AI and the Future of Risk with Dan Chuparkoff

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Navigating Risk: A Career in Technology

This chapter explores the speaker's extensive career in technology, focusing on their experiences in risk management across various organizational settings. It highlights the interplay between risk management and leadership, as well as the importance of public speaking in sharing knowledge and insights.

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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 Reinvention Labs to helping organizations reinvent work with the power of AI.

[12:15] Dan was an intern at an architecture firm when he was 17. One architect had AutoCAD, and all the others were drawing on paper. The architect with AutoCAD used copy-and-paste to accelerate his work. That changed the way Dan looked at technological change.

[12:39] From the age of 17, Dan started looking for those copy-and-paste moments. He found them, over and over again. Spreadsheets improved our analysis. The internet improved our ability to look for information. AI improves our ability to juggle more data than before.

[12:58] All those things were coming at a predictable cadence. It takes about five years for new technology to become part of the infrastructure. Dan realized that you have about five years to tackle something new before the next new thing comes at you.

[13:21] People wait for the dust to settle. They don’t start figuring out how to build this new thing into the way they work. You’ll get passed by. You’ll be working too slowly, and your customers will expect more of you. Or you’ll do it too quickly, make mistakes, and create unnecessary risk.

[13:44] Figuring out how to manage these five-year cycles of change became Dan’s strength.

[13:57] Dan will expound on his copy-and-paste moments in his November keynote. This was a preview. It was the moment that changed the way he thought about tools and technology, and their impact on the way we work.

[14:23] Justin says Dan takes complex topics and makes them simple and useful for a non-technical audience. Dan says a lot of people are talking about AI now.

[14:52] AI is an umbrella term that includes a lot of things. It’s on the level of “math.” You don’t say, “We’re implementing math at work, right now.” Math is part of everything we do.

[15:09] One of the things Dan helps people do is to start breaking AI down. Are we talking about a chat interface on top of our customer service knowledge base? Are we talking about a sophisticated AI image-recognition system to look at MRI scans? Those are different things.

[15:29] They’re both using AI, but as you’re evaluating the risk of AI features, AI deployment, and AI use cases, it will be helpful to understand the difference between a chatbot, image recognition, and AI-based research. They all have different amounts of risk.

[15:49] If you try to have a single AI policy that covers all those things, it will be challenging. That’s how Dan helps to break it down.

[16:14] Dan will have 60 minutes for his keynote. He will spend 45 minutes covering content he thinks is important for risk management professionals and about 15 minutes of open Q&A. He will also be around all day, if people want to talk to him in the hallway or at lunch.

[16:44] Final Break! The Spencer Educational Foundation’s goal to help build a talent pipeline of risk management and insurance professionals is achieved, in part, by its collaboration with risk management and insurance educators across the U.S. and Canada.

[17:03] Since 1999, Spencer has awarded over $2.9 million to create more than 570 Risk Management Internships. The Internship Grants application process is now open through October 15th, 2025.

[17:20] To be eligible, risk managers must be based in the U.S., Canada, or Bermuda. A link to the Internship Grants page is in this episode’s show notes. You can always visit SpencerEd.org, as well.

[17:33] Let’s Conclude Our Interview with ERM Conference Opening Keynote, Dan Chuparkoff!

[17:53] Dan says the fundamental and most important thing to remember is that AI shouldn’t make your decisions for you. Ask AI for 10 things that you should do, and you decide which one of those things is the right thing. You have a lot of things in your head that AI doesn’t know.

[18:20] You have things you remember from your first job, the things you remember your mother telling you when you were nine. Those things influence your decisions, and AI doesn’t know any of them. Always use AI as a recommendation and make your own decisions.

[18:43] Dan almost always says to give him 10 of whatever he is looking for. Some answers are too conservative, some are too risky, and some can work. No one is good enough at prompt engineering to put all the context in. Dan asks for choices and picks the one that feels right.

[19:43] Why is there a gap between crafting an AI policy and putting it into practice? Some people are creating policies with a different level of understanding of what AI is capable of doing and what it is not. Sometimes, policies are just early in their maturity.

[20:17] Three years from now, it will be a better policy that understands some of the discrepancies a little bit more, and that gap will start to close.

[20:25] Some people have policies, and their people are ignoring them. When ChatGPT came out in November 2022, students started using it for homework. It became a part of their lives. They didn’t stop using it when they went to work, regardless of the company policy.

[21:14] There’s a shadow AI use at a lot of organizations. The more your AI policy is crowdsourced, and you’re asking your people what they need, what they want, and what they’re doing already, the better your policy will match what’s happening in your organization. It evolves.

[21:44] Dan adds that email is already susceptible to IP leakage, but because of user training and judgment, people in the organization know what data to keep out of the email system. With training, people will learn what data to keep out of the AI system.

[22:48] The best add-on to email, according to Dan, is sending calendar invites. Justin says the best add-on is scheduled send. He loves how people think he sends an email at 5:01. Dan says an AI tool, Fixer, will draft a reply to every message you get, and you can send or edit it, or not.

[24:00] Dan foresees AI-powered email things that will be life-changing. Justin says Google will already generate a message for you if it’s something simple.

[24:37] Dan says before every keynote, he tries to get a deep understanding of the audience and what they care about. He goes through their website, watches videos, reads blogs and articles, and listens to podcasts. All those things influence the research and the content he brings.

[25:04] What Dan will do for his keynote is dig into the ways AI is changing the work that risk management professionals are doing now and how that will continue to change over the near term.

[25:15] Dan won’t talk about 20 years from now, but about six months to three years from now, what that’s going to look like, so that people can start anticipating the future and building a safe, risk-controlled future that they’re trying to build.

[25:38] I’m looking forward to it. You’ve been a wonderful guest. You’ve piqued the interest of a lot of our audience, and we hope they’ll make it out to Seattle on November 17th, when you kick off the conference for us.

[25:56] Dan looks forward to hanging out with everybody in Seattle. His parting advice is to tell AI, “Give me one thing every Monday that I should learn about AI.” Every week, you’ll be a little smarter about AI. You don’t have to do the things, but they’re little nudges along your AI journey.

[26:30] Special thanks again to Dan Chuparkoff for joining us here on RIMScast. We are so excited for him to kick off the RIMS ERM Conference 2025 in Seattle, Washington, on November 17th. The registration link is in this episode’s show notes, or visit the Events page of RIMS.org.

[26:50] We want to see you on November 17th and 18th. We will have more ERM Conference presenters on RIMScast in the next six weeks. Be sure to subscribe to RIMScast through your favorite podcasting app and catch all the risk management goodness!

[27:05] Plug Time! You can sponsor a RIMScast episode for this, our weekly show, or a dedicated episode. Links to sponsored episodes are in the show notes.

[27:34] RIMScast has a global audience of risk and insurance professionals, legal professionals, students, business leaders, C-Suite executives, and more. Let’s collaborate and help you reach them! Contact pd@rims.org for more information.

[27:52] Become a RIMS member and get access to the tools, thought leadership, and network you need to succeed. Visit RIMS.org/membership or email membershipdept@RIMS.org for more information.

[28:10] Risk Knowledge is the RIMS searchable content library that provides relevant information for today’s risk professionals. Materials include RIMS executive reports, survey findings, contributed articles, industry research, benchmarking data, and more.

[28:26] For the best reporting on the profession of risk management, read Risk Management Magazine at RMMagazine.com. It is written and published by the best minds in risk management.

[28:41] Justin Smulison is the Business Content Manager at RIMS. Please remember to subscribe to RIMScast on your favorite podcasting app. You can email us at Content@RIMS.org.

[28:53] Practice good risk management, stay safe, and thank you again for your continuous support!

Links:

RIMS ERM Conference 2025 — Nov. 17‒18

Spencer Internship Program — Registration Open Through Oct. 15.

10th Annual Chicagoland Risk Forum — Sept. 18 | Registration open!

RIMS Western Regional — Oct 1‒3 | Bay Area, California | Registration open!

RISKWORLD 2026 — Members-only early registration through Sept 30!

Spencer Educational Foundation 2025 Funding Their Future Gala — Sept. 18, 2025, in NYC!

RIMS-Certified Risk Management Professional (RIMS-CRMP)

The Strategic and Enterprise Risk Center

RIMS-CRO Certificate in Advanced Enterprise Risk Management — Featuring Instructor James Lam! Next bi-weekly course begins Oct 9.

RIMS Diversity Equity Inclusion Council