Caitlin MacGregor
CEO | Plum
In this interview, we spoke with Caitlin MacGregor, Co-Founder and CEO of Plum, a platform designed to unlock human potential by aligning people with roles that match their strengths.
Caitlin shared how Plum evolved beyond hiring into a full talent management solution, the importance of durable skills, and her leadership journey.
Plum started with a focus on hiring and grew into a full talent management platform. What was the turning point that made you realize the opportunity was bigger than pre-hire?
I think it’s a combination of two things. First, when we started Plum, we wanted to differentiate in three ways. There were decades of psychometric assessments out there, but they were expensive, required costly consultants, and provided a poor user experience. We wanted to democratize access to this highly predictive data — data that’s four times more accurate than a resume for predicting success — so anyone could be matched to any role.
We designed an assessment people actually enjoyed taking. Creating a Plum profile is like a LinkedIn profile, but focused on what you could do if given the opportunity. We never limited it to job seekers. Employees started taking it organically, showing us it was useful beyond hiring.
The second pillar was best-in-class science. Our science isn’t just for selecting candidates — it predicts long-term performance and retention. That’s valuable for both hiring and managing talent.
The third pillar was scale — how to match people to roles quickly and efficiently without costly consulting. Our enterprise customers started saying, “This is great for hiring, but we also need it for reorgs, upskilling, internal mobility.”
Three customers asked to use Plum with existing employees. I said, “Go ahead.” That was always the goal — match anyone to any role. We hadn’t built the talent management interface yet, but it worked.
Those pilots proved the model. Customers were thrilled. “We never would’ve selected these people without Plum surfacing them.” In 2021, we officially expanded the platform to include talent management. That’s where real scale happens — one universal dataset unifying all your people and matching them to all your roles.
You talk a lot about unlocking human potential. What’s one underrated signal or data point you believe companies should be paying closer attention to?
I think the opportunity is thinking through hiring and growing talent through a different lens than traditional organizations have. Historically, resumes were checked for things like knowing Microsoft Word, coding in Python, using Salesforce. That made sense 20 years ago.
But today, I don’t care if you’ve used a desktop for 20 years. I want an AI-first approach. How do you produce 2, 3, 4 times the output using AI? It’s not about starting from old ways and layering on AI — it’s about approaching it AI-first from day one.
You won’t find those signals on a resume. You won’t see “prompt engineer” experience. Even if someone took an AI course, that doesn’t tell you they’re adaptable or innovative. There’s an opportunity to focus on durable skills — skills like innovation, communication, execution, adaptability. Those will endure no matter how jobs evolve.
Technical skills are perishable. A report last year said their shelf life is 2.5 years — some now say it’s months. If I want to be good at Excel, I can ask ChatGPT to write formulas. I can learn on the job.
We need to prioritize durable skills because they’re four times more predictive of performance and retention. Perishable skills should be a minimum requirement — like needing a driver’s license to drive. Durable skills should be the focus. That shift changes who we screen in, who we interview, how we look at talent.
You’ve been vocal about the flaws in traditional hiring systems. What do you think is the biggest myth companies still believe about assessing talent?
I think the biggest myth is that candidates don’t want to take an assessment. We have 93% completion rates for Plum profiles, and 94% of people say it gives them enormous value. People share their results on LinkedIn by the minute.
Gen Z, especially early career talent, is hungry to be seen for their potential — not just what they’ve done. They want to stand out for more than internships or degrees. They want to be seen for what makes them exceptional and likely to succeed long-term.
Assessments are a win-win for candidates and employers. They also enhance the employer brand — showing you care about setting someone up for long-term success.
As a leader, how do you make sure your own team is placed in roles that energize them and align with their strengths?
We drink our own champagne. Every person applying for a role at Plum completes a Plum profile. We interview those with the strongest matches who meet the minimum requirements.
During onboarding, we review their Plum profile together: “How do you like to work? Communicate? How can you be supported?” We set development goals.
Twice a year, we revisit their profile for developmental conversations. “What’s driving you? What’s draining you? Where do you want more support? Where are new opportunities?”
I can reference team members’ profiles to coach managers, or support individuals when I see they’re drained by something. If decision-making is draining a team, and that’s one of my top talents, I step in.
It’s about matching people to roles they’re statistically suited for, using it in conversations, and destigmatizing the fact we’re all energized by different things. It’s about making it common language so people feel supported and positioned for success.
Building Plum required not just innovation, but education. How did you convince enterprise clients to embrace a new way of thinking about talent?
A lot of it was building proof points — like a 93% completion rate. We’d show testimonials of people thanking employers for the opportunity, sharing their profiles on LinkedIn.
We showed scientific validity. We did bias audits to comply with New York law and prove no adverse impact on protected groups. We’d provide reports showing no bias, predictive validity, and user satisfaction.
Working with highly regulated industries like financial services gave us credibility. Their teams of psychologists, compliance officers, privacy and security teams vetted us.
Education was about proving the product, showing scientific validation, and having third-party audits. Those proof points reduced fear for new clients because they saw we’d already passed rigorous standards with other large institutions.
You’ve received major recognition for your leadership. What’s one personal habit or mindset shift that’s helped you grow as a CEO over the past decade?
I’ve been lucky to work with executive coaches throughout my career. One of the biggest shifts came before COVID, when a coach helped me realize my self-worth was tied to getting things done — overachieving, exceeding expectations.
That mindset made me transactional at work. I left other parts of myself — the caring, supportive side — at home. I focused only on completing tasks, moving quickly.
But great leadership is relational, not transactional. It’s about caring whether people feel safe, supported, able to succeed. My coach helped me see that I already knew how to be relational outside of work — as a mother, wife, friend — but wasn’t bringing that into work.
Integrating those sides of myself changed how I lead. I became more authentic, more supportive. I started leading with empathy, care, and vulnerability — not just command and control.
During COVID, we learned if you only focus on the bottom line in crisis, people won’t be able to show up. You have to care about people first. I’ve carried that forward, and it’s shaped how I build culture and support my team.
Caitlin’s approach to leadership, talent, and human potential challenges companies to rethink how they measure and support success. Her insights remind us that building strong, future-ready workplaces requires prioritizing durable skills, authentic leadership, and a people-first mindset.
Interested in sharing your story? Contact us at info@fip.agency to be featured.
Dilara Cossette
Founder
Dilara Cossette is the founder of FIP, a boutique demand generation agency helping HR tech companies accelerate growth. With deep experience in B2B, she partners with HR tech companies to build strategies that drive demand, grow pipeline, and strengthen brand presence. Passionate about workplace culture, Dilara spotlights insights from HR tech innovators through the HR Connect interview series.
