Turning AI Pilots into Enterprise Wins with Rob Pettman

Jack Sharry: Hello everyone, and welcome. Thank you for joining us for this week’s edition of WealthTech on Deck. I’m very pleased to have our friend and colleague, Rob Pettman, on today’s podcast. Many of you know Rob from his nearly 20 years at LPL Financial, where he held various leadership positions and ultimately headed Wealth Management Solutions. Rob played a key role in the firm’s rapid expansion, helping grow assets from $1.4 trillion to significantly more since his departure—though they still miss him. He supported a network of more than 22,000 advisors and also led a research organization overseeing more than $70 billion in AUM. Rob currently serves as President at TIFIN, where he works with industry-leading firms on embracing and leveraging technology, specifically artificial intelligence. Rob, welcome to WealthTech on Deck.

Rob Pettman: Thanks, Jack. What a lovely introduction. Although I’m sure LPL is doing just fine without me—they’re a rocket ship. But it’s not quite the same without me there, at least from my perspective. It’s good to be here with you.

Jack Sharry: So, Rob, you’ve lived on the inside looking out, and now you’re on the outside looking in. All firms are trying to figure out how to grow revenues, keep expenses in check, and every conversation these days seems to be about AI. Where are we in the learning and adoption curve around AI?

Rob Pettman: We’ve been on quite a journey with firms implementing AI. Initially, it was about governance—how to approach AI responsibly. Now, firms are piloting, experimenting, and moving toward implementation. The key is intentionality: combining domain-level expertise with technology expertise to solve specific problems. Doing AI for its own sake doesn’t create value. Some firms succeed internally, others partner, and many do both.

Jack Sharry: Talk a little bit more about that strategic, partner-oriented approach.

Rob Pettman: When firms partner, they look at what the partner can do to create outcomes faster, influence internal initiatives, and speed time-to-market. Many deepen relationships, even investing in partners, to accelerate AI capabilities and gain competitive advantage.

Jack Sharry: Let’s talk about results. What are you seeing from early adoption and experimentation?

Rob Pettman: Results matter. Cost-cutting use cases are easier to measure—like reducing headcount or expanding capacity. Growth is harder but possible. At TIFIN, some clients have achieved more than $2 billion in net new assets through AI-driven growth solutions. It requires adoption, systems, and process alignment.

Jack Sharry: Can you give a concrete example?

Rob Pettman: For wealth managers, AI analyzes external and custodial data to estimate client net worth, income, and wallet share. It identifies opportunities to expand relationships with prioritized, explainable signals. For asset managers, AI unifies data so wholesalers know which advisors to focus on and why. This makes conversations more meaningful and improves flows.

Jack Sharry: How do firms refine and improve results over time?

Rob Pettman: We use machine learning. At delivery, the algorithm is the worst it will ever be, because it learns and improves. Feedback loops—like rating usefulness—feed back into the model. That improves adoption and results.

Jack Sharry: Where are we now in the adoption curve, and what’s next?

Rob Pettman: Most firms are focused on efficiency—expanding coverage or reducing cost. Agentic AI is emerging, enabling real workflows like automating ACAT processes or unifying portfolio, CRM, and planning data into holistic client views. That’s where the real value is.

Jack Sharry: Sports analogy—where are we in the game?

Rob Pettman: As an Englishman, I prefer soccer halves to baseball innings. But we’re still in the first half. Most adoption is still focused on cost-cutting. Growth adoption will be the second half.

Jack Sharry: What distinguishes the firms that are ahead?

Rob Pettman: They move quickly, minimize bureaucracy, and encourage experimentation without punishing failure. Bold leadership helps, but so does a culture that empowers mid-level decision-makers to innovate.

Jack Sharry: Any final thoughts before we wrap up?

Rob Pettman: Beyond pilots and experimentation, real commercial use cases are surfacing. The big question for firms is: how do I move from cost-cutting to growth with AI?

Jack Sharry: And what about ROI?

Rob Pettman: It often starts with a client willing to take a risk without proof points. Once results are shown, others follow and forecast ROI from those proof points.

Jack Sharry: Rob, as always, I’ve learned a lot. Before we go, what do you do outside of work that listeners might find surprising?

Rob Pettman: This Christmas, I’m going to Australia with my dad for his 70th birthday. We’re joining the Barmy Army—the fanatical English cricket supporters—to watch England versus Australia on Boxing Day. I was born and raised in England, moved to the U.S. at age 11, and eventually had to Americanize my accent as a financial advisor because cold-calling with a British accent didn’t work. But I’m still a proud Brit when it comes to cricket.

Jack Sharry: Fantastic. Rob, thanks again. This has been a terrific conversation.