About SkillCycle

After a combined 20+ years working in HR, SkillCycle’s future CEO Kristy McCann Flynn sat down with future CCO Rebecca Taylor over homemade ice cream at a NY steakhouse and, ready to flip the script (or tear it to pieces in frustration), decided to build a tech platform that actually answered the problems that HR and organizations were running into time & time again. With their deep insight into HR pain points, knowing as buyers what types of platforms weren’t working and why, they built SkillCycle as an answer to those repeated frustrations.

Built by talent development experts, SkillCycle’s unified tech delivers a seamless platform for companies that helps solve greater organizational challenges, builds stronger teams, and resets the way we all measure business success.

Trusted By 100+ Companies

Experiencing ROI Like You've Never Seen Before

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Improvement in Performance

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Improvement in Communications Skills

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Growth In Revenue For Aligned Companies

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The SkillCycle Way

Take a look at how we bring you success

Our Values


We empower all those we work with by meeting them where they are and partnering to help them grow in line with their needs and goals. We empower our clients by guiding, counseling, and supporting them in reaching their best outcomes by providing them with the support, skills, and tools they need to be successful. We center our learners, our client partners, and our team, first and always.


We care for each other, our customers, and our communities. By working with and for each other, we nurture a trust that serves as a foundation for healthy relationships. A culture of trust provides space for ideas to flourish and inspire innovation, propelling SkillCycle forward as leaders and visionaries.


We recognize that change is constant and healthy and that the need to successfully navigate it is fundamental to growth. We foster the skills needed to embrace change and effectively lead others through it. We do this for ourselves and our customers so we may thrive in the face of adversity and make happen the change we want to see.


We live in a constant growth mindset, always asking questions about how something can be better or why something is the way that it is. We face challenges with deep questions that lead us to the root of the issue, allowing effective problem solving and resolutions. We ask before we assume and intentionally strive to understand perspectives that are different from our own. “What if?” and “Why?” drive our best ideas.


We encourage our team to get creative to find new and better ways to solve problems. We know that doing things “how they’ve always been done” leads to stagnation, and we constantly seek to innovate in support of our mission, our clients, and our learners. Our team thinks outside the box to express new ideas and fuel innovative products, services, and processes.


We, as a company and as individuals, always strive to pursue actions that benefit our company, peers, and customers on a level that establishes trust and clearly demonstrates our values and morals. We serve others in meaningful, thoughtful ways by always striving to demonstrate that our commitment to their success and to each other is always true


During her 20+ years of experience as a Strategic Human Resource Leader, Change Manager and Organizational Development Expert, Kristy has served in senior leadership positions throughout her career – most notably with Pearson Education and Constant Contact. Kristy brings a big picture perspective and a hands-on, tactical approach to her leadership at SkillCycle. Kristy’s goal is to help companies to meet their  goals by empowering their employees to take ownership of their career.

Kristy McCann Flynn

Co-founder and CEO

Rebecca brings her years of experience in the HR and People space to SkillCycle as the first official employee and Co-founder. Throughout her 10 years in HR, she developed and spearheaded People strategies that made her companies successful and protected their most valuable asset – the people. Her goal is to empower people to invest in themselves and their teams, to increase employee engagement, retention, and performance.

Rebecca Taylor

Co-founder and CCO

Jeff joined SkillCycle in 2021 to lead the continued evolution of the SkillCycle platform that makes it easy for employers to provide their employees with seamless access to personalized, continuous learning. He brings over 15 years of experience delivering innovative and market-leading solutions across e-learning, assessments and analytics, with experience leading product development efforts at Pearson, McGraw-Hill, and Taskstream (now Watermark Insights).

Jeff Reid

Co-founder and COO

With 15+ years of B2B technology sales experience, Jason focuses on optimizing the customer lifecycle, driving go-to-market strategy, and supporting sales and marketing alignment. His mantra is simple: provide consistent and simple buying experiences through insights, process, and technology. Jason served as the VP of Revenue for Localist and held senior leadership roles at RNL and CEB (now Gartner). When offline, he enjoys chasing around his two children and being a local tourist in the nation’s capital.

Jason Finney


Board of Advisors

Elise James DeCruise, Chief Equity Officer, Ad Council — Learning and D&I Strategic Advisory

Angela Schwers — Human Resources Advisor 

Ted Brodheim, President, Altimira Advisors — Education Strategic Advisor

Tarek Pertew, CEO, Uncubed — Sales Strategic Advisor

Navarrow Wright, Senior Director Product Marketing, Meta — Tech Advisor


Show us your skills and grow them at the same time by joining our team.

All job postings can be found here on our LinkedIn page. Check there for the latest updates!