This tech founder helps make work feel less like a chore

Plum CEO Caitlin MacGregor helps match job candidates with roles where they’ll flourish.

Imagine having a job you love so much that each morning, you jump out of bed excited to start your work day. While that experience may be somewhat rare, Caitlin MacGregor is one of the fortunate few who are familiar with that feeling. She believes anyone can find deep fulfillment in their work — as long as their job aligns with their skills.

MacGregor is the CEO and co-founder of Plum, a Waterloo, Ont.–based online talent platform that helps companies hire candidates who are best suited to the positions on offer. In addition to assessing work experience and education, the software analyzes innate skills, such as how well a person might communicate and collaborate with others, and then matches them to roles where they’ll flourish. Plum also provides employers with data that can help them develop their teams and transform workplace culture.

Prior to launching Plum, MacGregor helped build two businesses: a clothing company and an educational software company for students with learning disabilities. Those experiences taught her that hiring the wrong person can be a costly mistake — and that there can be discrepancies between how a candidate comes across on paper and how they perform on the job. In response, MacGregor and her husband, Neil (who was also her coworker at the time), decided to devise a better way of connecting people with meaningful jobs. They realized they could rework the assessment functionality in their edtech software so that it could be used as a tool to match job-seekers with ideal opportunities. After the pair rebuilt their intellectual property from the ground up, they launched Plum in 2012.

Since then, the company has played professional matchmaker for many major clients, including Whirlpool and Citibank; its current roster includes Scotiabank, Syneos Health and Protexxa. Here, MacGregor shares her thoughts about how to help employees flourish, how to optimize hybrid work arrangements and how to read between the lines of a resume.

What valuable information does a resume leave out?

When I made my first hire for the education tech company, my executive coach said that if I screwed up, it would result in a loss of $300,000. I ended up using a personality and cognitive assessment tool that helped me screen all 80 applicants. Two candidates stood out. One was perfect on paper: He had a master’s degree in education and five years of relevant work experience. The other person had two art degrees and her only work experience was seven years of waitressing, but she scored in the top third percentile of the workforce for her overall productivity. I ran an experiment and hired them both. Within three months, the guy was only doing 10 percent of his work; he was let go. The woman was doing all of his work, plus her own. Within a year and a half, she replaced me as acting president. If I had relied on a resume, there’s no way I would have shortlisted her for that interview, let alone hired her.

How is the tight job market affecting how companies think about employee growth?

In this post-COVID 19 era, there’s a realization we need to invest more in employees. It is so much more cost-effective to retain the people you have — but that takes effort. There has to be an investment in things that matter to people, and a big part of that is career development — individual growth as well as career mobility opportunities. In the past, talent management didn’t receive as much attention as talent acquisition, but we’ve seen an increase in the number of people who are excited to use our data in talent management so that they’re better able to support employee development. Plus, a lot of the jobs that we’re going to see emerge over the next 10 to 20 years don’t exist in the market right now. Companies are going to have to upskill those roles. Do you want to upskill complete strangers, or do you want to upskill the people you already have?

What can leaders do to encourage the best performance from employees?

The best way is to align their strengths to the strengths that are needed on a daily basis. For example, if somebody feels fulfilled because they were able to come up with an out-of-the-box idea, then put them in a job where innovation is a top priority. That sense of accomplishment will motivate them to continue to do better and stay longer. You can also measure key behavioural indicators like key performance indicators. What are the behaviours that drive success in a role? Plum analyzes individual skills and behaviours to determine a person’s top talents, potential job performance and fit. The idea is to align the workforce around operational goals. If you align those to the behaviours that a person innately has — that’s your recipe for productivity.

Happy employees make for healthy companies. How can employers foster a positive work culture?

Our motto at Plum is “When people flourish, business thrives.” Supporting your people allows them to support the success of the business. The most important thing is consistency with what you say and what you do. People lose engagement when they hear one thing and see something else. There’s often a top-down approach where HR tries to disseminate information. The command-and-control days of leadership and culture are over, and it’s much more about having a bottom-up strategy that is evidence-based. For example, if you are prioritizing automation and implementing generative AI, do you know what departments or individual contributors can be the early adopters and show examples of success to late adopters? Or are you treating everybody exactly the same and trying to get everyone to just obey the new direction of the company? If you can align strategy, culture and people in the right roles, you’ll be able to accomplish your business outcomes far more efficiently.

There’s a growing push to have employees physically in the office more often. What can employers do to ensure the commute is worth it?

Consider what you are trying to accomplish in person that you can’t accomplish remotely. When you’re coming in three days a week, are people in back-to-back meetings with external stakeholders where they’re on a computer the entire time anyway? Or are there specific things that are happening in person that you can’t replicate over Zoom? What is the unique value proposition that you are trying to accomplish by having people in the office, and are you truly leveraging that? Are you using that time to foster cross-departmental interactions and build trust?

What was the best lesson you learned from a boss early in your career?

The advice I was given by my first boss, Oliver Madison: “Hire people for their potential and then grow them on the job.” Oliver showed me this in practice when he hired me. I had never built a business from scratch. But he saw my potential. He hired me and then kept giving me more responsibility, never putting a glass ceiling on me. I’m not sure I’d be the CEO of my own tech company if Oliver hadn’t seen my potential.

 
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