Kristy McCann Flynn – Job Board Doctor

Author

Kristy McCann Flynn

Kristy McCann Flynn is a CEO, Founder, and CHRO who has spent 25+ years at the intersection of people, culture, and technology, building companies, transforming enterprises, and coaching leaders at every stage.

As Co-Founder and CEO of SkillCycle (formerly GoCoach), she raised $15M+, built a global AI-powered coaching platform, achieved 400% ARR YoY growth, and earned Inc. 5000 Fastest Growing recognition in 2023 and 2025, and Inc. Best Workplaces recognition in 2024.

Today, through 127 Ventures, she advises and invests in the Work Tech space, including Granted, Relate, and Previ, and brings the full weight of her founder, operator, and coaching expertise to executives, HR leaders, and startup founders ready to lead differently.

She also advises organizations on AI ethics and efficacy guardrails — building the governance frameworks that ensure AI adoption in the workforce is responsible, measurable, and human-centered.

Financials, Leadership, Thought Leadership

Startup Founders Beware: The Loan-to-Own Playbook, and How to See It Coming

by Kristy McCann Flynn July 23, 2026 0

(Note from the Doc: Happy Friday, Job Board Doctor friends! In the past year since the bankruptcy of Monster and Careerbuilder, followed by the Job.com bankruptcy,... Read more.