Tag: Wealth Technology
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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From Franken-Stacks to AI Agents: The Annual WealthTech Outlook with Davis Janowski

From Franken-Stacks to AI Agents: The Annual WealthTech Outlook with Davis Janowski

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For three years running, the WealthStack season has officially started the same way: with an unfiltered wealthtech outlook conversation between Shannon Rosic and Davis Janowski, senior technology editor and research analyst at Wealth Management. If 2025 was the year firms finally started using AI, 2026 is shaping up to be the year we find out whether all that tech actually pays the rent.

In this annual tech vibe check, Shannon and Davis dig into how AI notetakers quietly reshaped advisor workflows, why agentic AI and “AI operating systems” are the next wave, and what this all means for junior talent, firm structure and the future “Chief AI Officer.”

They also explore whether Franken-stacks are really dying, how niche platforms and new lead-gen tools are redefining value, and why cybersecurity and deepfakes may be the biggest underpriced risks on every CTO’s roadmap. 

Key takeaways:

  • What under-the-radar innovations to watch in the 2026
  • How data fragmentation limits real AI adoption despite rising tech budgets
  • What agent-based platforms signal about the future of advisor software
  • Why critical thinking remains more valuable than pure AI skills
  • How cybersecurity risks are growing faster than regulatory responses

Resources:

Connect with Shannon Rosic:

Connect with Davis Janowski:

About Our Guest:

Davis Janowski is a New York-based technology journalist whose work spans consumer, business and the FinTech sectors.

Prior to his six years with WM, Janowski worked for Forrester Research as an analyst covering Digital Wealth Management. In edition, he has worked for two FinTech startups, Wealthfront and New York-based FeeX, Inc. (now Pontera). His work covering the advisor tech space began in 2007 when he joined InvestmentNews as the advisor industry’s first dedicated technology reporter. His start in tech journalism began as an editor with PC Magazine in 1999 where he later served as an analyst and reviewer.

His work has appeared in The New York Times, Wealth Management, Financial Planning, RIABiz, InvestmentNews, PC Magazine, numerous blogs and several books, including Technology Tools for Today’s High Margin Practice. He has also been a speaker and moderator at numerous industry conferences.

Outside his day-to-day he is a senior guide for Manhattan Kayak Company in New York City.

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The WealthStack Podcast: Jason Pereira’s Unfiltered Take on 2025 Wealthtech Wins and Wipeouts

The WealthStack Podcast: Jason Pereira’s Unfiltered Take on 2025 Wealthtech Wins and Wipeouts

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Technology promises speed and clarity, yet frustration keeps showing up instead. Many firms buy tools expecting instant results, only to find the real challenges start after launch.

In this episode of The WealthStack Podcast, host Shannon Rosic speaks with Jason Pereira, senior partner and financial planner at Woodgate Financial, about what actually broke in wealthtech adoption this year. They unpack why most failures are human, not technical, how unrealistic expectations derail implementation and why AI often complicates workflows before helping. 

They also explore where AI truly adds value, why surface-level integrations fall short, and what advisors should focus on before buying the next shiny tool.

Key takeaways:

  • Why most tech “fails” at the human level
  • The rise and risks of vibe coding and DIY tools
  • AI’s real wins and painful misfires in 2025
  • The danger of treating complex tools like plug-and-play appliances
  • What advisors should actually do heading into 2026

Resources:

Connect with Shannon Rosic:

Connect with Jason Pereira:

About Our Guest:

Jason Pereira is a financial planner who has lived and breathed financial planning for over 20 years. Over that time, he has become a recognized writer, commentator, speaker, podcaster, teacher, and voice in financial planning, practice management, and fintech. He has earned two degrees, nine professional designations, been nominated for or received more than 30 industry awards, and produced over 750 articles, podcasts, and interviews. JasonPereira.ca serves as his platform for sharing the insights, perspectives, and lessons he has gathered throughout his career.

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