On the TechTO stage ×2
Caitlin MacGregor of Plum presents Keeping The Lights On
Watch on YouTube ↗Early-Stage Startup Lessons Learned
Watch on YouTube ↗First seen on a TechTO stage in 2016. Every TechTO talk is searchable — ask the archive about Caitlin ↗
In their words
The biggest responsibility of being the CEO is keeping the lights on, because overnight success does not happen overnight.
How much sales training did I get in my first two years of business? Zero. And I could tell you that all the energy that was put into learning how to fundraise and learning how to speak to investors — if even half of that had been put into sales training for myself and my team, we probably would have got that hockey-stick sales growth a lot sooner.
Go where your competition can't follow. It took me a long time to realize I needed to get out of the very crowded space of talent acquisition into an underserved part of the market, which is talent management.
Around the web ×2
Quick answers
What is Caitlin MacGregor known for?
Co-founding Plum in 2012 and building it into a psychometric assessment platform used by large employers including Hyundai, Scotiabank and Whirlpool. Phenom acquired Plum in April 2026.
What did Caitlin MacGregor do before Plum?
She built two businesses for other people before starting her own, as she told the TechTO stage in 2019 — a clothing company and an educational software company for students with learning disabilities, according to MaRS. Plum grew out of reworking the assessment functionality in that edtech software.
What has Caitlin MacGregor said on the TechTO stage?
In 2016 she argued that a CEO's first job is making payroll and that founders are coached on pitching investors when they should be trained on sales. In 2019 she said chasing small businesses cost her years, and that the answer was going upmarket to enterprise — where the competition couldn't follow.