Ep. 576- Tilt COO Taylor McLemore - How To Approach Leave Management and Organizational Performance

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.

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

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.

🔗 LinkedIn | Website

• Techstars
• Rippling
• Paycor
• Paylocity
• Workday
• Ray Dalio – Weighted Believability
• SOC 2 Compliance
• Short-Term Disability (US HR context)

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

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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.

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