How do you go from Director to CIO? Host Matt Peters, CEO of Fixify, sits down with IT executives who've made the climb to unpack the pivotal decisions, career-defining moments, and hard-won lessons that got them there. If you're a VP or Director of IT looking for practical advice to reach the C-suite, this is the podcast that finally focuses on your journey—not just the latest tech trends. Real stories. Real strategies. Real career growth.
How radical transparency built a team that followed me for three companies | Robert Former
Robert Former (https://www.linkedin.com/in/robertformer/) spent years losing the risk argument, until he found a way to say it in the language executives speak, dollars. As Chief Information Security Officer at Acquia (https://www.acquia.com/), he uses the FAIR methodology to turn security risk into one number the business can weigh against its appetite.
He talks with Matt Peters about the two paths into the CISO seat, why compliance is an outcome of security and not its driver, and how radical transparency built a team that followed him through three companies. Accepting risk, he argues, is the business's decision, never his.
Topics discussed:
- Turning security risk into a dollar figure with FAIR
- Why compliance is an outcome of security, not a driver
- Two paths to the CISO chair, technical and business
- Leading every function only after doing it yourself
- Building trust through radical transparency and demonstrable honesty
- Making risk acceptance the business's decision, not security's
- Navigating the shared security responsibility model in PaaS
- From security orthodoxy to weighing the upside of risk
Listen to more episodes:
Apple (https://podcasts.apple.com/us/podcast/climbing-the-stack/id1850604017)
Spotify (https://open.spotify.com/show/5fJOhXU3qrODBA2BJcHQC9)
YouTube (https://www.youtube.com/@FixifyHelpDesk)
29 Sept 2026
Don't break into jail: How to present technology to the board | Brad Lontz
You can spot a CIO who has made the climb by sitting in on their leadership team, where you cannot tell who runs technology. Brad Lontz (https://www.linkedin.com/in/bradlontz/), EVP and Chief Information Officer at CSAA Insurance Group (https://careers.csaa-insurance.aaa.com/us/en), got there by leading with the business first.
He walks Matt through the counterintuitive move that broadened his career, taking a smaller team to land his first CIO seat, how he learns a new business by starting with the value chain instead of the CFO, and why he keeps no separate AI strategy.
Topics discussed:
- Taking a smaller team to reach your first CIO seat
- Trading quick technical wins for longer-term leadership problems
- Connecting every technical role back to business impact
- Learning the business by starting with the value chain
- Building relationship capital before you need to spend it
- Telling the right story for the board versus the team
- Why AI belongs inside your business strategy
- Becoming the leader nobody identifies as the technology person
Listen to more episodes:
Apple (https://podcasts.apple.com/us/podcast/climbing-the-stack/id1850604017)
Spotify (https://open.spotify.com/show/5fJOhXU3qrODBA2BJcHQC9)
YouTube (https://www.youtube.com/@FixifyHelpDesk)
15 Sept 2026
Trust your gut: The leadership advice I'd give my younger self | Darragh Curran
Darragh Curran (https://www.linkedin.com/in/darraghcurran/) spent 14 years helping Fin (https://fin.ai/), formerly Intercom, grow from six people to around 1,400. His sharpest lesson for engineers now is that writing code has become the trivial part, while deciding what to build is where the value sits.
He talks with Matt about distilling engineering values after early hires stopped working out, why he hires for durable traits, and how he pushed his team to treat AI as an advantage rather than a threat. He also makes the case that craft now shows up everywhere.
Topics discussed:
- Trusting your gut and acting on conviction
- Hiring for traits over skills or experience
- Distilling implicit team values into explicit principles
- Why writing code became the trivial part
- Reframing AI from threat into an advantage
- Owning problems end to end as a product engineer
- Where craft lives in AI-assisted engineering
Listen to more episodes:
Apple (https://podcasts.apple.com/us/podcast/climbing-the-stack/id1850604017)
Spotify (https://open.spotify.com/show/5fJOhXU3qrODBA2BJcHQC9)
YouTube (https://www.youtube.com/@FixifyHelpDesk)
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