Chart
Command
Your Course.
Your Career.
Keynotes & panels that hand you
the map, pep you up, and launch
you straight into unstoppability.
Why Jen Bailey?
You get 25 years of rock-solid corporate strategy plus a splash of “Jen in the Wild” unpredictability. She’ll make you laugh, make you think, and—most importantly—help you identify exactly what to do next.
Blueprint Mindset
Swap confusion for a clear, three-step game plan.
Boardroom Command
Walk into any meeting, project unwavering poise, and influence the outcomes.
Lasting Impact
You won’t just feel inspired, you’ll have an action list to prove it.
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I hope she continues to inspire!
The negotiation workshop Jen led, has been essential for my professional growth.
Jen was able to teach multiple students with zero negotiation experience from the ground up, gave us tips on when to negotiate, and offered real world example of how negotiations benefit candidates.
I hope she continues to inspire others as much as she has inspired me!
Edgar Gonzales Reyes
HR Intern/ Candidate for MHRIR 2026 -
Jen's energy is contagious!
Jen's energy is contagious. She is very intentional with the way she communicates and engages with the audience.
Her unique insights in combination with her life experiences helped the audience draw a clear picture of the ways Allina was enhancing their employee wellbeing from implementation to results.
I cannot recommend Jen enough for any speaking opportunities!
Melissa Donaldson
Center for Human Resources and Labor Studies -
she makes audiences feel like they are part of a conversation
Jen Bailey shares new insight wherever she speaks. She is bright, funny and intelligent!
As a keynote speaker, she makes audiences feel like they are part of a conversation instead of a lecture.
Jen’s positivity brings so much great energy to the stage and instantly elevates any panel or event she is a part of.
Kelly Jahner-Byrne
CEO of The HOW Conference™
Signature Keynotes & Panels
SMART Career Planning
Plot your strengths, set your milestones, and power-up your promotion strategy.
Negotiating Your Value
Speak up, claim your worth, and walk away with the compensation you deserve.
Conference Prep Class
From killer intros to post-panel follow-ups, learn the ✨ secret sauce ✨ of conference success.
Get in the Game Workshops
SMART College Planning
Your campus-conquering blueprint—pick majors, snag internships, and make the dean notice you.
Conference Confidence Prep 101
Role-play, mic drop practice, and belly–laugh your way to event-floor domination.
Mentorship
3 Months, 5 Power Sessions
Spend five one-hour deep dives over three months with Jen.
Identify your superpowers, sharpen your interview swagger, and network like a pro.
E-mail support between calls keeps you on track.
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A true anchor during a time of transition
Jen’s mentorship has been a true anchor during a time of transition for me. She has offered invaluable advice in the field of HR, taught me meaningful life lessons, and been a constant source of support whenever I’ve had questions.
She inspires me to leave a legacy like she did for me, and she is such a representative and inspiration for young women, including me, who may not even know that business is a career avenue.
Audrey Gilmore
MHRIR Masters Student -
Great advice and boundless positive energy
With Jen’s mentorship, I’ve learned how to be an advocate for myself, to take ownership of my learning and professional growth, and to embrace opportunities to step outside my comfort zone.
In my role today, I am actively seeking out ways to take on more leadership and ownership of key projects - Jen has been instrumental in building the confidence to do so.
Maybe most importantly, Jen has shown me that being a polished professional doesn’t mean leaving your personality behind. She is living proof that bringing your authentic self to work can be one of your greatest assets.
Laura Gale
Senior Total Rewards Analyst -
game-changer in my professional journey
I came to Jen when I was unsure of what my next career step should be. Jen empowered me to be confident in the workplace by helping me identify my strengths, interests, and establishing what I want from my career.
Through working with Jen, I am confident I have the tools I need to succeed in my current role and beyond.
Samantha Pierce
Financial Analyst
Your Takeaway Toolkit
An Actionable Strengths Roadmap
Three Concrete Goals (with milestones—no guesswork)
A Practical Game Plan you can put into motion immediately
Unshakable Boardroom Presence that amplifies your influence