Tag: Automation
The WealthStack Podcast: Rethinking Technology, AI and the Advisor Experience with Freedom Dumlao

The WealthStack Podcast: Rethinking Technology, AI and the Advisor Experience with Freedom Dumlao

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Technology in wealth management isn’t just changing, it’s colliding with reality. Advisors are expected to deliver deeply personalized experiences, operate at consumer-grade speed and navigate increasing complexity, all on top of legacy systems never designed for this moment. As AI accelerates what’s possible, the real challenge isn’t adopting new tools, it’s rethinking how technology supports the advisor experience from the ground up.

In this episode of The WealthStack Podcast, host Shannon Rosic sits down with Vestmark CTO Freedom Dumlao to go behind the curtain of modern wealthtech and unpack why advisor experience, data integration and agentic AI are now the real battlegrounds for scaling RIAs. 

Key takeaways:

  • Why consumer software experiences are redefining advisor expectations at work
  • How integration challenges quietly drain time and limit true personalization
  • Why agentic AI is the real leap forward
  • Why the advisor’s moat is validation, not information
  • How compliance doesn’t kill innovation, it sharpens it

Resources:

Connect with Shannon Rosic:

Connect with Freedom Dumlao:

About Our Guest:

Freedom Dumlao is the Chief Technology Officer at Vestmark, where he leads the firm’s technology strategy with a focus on resilience, scalability, and building long-term client confidence. He brings a disciplined, hands-on approach shaped by senior leadership roles at Amazon, Zipcar, Flexcar, Wayfair, and Drift, including his work on the Alexa machine learning and AI platform. A strong advocate for open-source communities, Freedom also serves as a board member and treasurer of Ruby Central. Outside of work, he enjoys woodworking, cooking, and spending time with his two daughters building robots and experimenting with electronics.

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The WealthStack Podcast: Portfolio Personalization Without the Ops Headache with Wes Caywood

The WealthStack Podcast: Portfolio Personalization Without the Ops Headache with Wes Caywood

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As advisors race to deliver “personalized” portfolios at scale, a hard reality is setting in: most personalization is still just a model tweak with a nicer label. Meanwhile, clients want more hands-on service, more transparency and more customization, while firms are trying to grow without hiring an army of operations and investment staff. The result is a widening gap between what clients expect and what legacy portfolio tools can realistically deliver. The firms that win won’t be the ones stacking more complexity. They’ll be the ones using automation to deliver truly bespoke outcomes, with clearer decisioning, tighter risk controls and better records behind every trade.

In this episode of The WealthStack Podcast, host Shannon Rosic sits down with Wes Caywood, head of distribution at Pave Finance, to unpack what “real personalization” actually means in 2026, why portfolio complexity rarely translates into client-perceived value and how automation can make portfolio management more defensible, not less. 

Key takeaways:

  • How to modernize portfolio management with “blowing up” your existing workflows
  • Where AI actually fits in portfolio management
  • Where the personalization gap shows up most clearly (and why it becomes an ops and time problem fast)
  • What automation should capture for compliance, auditability, and transparency 
  • The biggest mistake firms make when evaluating portfolio tech

Resources:

Connect with Shannon Rosic:

Connect with Wes Caywood:

About Our Guest:

Wes Caywood is the Head of Distribution at Pave Finance, where he works closely with advisors and firms to modernize portfolio management through thoughtful use of technology and automation. With more than 20 years in financial services, Wes brings deep experience working with sophisticated clients, family offices, and advisory teams. A U.S. Naval Academy graduate and former Navy officer, he is driven by a service-oriented mindset and a focus on helping advisors deliver personalized, well-prepared client experiences at scale.

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The WealthStack Podcast: The Strategy Behind Allworth’s 40+ AI Initiatives

The WealthStack Podcast: The Strategy Behind Allworth’s 40+ AI Initiatives

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As artificial intelligence becomes table stakes, RIAs and enterprises alike are experimenting with tools to streamline workflows, improve client experiences and scale smarter. But while many firms are testing isolated tools, the real opportunity lies in weaving AI into the very DNA of a business, transforming it from a tech experiment into a strategic advantage. 

In this episode of the WealthStack Podcast, host Shannon Rosic speaks with John Bunch, CEO of Allworth Financial, to explore how one of the industry’s rapidly growing RIAs is pushing AI beyond pilot programs. With more than 40 active initiatives and an internal AI Council guiding adoption, Allworth is proving that the future of advice isn’t just about efficiency, it’s about strategy, culture and client impact.

John discusses:

  • Why Allworth launched 40+ projects
  • How AI can elevate client relationships 
  • The role of the AI Council in driving adoption and ROI
  • His “fail fast, fix it or ditch it” approach to innovation and automation beyond AI
  • What it takes to align business strategy and tech strategy in practice

Resources:

Connect with Shannon Rosic:

Connect With John Bunch:

About Our Guest:

John Bunch is the Chief Executive Officer at Allworth Financial. Universally recognized within the wealth management industry, he has accumulated an extensive 30-year history of successfully leading and expanding award-winning organizations that serve both retail and institutional clients.

Before coming to Allworth, John spent over three years as the Chief Financial Services Director at Evelyn Partners (formerly Tilney Smith & Williamson), a leading integrated wealth management and professional services firm headquartered in the United Kingdom. Prior to that, he was the Chief Operating Officer and Executive Vice President of Edelman Financial Engines – where he oversaw 130 branch offices – and the Chief Executive Officer of The Mutual Fund Store. Before that, he held several key institutional sector leadership positions, including Executive Vice President at TD Ameritrade and Divisional Senior Vice President at Charles Schwab & Co.

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