Skills
About
Caitlin MacGregor, CEO and Co-founder of Plum, is passionate about helping people reach their true potential. That’s why, after building two businesses for other people, she founded Plum – to help organizations fully leverage the human potential within their workforces. With Plum, business leaders gain access to vital talent data that aligns employees with roles where they’ll flourish, setting the stage for the entire business to thrive. She is a regular speaker at global events, including CES, Human Resource Executive HR Technology Conference & Exposition, Americas’ SAP Users’ Group (ASUG) Women Connect, HRCI Higher Standards Summit and more. She is also a sought-after guest on podcasts, including Recruiting Daily, The Recruitment Flex Podcast, and 3Sixty Insights. In addition, she has been quoted in the NY Times, Financial Post, The Globe and Mail, The Record, Global News, Human Resource Executive, and Benefits Pro. Caitlin was selected for the EY Entrepreneurial Winning WomenTM and the Worthy 100. She is also a Bronze Stevie® Winner for Best Female Entrepreneur in Canada and a gold GLOBEE® Women World Awards winner for Achievement in Innovation. She was named an Inspiring Leader by InspiringTM Workplaces. Before founding Plum, Caitlin was the first employee at a social enterprise called Me to We Style, where she built the company from scratch as Director of Operations. She then joined goQ Software, an educational technology company, as President, where she opened and ran the new U.S. Head Office. Caitlin is passionate about equipping business leaders with the talent data they need to match their talent to the right roles, as companies adapt in the age of automation. Caitlin is a regular speaker at women entrepreneur events, and she was selected by Springboard enterprises NYC as one of the top 10 businesses led by women.
Caitlin MacGregor
Published content
expert panel
AI is a powerful tool—one requiring strong guardrails to ensure responsible use. CISOs play a key role in making this happen. As artificial intelligence becomes more integrated into daily operations, the need for strong governance grows alongside it. For many companies, that responsibility increasingly falls to the Chief Information Security Officer (CISO). But effective AI governance isn’t just about risk mitigation—it’s about building systems that are transparent, secure, and aligned with business and regulatory expectations from the start. Below, the members of Fast Company Executive Board share how CISOs can help shape compliant, ethical AI adoption without stifling business innovation.
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Building bridges behind your screen is easier than you think. Introverted leaders often thrive in quiet, reflective environments, but the challenge of leading remote teams may sometimes feel cumbersome. In a fully virtual company where in-person interactions are limited, creating a sense of community and connection is essential, but engagement is still incredibly difficult for those who prefer to keep their head down, letting their work speak for itself. However, when introverted leaders need to step out of their comfort zones, there are strategies they can apply to foster a stronger, interactive virtual team. If you consider yourself an introvert and are trying to establish better points of contact with your virtual team, the leaders of Fast Company Executive Board each share their best practices for building a stronger digital community, creating more deliberate, thoughtful, and personal connections on the job.
expert panel
Mar 6, 2025
17 lessons on a mind shift in strategy and the future of innovation The implementation of artificial intelligence is here to stay. For most companies, it is redefining their leadership approach to engaging in business and uncovering innovative solutions to assist customers with their pain points like never before. However, business leaders still agree that human insight alongside AI usage is still a key factor in maintaining the proper balance of ethical practices in handling data analysis and compliance updates. Below, 17 leading experts from Fast Company Executive Board each share how the rapid advancement of AI has reshaped their company's business model and what other leaders can learn from it.
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Feb 27, 2025
Here's why you should sack "quality of hire" and focus on retention instead.
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Despite DEI rollbacks, some company leaders remain rooted in their initial choice to prioritize inclusivity for their customers and staff. Amid recent pushback on DEI policies across the federal government, private company executives are also rolling back on their organizations’ earlier commitments to invest in DEI program initiatives for employees and the communities they serve. However, other brand leaders are determined to remain connected with a broader, stronger, and more diverse audience base to fuel company growth. And whether it relates to team functionality or delivering high-value products and services, these 10 experts from Fast Company Executive Board know just how important it is to build personalized, user-friendly products and processes that benefit all. Below, featured members each share one way for companies to embed DEI into business design for more inclusive products and work environments.
expert panel
Learn how to leverage your unique strengths and community connections to unlock personal and professional growth. Leaders often succeed by building on their unique strengths and tapping into the power of their communities. Whether through strategic collaborations, mentoring others, or applying specialized skills in new ways, leveraging these resources can accelerate personal growth and professional advancement. However, identifying the best ways to harness your talents and network effectively can feel overwhelming without the right guidance. To help, Fast Company Executive Board members offer practical strategies for using your unique skill sets and community connections to create meaningful growth opportunities.
Company details
Plum
Company bio
Revolutionary talent assessment provider Plum knows when people flourish, business thrives. With a universal design, Plum uses objective data to measure and match human potential to job needs, enhancing talent decisions across the employee lifecycle. Featuring unmatched scalability, Plum empowers organizations to quantify job fit, improve quality of hire, identify potential, provide personalized career insights and create high-performing teams from one platform. Plum has been named a Top HR Product of the Year by Human Resource Executive, won an HR Tech Award from Lighthouse Research & Advisory and secured High Performer status with G2.