What would your workplace look like if every single leave of absence became a chance to build legendary loyalty and turbocharge retention?
Sivana Brewer sits down with Taylor McLemore, COO at Tilt, for a conversation that slices through HR noise and exposes the uncomfortable truth: most companies fumble leave policies and lose their best people as a result. This episode unpacks the hidden costs (and wild upsides) of leave done right.
From the real-world pain operators feel managing compliance chaos, to how AI is shaking the industry, and the “roles, responsibilities, expectations” framework that creates lasting clarity, this is actionable COO gold.
Miss this, and you risk bleeding talent, tanking culture, and getting steamrolled by change. Listen now for raw lessons, war stories, and tested tactics you won’t hear anywhere else.
Timestamped Highlights
00:40 – The brutal truth about why leave management is your hidden loyalty driver
02:07 – The jaw-dropping time and complexity HR teams actually face
08:20 – A career-changing moment: what empathetic leave really looks like
13:16 – The overlooked ROI of doing leave brilliantly
14:23 – Why Tilt planted the flag as the AI leader (and what that really means)
16:43 – The four principles that keep AI both fast and safe inside HR
22:40 – The surprisingly simple doc that ends CEO-COO confusion
29:15 – The unexpected power of letting people define “winning” in their own role
About the Guest
Taylor McLemore is the COO of Tilt, revolutionizing employee leave with empathy and technology. Taylor is the founder of the Human Potential Summit. Previously, he was an EIR at Stand Together. Taylor is a venture builder, scale operator, community connector, and investor. Taylor served on the Colorado Banking Board and the Board of Trustees for Colorado PERA. Previously, he launched and built the Techstars Workforce Development Accelerator as a Managing Director at Techstars. Taylor was the Co-Chair of the DAV National Veterans Entrepreneurship Council. He previously served as an advisor to SHRM Labs and sits on a number of startup boards. Previously, he was Managing Director of Able, a venture and product studio. While at Able, he was a co-founder and investment lead for Codeable, a coding school in Latin America. Taylor was the founder and a board director for Patriot Boot Camp, a nonprofit that supports military veteran and military spouse entrepreneurs. Patriot Boot Camp was acquired by DAV in 2021.
Mentioned Resources
- Techstars
- Rippling
- Paycor
- Paylocity
- Workday
- Ray Dalio – Weighted Believability
- SOC 2 Compliance
- Short-Term Disability (US HR context)
About the Co-Host
Sivana Brewer is a Fractional COO for Remote Teams and former COO at Closers.io, where she helped scale the company to multiple eight figures and built over 500+ sales teams in just 2.5 years. She specializes in leadership development, remote operations, and systems that empower teams to grow sustainably.
? Connect with Sivana on LinkedIn
Important Links
- Connect with Cameron: Website | LinkedIn
- Explore the COO Alliance – The World’s Leading Community for Seconds in Command
- Get Cameron’s book: Second in Command: Unleash the Power of Your COO Book
- Take his course: Invest In Your Leaders Online Course (Use promo code PODCAST10 before the end of the month for 10% off)
- Chat or video call with AI Cameron via Delphi
The Second in Command Podcast is an original production hosted by Cameron Herold. Brought to you by COO Alliance. Production and editing by Podcast Your Brand.
Sponsored by
STS Capital – A global M&A advisory firm helping entrepreneurs achieve maximum value when selling their business, with a focus on strategic buyers and life-changing exits.
Learn more:https://stscapital.com
