Jack Sharry: Hello everyone, and welcome to this week’s edition of WealthTech on Deck, where we explore the trends, technologies, and ideas shaping the future of wealth management. For today’s conversation, we’re going to talk about what everyone is talking about—artificial intelligence. And I can think of no one better than Rob Pettman, President and Chief Revenue Officer at Tiffin, to cut through the noise and get to what really matters. Tiffin is one of the most active firms at the intersection of AI and wealth management, with a unique model spanning asset management, distribution, and advisor technology. We’re going to examine what’s real versus hype, what winners are doing differently, and where we’re headed. Rob has been on WealthTech on Deck before, and it’s great to have him back. Rob, welcome back.
Rob Pettman: Thanks, Jack. Pleasure to be here. I’ve got to say, I’ve had a hard time with AI—it used to stand for alternative investments. Now what do we say?
Jack Sharry: I’m with you. I’ve found myself talking about alternatives a lot lately, and when I write “AI,” I have to stop and think about what it stands for. Let’s start at a high level. There’s a tremendous amount of conversation about AI in wealth management right now—arguably more noise than clarity. From where you sit at Tiffin, how would you characterize the current state of AI adoption in our industry?
Rob Pettman: We’ve gone through a progression—initial curiosity, then experimentation, and now we’re moving from experimentation into production. What you’re seeing is different shades of production depending on where firms fall on the risk and sophistication spectrum. On one end, you have lower-risk, more basic implementations like Microsoft Copilot. On the other end, you’re seeing firms using AI agents to rewire internal workflows. That’s where a lot of the future is headed, and there’s a big space in between.
Jack Sharry: I’m seeing that myself. I’ve been using Copilot to help construct questions for this podcast. It gets me part of the way there, but I still need to refine it. Let’s get practical. There’s a big gap between AI as a concept and AI that actually drives measurable outcomes. Where are you seeing AI really working today?
Rob Pettman: There are three major areas. First is productivity. Firms are using AI for note-taking, meeting prep, and content creation. It’s saving time and improving efficiency, although it’s harder to measure the direct commercial impact. As these tools evolve and connect—bringing together CRM data, financial planning, and portfolio systems—you start to build a unified “brain” that understands the client holistically. That’s where you start to see real outcomes. Second is growth and distribution. Firms are leveraging large data sets to generate signals—whether that’s increasing wallet share, identifying new prospects, or helping asset managers determine which advisors to prioritize. These use cases are generating measurable commercial results. Third is workflow and operations. This is the frontier. We’re seeing real progress in areas like advisor transitions, M&A onboarding, and operational workflows. Compressing timelines, improving data accuracy, and accelerating time to revenue are all key benefits. There are also big opportunities in supervision, OCIO functions, and insurance operations—particularly around reducing cost to serve.
Jack Sharry: What I’m hearing—and what I’m experiencing myself—is that AI is streamlining what we do and accelerating outcomes. How does Tiffin help firms actually implement this effectively?
Rob Pettman: It starts with the commercial outcome you’re trying to solve for. Too many firms focus on data problems without defining the outcome. You’ll often hear, “We can’t do AI yet because our data isn’t ready.” But modern technology has changed how you solve those issues. If you don’t anchor your efforts to a specific outcome, you won’t make meaningful progress. Focus on the problem first, then engineer around it.
Jack Sharry: Let’s talk about the advisor level. Advisors are inundated with tools, and now AI is layered on top. What’s actually resonating versus being ignored?
Rob Pettman: At the end of the day, advisors just want to do right by their clients. Not every advisor wants to grow. Some may have the capacity to serve more clients but choose not to. Enterprises may want growth, but advisors have their own priorities. What really resonates is the ability to unify systems and provide a comprehensive view of the client. Today, getting that information can be slow and fragmented. AI creates a more efficient, personalized experience.
Jack Sharry: Firms want advisors to grow, but many advisors don’t seem motivated to do so. How do you approach that challenge?
Rob Pettman: There’s a missing piece—advisors don’t always understand what growth looks like with a new set of capabilities. This is where change management becomes critical. Simply deploying tools isn’t enough. You need to help advisors adapt their behavior. We’ve seen this play out in pilots where advisors were given AI-driven signals—like identifying wallet share opportunities or life events—and encouraged to ask different questions. Initially, there’s resistance. Advisors think they already know their clients. But when they engage with the process, the results can be significant. In one case, advisors in the pilot grew three times more than those outside of it. Without strong change management, those results don’t materialize.
Jack Sharry: What are the most successful firms doing differently when it comes to AI?
Rob Pettman: The most successful firms have strong leadership from the C-suite. They’re not just declaring AI a priority—they’re pushing through structural barriers that would otherwise prevent success. Most firms aren’t set up organizationally to fully realize AI’s potential.
Jack Sharry: What do you mean by structural barriers?
Rob Pettman: Historically, business teams have deferred technology decisions to IT. But AI isn’t just a tool—it’s a shift in the operating model. If technology leads without deep business involvement, it won’t work. You need a business-led, technology-enabled approach, with both sides collaborating toward a shared outcome.
Jack Sharry: Let’s make a distinction between AI as a tool and AI as an operating model.
Rob Pettman: The real value emerges when cost savings, growth, and scale come together. For example, in advisor transitions, operations teams used to handle everything manually. Now, they’re reviewing dashboards, focusing on exceptions, and processing multiple cases in parallel. That’s a fundamental shift in how the work gets done.
Jack Sharry: Let’s talk about personalization. How is AI changing that in wealth management?
Rob Pettman: AI enables true personalization at scale. You can now create personalized portfolios more efficiently and connect them to client goals, preferences, and changing circumstances. It’s not just about implementation—it’s about continuous insight and better communication with clients.
Jack Sharry: We’re seeing an explosion of AI point solutions while firms are also trying to rationalize their tech stacks. How do you see that dynamic playing out?
Rob Pettman: This industry moves in cycles—between point solutions and platforms. We’ve moved toward a platform approach because clients want integration. That said, flexibility is critical. Firms may have their own systems and agents, so platforms need to integrate rather than replace.
Jack Sharry: Looking ahead 12 to 24 months, what will change most meaningfully?
Rob Pettman: A lot of the operational drudgery in wealth management will go away. There’s a huge amount of manual work that doesn’t add value, and AI will streamline that. More broadly, I think we’ll see better outcomes for investors as firms and advisors become more effective.
Jack Sharry: Quick lightning round. What’s one AI use case every firm should prioritize?
Rob Pettman: It depends on the firm, but common areas include operations, supervision, and transitions—especially where you can align growth, cost savings, and scale.
Jack Sharry: Biggest misconception about AI in wealth management?
Rob Pettman: The gap between what’s possible and what people think is possible. That misunderstanding limits adoption.
Jack Sharry: Let’s close with something personal. How do you recharge?
Rob Pettman: I haven’t quite embraced meditation yet, but I do long runs and long bike rides—that’s my version of it.
Jack Sharry: That counts. Rob, this has been a great conversation. Thanks again for joining us. And to our audience, thank you for tuning in. If you enjoyed the podcast, please rate, review, subscribe, and share. You can find us at wealthtechondeck.com and wherever you get your podcasts. Rob, thanks again.
Rob Pettman: Thanks, Jack. Appreciate it.
