Kendall Roy
Co-CEO (on sabbatical) | Digital Transformation Evangelist | Future-Proof Narrative Architect
New York, NY
About
I’m Kendall Roy, strategic operator, turnaround optimist, and firm believer that next is the only direction worth moving in. I’ve spent my career inside a global media empire translating legacy assets into future-facing narratives, managing high-stakes deal environments, and trying to drag entrenched institutions toward relevance. My style is high conviction, high urgency, and maybe occasionally too much honesty. Currently exploring post-Waystar opportunities at the intersection of media, tech, culture, and personal evolution.
Experience
Co-Chief Executive Officer
Waystar Royco
2023 - Oct 2023 · 9 mos
Manhattan, NY
Co-led a $70B media conglomerate through board pressure, succession drama, and transaction volatility
- Accelerated streaming ARPU +38% in 2 quarters by green-lighting the Living+ pre-launch roadshow, generating 11.4M impressions before the product existed.
- Drove a 9,000% week-one media coverage ROI with a single shareholder-meeting performance that was either leadership or a cry for help.
- Reduced executive complacency 73% by forcing sharper internal debate and a much higher tolerance for uncomfortable truths.
Founder & CEO
The Hundred (Stealth Content Lab)
2022 - Dec 2022 · 11 mos
Brooklyn, NY
Incubated a premium ideas platform for culturally influential moderates and adjacent thinkers
- Built a 38-page vision deck that secured verbal commitments totaling $300M, subject to diligence, market conditions, and vibes.
- Achieved 1,100% prototype engagement across a very narrow but emotionally invested beta group.
- Sunset the concept before launch and successfully recycled 92% of the language into subsequent leadership conversations.
Chief Operating Officer, Global Media
Waystar Royco
2014 - Dec 2021 · 7 yrs 11 mos
New York, NY
Oversaw a 46K-employee portfolio spanning news, cruises, parks, and international media assets
- Led the $5.8B Vaulter acquisition, then pivoted decisively once synergy capture stalled at a breathtaking 0.9%.
- Negotiated a bear-hug offer with a major rival, pushing the stock up 22% intraday and briefly making everyone in the family intolerable.
- Modernized the crisis-communications playbook, cutting scandal-to-settlement cycle time by 35%.
Director of Digital Strategy
Waystar Royco
2008 - Dec 2013 · 5 yrs 11 mos
New York, NY
Helped push a legacy media business from cable-era thinking toward digital distribution
- Launched Waystar News App V1, reaching #2 in the News category and temporarily convincing leadership we understood mobile.
- Grew streaming hours 600% by repackaging catalog assets with just enough exclusivity to sound innovative.
- Earned the informal title of Most Improved Roy from 2011 to 2013, which still counts to me.
Education
Harvard University
AB, Government
Co-founded campus media fund • Wrote 118-page thesis draft on power, morality & morning cable ratings
Honors & awards
Forbes 30 Under 30 (Media)
Forbes
Issued 2011
Recognized for aggressively transforming a $60B family corporation into a $60B family corporation, now with Wi-Fi.
