Alex: Hey everyone, welcome to another episode of The Curiosity Code podcast. I’m Alex Khomyakov, and today I’m joined by not one but two incredible guests—Will Prest, Managing Partner at KWP Growth Partners, and Lisa Kottler, a 401(k) fintech strategist and digital transformation leader. Together, they’ve been deep in the trenches exploring the retirement technology space and are here to share key insights from their upcoming Next Gen 401(k) Report. Will, Lisa—welcome!

Will: Thanks, Alex, thrilled to be here.

Lisa: Likewise, thanks for having us.

Alex: So let’s start with the big picture. What’s going on in the 401(k) space that made you two want to dive in and put this report together?

Will: It started from conversations with fintech founders, enterprise leaders, and investors all hitting similar walls. There’s real momentum in the retiretech ecosystem—but also serious friction. A lot of folks want to innovate in this space but are running into outdated infrastructure, complex compliance, and a fragmented landscape. We wanted to map the space and identify where the real opportunities and gaps are.

Lisa: Exactly. I’ve spent 20+ years in retirement, working with everything from recordkeepers to fintechs. And I kept seeing the same thing—new products solving real problems but struggling to scale. There’s a huge opportunity to modernize how we engage plan sponsors and participants, but it takes coordination and a better understanding of the ecosystem. That’s what this report is about.

Alex: So what did you find in the research? What’s the most surprising insight?

Will: One thing that really stood out: most innovation is still focused on accumulation, not income. Everyone’s optimizing savings and investment options, but not nearly enough is happening around how people decumulate, convert savings into reliable income, and feel secure in retirement. That’s a big white space.

Lisa: And related to that, personalization is lagging. We talk about personalization in wealth management, but in retirement? Most people still get a generic portal with 10 funds and a risk questionnaire. That’s not enough. Fintechs are starting to change that—bringing in behavioral data, AI, more tailored advice—but it’s early.

Alex: Let’s pause there. I want to get into the distribution side of this next.

Alex: Distribution is always the elephant in the room with fintech. What’s different or uniquely difficult about distribution in the 401(k) space?

Will: Two things. First, the channel is complex—it’s not just selling to the end participant. You have recordkeepers, plan sponsors, advisors, sometimes TPAs. Each of those layers has its own incentives and tech stack, and that creates friction. Second, trust. Retirement is personal and highly regulated. You can’t just show up with a slick UX and expect adoption. You need to earn credibility, show compliance rigor, and integrate well with existing workflows.

Lisa: Exactly. And we found that fintechs who partner well—with recordkeepers, with advisors, with employers—see faster adoption. It’s not about displacing the current players; it’s about enhancing what already exists. That mindset makes a huge difference.

Alex: So what are the models that actually work? Who’s getting it right?

Lisa: Companies like Vestwell and Guideline are interesting—they’ve built vertically integrated stacks that make it easier for SMBs to offer plans. Others like Human Interest are leveraging payroll integration as a wedge. And then you have infrastructure plays like Pontera, helping advisors serve retirement assets more holistically. These aren’t just flashy interfaces—they’re solving structural issues.

Will: And we’re also watching companies outside retirement—like in payments or embedded finance—that may move into this space. If Stripe or Square decided to wrap retirement offerings into their ecosystems, that could be game-changing. There’s a lot of convergence happening.

Alex: That’s a good segue. You mentioned embedded earlier—what role does embedded finance play in the future of retirement?

Will: Huge. We think retirement benefits will become more contextual. Instead of making people log in to a dusty portal once a year, you meet them where they are—inside payroll, inside benefits platforms, inside banking apps. We’re already seeing early signs of this, but it’s going to accelerate.

Lisa: And that’s where APIs and infrastructure matter. The more retirement providers can expose capabilities through APIs, the more innovation can flourish around them. That’s how you enable personalization, smarter defaults, and proactive nudges based on behavior—not just static plan menus.

Alex: So how far are we from that vision? What’s holding us back?

Lisa: Recordkeeping architecture is still a major bottleneck. Many systems were built decades ago and aren’t API-native. But that’s changing. Newer recordkeepers are taking a more modern, modular approach, and even some legacy players are opening up. Regulation is another piece—safe harbor guidance, data privacy—but that’s evolving too.

Will: I’d add that we need more ecosystem thinking. Fintechs can’t solve this alone. It’s going to take collaboration—between providers, regulators, tech platforms, and employers. The good news is there’s more momentum and funding in the space than ever before. Now it’s about execution.

Alex: Love that. Let’s wrap up with one final question. What advice do you have for fintech founders looking to break into the retiretech space?

Will: My advice is simple—do your homework. Retirement is a regulated, multi-stakeholder environment. If you don’t understand the compliance side or the ecosystem players, you’ll burn time and credibility. Find smart advisors early, understand the incentives in the channel, and design your product to fit the workflows that already exist.

Lisa: I’d add—focus on real problems. There’s no shortage of pain points in this space, but not all of them are solvable with tech alone. Talk to plan sponsors, advisors, participants. Find the intersection of need, feasibility, and business model. And don’t try to boil the ocean. Start with one segment—like gig workers, or pooled plans, or decumulation—and build from there.

Alex: That’s excellent advice. And for those listening who want to dig deeper, when is the full Next Gen 401(k) Report dropping?

Will: We’re aiming to release it later this quarter. It will be available on our website, and we’ll be sharing key insights on LinkedIn and through our networks.

Lisa: And we’re excited to get feedback. This is meant to spark conversation and collaboration, not just sit on a shelf. If you’re building in this space or thinking about it, we’d love to connect.

Alex: Fantastic. Will, Lisa—thank you both so much for being here and for sharing your deep knowledge on where retirement tech is headed. This has been a super insightful conversation.

Lisa: Thanks, Alex, really enjoyed it.

Will: Likewise, thanks for having us!

Alex: And to all our listeners—thank you for tuning in. If you found this episode valuable, be sure to subscribe, rate, and share it. And as always—stay curious. See you next time on The Curiosity Code.