Caitlin MacGregor: Redesigning the hiring process and transforming company culture.


Caitlin MacGregor is the Co-Founder and CEO of Plum, which combines advanced Industrial/Organizational Psychology with AI to help organizations predict the quality of their hires, develop their employees, and transform company culture. Thanks to Caitlin’s vision, Plum customers can spur employee success, diversify their teams, and align talent to business needs by predicting potential.

1.  Plum started in 2012 and is now considered a leader in Canada’s tech sector. Tell us about the Plum Journey.

Before starting Plum, I built two businesses for other people. As I was building the second business, I saw so clearly how broken the hiring process was. I began to see and learn about psychometrics and how valuable they can be in the hiring process. It was part of the formula we were using – but we were tapping into a very expensive consulting model. I saw I could use the science – more specifically, Industrial/Organizational Psychology – that’s often used only for executives and senior leaders, for the whole workforce. In short, I saw an opportunity to democratize best practices with a subscription-based software model. Industrial/Organizational Psychology is an entire academic field with the sole purpose of helping companies recruit top talent – but it was so limiting with respect to both cost and reach. At Plum, our software provides all levels of hiring access to incredible science and technology.

A little bit about the journey…

When you run a start-up, what you’re looking to build will take more time and resources than you could have ever imagined. Two years in, when we were faced with a particularly difficult season, my co-founder Neil turned to me and said, “You’ve run two businesses for other people. If you walk away, and you end up building another company, do you feel confident in anything you do without Plum?” I realized that if I want to continue to build great businesses in the future, I can’t build them without Plum’s human potential quantification capabilities, because I know from my own experience that great businesses are built on great people.

Now, to any aspiring entrepreneurs I talk to, I advise them to ask themselves the question, “If I wasn’t doing this, what would I be doing instead?” Whenever I ask this question to myself, I always realize that Plum is the absolute best thing I could be doing. If I wasn’t at Plum, I’d be running businesses that wouldn’t be successful because I wouldn’t have the best people. That was the perseverance I needed to go through all the highs and lows that came with starting a business. And yes, there are a lot of lows. But now, six years into Plum, we have gone from surviving to thriving –  and I’ve seen the idea I believed so passionately in for so long has come into fruition.

2.  You are clearly passionate about helping companies find the right people for various roles, and helping job seekers understand themselves, and market themselves more effectively. Does this passion come from a personal experience?

When I was building that second business, we kept on hiring diamonds in the rough using the expensive (but clearly effective) consultant model. I just knew this idea could expand beyond the small market it was serving. And now I see, when you start using a predictive tool like Plum, you also end up with a much more diverse group of applicants.

3.  Share your top three insights about Hiring for Diversity.

#1: As I learned from the book What Works: Gender Equality by Design by Harvard Kennedy School professor Iris Bohnet, if we truly want to hire a diverse group of people, we need to redesign the process. The traditional resume-first hiring process simply cannot predict the best future hires, nor can it fix the lack of diversity in so many industries. For instance, if you shortlist 30 applicants out of 300 based on resumes alone, you’ll ultimately end up with a homogeneous group narrowed down by subjective biases triggered by a 6 second scan of a resume.

#2: Use the job description as a tool to encourage people to apply, not as a tool to weed people out. The traditional method of using criteria in a job description is limiting and results in certain people self-selecting out of the process. We need to properly define what success looks like – beyond the job description – and then we can’t let subjective elements get in the way of the hiring decision.

#3: Don’t just stop at hiring. Customers are asking us to help them optimize their existing staff. We’ve listened carefully and in the last 18 months, we’ve moved beyond a hiring tool. We can now help companies optimize their current employees for success – and ensure diversity remains front and centre.

4.  Tell us about your journey to raise capital. What’s on the horizon as we speak?

We raised two million dollars with a seed round with angel groups and institutional investors. It was a long journey that took two-and-a-half years. It was a slow trickle – we didn’t raise it all at once. I learned that you can’t get as far because you are growing more slowly than you would if you had raised a large sum all at once. The benefit is that we had the opportunity to take the time to see what worked and what didn’t. But it was also harder because we were compared to businesses that raised large sums all at once.

Ultimately, we were able to be successful with what we raised and we’ve had great momentum and growth. We’re currently on the journey of funding our next round. This time, we’re motivated to raise a larger sum in one go so we can invest in some big bets.

5.  How does it feel to be seen as someone who is “making waves” and “breaking the glass ceiling”?

Amazing. Five years ago, I was accepted into the Communitech Hyperdrive Accelerator Program (now called Rev) in Waterloo to help grow Plum. It was a great opportunity, but I was constantly asked to speak on panels because I was one of two female CEOs (out of eleven total) in the program. Now, thanks to organizations like Fierce Founders, there’s been a complete shift – there are a lot more women CEOs who are great role models for the tech and start-up communities, and beyond. It was an honour to be a role model 5 years ago when women CEOs were so rare, but it’s even more amazing to be a mentor to women and help change those numbers.

And as much as I’m a role model for others, I also need role models. My hope is that one day there will be a female equivalent of Mark Zuckerberg in the start-up world.

6.  What have been your favourite and most challenging parts about being a tech entrepreneur?


I spent many years building businesses for other people. Now I finally get to do it for myself. And I’ve demonstrated that I can do it – the survival part is behind us. Nothing is more rewarding than overcoming such a huge challenge.

Most challenging:

To get out of survival mode and into sustained success. It was a long five years. There’s a belief out there that it happens in three years, and if it doesn’t, you should fail fast and something is wrong. But that’s a myth. My hard work and determination paid off and I’m one of the statistics for success, not failure.

7.   What’s next for Plum?

Plum’s mission is to provide every employer with the data they need to predict with certainty the quality of their hires, develop their employees, and transform their company culture – in other words, quantify human potential at every stage of the employee journey.

Moving forward, it’s all about scaling – our products, the market, our R&D beyond psychology to AI/machine learning. We’ll work with larger and larger companies and we’ll continue to grow our amazing team.

Guest writer: Jori Lichtman

articleElektra Simms