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
You have more control over your travel schedule than you realize. Apply these expert tips to emulate aspects of your normal routine. While some executives look forward to engaging in business travel opportunities, enabling them to see the world while representing their establishments and growing their network, other professionals dread being away from their families for any amount of time, feeling out of sync from their daily routines, and having to play catch up on specific workflow tasks once they've returned to the office. To help these leaders adopt a proactive (rather than reactive) approach to planning their short- or long-term business trips, the members of Fast Company Executive Board provide 17 strategies to help any colleague build a better work-life balance on the go, and remember to prioritize self-care at the top of their list.

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Looking ahead, with a whole new type of candidate in mind, here’s what businesses should be considering sooner rather than later.

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Your brand's reputation doesn't have to waver just because the market does. In an unpredictable market, your brand’s reputation can feel simultaneously more fragile and more important than ever. A single misstep, a poorly handled crisis, or a lack of clear communication can erode trust faster than it’s built. To help you avoid a PR crisis, 20 Fast Company Executive Board members share their best practices for managing brand reputation. Follow their advice to strengthen and protect your brand, no matter the external circumstances.

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Some executives are energized while others are cautious, but all agree that adapting to rapid innovation is essential to thriving in today's marketplace. The world is moving faster than ever, and technological innovation is at the center of it all. From generative AI to data-driven automation, change is happening at lightning speed—and business leaders are faced with a choice: embrace it, resist it, or try to strike a balance. Below, 18 Fast Company Executive Board members share how they really feel about the current pace of tech change, and what it means for their industries, their teams, and their leadership mindset.

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To bring out the best in their remote teams, managers must adapt their leadership styles to meet each employee’s unique needs, preferences, and work habits. Flexibility is essential to effective leadership, especially in remote and hybrid work environments. But flexibility doesn’t mean being hands-off or vague—it means knowing your people well enough to lead them intentionally, based on who they are and how they thrive. To that end, 20 Fast Company Executive Board members offer advice on how today’s managers can adapt their leadership approach to meet the needs of remote team members. From customizing communication styles to co-creating expectations, these strategies offer practical guidance for leading with empathy, clarity, and results.

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Your first big interview with the press can feel intimidating, but the right preparation can turn it into a defining moment for you as a brand leader. Whether it’s a podcast, panel, or live social media event, stepping into the spotlight for the first time as a brand leader can feel like walking into a conversation where everyone else already knows the script. But with the right preparation, these moments can become powerful opportunities to share your story, connect with your audience, and elevate your company’s message. From refining your talking points to embracing authenticity and learning to handle tough questions, small adjustments can make a big impact. To help you feel confident and prepared, 20 Fast Company Executive Board members share their best advice for first-time brand leaders getting ready for a media interview or public appearance.
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.