Category: Finance
The WealthStack Podcast: AI’s Client Engagement Frontier with A.J. De Rosa

The WealthStack Podcast: AI’s Client Engagement Frontier with A.J. De Rosa

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Everyone in wealth management is talking about artificial intelligence, but too much of the conversation still centers on efficiency. Yes, saving time matters. But the bigger opportunity is moving firms from disconnected tools, dashboards and workflows into a world where AI can help deliver timely insights, proactive engagement and more personalized communication at scale.

In this episode of The WealthStack Podcast, host Shannon Rosic sits down with A.J. De Rosa, CEO and co-founder of Intellebox, to explore what separates AI as a feature from it as a firmwide strategy, why agentic workflows are not the same as basic automation, and how compliance may become stronger, not weaker, when AI is designed with the right guardrails.

Key takeaways:

  • How client engagement and personalization have become the new bottlenecks in wealth management
  • Why AI needs to evolve from point solutions into agentic operating systems
  • How compliance could become stronger with AI-powered oversight and human review
  • Why the future is not human versus AI, but human judgment plus machine intelligence
  • Why efficiency alone is not a growth strategy for advisory firms

Resources:

Connect with Shannon Rosic:

Connect with A.J. De Rosa:

About Our Guest:

AJ DeRosa is the Co-Founder and CEO of Intellebox.ai, where he leads the company’s mission to redefine wealth management through agentic AI and a next-generation client engagement platform. His extensive experience in startup leadership, capital formation, and enterprise scaling has positioned him exceptionally well for this next chapter, building an industry-transforming company at the intersection of AI and wealth advisory.

AJ brings over 29 years of revenue and operations leadership across finance, AI, and technology. He joined Intellectus Partners as a Partner and CEO-in-Residency, specifically recruited to incubate and launch Intellebox.ai. During his time at Intellectus, AJ helped shape the firm’s growth strategy while architecting the vision, commercial model, and market approach that became the foundation of Intellebox.

Before launching Intellebox.ai, AJ played integral roles in five venture-backed startups. Most recently, as Chief Revenue Officer and Section 16 Officer at Evolv Technologies, he helped lead the company through hyper-growth and its successful NASDAQ public listing in 2021. Prior to Evolv, AJ served as Chief Revenue Officer at Orbital Insight, where he secured over $120 million in venture capital from firms including Sequoia, Google Ventures, and Lux Capital, relationships he continues to support as an advisor.

Earlier, AJ spent more than a decade at Eze Software Group, where he contributed to major private equity transactions and served as Co-Head of Global Sales, solidifying his deep roots in the investment management and hedge fund ecosystem.

AJ holds a B.S. in Economics from Lehigh University.

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The WealthStack Podcast: How Delegating Drives Growth & Better Client Experiences with Brooke Cecil

The WealthStack Podcast: How Delegating Drives Growth & Better Client Experiences with Brooke Cecil

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Sometimes, the biggest growth lever is hiding in plain sight: the client experience advisors are already delivering every single day.

In this episode of The WealthStack Podcast, host Shannon Rosic speaks with Brooke Cecil, vice president of client relations and talent at BELAY Solutions, to unpack why operational support, delegation and consistency are becoming critical pieces of the modern advisory firm. Brooke also shares practical ways to measure delegation, reduce burnout and create more room for client-facing work.

Key takeaways:

  • Where operational breakdowns most often happen inside advisory firms
  • How delegation helps advisors create more capacity without sacrificing service quality 
  • How advisors can identify the first tasks they should hand off
  • BELAY’s “six Ts” framework for identifying what advisors should stop doing
  • Why inbox zero may be overrated 

Resources:

Connect with Shannon Rosic:

Connect with Brooke Cecil:

About Our Guest:

Brooke Cecil is the Vice President of Client Relations and Talent at BELAY, where she works closely with financial advisors and organizations to strengthen their operational support and improve client experience. With nearly 13 years at BELAY, she brings a strong focus on helping firms balance growth with consistency by freeing advisors from administrative bottlenecks. Brooke’s work centers on building systems and support structures that allow advisors to spend more time on relationships, which she sees as the core driver of referrals and long-term growth.

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The WealthStack Podcast: AI, Capacity and the Future of Advice with Mark Swan

The WealthStack Podcast: AI, Capacity and the Future of Advice with Mark Swan

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Everyone in wealth management is talking about artificial intelligence, but the more important question is what happens when it stops being just another feature and starts becoming the operating layer for the firm. Not just a notetaker. Not just a chatbot. Something that can actually help advisors scale capacity, reduce operational drag and make the tech stack feel a whole lot less fragmented.

In this episode of The WealthStack Podcast, host Shannon Rosic chats with Mark Swan, CEO and co-founder of Nevis, to explore what it really takes for AI to move beyond point solutions and into the core infrastructure of a modern RIA. He unpacks the difference between horizontal AI tools and vertical AI platforms, why voice may become the next major interface in advisor technology, and how firms can start thinking about AI not as a collection of disconnected tools, but as a system for orchestrating work across the front, middle and back office.

Key takeaways:

  • Why the real bottleneck in wealth management is advisor capacity, not demand
  • The difference between AI point solutions and a truly unified platform
  • What lessons from digital banking can teach wealth firms about scaling and reducing costs
  • Why voice could become a much more natural way for advisors to interact with their technology 
  • How lowering the cost to serve could make professional financial advice accessible to more clients

Resources:

Connect with Shannon Rosic:

Connect with Mark Swan:

About Our Guest:

Mark Swan is the CEO and Co-founder of Nevis, an AI platform built specifically for wealth management firms. Originally from Scotland, he brings a global perspective shaped by his experience helping scale Revolut into one of the largest digital banks in the world. At Nevis, Mark is focused on reducing the administrative burden that limits advisor capacity, using AI to streamline workflows and improve how firms operate. His work centers on helping advisors spend less time on processes and more time with clients, while also expanding access to financial advice through more efficient and scalable systems.

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The WealthStack Podcast: Are You Hiring AI or Just Buying Tools? with Subatomic’s Sam Sova

The WealthStack Podcast: Are You Hiring AI or Just Buying Tools? with Subatomic’s Sam Sova

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Everyone in wealth management says they’re using AI right now. But if we’re being honest, most of it still looks like faster note taking, cleaner CRM updates or slightly better workflows. Helpful? Yes. Transformational? Not even close.

In this episode of The WealthStack Podcast, Shannon Rosic sits down with Subatomic CEO Sam Sova to unpack the much bigger shift happening beneath the surface: AI that doesn’t just assist advisors, but actually works alongside them.

He explains why the industry is still stuck in a “1995 internet moment,” what it really means to move from AI tools to AI coworkers, and how leading RIAs are already using agentic AI to orchestrate workflows, unlock growth and fundamentally rethink how their firms operate.

Key takeaways:

  • Why most AI in wealth management today is just incremental improvement, not transformation
  • The difference between AI tools and true agentic AI coworkers
  • How AI orchestration creates a single, intelligent view of the client
  • What “hiring AI” looks like inside a modern RIA
  • Why operational efficiency is just the starting point and growth is the real unlock

Resources:

Connect with Shannon Rosic:

Connect with Sam Sova:

About Our Guest:

Sam Sova is the Co-Founder and CEO of Subatomic, where he focuses on helping wealth management firms rethink how they operate through AI-driven systems. With over two decades of experience inside large organizations such as Fiserv, TIAA, AT&T, and Johnson Controls, he has led transformation efforts centered on solving complex operational challenges. Today, he brings that background into the evolving AI space, working with firms to move beyond traditional tools and adopt AI coworkers that can streamline workflows, unify data, and support more meaningful client engagement.

 

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The WealthStack Podcast: Elevating the Client Meeting with Dan Zitting

The WealthStack Podcast: Elevating the Client Meeting with Dan Zitting

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Client meetings remain the heartbeat of the advisory relationship, but the expectations around them have never been higher. Advisors are under pressure to show up prepared, deliver deeply personalized guidance and answer increasingly complex questions on the spot, all while navigating a fragmented tech stack and rising client expectations shaped by artificial intelligence.

In this episode of The WealthStack Podcast, host Shannon Rosic sits down with Nitrogen CEO Dan Zitting to unpack how technology is reshaping the before, during and after of client engagement. Fresh off Nitrogen’s Fearless Investing Summit, Zitting shares why the real opportunity in wealthtech isn’t replacing advisors with automation, but amplifying their expertise through connected workflows, compelling visuals and agentic AI.

Key takeaways:

  • Why the client meeting is becoming the most important battleground for advisor value
  • How Nitrogen rebuilt its platform around its Nucleus AI engine to automate advisor workflows
  • Why tax conversations may spark the next generation of “catalyst moments” for clients
  • Why persuasive visuals can transform client understanding and engagement
  • How AI tools could help advisors manage larger client books while offering deeper planning insights

Resources:

Connect with Shannon Rosic:

Connect with Dan Zitting:

About Our Guest:

Nitrogen CEO Dan Zitting is a SaaS entrepreneur & operator, with a passion for software that enables a bold vision, especially one as bold as empowering the world to invest fearlessly. Prior to Nitrogen, Dan spent 13 years in enterprise SaaS for governance, risk management, and compliance (GRC). That journey started with founding Workpapers.com, the first true cloud software for audit & compliance management, which was acquired by Galvanize (then ACL) in late 2011. Then, leading Galvanize, Dan oversaw growth into the industry-recognized leader globally in GRC as recognized by analysts, investors, and (most importantly) customers alike. Galvanize was ultimately acquired by Diligent in a $1B transaction that created by far the world’s largest company in GRC software, a $650m+ revenue SaaS business serving 25,000 customers in 130+ countries. Dan’s lessons along the way have been published in Forbes, The Wall Street Journal, Bloomberg, Business Week, Reuters, The Street, CNBC, etc., as well as from the stage at hundreds of professional speaking events.

Dan graduated with a BSBA in Information Systems and Finance from Colorado State University and received a Master of Accountancy from the University of Notre Dame. Dan believes his purpose is to challenge the planet’s organizations to maximize impact by operating with a conscience, and he’s found cloud software to be his best contribution to that personal mission.

 

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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: Beyond the Model & Scaling Personalized Portfolios with Joshua Allen

The WealthStack Podcast: Beyond the Model & Scaling Personalized Portfolios with Joshua Allen

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“Personalization” has become one of the most overused words in wealth management and one of the hardest promises to actually deliver. Clients want portfolios that reflect their goals, values, tax realities, and life events. Firms want scale, efficiency, and fewer operational landmines. Too often, those two goals collide.

In this episode of The WealthStack Podcast, host Shannon Rosic sits down with Joshua Allen, CEO of TCP Asset Management, to unpack what real portfolio personalization looks like inside a fast-growing RIA and why most firms underestimate the operational cost of getting it wrong. Josh shares how TCP moved beyond model-only workflows, where automation actually helps (and where it doesn’t), and why saying no to most technology is critical to scaling personalization without creating an ops headache.

Key takeaways:

  • How hiring a director of advisory services strengthened tech integration
  • Why deeper use of existing tech beats adding more tools to the stack
  • How personalized portfolios are driving referrals across generations
  • Why most “personalized portfolios” still feel identical to clients
  • What’s real vs hype when it comes to AI in portfolio management

Resources:

Connect with Shannon Rosic:

Connect with Joshua Allen:

About Our Guest:

As a founding Partner and  Chief Executive Officer of TCP Asset Management, Josh Allen is charged with leading a team of wealth advisors in practice management, business development, and innovative planning solutions. These solutions have provided our clients with the resources and flexibility needed to deliver a personalized financial planning experience that is fluid and dynamic. Josh and his team have developed and refined a process that is comprehensive in nature and ties together: investment management, risk management, retirement income planning, estate planning, business and family legacy planning, and philanthropy. This exclusive process allows them to put together all the pieces of the financial puzzle for their clients as their lives unfold and be engaged when their needs evolve.

Josh received a Bachelor of Science degree from The Ohio State University in Family Resource Management. He also received a certificate in Financial Planning from Boston University. Upon completion of the education, examination and experience requirements, Josh obtained the Certified Financial Planner™, CRPC® and CRPS® designations. His securities licenses include the series 7,9,10 and 66 and State of Ohio insurance license.

Josh is married to Branda, who is also one of his business partners. They together have three children, two dogs and two cats. As a family they love the outdoors, whether it is on the beach or in the mountains, they are always up for an adventure.

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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: Tech Meets Behavioral Finance with Dr. Joshua Wilson

The WealthStack Podcast: Tech Meets Behavioral Finance with Dr. Joshua Wilson

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As artificial intelligence-powered tools flood the market and marketing becomes faster, cheaper and easier to automate, advisors are discovering an uncomfortable truth: more tech doesn’t automatically create more trust. In an industry that’s louder and more crowded than ever, growth is no longer a tactics problem; it’s an attention, resonance and differentiation problem. The firms that win will be the ones that understand how technology amplifies identity, not replaces it, and how behavioral finance and neuroscience shape decisions long before a prospect ever takes a meeting.

In this episode of The WealthStack Podcast, Shannon Rosic sits down with Dr. Joshua Wilson, founder of NeuBeFi, to explore where tech, behavioral finance, and human psychology actually intersect, and why most advisors are focusing on the wrong side of the decision-making process.

Key takeaways:

  • Why most firms have a marketability problem, not a marketing problem 
  • How technology amplifies identity rather than creating differentiation
  • What “signal discovery” means and how it turns sameness into differentiation
  • Why growth fails when treated as a checklist instead of a diagnosis
  • How clarity and cognitive relief drive trust in money decisions

Resources:

Connect with Shannon Rosic:

Connect with Dr. Joshua Wilson:

About Our Guest:

Dr. Joshua Wilson is the pioneer behind Neuro-Behavioral Finance—a transformative approach that fuses behavioral finance, neuroscience, narrative strategy, and decision science to help advisors and FinTechs become the only option their ideal clients feel drawn to.

Before becoming a sought-after strategist to RIAs and FinTechs, Joshua spent nearly two decades inside the arena where he achieved significant success. Joshua has personally closed hundreds of millions in AUM both virtually and in person.

During his time with TD Ameritrade, he was a highly decorated advisor, National Coach of the Year, led the national sales training program, and traveled the country representing the firm.

After transitioning to the independent RIA world, he built and grew his advisory practice from $0 AUM and no base salary. After selling his book, he led another RIA from turnaround to rapid expansion to acquisition as CEO. In addition to guiding wealth advisors and FinTechs, his expertise has been sought by $20+ billion asset managers, platforms backed by Y Combinator, marketing agencies, and venture capital firms.

His programs have reshaped firms that later appeared in Forbes, Financial Times Top 300 RIAs, the RIA Database’s Top 100 Emerging Wealth Managers, and more. Individually, Joshua has been named to multiple Forbes lists honoring America’s top financial advisors and recognized multiple times as a 5 Star Wealth Manager.

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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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