The WealthStack Podcast: Portfolio Personalization Without the Ops Headache with Wes Caywood
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:
- Listen to WealthStack on Wealth Management
- Subscribe and listen to WealthStack on Apple Podcasts
- Subscribe and listen to WealthStack on Spotify
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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