Kristy McCann Flynn
Leaders hire me
for the hard part.
Founder & CEO CHRO Operator Prosci Certified
I advise HR tech, work tech and ed tech startups on go to market, product evolution and voice of customer. I coach the founders and CHROs running them. And when a change lands without a plan, I am the one who builds the plan.
Three chairs, one operator
I have sat in all three, so I know which one you are in
Most advisors have held one of these jobs. The reason the advice lands is that I have held all three, and they teach you completely different things.
Founder
Creator and builder
Zero to one. The idea, the first ten customers, the first ten hires and the raise. Making something exist before anybody agrees it should.
I know what it costs to turn down revenue that does not fit, and how to tell whether the thing not working is the product, the pitch or the person doing the selling.
CEO
Scaler and operator
Turning a thing that works into a thing that works repeatedly. Numbers, sequencing, the board, and the calls nobody else can make for you.
I have run the board meeting where the number missed. I can tell you which levers move it this quarter and which ones only look like levers.
CHRO
Strategy and balance
Holding the business case and the human cost in the same hand. Org design, comp, performance and what the company becomes while it grows.
I can price the people cost of a decision before you make it, and tell you which culture problem is real and which is a manager problem wearing a costume.
Open for enrollment
The Change Management MasterClass
AI tools deployed before anybody wrote a policy. Notetakers in meetings nobody consented to. Company IP walking into a model on a work email. Layoffs announced and reversed. Every one of those is a change somebody made without a plan and then handed to their people to absorb.
I am Prosci certified, I have run change on the inside as a CHRO and on the outside as a founder, and this is practical skilling rather than a framework tour. Three Fridays. Small cohort. You bring the change you are actually running and we work it live.
- 01Reading the changeWho is affected, what they actually lose, and where resistance is already showing up before anybody names it.
- 02Building the planSponsorship, sequencing, communication, and the decisions you make once so you stop relitigating them.
- 03Landing itManagers, measurement, and what to do when it goes sideways in week three. Because it does, and nobody teaches this part.
Where most of my time goes
Startup advisory for HR tech, work tech and ed tech
This is the bulk of the work. I take a small number of companies and go deep: go to market, product evolution, voice of customer and brand awareness. I am in the roadmap conversation and the pipeline conversation, and I talk to your customers myself.
HR Tech
Hiring, development, compensation and retention. The category I have both bought from and built inside.
Work Tech
How work gets coordinated, measured and experienced, including the systems quietly deciding who gets noticed.
Ed Tech
Skilling and credentialing, and the growing distance between what people are taught and what the job now requires.
What I actually do inside the company
01
Go to market
Ideal customer profile, positioning, pricing and channel strategy. Pipeline design that survives contact with a real sales cycle rather than a spreadsheet.
02
Product evolution
Roadmap strategy, feature prioritization, adoption and AI ethics guardrails. Built with buyers who have to defend the purchase internally, because I have been that buyer.
03
Voice of customer
I talk to your customers and bring back what they said rather than what the survey scored. The gap between those two is usually the whole problem.
04
Brand awareness
Narrative, founder visibility and getting the company into the rooms and shows where its buyers already are. I have spent 20 years in those rooms.
Currently advising
Strategic advisor
Relate
Trust intelligence for meetings. Coaches the person who was in the room. I co-host Trust Issues with their Tom Keenan.
relate.us
Strategic advisor
Sherlock AI
Coaching native AI that reinforces the right behaviors in the flow of work, before the gap shows up in the metrics.
sherlockperformance.com
Strategic advisor
Granted
Funding intelligence for workforce ecosystems.
grantedapp.co
About
25 years where people, culture and technology collide.
I co-founded and led SkillCycle, raised more than $15M, and grew ARR 400 percent. Before that I served as interim CHRO for Richemont, MoneyLion, WeWork and Western Asset Management, ran enterprise change management at Eli Lilly, and led global HR strategy through acquisitions at Pearson.
I have hired and I have laid people off. I have sat across from a board that wanted a different answer than the one the numbers supported. I have raised money in a good market and in a terrible one. Every framework I teach has survived a real quarter, and the ones that did not survive I throw out rather than sell.
Today I coach founders, CEOs and CHROs through the parts nobody warns them about, serve as strategic advisor to a small group of work tech, HR tech and ed tech companies, and speak about what the last three years have actually done to the people doing the work.
Expertise
Seven things I am actually good at
All seven earned in an operating role before they became something I teach.
- 01 Founder & CEO leadershipZero to one, the raise, the board, and the moment the plan stops working.
- 02 People & culture strategyOrg design, performance, comp philosophy, and what people conclude from watching who gets promoted.
- 03 AI & HR tech innovationBuying it, building it, rolling it out, and measuring whether it changed anything.
- 04 Change managementProsci ADKAR certified. Run at enterprise scale at Eli Lilly and at startup speed since.
- 05 Executive coachingFounders, CEOs and CHROs. More than 100 leaders through promotions, reorgs, fundraises and exits.
- 06 M&A & org designMore than $597M in acquisitions. Integration, retention, redundancy and the culture question.
- 07 AI ethics & efficacy guardrailsConsent, monitoring, IP, bias, and what your people are owed before a tool joins the meeting.
Services
How we work together
Pick the one that fits the problem. If you are not sure, the quiz below sorts it in a minute, or write to me and I will tell you straight.
Keynote & speaking
Conferences, corporate events, university summits and workshops. Talks built for the room in front of me rather than a deck I reuse.
Executive coaching & advisory
One to one coaching, facilitation and strategic sessions for founders, CHROs and senior leaders. Book 30 minutes or find me on Intro. No waitlist.
Change management enablement
The MasterClass for cohorts, and private engagements when a company is running a transformation and the plan needs to be real.
Brand & content creation
Executive thought leadership, company narrative, messaging frameworks and editorial strategy. Forbes Coaching Council contributor.
Startup advisory
Go to market, product evolution, voice of customer and brand awareness, on a retainer. See the detail.
Startup expertise & founder advisory
Zero to one through private equity backed scale. People strategy, org design, fundraising narrative and the culture you are actually building.
The show
Trust Issues
A show about what happens to work when trust runs out, and what it takes to rebuild it. I co-host it with Tom Keenan of Relate, one of the companies I advise, which means the conversation comes from two people who work on this problem for a living rather than two people with opinions about it.
Real conversations with people who were in the room when it broke, without the sanitized version companies put in the press release.
Grab 30 minutes on my calendar and pitch me. I want the episode nobody else will run.
Speaking & media
Stages, shows and bylines
More than 20 keynotes and 50 media features. A sample of where the work has landed.
Keynotes & stages
- HR Transform
- University of Michigan
- TechCrunch
- HR UnCubed
- HR.com
- Human Capital Institute
- Association for Talent Development
Podcasts & shows
- Trust Issues, host and creator
- HR Confessions, host and creator
- Chad & Cheese
- HR Morning Show
- The Job Doctor
- Punk Rock HR with Laurie Ruettimann
- HR Heretics
- Troop HR
Writing & features
- Forbes Coaching Council, contributor
- CEOWORLD Magazine
- Nasdaq
- Troop HR
- Job Board Doctor
- HRCI Webinars
- HRTech Cube
- People & Progress, my own report
Investment
What it costs, before you get on a call
Tap the one you are thinking about. Final numbers depend on scope and availability, and if what you need is not here I will tell you rather than invent a package for it.
-
The Change Management MasterClass
Three live Fridays in October, recorded, small cohort
$999for all three sessions
Reserve a seat → -
Executive coaching
60 minute one to one session, founders, CEOs and CHROs
$450per session
Book 30 minutes first → -
Startup advisory
Ongoing retainer. GTM, product evolution, voice of customer, brand awareness
$7K–$10Kper month
Talk about your company → -
Keynote speaking
Conferences, corporate events and university summits
Customdepends on scope and travel
Check my availability → -
Workshops & seminars
Half day or full day, built for your team
Customby team size and length
Tell me about your team → -
Facilitation
Offsites, leadership teams and the hard conversations
Customby session
Start a conversation → -
Content & thought leadership
Narrative, messaging and editorial strategy
Customby project
Send me the brief →
Not sure which one? The quiz sorts it in a minute.
Find out
The Ready to Work Quiz
Five questions, about a minute. It tells you which kind of help would actually move something right now, and it will tell you when the answer is none of mine.
Question 1 of 5
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Get in touch
Tell me what is actually going on
Write to me directly. Not a form that routes to nobody. I answer within 48 hours, and if I am not the right person I will say so and point you at who is.
Straight to me
Best for speaking, advisory, coaching and anything with a deadline.
Where I post
The writing lives here first. Fair warning, I say what I think.
Book time
Grab a slot, no waitlist
Executive coaching runs $450 for 60 minutes. The 30 is free and it is where most people start.
Or start with October
Three Fridays, a small cohort, and the change you are running right now taken apart in the room.
Reserve your seat · $999 →Questions, or buying seats for a team? Email me directly.