregor, Co-Founder and CEO of Plum

Caitlin MacGregor co-founded Plum in 2012 and has been an earlier guest on my podcast (#54 in February 2019).

She was voted "most likely to save the world" in her high school yearbook, foreshadowing her future as an innovative entrepreneur.

Before founding Plum, Caitlin built two other businesses, which gave her insights into the need for change around talent processes in the age of automation.

Fast forward, she was recently selected for the EY Entrepreneurial Winning Women™ North America Class of 2024, a program that supports high-potential women entrepreneurs.

Caitlin's drive to democratize access to psychometric data so that no one would have to rely on luck for someone to realize their superpower still underpins the core of the company - although how this is brought to market has evolved a lot.

And it's noticed - HR Tech voted Plum the best Talent Intelligence solution in the market in 2023

This inspired me, and hence I invited Caitlin back to my podcast. We explore the journey over the past 5 years. How did the market change in general - in particular in relation to how we attract and manage talent? She also shares what this means to all of us in the coming years. She then drills into how this has changed their priorities around product strategy and Go To Market. As we discuss this, she reveals some valuable lessons learned in product development, positioning, and segmentation, and how her role as CEO changed in this period of rapid change.

Here's one of her quotes

12 months ago, we were working on how we best resonate. It was really just about how you get to that Aha moment, and it really has nothing to do with the product and the solution. It was really like the Why. Why should you care about Plum? How do we align to a top three boardroom problem? And how do we connect to that strategic problem [....] so we were able to get into a strategic conversation with the right people that had the power to decide to do things differently.

During this interview, you will learn four things:

1. How Plum expanded from talent acquisition to full employee lifecycle management
2. What made them decide to bet on Enterprise instead of SMBs
3. What internal capabilities organizations need to develop and prioritize to gain competitive advantage and become the winners of the future?
4. How her role as a CEO had to change to effectively lead the rapidly growing organization that Plum is today.

For more information about the guest from this week:

• Caitlin MacGregor
• Website: Plum
• Plum Flourish Assessment

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