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“Comparison isn’t how you become successful; In fact, it’s probably the biggest distraction on the road to success” With Penny Bauder & Caitlin MacGregor

Comparison isn’t how you become successful. In fact, it’s probably the biggest distraction on the road to success. When I first started building Plum, I felt like I was doing something wrong because everyone around me seemed to be building a business better and faster. It wasn’t until I got to the other side of […]

Comparison isn’t how you become successful. In fact, it’s probably the biggest distraction on the road to success. When I first started building Plum, I felt like I was doing something wrong because everyone around me seemed to be building a business better and faster. It wasn’t until I got to the other side of successfully raising venture capital that I came to realize that there’s a lot of glamorization of startup culture, but not enough discussion on how pain-staking the journey really is, especially for entrepreneurs who don’t fit that well-recognized startup leader mold.


As part of my series about “Lessons From Inspirational Women in STEM and Tech,” I had the pleasure of interviewing Caitlin MacGregor, the CEO and co-founder of Plum. Caitlin has always been passionate about identifying people’s potential. That’s why, after building two businesses for other people, she founded Plum. Plum uses the power of Industrial/Organizational Psychology and AI to prepare enterprises for the future of work by unlocking the potential of their workforce. Caitlin is particularly passionate about supporting women to reach their full potential; she’s a regular speaker at women entrepreneur events and a champion of #movethedial, an initiative dedicated to increasing the leadership of women in tech. Caitlin was selected by Springboard Enterprises NYC as one of the top 10 businesses led by women.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I didn’t always know I wanted to be an entrepreneur; I studied international development in university. After I graduated, I started doing informational interviews with people with similar backgrounds who were in jobs that I found interesting. It was through one interview that I was presented with the opportunity to be the first employee building a social enterprise. By building that business from the ground up, I realized I had a knack (and passion) for entrepreneurship, which I never would have discovered if someone hadn’t seen that potential in me. That’s what inspired me to found Plum — to give every person the opportunity to be placed in a role where their potential and innate strengths can shine.

Can you share the most interesting story that happened to you since you began at your company?

What’s interesting is that everything about building a business has been so hard — except for the one thing that completely changed the direction of our company.

About a year and a half ago I was in the thick of raising venture capital, and an investor from the enterprise software giant SAP reached out on LinkedIn. She wanted to learn more about investing in us, and I assumed it would be a better use of time to speak to her in 6 months, so I said “no.” But she persisted, so I caved and said I would give her one phone call. And by the end of the phone call, it was clear that I didn’t need to sell her the vision of Plum — she was selling me on the future of Plum and how it would impact people’s lives in the future of work. She became an advocate and a champion, ensuring that everyone else in the investment process understood the value of Plum.

Not only did this relationship result in their fund investing in us financially, but we soon became part of their product App Center, our product became integrated with their human capital management system SuccessFactors, and we were selected as a part of their partner go-to-market strategy. Our partnership with SAP is now a key business strategy and impacts everything we do as a company. I can’t believe I almost closed the door on that investor, but I’m so glad she stuck her foot in the threshold, because it’s been the most important door I’ve ever opened.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Well, one night at 3 am I sent off an email to a potential investor introducing Neil, our Director of Product. Except I introduced him as our Director of Produce — which is particularly comical considering our company is named after a fruit. Lesson learned: don’t send important emails to investors at 3:00 in the morning!

Are you working on any exciting new projects now? How do you think that will help people?

Plum launched as a solution to help enterprises make better hires. We are now moving into the next phase of our vision — enabling employers to access predictive talent data at every stage of the employee lifecycle. This includes internal mobility, succession planning, learning & development, and identifying emerging leaders.

We’re able to do this because we offer the enterprise-grade scalability and scientific validity that allows our psychometric data (data capturing predictors of job success, like problem-solving ability, social intelligence, and personality) to touch 100% of the organization.

If organizations wanted to access psychometric data to make predictive talent decisions, they have traditionally had two choices. First, they could invest in consulting services. Due to their cost and lack of scale, organizations tend to reserve these consulting services only for vetting senior leadership candidates — the top 10% of an organization. Second, enterprises could invest in a pre-employment assessment. Unfortunately, these assessments require a high volume of people to already be functioning in the role who can take the assessment and create a benchmark for success. That’s why pre-employment assessments don’t often get leveraged beyond the bottom 20% of an organizational structure.

By scaling Industrial/Organizational Psychology practices with AI, Plum unlocks the potential of the middle 70% of the workforce previously untouched by psychometrics.

Ok super. Thank you for all that. Let’s now shift to the main focus of our interview. Are you currently satisfied with the status quo regarding women in STEM? What specific changes do you think are needed to change the status quo?

I am not satisfied with the status quo of how women in STEM are viewed and treated. The way I see it, the problem comes down to unconscious efforts to de-risk decision-making. You see it all the time in the venture capital world — when investors are making a decision of who they want to put capital behind, they are going with what they know. Steve Jobs, Mark Zuckerberg, Bill Gates — these are very clear-cut examples of successful entrepreneurship. As women, we don’t fit that mold. We sound different, we look different, we express ourselves differently, and we tend to lead differently. And as such, women can feel like they don’t fit the STEM status quo.

That’s why I believe in the power of example. I take every opportunity I can to speak to women in STEM and women in leadership to prove that there isn’t just one limited definition of what “success” looks like. And when we see more diverse examples of what success looks like, our cultural understanding of success will change.

In your opinion, what are the biggest challenges faced by women in STEM or tech that aren’t typically faced by their male counterparts? What would you suggest to address this?

Women’s leadership styles tend to come under more scrutiny than men’s. Ironically, there is a lot of research coming out stating that traits that have conventionally been marked as more “feminine” are actually the most sought-after leadership qualities — traits like kindness, supportiveness, trustworthiness, and integrity. In fact, the CEOs of over 180 companies — including JPMorgan and Amazon — recently signed a pledge committing to conscious leadership principles that include delivering value to customers, investing in employees, dealing ethically with suppliers, and supporting the communities where they work. When women’s voices are brought to the table, so are these priorities. Businesses shift from a mindset where the bottom line comes first at the expense of the people, to a place where the love and care of the people is the number one priority — and financial profit is a result.

What are the “myths” that you would like to dispel about being a women in STEM or tech? Can you explain what you mean?

A lot of women tech leaders start their companies with and/or lead alongside their husbands, and there is a lot of stigma surrounding that decision. What they don’t realize is that founding a company with your spouse builds an automatic support system to tackle the challenges of entrepreneurship. I have found it critical in protecting my mental health, especially since startup founders are twice as likely to suffer from depression, 10 times more likely to suffer from bipolar disorder, and twice as likely to have suicidal thoughts.

The same stigma is directed towards women leaders who choose to continue leading their business while having children. People see starting a family as a step back. But it’s actually another secret weapon! Building a business while starting and raising a family has widened my capacity for everything — my capacity to care, my capacity to multi-task, my capacity to persevere when things get tough. And the rewards of pursuing both passions — family and business — without sacrificing one for the other are so worth it.

What are your “5 Leadership Lessons I Learned from My Experience as a Woman in STEM or Tech” and why?

1. Comparison isn’t how you become successful. In fact, it’s probably the biggest distraction on the road to success. When I first started building Plum, I felt like I was doing something wrong because everyone around me seemed to be building a business better and faster. It wasn’t until I got to the other side of successfully raising venture capital that I came to realize that there’s a lot of glamorization of startup culture, but not enough discussion on how pain-staking the journey really is, especially for entrepreneurs who don’t fit that well-recognized startup leader mold.

2. Surround yourself with the right examples. This is related to the pervious point; when I was striving to be a better leader, I felt different from the examples presented before me. That felt very lonely. It was when I was introduced to the concept of conscious leadership and discovered examples like Whole Foods and Patagonia, who are committed to their impact on their people and the planet — just like me. I learned that striving to go beyond the status quo in my leadership style didn’t make me wrong — I just had to surround myself with the right examples that I could learn from and strive to be like.

3. It’s not enough just to find a problem you can solve — you need to believe that it’s a problem worth putting everything on the line to solve. I have the perseverance to get through the hardest seasons of running a business because I know our cause is worth it. The consequences of Plum not being available to enterprises are too great. I don’t want to live in a world where people are without work because organizations have not figured out how to unlock the potential of their applicants and employees. When you have a cause like that — a cause that’s too important to you that you can’t not do anything about it — that’s what will give you the perseverance to keep going, in the highs and lows of entrepreneurship.

4. Building a business isn’t a sprint; it’s a marathon. And believe me, it’s almost always a longer marathon than you expect. You have to take care of yourself mentally, physically, and emotionally. You have to have long-term support and balance because there is nothing that is a bigger threat to your business than burn-out. For me, that meant not putting my family life on-hold for my business. That way, even on the days when it felt like everything was going wrong building Plum, there were things outside my company that were still fulfilling me.

5. Take time for the things that matter. This lesson is related to the previous point; as an entrepreneur, there are always things you can be doing to make your business better. But you have to upkeep healthy boundaries and take time for what fills you up because time is a limited resource that you’ll never get back. In the beginning stages of building Plum, I took a pause to take a trip with my mom, and two years later she passed away. Even though at the time I thought I physically could not take the time to travel with my mom, I never once regretted doing it.

What advice would you give to other female leaders to help their team to thrive?

I always emphasize the importance of relationships. So much success in the tech industry comes from people believing in your potential and advocating for you. And that starts by building a strong network. As women, we enter the tech space at a disadvantage because our networks tend to be a fraction of the size of our male counterparts’ simply because we’re the outliers. As women, we need to intentionally spend the time building a network that can support us, connect us, and advocate for us.

What advice would you give to other female leaders about the best way to manage a large team?

To drive business outcomes, you need to have alignment. When you design your operation plan, you need to think about it as a collaborative operating system. A lot of the time, when business leaders design how they run their organization, they start from a place of trying to track completion rates — in other words, answering the questions, “Are people working? Who is slacking?” Instead, leaders should approach their operation plans answering the question, “How do we unlock the potential of our people to keep everyone aligned?”

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped you get to where you are? Can you share a story about that?

I am so thankful for Jodi Kovitz, founder and CEO of #movethedial, a movement dedicated to advancing women in tech. When I decided to raise venture capital, I knew I didn’t have the necessary connections or network and that the odds were stacked against me. I reached out to Jodi as she was starting #movethedial. I helped her as she began her journey as an entrepreneur, and she helped me by advocating for me and giving me credibility as I began to interact with future enterprise customers. She set up a 30-minute meeting between me and an investor. The investor only expected to give me some advice and offer to connect me with some of her contacts, but after that 30-minute meeting, she knew she wanted to invest.

How have you used your success to bring goodness to the world?

My mission is to make Plum a workplace where people are given opportunities based on their potential, not past performance or what they look like. 50% of Plum’s employees are women — a group that tech companies in particular tend to exclude. Of those women, almost all of them come from backgrounds that aren’t technology. We have HR practitioners and consultants turned product managers, retail specialists turned customer success managers, and moms re-entering the workforce who took working at Plum as an opportunity to enter tech for the first time. In fact, 95% of the women at Plum had never previously worked in tech before starting at Plum. Very little on their resume indicated that they would be a good fit, yet we were able to dig beneath the surface to unlock their potential — and now these women are thriving in their careers.

Plum’s vision is to make the world a better place by bringing the power to unlock workforce potential to every single organization.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I would advocate for a movement that banned resumes from the hiring process altogether. Resumes only demonstrate a semblance of someone’s past performance and have absolutely no predictive ability into someone’s future potential. Not to mention, they’re incredibly biased. One study found that resumes with Asian-origin names are 28% less likely to be shortlisted for an interview than resumes with Anglo-origin names.

At Plum, we’ve seen firsthand that this movement could work. One of our customers banned resumes from their hiring process altogether…and ended up finding better candidates. As a result, their number of failed hires dropped and their annual turnover rate went from 30% to 6%.

Can you please give us your favorite life lesson quote? Can you share how that was relevant to you in your life?

It’s not a quote per se, but the way my mom lived her life is my biggest life lesson. My mom kept growing as a person. She got better as she aged. She was also someone who inspired others, including me. My mom passed away two years ago now, and I want to carry on her ability to grow and inspire others.

Is there a person in the world with whom you would love to have a private breakfast or lunch with, and why?

I would love to get the opportunity to meet Jeff Bezos. This past summer, Amazon committed to upskilling 100,000 employees to future-proof their workforce. I have a feeling that if I had the chance to tell Jeff Bezos what we’re doing at Plum to prepare enterprises for the future of work by unlocking people’s potential, the result would be a kickass partnership!

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