Roselle Safran: So much opportunity. [Entrepreneur] [Career Notes] - CyberWire Daily

Summary5 min read

Episode Overview

Podcast: CyberWire Daily
Guest: Roselle Safran, CEO and Founder of KeyCaliber
Episode Title: Roselle Safran: So much opportunity. [Entrepreneur] [Career Notes]
Release Date: September 21, 2025

In this episode, Roselle Safran discusses her unconventional career path into cybersecurity, her leadership philosophy, and her entrepreneurial ventures. She shares concrete advice for those entering the field, particularly encouraging women to apply their talents in cybersecurity. Roselle’s story is a testament to adaptability, resilience, and the immense opportunities present within the cybersecurity industry.

Key Discussion Points & Insights

Roselle’s Career Evolution (01:14 - 03:40)

Early Ambitions and Transition:
- As a child, Roselle aspired to a variety of professions but gravitated to technology after studying civil/environmental engineering at Princeton.
- “I think when I was in about fifth or sixth grade, I wanted to be about six different professions ranging from doctor to ballet dancer and everything in between.” (Roselle Safran, 01:16)
- Her first foray into tech was at a startup after college, which sparked a sustained interest in the startup environment.
Entry into Cybersecurity:
- Found an opportunity as a computer crime investigator at a law firm with no prior background, convincing the hiring manager of her ability to learn on the job.
- “I had no background in any of the skills required, but the job sounded fascinating and I was able to convince the hiring manager that I would learn all the skills on the job and that's what really started to take me down the cybersecurity path...” (Roselle Safran, 01:52)
- Earned one of the earliest NCASE certifications in computer forensics.

Public Sector Experience (03:40 - 04:50)

Roles at DHS and the Executive Office of the President:
- Led forensic and malware analysis teams at the Department of Homeland Security.
- Managed all security operations at the Executive Office of the President, highlighting both the honor and stress involved:
  - “I was honored to have the opportunity to work there. It was a very stressful experience because I was always concerned that there would be a major breach that would be front page news that did not happen under my watch.” (Roselle Safran, 03:58)
- Discussed challenges during the 2013 government shutdown, including taking night shifts herself:
  - “At one point, half of my team was furloughed and so I went back to working on the night shift doing analysis.” (Roselle Safran, 04:33)

Entrepreneurial Journey (04:50 - 05:30)

Startup Ventures and Problem Solving:
- Founded her first startup, Up Level Security, after identifying gaps in cyber-ops during government service.
- Keycaliber is her second cybersecurity startup, driven by a “circuitous path” and a continual desire to solve real operational challenges.

Leadership Philosophy (05:30 - 06:15)

Teamwork and Collaboration:
- Values open communication, creativity, and empowering team members.
- “I am very focused on collaboration, making sure that everyone has a voice because everyone has great ideas. I certainly do not have a monopoly on great ideas.” (Roselle Safran, 05:39)
- Emphasizes that the Keycaliber team is “incredibly supportive and collaborative and communicative.”

Reflections on Failure and Resilience (06:15 - 06:55)

Learning from Setbacks:
- Redefines failure as a temporary blip and credits resilience for recurring success.
- “Once you have in your mind failed and picked yourself back up from it, it's not hard to do it again and again because you know, you have that resilience and you're not afraid of failing.” (Roselle Safran, 06:21)
- Urges entrepreneurs to “pat yourself on the back” for progress but never to rest on laurels.

Advice for Aspiring Cybersecurity Professionals (06:55 - 08:00)

Encouragement to Enter the Field:
- Strongly endorses cybersecurity as a career path, especially for women:
  - “Anyone who is in college or looking at a career change, I always tell them, go into cybersecurity. There is so much opportunity that's not changing anytime soon.” (Roselle Safran, 07:10)
- Counsels against unnecessary hesitation:
  - “I often hear people say that they feel that they need more education before they can even apply for jobs in cybersecurity. And I tell them, just apply, just learn it on your own and download free demo versions of every open source product you can get your hands on and then just start applying...” (Roselle Safran, 07:32)
- Stresses the industry’s need for passionate learners and advocates for boosting diversity:
  - “If you have the will and the capability to learn and learn quickly, that's what's needed... For everyone in cybersecurity, they should encourage one person to get into cybersecurity. We need to spread the word more because it's an exciting industry that needs more talent in it.” (Roselle Safran, 07:48)

Notable Quotes

On Self-Discovery and Careers:
“It wasn't until much later that I had a better understanding of where there were opportunities and what was a good fit for me.” (Roselle Safran, 01:21)
On Breaking Into Cybersecurity:
“I had no background in any of the skills required, but the job sounded fascinating... that's what really started to take me down the cybersecurity path.” (Roselle Safran, 01:52)
On Handling Stressful Leadership:
“There was never a dull moment and we were a 24 by 7 shop and there was never an evening where I slept through the night.” (Roselle Safran, 04:17)
On Fostering Innovation:
“I like to give people as much room to be creative and as innovative as possible and then hear everything that they have to say.” (Roselle Safran, 05:51)
On Resilience:
“You know that this is a momentary blip. I'm down per minute, but I'm going to get up and I'm going to do something else that's super exciting.” (Roselle Safran, 06:29)

Timestamps for Important Segments

01:14 — Roselle’s early ambitions and introduction
01:52 — Entry into cybersecurity and computer forensics
03:40 — Department of Homeland Security and Executive Office of the President roles
04:33 — Challenges during government shutdown
05:30 — Shifting to entrepreneurship
05:39 — Leadership and collaboration philosophy
06:21 — Thoughts on failure and resilience
07:10 — Advice for aspiring cybersecurity professionals
07:32 — Overcoming hesitation and self-education
07:48 — Industry needs and call to action

Final Takeaways

Roselle Safran’s journey underscores that with curiosity, persistence, and a willingness to learn, individuals from any background can thrive in cybersecurity. Her advocacy for inclusivity and continuous learning reflects the spirit of the evolving industry: “There is so much opportunity that’s not changing anytime soon.” (07:10)

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[01:14]
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Hello, my name is Roselle Saffran and I am the CEO and founder of Keycaliber. I think when I was in about fifth or sixth grade I wanted to be about six different professions ranging from doctor to ballet dancer and everything in between. It wasn't until much later that I had a better understanding of where there were opportunities and what was a good fit for me. My undergrad degree from Princeton is in civil engineering, specifically focus in environmental engineering and I did that for a year after school and then switched to more of a tech type role at a startup and I kind of got the bug for startups and this was dating myself here, but back at the end of the original.com boom then I saw this really interesting position as a computer crime investigator posted for a law firm. I had no background in any of the skills required, but the job sounded fascinating and I was able to convince the hiring manager that I would learn all the skills on the job and that's what really started to take me down the cybersecurity path because I was doing computer forensics. I think I was 600 and something in the world to have an NCASE certification and once I had that background in computer forensics, then it's actually really easy to get jobs after that. So then I eventually moved to the Department of Homeland Security and there I was leading the forensic and malware analysis teams. And then from there I moved to the Executive office of the President and there I was leading all the security operations. I will say it was a phenomenal experience. I was honored to have the opportunity to work there. It was a very stressful experience because I was always concerned that there would be a major breach that would be front page news that did not happen under my watch. There was never a dull moment and we were a 24 by 7 shop and there was never an evening where I slept through the night. I was there during the government shutdown in 2013. At one point, half of my team was furloughed and so I went back to working on the night shift doing analysis. It was a fantastic experience. It really helped me understand where there were technology gaps that needed filling. My job since then have been around helping to fill those gaps and improve security operations. And then my entrepreneurial bug came back because I had had all these experiences in cybersecurity operations, learning what worked, what didn't work. And that led me to found my first cybersecurity startup, which was called Up Level Security. Keycaliber is my second cybersecurity startup. So very circuitous path to get to where I am. I am very focused on collaboration, making sure that everyone has a voice because everyone has great ideas. I certainly do not have a monopoly on great ideas. I like to give people as much room to be as creative and as innovative as possible and then hear everything that they have to say. And I'm very thankful with the team that we have at Keycaliber is it's just incredibly supportive and collaborative and communicative. The definition of failing is very different for each person. But once you have in your mind failed and picked yourself back up from it, it's not hard to do it again and again because you know, you have that resilience and you're not afraid of failing. You know that this is a momentary blip. I'm down per minute, but I'm going to get up and I'm going to do something else that's super exciting. I think the biggest challenge for entrepreneurs, especially when they're just starting out, is that fear of failure. It's great to just take a moment to pat yourself on the bag and say, hey, this was fantastic. And then you keep pushing forward. You can't rest on your laurels at any point. Anyone who is in college or looking at a career change, I always tell them, go into cybersecurity. There is so much opportunity that's not changing anytime soon. And you can take it in all sorts of different directions. I really try to encourage people to enter the industry, especially women. We really need more women in cybersecurity. I often hear people say that they feel that they need more education before they can even apply for jobs in cybersecurity. And I tell them, just apply, just learn it on your own and download free demo versions of every open source product you can get your hands on and then just start applying, start applying, start applying. Because there's just so much opportunity. If you have the will and the capability to learn and learn quickly, that's what's needed, I'd say, for everyone in cybersecurity, they should encourage one person to get into cybersecurity. We need to spread the word more because it's an exciting industry that needs more talent in it.
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