Maeve Security Podcast

In this episode, Kendra sits down with Coleen Coolidge, a two-time CISO with over 25 years in tech (20 of them in security), who built security and trust programs from the ground up on the belief that great security is a team sport. Now a self-described "recovering CISO," Coleen invests in early-stage startups and works as a Field CISO at formal.ai, all while thinking hard about what AI means for both defenders and attackers.
 
Coleen's origin story is one many in security will relate to: she didn't choose this field, it chose her. What started as a mortgage data project in 2004 turned into a career-defining moment when a security reviewer named Ian showed up, tore the project apart, and changed the entire trajectory of her career.
 
In this episode, Coleen shares:
- How being "tricked" into security by a mentor led to two decades in the field
- Why the best security leaders are well-versed generalists, not narrow specialists
- The real day-to-day of being a CISO (hint: it's more politics and advocacy than pure technical work)
- Retiring, and immediately getting pulled back in by founders who wouldn't let her leave the industry alone
- Becoming a Field CISO and what that role actually looks like
- Why people skills matter more than technical expertise when it comes to getting things done
- The Security Padel community she started to get security people off their screens and away from unhealthy happy-hour culture
- The surprising parallels between sales teams and security teams, and what security can learn from GTM
- How the experience of being a woman in security has shifted since she started in 2005
 
This conversation is packed with hard-earned wisdom on burnout, mentorship, and building a career that outlasts any one job title.
 
🔗 Connect with Coleen: Find her on LinkedIn under Coleen C
Learn more about formal.ai, a protocol-aware proxy security company

This week, the tables turn as Kendra welcomes a fellow podcast host to the show: Dawn Butler, host of Bytes, Bits, and Brilliance and a 23-year veteran of senior leadership at Citi, most recently in Global Identity and Access Management under the CISO organization.
Dawn's path into cybersecurity started far from where it ended up: an electrical engineering degree, and nearly two decades as a software engineer before pivoting into governance and policy. Her story is candid, funny, and refreshingly honest about the messier parts of a "successful" career.
In this episode, Dawn shares:
- How a college friend's phone call led her into a computer programming job she never expected to take
- Teaching herself Oracle databases in a single intense weekend
- The shift from hands-on technical work to global governance and leadership, and the mental adjustment that came with it
- Getting physically burned out early in her career (including tendonitis from overwork) and what it taught her about limits
- Getting laid off in 2024 while on leave, and the surprising relief that came with it
- From Pause to Power, the healing circle she created to support women navigating layoffs, unemployment, and career transitions
- Why representation and visibility still matter, and her call for more women and people of color to show up and be seen in this industry
 
This is a conversation about burnout, reinvention, and giving yourself permission to not have it all figured out, even 20+ years into a career.
 
🔗 Connect with Dawn: Podcast: Bytes, Bits, and Brilliance (wherever you listen)
Find her on LinkedIn Reach out directly to learn more about From Pause to Power

Welcome to the very first episode of the Maeve Security Podcast! Host Kendra sits down with cybersecurity analyst and researcher Cheryl Biswas for a conversation that's equal parts inspiring, honest, and hard-won wisdom.
 
Cheryl's path into cybersecurity is anything but traditional. She holds a degree in political science, was once told she "couldn't learn computers," and worked her way up through help desk, admin, and mainframe roles before landing in the threat intelligence world — where she now tracks APTs, ransomware, botnets, and supply chain risks to critical infrastructure.
In this episode, Cheryl opens up about:
- Her unconventional career journey — from being discouraged in math class to becoming a leading voice in threat intel
- Getting laid off after a long career at a bank, and how she's navigating the job search with resilience
- Her passion project on critical infrastructure resilience and a talk on Arctic sovereignty and cybersecurity for Canada
- Burnout, isolation, and mental health in cybersecurity — and why checking in on people who go quiet matters
- Her work as a founding board member of The Diana Initiative, supporting women, transgender people, and neurodivergent folks in security
- The power of mentorship, community, and just saying "yes" to opportunities Whether you're new to cybersecurity, considering a career change, or just need a reminder that persistence pays off, this conversation is packed with heart and hard-earned advice.
 
🔗 Connect with Cheryl:
Blog: cyber-watch.ca
Find her on LinkedIn Catch her at DEF CON's Adversary Village and Hackfest
🔗 Learn more about The Diana Initiative: supporting women and underrepresented groups in cybersecurity through mentorship and an annual conference in Las Vegas.