You need someone who has built companies, led through acquisitions, raised capital, and coached the leaders doing it right now. Not a consultant who studied it. Someone who lived it. That is what 127 Ventures brings to every engagement.
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, before a PE-backed transition.
She has served as Interim CHRO at Richemont, MoneyLion, WeWork, and Western Asset Management, led enterprise change management engagements at Eli Lilly and other Fortune-scale organizations, and directed global HR strategy at Pearson through $497M+ acquisitions. A Forbes Coaching Council contributor featured in 50+ media outlets.
Today, through 127 Ventures, she advises and invests in the Work Tech space, including Granted, Relate, RallyBright, 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.
25+ years of driving revenue growth, building people product roadmaps and designing the people and culture strategies that make organizations actually perform.
From zero-to-one to PE exit, the full founder journey including fundraising, team building, product strategy, and scaling a SaaS business to Inc. 5000 recognition.
Designing organizations where people thrive, talent architecture, DEI, performance management, engagement, and workforce transformation at every stage of growth.
Bridging the gap between cutting-edge technology and human-centered work, from AI-enabled coaching platforms to next-gen HR tech stack strategy.
Prosci ADKAR-certified practitioner with a track record of leading complex transformations, M&A integrations, digital adoptions, and culture shifts, at global scale.
executive coach working with founders, CHROs, and senior leaders to unlock potential, navigate inflection points, and lead with clarity and purpose.
Led integrations across $597M+ in acquisitions, designing the structures, processes, and cultures that make combinations actually work at scale.
Designing the frameworks, policies, and governance structures that ensure AI adoption in the workforce is responsible, equitable, and effective — building AI-centric organizations that perform without compromising human dignity, compliance, or trust.
Every engagement is built around your goals, a keynote that reframes the room, a coaching relationship that rewires how you lead, or a workshop that builds skills that stick.
Compelling keynotes on the future of work, HR tech, AI adoption, and resilient leadership — delivered at HR Transform, HR UnCubed, TechCrunch, University of Michigan, HR.com, HRCI, and the Human Capital Institute. Tailored for conferences, summits, corporate events, and leadership retreats.
One-on-one executive coaching for founders, CHROs, and senior leaders navigating complexity, career transitions, or their next big move. Expert facilitation of strategic planning sessions, leadership offsites, and board retreats. Available instantly on Intro — no waitlist.
Hands-on GTM strategy and pipeline engine design for HR Tech, Work Tech, and B2B SaaS companies — built by a founder who has done it. From ICP definition and positioning to channel strategy, outbound, inbound, and community-led growth. Grounded in 25+ years of real buyer insight as Voice of Customer for B2B SaaS and AI.
Building brands that stand for something and content that earns attention — from executive thought leadership and company narrative to messaging frameworks and editorial strategy. Forbes Coaching Council contributor with 50+ media features and a proven track record of building platforms that open doors.
Advising HR Tech companies on how to evolve their products with an AI-native mindset — not AI bolted on, but AI built in from the ground up. Product roadmap strategy, feature prioritization, user adoption, change management, and AI ethics & efficacy guardrails. Built on firsthand experience founding and scaling an AI-powered HR Tech platform.
Strategic advisor and investor in the Work Tech space — Granted, Relate, RallyBright, and Previ. Founder and investor in SkillCycle (formerly GoCoach). Board-level guidance for HR Tech, Work Tech, and Ed Tech companies. Chief HR Evangelist & Voice of Customer for B2B SaaS and AI — bringing the operator and buyer perspective to product, GTM, and positioning.
From zero-to-one to PE-backed scale — Kristy has built it, raised it, and led it. Advising startup founders and early-stage teams on people strategy, org design, fundraising narrative, culture, and the operational decisions that determine whether a company thrives or stalls. Real founder experience, not theory.
Helping organizations understand and adopt the platforms, processes, and practices that define modern work, from remote infrastructure to AI-enabled productivity.
Bridging learning technology and meaningful skill development, guiding organizations to build cultures of continuous growth and career ownership.
Advising on the selection, implementation, and optimization of HR technology that genuinely puts people first, not just people data.
From global HR conferences to university keynotes, top-ranked podcasts, and leading publications, Kristy brings energy, candor, and hard-won insight to every platform.
Whether it's a keynote, a coaching engagement, or a 1:1 strategy session, let's make it happen.
Bring Kristy to your conference, summit, or corporate event for a talk that reframes how your audience thinks about the future of work.
Ongoing coaching relationships for founders, CHROs, and senior leaders. Facilitation, workshops, and strategic advisory also available.
Need focused advice now? Book a direct paid session on Intro, no waitlist, no middleman. Available to startup founders, CEOs, and HR leaders.
Whether it's a keynote, a coaching engagement, or a quick conversation, reach out and let's make it happen.
Every engagement is built around your goals. Here is what working together looks like.
Compelling keynotes on the future of work, AI adoption, HR leadership and resilient cultures. Tailored for conferences, corporate events, university summits and leadership retreats.
Hands-on, interactive learning experiences that leave teams with practical tools they can use immediately. From AI readiness to leadership development and change management.
One-on-one executive coaching for founders, CHROs and senior leaders navigating inflection points, career transitions or their next big move. Available on Intro for instant booking.
Ongoing strategic advisory for Work Tech, HR Tech and Ed Tech companies. Board-level guidance, people strategy, AI adoption and organizational design. Equity optionality available for early-stage companies.
Expert facilitation of strategic planning sessions, leadership offsites, board retreats and team alignment workshops. Creating space for the conversations that move organizations forward.
Articles, white papers, webinars and podcast appearances across Work Tech, HR Tech and the future of work. Forbes Coaching Council contributor with 50+ media features.
All pricing is subject to scope and availability. Reach out to discuss what the right engagement looks like for you.
Five questions. One minute. Find out exactly what kind of support would move the needle for you right now.