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

Learn more about your ad choices. Visit megaphone.fm/adchoices

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

Learn more about your ad choices. Visit megaphone.fm/adchoices

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

Learn more about your ad choices. Visit megaphone.fm/adchoices

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

Learn more about your ad choices. Visit megaphone.fm/adchoices

This week, we're rocketing into the cosmic realm of Legal Ops 3.0 with the ever-brilliant Jenn McCarron, President of the Board of Directors at CLOC and host of the CLOC Talk podcast. As we unravel Taylor “Seeking the Stars” from Tacoma's plea for guidance, Jenn helps us explore the expansive frontier where strategy, innovation, and artificial intelligence intersect. From leveraging AI for data-driven storytelling to mastering the next era of legal ops, Jenn's insights will illuminate the path forward for anyone feeling adrift in their career. Tune in as co-hosts Tom and Tommie join Jenn on this interstellar journey, providing the stellar advice needed to propel your career into the future. Grab your spacesuit and prepare for lift-off into a universe of knowledge, laughs, and cosmic revelations. 

LinkedIn: @jennmccarron 

Website: www.jennmccarron.com 

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

Learn more about your ad choices. Visit megaphone.fm/adchoices

This week we’re getting anonymously comfy with Melody “Master-or-Mix” from Memphis and the legendary Jenn McCarron, President of CLOC & host of the CLOC Talk podcast. As we lip sync our way through the classic debate of generalist versus specialist, we’ll explore the high notes and harmonies of both paths in the corporate & tech startup world. From mastering multiple instruments to hitting every note perfectly on one, Jenn helps us find the rhythm that suits our careers best. Remember, the greatest achievements come from daring to play your own tune. So tune in for this jam session that promises laughs, insights, and a few unexpected riffs along the way.   

Jenn McCarron, Corporate Legal Operations Consortium (CLOC)’s Board President 

LinkedIn: @jennmccarron 

Website: jennmccarron.com 

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

Learn more about your ad choices. Visit megaphone.fm/adchoices

This week we are live from Las Vegas at CLOC’s Global Institute, in the CLOC Talk Studio. As we open our anonymous letter from Dora the Dear Legal Ops Explorer, who’s gearing up for her first trek to the CLOC Global Institute aka CGI. With her backpack strapped and boots laced, Dora asks, “How do I navigate through this labyrinth of knowledge to ensure I discover the hidden treasures and make the most out of this incredible conference experience?” Join co-hosts Tom and Tommie as they divulge starategies for maximizing any conference experience, insights on making meaningful connections, and turning conference learnings into actionable steps for your legal ops journey back home. Whether you’re a first-time attendee or a seasoned conference-goer, get ready to navigate the untold hacks of conference-going with confidence. 

Special thank you to CLOC for giving us time in the CLOC Talk Studio and Jenn McCarron, CLOC’s President and CLOC Talk’s host. 

CLOC: https://cloc.org/ 

CLOC Talk: https://cloc.org/cloctalk/ 

This episode was made possible by our sponsor, Legal.io. 

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

Learn more about your ad choices. Visit megaphone.fm/adchoices

This week we're getting comfy with David Cowen, a legendary connector and the mind behind the SOLID Legal Summit. As we open our anonymous letter from a consulting composer, we'll explore the musical world of career development—where the art of improvisation plays the lead role in the symphony of success. David shares his expertise on the power of networking, mentorship, and embracing the jungle gym philosophy of career growth. Join co-hosts Tom & Tommie as they discuss cultivating radical curiosity, embracing the diversity of thought, and finding processes that foster personal and professional advancement. Whether sipping your morning brew or unwinding with an evening drink, prepare to get jazzed up while learning how to harmonize your aspirations with life's unpredictable yet exhilarating rhythms. 

This episode was made possible by our sponsor, Legal.io. 

David Cowen (President, Cowen Group) 

LinkedIn: @davidcowen 

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

Learn more about your ad choices. Visit megaphone.fm/adchoices

This week, we're getting anonymously comfy with Kim Brown, Project Manager at Netflix while pairing pencils with pinot as we explore the synergistic synergy between educational leadership and corporate management excellence. As we open our letter from Richard 'Detention to Direction' Belding, we'll uncover how principles of teaching and learning can shape and energize a career pivot from the classroom to the corporate boardroom by creating a symbiotic environment where strategy and collaboration flourish. Ready your notebooks and sharpen your minds as we translate teaching triumphs into corporate victories, proving that a good leader can inspire any audience, anywhere. 

This episode was made possible by our sponsor, Legal.io. 

Kim Brown (LinkedIn: @ kbbrown17) 

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

Learn more about your ad choices. Visit megaphone.fm/adchoices