My name is Kaishon Holloway and I believe advocacy is not just a noun, it's a verb. And I show up every single day to prove it.
I don't just give keynotes. I start conversations.
I'm a Keynote Speaker and Culture Transformation Strategist who turns ordinary events into conversations people are still talking about long after they end. I thrive in keynote, fireside chat, and panel discussion environments where the topic meets the audience exactly where they are. I don't speak at audiences. I speak with them. My sessions are warm, a little witty, deeply human, and grounded in over a decade of experience going from retail cashier to leading global programs and multimillion dollar client relationships at some of the world's most recognizable companies.
My story starts as a cashier in retail at 17. At 19, I started interning in the tech industry while still working retail, building both worlds at once until I transitioned fully into tech full time after graduation. From there, I went on to lead multiple global people programs across Customer Advocacy, HR, Employer Branding, Employee Advocacy, Culture and Belonging, Marketing, Go to Market Strategy, and Social Impact at Indeed and Peloton, interfacing directly with senior executives at some of the world's most prominent organizations. I didn't get there through credentials and job title alone. I got there by building real relationships with real intention, and that is the framework I now teach from the stage.
My signature topic:
▪ From Cashier to Corporate Superstar: Build Your Career Authentically One Relationship at a Time
Organizational belonging and individual career growth are the same story, told from two sides. I help organizations turn belonging into a business advantage that strengthens retention, engagement, and performance, and I help the professionals inside those organizations accelerate their careers by building genuine relationships that create promotions, opportunities, and influence.
I live openly as a proud Gay, Black man with Bipolar Disorder and document that journey in my blog, Kaipolar Diaries. I don't share that to be brave. I share it because psychological safety is not a buzzword to me. It's personal. And when I stand on your stage, your audience knows that I mean it.
Past Clients Include: Salesforce, Sony, McDonald's, Unilever, National Urban League, Casper, University of Connecticut, Out & Equal, New York Urban League Young Professionals, and Out in Tech
Featured On: Business Insider, CNBC, and CNBC Make It
My life's mission is to use my voice to effect positive change for the most vulnerable communities in our society. My passion sits at the intersection of belonging, career growth, and self-actualization.
My goal is simple: to empower myself and others one day at a time while building a better future for ALL.
Take care of yourself and be kind to others.
Speaker inquiries: kaishon@kaishonholloway.com
Blog: kaipolardiaries.com
Speaking Topics
▪ From Cashier to Corporate Superstar: Build Your Career Authentically One Relationship at a Time: Organizational belonging and individual career growth are the same story, told from two sides. I help organizations turn belonging into a business advantage that strengthens retention, engagement, and performance, and I help the professionals inside those organizations accelerate their careers by building genuine relationships that create promotions, opportunities, and influence. When people learn to build sincere connection, cultivate strategic visibility, and practice active advocacy, they grow their careers, and they build the kind of culture organizations are fighting to keep.
Speaking Engagements
2020 - 2026
▪ Unilever: "Addressing Non-Inclusion" Panel
▪ Execs in the Know (CX Summit): "Empowering Employees through Technology" Panel
▪ East Coast Executives: "The Future of Work Conversation: Black Male Edition"
▪ McDonald's and Out & Equal: "Intersectionality: The Black & LGBT Experience" Panel
▪ Wonsulting (Amplify Virtual Conference): "LGBT+ Professionals" Panel
▪ Casper: "Building Inclusion" Panel
▪ National Urban League (Digital Career Success Series): "Escaping The Resume Black Hole"
▪ SONY: OutLoud Presents | The Grit and Glamour: The LGTBQ+ Experience at Work with Kaishon Holloway
▪ Business Insider: Skills You Need to Land a Job in Diversity and Inclusion
▪ CNBC: Why Being Single Is So Expensive In The U.S.
▪ New York Urban League Young Professionals: "Navigating Your Career & Mental Health Journey" Panel
▪ UConn Stamford Micro Internship Program: Professional Development Fireside Chat
▪ Out in Tech Miami: Diversity, Equity, and Inclusion in Tech Panel
▪ Out in Tech x Pridelines: LGBTQ+ Professionals & Entrepreneurs in Tech Panel
2019
▪ University of Connecticut Career Day
▪ Circle of Change Leadership Conference
▪ Pluto: "Intersections of Workplace Diversity & Inclusion" Panel
▪ Salesforce: "Imposter Syndrome: Myth or Reality?" Panel
2018
▪ IAMPHENOM (VX Conference): "Marketing the Employer Brand in a Candidate-Driven Market" Panel
See me in action
CNBC: Why Being Single Is So Expensive In The U.S.
The number of single Americans has been steadily rising for several decades. Today, 46.4% of U.S. adults never married, are divorced, or widowed. But a single life today can come with an additional challenge: financial anxiety. A 2023 survey by Match revealed that the top three stressors for single Americans, excluding Gen Z, were all financial. So what’s causing so much financial anxiety among single Americans?
I had the privilege of participating in the Urban League Jobs Network Digital Career Success Series segment, “Escaping The Resume Black Hole”. Kenneth L. Johnson (East Coast Executives) and discussed the best strategies to get your resume past the Applicant Tracking System (ATS) and in the possession of a Recruiter.