A Day in the Life: Jason Rebholz

We are taking a look at the typical workday and aspirations of insurance professionals at different companies and in different stages of their career.

In this edition of A Day in the Life, we explore the role of a co-founder and CEO of a cybersecurity startup, Jason Rebholz.

Background

What is your current position? How long have you been in it? How did you find it? 

I’m the co-founder and CEO of Evoke Security, the EDR for AI agents. I started Evoke Security in June of 2025 after seeing the trajectory of where AI was going. I saw a fundamental underlying security issue in the approach and that we were about to repeat the same security mistakes we made with every new emerging technology. The challenge to get ahead of that pain is what found me.

Please give a description of your current position, something that explains your role in the insurance marketplace and how you interact with others:

As the CEO, it’s my responsibility to plot the course and enable our team to deliver on it. A lot of that involves educating others on the emerging risks and enabling them to get ahead of it. As the former CISO at Corvus Insurance, I spent a lot of my time working with brokers and policyholders to educate them on where cyber attacks were going, including the early days of deep fake technologies. Today in my role at Evoke, I continue to spend time with carriers and brokers to educate them on how the risks of AI agents are evolving and what it means for their customers.

What positions have you held to date? Why did you get into the insurance industry?

I started my career in incident response at Mandiant as their first college hire. It was an incredible opportunity to gain hands-on experience responding to incidents. It was there that I had my first exposure to working with cyber insurance on their panels. From there, I continued to work in various incident response startups including Crypsis Group and MOXFIVE, where I continued to build relationships within the cyber insurance ecosystem. That led me to become the CISO at Corvus Insurance, where I was able to secure Corvus’s environment and support securing our policyholders through innovative early alerting of emerging vulnerabilities and compromised credentials.

What do you love most about your position?

I love being at the edge of where technology is going and doing my best to play a part in securing that for organizations. I spent over a decade responding to the pain of cyber incidents. It’s energizing for me to work to get ahead of the next wave of pain organizations will face.

What skills make someone successful in your position?

Curiosity and a willingness to pave your own path is what makes someone successful in my position. Much of my time is spent navigating unpaved roads. You must have an innate curiosity to dig deep into problems and an intuition of what the right path forward is. Most importantly, it’s the courage to get started. You can’t steer a parked car; you have to get moving and adjust course as you go.

 

Daily Structure

Please describe your typical workday.

A lot of meetings with customers, partners, and internally.

What is your favorite part of the day and why?

Talking with customers. It’s the perfect way to gather more insights into their challenges and helps inform what we do to make ourselves better.

What is the most challenging part of your day and how do you tackle it?

My morning workouts. Pushing yourself physically also pushes yourself mentally. After a hard workout, the rest of the day seems easy in comparison.

How do you achieve work life balance?

I have a strict morning routine for consistency. While my work can stretch into the early evening and weekends, I do my best to time box work. Anything on the personal side, I treat as a calendar block to ensure its respected. Most importantly, work life balance for me ebbs and flows. I recognize I will never have something that is perfect, so I focus on managing my energy and knowing when I have to pull back.

What do you do to ensure you are progressing in your career and continuously learning?

Reading to understand is key to leveling up. It’s easy to read a headline and assume you understand what happened. Reading leads to understanding which leads to leveling up.

 

Aspirations

What professional advice would you give your younger self?

Your network is your superpower. I always heard it but never truly appreciated it until later in my career.

What is one of your goals you are working towards and have not yet accomplished?

I made the switch to working out every day. It stops the negotiation you have with yourself about when you will work out. I’m nearly three years in on this never-ending goal. The accomplishment is in the journey, not the end, and that’s what I love about it.

 

Other Questions

How do you prioritize when everything feels urgent?

I’m a huge fan of the Eisenhower matrix, where you separate tasks by urgency and importance and take actions on them appropriately. It helps distinguish the fires you need to tackle yourself the ones you can delegate and the ones you can let keep burning.

What tools or software do you use daily?

Claude. Easy.

How do you collaborate with other teams (e.g., underwriting, claims, brokers)?

Virtual meetings and in-person whenever possible.

Do you work remotely, in-office, or a mix of both? How does that shape your day?

I have worked remotely since 2018. It allows me to maximize my day and make the most out of the time when I travel.

How do you stay connected with colleagues or clients?

I’m very active on LinkedIn and love catching up with people on virtual calls or coffees when I’m traveling.

If you could describe your job in three words, what would they be?

Secure the agentic workforce.

 

Typical Day in the Life

5 am – 6 am: Wake up, walk my dog with my wife.

6 am – 7 am: Work out, either strength training, cycling, or Pilates.

7 am – 8 am: Get ready, make some coffee, and prepare for the day.

8 am – 10 am: Focus time. Try to knock out my most creative items when I’m fresh.

10 am – 12 am: Meetings with customers, partners, or employees.

12 pm – 1 pm: Walk my dog. Eat lunch.

1 pm- 5 pm: More meetings and customer demos.

5 pm – 7 pm: Catch up on administrative items.

7 pm – 9 pm: Quality time with my wife: walk the dog, dinner, and Netflix before I power down.