Dear Legal Ops

This week we're getting anonymously comfy with our favorite festive co-hosts as we trade our letters for a holiday highlight reel. On this special holi-slay episode, we're reflecting on a year that taught us sometimes the biggest transformations aren't in your tech stack—they're in having the courage to redefine what's possible. Join Tom & Tommie as they unwrap the greatest hits of 2024, spill the holiday tea on what's brewing for 2025, and remind us all why the Haus of DLO feels less like a podcast and more like chosen family. So grab that festive drink and ugly holiday sweater as we celebrate a year where every messy, beautiful, and gloriously unscripted moment helped write a chapter we'll never forget. 
 
Dear Legal Ops 
IG: @dearlegalops 
LinkedIn: @dearlegalops 
Facebook: @dearlegalops 
Twitter: @dearlegalops 
TikTok: @dearlegalops 
www.dearlegalops.com 
 
Tommie Tavares-Ferreira 
Linkedin: @tommie 
IG: @suttontell 
 
Tom Stephenson 
LinkedIn: @tstephenson1 
IG: @tacotacotomtom 
 
This is a Redd Rock Music Podcast 
IG: @reddrockmusic 
www.reddrockmusic.com
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In this milestone 50th episode of Dear Legal Ops, we welcome Mary O’Carroll, Chief Operating Officer at Goodwin, for a thought-provoking conversation on navigating the highest peaks of a legal ops career. With a career journey that spans Google, Ironclad, and the founding of CLOC, Mary has redefined what it means to lead and innovate in operations and community. Her path to the C-suite is a testament to vision, tenacity, and the power of betting on yourself. 
Mary shares her insights on leadership and how building communities creates lasting impact. Whether you’re just starting your climb or looking for new heights in your career, Mary’s story will leave you inspired and equipped to chart your own ascent. 
 
This episode was made possible by our sponsor, Sterling Analytics “Legal Billing Unlocked” 
 
Mary O’Carroll, Chief Operating Officer at Goodwin  
LinkedIn: @Mary O’Carroll 
 
Dear Legal Ops 
IG: @dearlegalops 
LinkedIn: @dearlegalops 
Facebook: @dearlegalops 
Twitter: @dearlegalops 
TikTok: @dearlegalops 
www.dearlegalops.com 
 
Tommie Tavares-Ferreira 
Linkedin: @tommie 
IG: @suttontell 
 
Tom Stephenson 
LinkedIn: @tstephenson1 
IG: @tacotacotomtom 
 
This is a Redd Rock Music Podcast 
IG: @reddrockmusic 
www.reddrockmusic.com
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This week, we’re getting anonymously comfy with Nail-biting Natalie, who’s preparing for her first big step into the C-suite spotlight. Tom and Tommie bring on the dynamic duo of Connie Brenton and Jeff Franke from LegalOps.com to explore what it takes to lead with confidence and clarity. Connie dives into her passion for mentorship, education, and paving the way for in-house leaders to level up their careers, while Jeff discusses the evolving role of AI and how it’s reshaping legal ops. We’ll unpack how to build connections across all the major players—without losing your voice—and why resilience and adaptability are the real keys to thriving in today’s legal landscape. 
 
Connie Brenton – LinkedIn: @conniebrenton 
Jeffrey Franke – LinkedIn: @jeffrey-franke-b84566 
 
Dear Legal Ops 
IG: @dearlegalops 
LinkedIn: @dearlegalops 
Facebook: @dearlegalops 
Twitter: @dearlegalops 
TikTok: @dearlegalops 
www.dearlegalops.com 
 
Tommie Tavares-Ferreira 
Linkedin: @tommie 
IG: @suttontell 
 
Tom Stephenson 
LinkedIn: @tstephenson1 
IG: @tacotacotomtom 
 
This is a Redd Rock Music Podcast 
IG: @reddrockmusic 
www.reddrockmusic.com
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This week, we’re getting anonymously comfy with Britney “Crossroads: The Sequel” Spears and our special guest, Steph Corey, Founder & CEO at UpLevelOps. As Britney stands at a career crossroads, contemplating a leap from in-house to entrepreneurial ventures, we’ll explore the tips, tricks, and trials of making a bold transition. From trailblazing beginnings to fostering mentorship and building your own company, Steph shares her insights on navigating the complex legal ops landscape while staying true to your community and values. Get ready to chart a new course as we dive into the future of executive roles, the ever-evolving career jungle, and the rise of GenAI. So, buckle up for this episode filled with forward-thinking strategies and a few career-defining decisions that will inspire you to make your next move with confidence. 
 
This episode was made possible by our sponsor, Legal.io. 
Stephanie Corey (CEO & Co-Founder at UpLevel Ops & LINK, Legal Innovators Network) 
LinkedIn: @ stephcorey-ulo 
 
Dear Legal Ops 
IG: @dearlegalops 
LinkedIn: @dearlegalops 
Facebook: @dearlegalops 
Twitter: @dearlegalops 
TikTok: @dearlegalops 
www.dearlegalops.com
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This week, we’re live from The Masters Conference Legal Power Skills, hosted by Rich Robinson. Co-hosts Tom and Tommie, joined by Cat Casey and a live audience, open an anonymous letter from Charlie "Champion-for-Change" Chapman from California. Together, they discuss navigating change and building personal brands in the legal industry, sharing experiences and insights from their careers. Whether battling impostor syndrome or looking to develop meaningful relationships, discover how power skills in the workplace can help you understand your audience, stay true to yourself, and balance data-driven insights with emotional intelligence.  
  
Special thanks to The Masters Conference and Rich Robinson for his expert moderation. 
 
Rich Robinson, Director, Legal Operations and Litigation Support at Toyota North America (LinkedIn: @RichRobinson-Toyota) 
 
Dear Legal Ops 
IG: @dearlegalops 
LinkedIn: @dearlegalops 
Facebook: @dearlegalops 
Twitter: @dearlegalops 
TikTok: @dearlegalops 
www.dearlegalops.com 
 
Tommie Tavares-Ferreira 
Linkedin: @tommie 
IG: @suttontell 
 
Tom Stephenson 
LinkedIn: @tstephenson1 
IG: @tacotacotomtom 
 
This is a Redd Rock Music Podcast 
IG: @reddrockmusic 
www.reddrockmusic.com
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