Welcome to RIMScast. Your host is Justin Smulison, Business Content Manager at RIMS, the Risk and Insurance Management Society.

 

In this episode, Justin interviews Dan Chuparkoff, the CEO and founder of Reinvention Labs, about his risk career, from an insight at age 17, leading at tech giants, to founding a startup to help organizations reinvent themselves with AI. Dan asserts that if you’re not keeping up with AI, you’re falling behind your industry. Dan previews his upcoming November 17th opening keynote address at the RIMS ERM Conference 2025 in Seattle, Washington.

 

Listen to learn more about AI, innovation, and staying ahead of the competition.

 

Key Takeaways:

[:01] About RIMS and RIMScast.

[:17] About this episode of RIMScast. We will be joined by the CEO of Reinvention Labs, Dan Chuparkoff. Dan will deliver the opening keynote at the RIMS ERM Conference 2025 on November 17th in Seattle, Washington. 

[:47] We will get a glimpse into Dan’s risk philosophies, when it comes to AI and innovation, and get a preview of his keynote. It’s going to be a lot of fun!

[:55] RIMS-CRMP Workshops! The next RIMS-CRMP-FED virtual workshop will be held on November 11th and 12th, and led by Joseph Mayo. Links to these courses can be found on the Certification Page of RIMS.org and through this episode’s show notes.

[1:16 ] RIMS Virtual Workshops! RIMS has launched a new course, “Intro to ERM for Senior Leaders.” It will be held again on November 4th and 5th and will be led by Elise Farnham. RIMS members enjoy deep discounts!

[1:33 ] The full schedule of virtual workshops can be found on the RIMS.org/education and RIMS.org/education/online-learning pages. A link is also in this episode’s notes.

[1:44 ] Several RIMS Webinars are being hosted this Fall. On September 18th, Origami Risk will present “Driving Better Incident and Claims Management with Data, Technology & Strategic Collaboration”.

[1:57 ] On September 25th, we will have a special webinar, hosted by Merrill Herzog, about active shooter preparedness in 2025 and beyond. That session will be complimentary for members and nonmembers. So, be sure to put that on your calendar for 1:00 p.m. Eastern Time.

[2:16 ] On October 9th, Global Risk Consultants 07returns to deliver “Natural Hazards: A Data-Driven Guide to Improving Resilience and Risk Financing Outcomes”.

[2:25 ] On October 16th, Zurich returns to deliver “Jury Dynamics: How Juries Shape Today's Legal Landscape”.

[2:33 ] On October 30th, Swiss Re will present “Parametric Insurance: Providing Financial Certainty in Uncertain Times”.

[2:42 ] On November 6th, Hub will present “Geopolitical Whiplash — Building Resilient Global Risk Programs in an Unstable World”. Register at RIMS.org/Webinars.

[2:54 ] On with the show! As you know, the RIMS ERM Conference 2025 will be held in Seattle, Washington, on November 17th and 18th. Our guest today will be kicking off the conference with his keynote, “AI and the Future of Risk Management.”

[3:11 ] His name is Dan Chuparkoff, and he is the CEO and Founder of Reinvention Labs. He’s going to talk to us all about innovation and how AI can enrich our risk management processes. This conversation today will be a preview of what he will bring to the stage in Seattle.

[3:30 ] Be sure to visit the link in this episode’s show notes to register. You can also visit RIMS.org/Events and click on the ERM banner. I had such a great time recording this interview, and I know you are going to love it. Let’s get to it!

[3:43 ] Interview! Dan Chuparkoff, welcome to RIMScast!

[3:52 ] Dan is super excited for this conversation. He says he doesn’t always get this chance before an event to dig into some of his thoughts about the event and the industry.

[4:37 ] Dan had a meandering career. He worked for 32 years in technology. He worked for some massive organizations, a 100-year-old company, McKinsey, some new startups, more mature startups like Atlassian, and Google.

[5:15 ] Working for major enterprises and new startups, Dan got exposure to risk management perspectives from both extremes. He built a blend of how he thinks about risk that mixes the best of both worlds. That has helped make him successful. He’ll talk about that in his keynote.

[5:44 ] Dan brings some things he learned from nimble startups about experimentation, and keeps his eye out for the pitfalls that are coming in the future, which the major enterprises had more risk awareness to avoid.

[6:08 ] Dan worked alongside risk managers, who were the Chief Legal Officer, or even the CEO, to figure out when they were taking smart risks and when they needed to stop doing something they had started.

[6:40 ] Dan learned of Enterprise Risk Management while working at a marketing services software development agency. They were building software for global enterprises. As they built software, the enterprise would have a review board evaluate it for quality and policy adherence.

[7:09 ] From 2002 to 2010, Dan got real exposure to global risk management. He learned things like the risk philosophy of European countries and the European Union, as it differs from American risk philosophy. 

[7:35 ] Dan notes that the risk management profession tunes you to be a systems thinker, not just a siloed thinker. You’re not just thinking about what your team is doing, but you’re thinking of the downstream ripple effects of every decision that you make.

[7:53 ] As you become a leader in charge of more of the organization, systems thinking prepares you to understand the ripple effect of your decisions and think about how decisions need to be coordinated across the different streams of the organization. That makes you a great leader.

[8:40 ] About 15 years into Dan’s career, he realized there were some things he knew deeply and was really passionate about. When those things came up in meetings, he was outgoing. He stood up and marked on the whiteboard.

[9:06 ] He had this passion, and he knew it would be helpful to share it. Before he started thinking about audiences and microphones, he started thinking about the content he was passionate about. That content was about people’s ability to change and adapt to new technology.

[9:29 ] Technology changes all the time. New technology is confusing and filled with risk. At some point, you have to get on that new bus, or the organizations in your industry will pass you by. Dan became excited about that. It became easier for him to talk in bigger groups.

[9:54 ] One day, Dan found himself onstage at a Gartner conference in front of 800 people, and that was the beginning of a journey he says is now the best job in the world.

[10:34 ] RIMS Events! On September 18th, the 10th Annual Chicagoland Risk Forum will be held at The Old Post Office in Chicago. Register at ChicagoRIMS.org.

[10:49 ] On October 1st through the 3rd, the RIMS Western Regional Conference will be held in North San Jose at the Santa Clara Marriott. The agenda is live. It looks fantastic! Visit RIMSWesternRegional.com and register today!

[11:06 ] RISKWORLD 2026 will be in Philadelphia, Pennsylvania, from May 3rd through the 6th. RIMS members can now lock in the 2025 rate for a full conference pass to RISKWORLD 2026 when registering by September 30th.

[11:21 ] This also lets you enjoy earlier access to the RISKWORLD hotel block. Register by September 30th, and you will also be entered to win a $500 raffle. Do not miss out on this chance to plan and score some extra perks.

[11:34 ] The members-only registration link is in this episode’s show notes. If you are not yet a member, this is the time to join us. Visit RIMS.org/membership and build your network with us here at RIMS.

[11:46 ] Let’s Return to Our Interview with ERM Conference Keynote, Dan Chuparkoff! 

[11:58 ] Justin asks how Dan’s experience of building and leading teams at Google, McKinsey, and Atlassian, delivering software to billions, informs his current approach as the CEO of R