Disclaimer: Yes, this post is long, so grab a coffee (or two). But hey, if TPAs can survive compliance testing season, you can survive this.

I never expected to find myself in the retirement industry.

A few years ago, if you’d told me I’d be swapping AI talk for 401(k) compliance chatter, I might have checked your temperature. Yet, here I am - deep in the trenches of third-party administration. The entry was anything but traditional: it involved a dash of skepticism, a couple of major pivots, and a whole lot of learning.

Let me share how I stumbled into the world of TPAs, fell in love with it, and why Stax.ai is here for the long haul.

What the Heck Is a TPA?

Back in 2021, I was introduced to a company named Pinnacle Plan Design. They introduced themselves as a TPA looking for help with automating some paperwork. Full disclosure: I had no idea what a “TPA” was. (Total Party Animal? I was clueless. By the way, I learned now that it might as well have been that...) A quick Google search later, I learned it stands for third-party administrator – an independent firm that handles the nitty-gritty of managing retirement plans for businesses.

These are the folks who keep 401(k) and pension plans running smoothly by tackling administrative tasks like record-keeping, compliance testing, and government filings.

In other words, they’re the behind-the-scenes heroes making sure your retirement plan stays legit.

I met with Pinnacle, a Tucson-based TPA, and they had a very specific pain point: thousands of brokerage statements arriving by mail, with staff spending hours scanning, sorting and filing them by client. They wondered if our AI tech could help. At the time, my company (Aptus Engineering, which later spun out Stax.ai) was building document automation for healthcare, not finance. But we launched it in November 2019, and COVID-19 was just a solid concrete wall blocking our growth in healthcare. We were scrambling to find a new market. So we thought - why not give it a shot? We configured our workflow tool to do the sorting and filing automatically. To Pinnacle’s delight, it worked – a job that took hours was now done in minutes.

That got my attention. Here was an industry I knew nothing about, yet our solution hit a bullseye on a real problem. What other headaches were TPAs quietly grinding away on, and could technology help? My skepticism about this “stodgy” sector started to fade. I began to wonder: if one TPA had this issue, how many others were in the same boat?

Conference Crashers

Fast forward to spring 2022. We caught wind (via a last-minute email blast from PensionPro) of a conference called NIPA NAFE 2022 – the National Institute of Pension Administrators’ Annual Forum & Expo – happening in New Orleans. It sounded like the place to learn about the TPA world. One problem: it was only three days away, and we hadn’t even registered.

My wife, Lindsay and I decided to go for it. We scrambled to put together some makeshift brochures about our product (an overnight print job Kinko’s would be proud of). With a mix of nerve and naiveté, I hopped on a plane. I was a newbie in a sea of seasoned retirement pros. We had no booth, no passes, and no clue – just enthusiasm and those freshly printed pamphlets. We walked into the hotel conference center acting like we belonged, determined to blend in.

Sneaking in turned out to be surprisingly easy – I just waltzed through the doors with a confident smile. To be honest, I didn't even know registration was required.

(Since then, I have apologized to NIPA and hoped that our string of sponsorships and advertising made up for this!)

I wandered the expo hall, introducing myself to anyone who would listen, and soaking up every conversation. When people asked who we were, we’d say, “Stax.ai – we do AI automation for TPA firms.” That usually got polite nods or puzzled looks. This wasn’t exactly a tech crowd; clearly we had to learn to speak their language.

By the end of the event, I had made a few friends and collected a stack of business cards. More importantly, we walked away with an education money can’t buy – an unfiltered look at the daily struggles of TPAs. Which leads me to…

Pattern Recognition

After countless conversations in those halls, a clear pattern emerged. Nearly every TPA I talked with had similar gripes about their workflows and tools. “We’re drowning in paperwork,” one person sighed. “Our software works, but it’s no spring chicken,” said another. The retirement industry, it turned out, was full of inefficiencies that no one had fully solved - and very few had even attempted.

We heard about offices drowning in paper and Excel files. We heard about data re-keyed into five different systems because nothing was integrated - the classic copy-paste gymnastics. One attendee joked their core software was “state-of-the-art… in 2005.” Ouch. Another admitted they spent more time chasing data and documents than actually helping clients.

In short, here were the recurring pain points we discovered:

• Document Overload: Too many papers and forms coming in from all directions, with staff manually sorting and filing each one.

• Archaic Software: Reliance on legacy TPA systems that looked and felt like they hadn’t updated since the flip phone era (no names mentioned, but a certain popular software got more than a few groans).

• Fragmented Tech Stack: Multiple systems for different tasks – one for plan docs, another for compliance, another for CRM – that don’t talk to each other, forcing repetitive data entry.

• Workflow Bottlenecks: Key processes (like annual compliance testing or trust accounting) that bog down because they’re handled with semi-manual workarounds.

It was the perfect storm begging for automation and better integration. My pattern-recognition neurons were firing. It struck me that TPAs are truly the backbone of the retirement industry, yet they were stuck with processes from a bygone era.

The incumbent software vendors had grown complacent, and nobody was tackling the big picture for these folks.

By the time I left New Orleans, my skepticism had evaporated. In its place was excitement (at the opportunity) and a bit of indignation on behalf of these professionals who clearly deserved better tools.

Falling in Love (With the Industry)

Here’s the plot twist: I went to that conference a cynic, but I left a convert.

Despite all the challenges they face, the people in this industry are passionate, genuine, and deeply committed to their work. These aren’t Wall Street fat cats or aloof tech execs; they’re small business owners, actuaries, compliance nerds (said affectionately), and client service reps who truly care about helping employees retire comfortably.

They take pride in making sure every employee’s retirement plan is in good shape.

It dawned on me that TPAs have been underserved and overlooked. When people talk about fintech, retirement plan administration rarely gets a mention. It’s a crucial niche that has flown under the radar. Yet, this community is the glue connecting all the stakeholders - employers, advisors, record-keepers, regulators - keeping plans running smoothly.

They’ve been holding it all together with duct tape and sheer willpower.

I fell in love with both the problem and the people. The decision practically made itself: we were going to pivot Stax.ai entirely into retirement plan tech.

It wasn’t easy.

It meant pulling back from other markets we’d been exploring, but my gut told me it was the right move. We already had one foot in the door thanks to Pinnacle and the TPAs they introduced us to, and now we were ready to jump in with both feet.

Back home, we immediately began reshaping our roadmap. No more half-measures.

Our AI company was becoming a full-fledged TPA tech partner.

In 2022 we onboarded more TPA clients (word spread that we had a nifty solution for that statement-filing headache). Each new client taught us more about the industry’s nuances. Instead of scaring us off, the complexities only reinforced our commitment. By mid-2023, we had phased out all non-retirement projects to focus entirely on the TPA market.

We had found our mission: make life easier for TPAs with modern technology.

Timing Is Everything

Life has a sense of humor.

As if our pivot journey wasn’t eventful enough, the universe added some personal plot twists at highly inconvenient times. Case in point: the ASPPA Annual Conference 2022 (ASPPA being the American Society of Pension Professionals & Actuaries). I was all set to attend my first ASPPA national conference in fall 2022 to continue my TPA education. Then, shortly before the event, our first child arrived - my son, Atlas was born. Talk about timing. Instead of networking with peers, I was at home learning to change diapers and function on two hours of sleep. I even slipped away for one day of the conference when I was giving a speech on AI and its impact on the world, but I was basically a zombie in the sessions.

Fast-forward two years to ASPPA Annual 2024. Wouldn’t you know it - child number two decided to debut that same week. Our daughter, Josie was born right before the conference, and I missed it entirely.

At this rate, I suspect my kids have an internal alarm set for major industry events – two for two so far!

I wouldn’t trade those moments for anything, of course. But it is ironic that the two times I was most eager to immerse myself in the community, I ended up on paternity leave instead. Thankfully, our team covered for me at those conferences, and this community is so tight-knit that I got plenty of updates on what I missed. On the bright side, I now have two adorable reminders of why we do this work: to build a better future for our kids (and everyone else’s).

Why We’re Here to Stay

If there’s one message I want every TPA to hear, it’s this: Stax.ai is all-in on TPAs. We’re not in this space as a quick side gig, and we’re not here to replace anyone. Our mission is to support and empower TPA firms, not sideline them.

Early on (well, and still now...), people asked if we’d ever try to sell our platform directly to plan sponsors (the employers) or to other providers. The answer remains no. Sure, chasing plan sponsors might sound tempting for a bigger market, but that’s not our game. We believe the best way to improve the retirement industry is to elevate the experts who are already doing the work - the TPAs - rather than bypass them.

TPAs possess a level of expertise, passion, and grit that is impossible to match, and is absolutely crucial to successfully administering retirement plans. Just look at the fintech TPA/record-keepers - they offer very basic plan designs, zero support, and when compliance tests fail, they just tell plan sponsors that they did it wrong. No wonder so many plan sponsors are leaving them to go to TPAs to save them.

This philosophy also sets us apart from some of the incumbent software providers.

A lot of the big TPA software players have been around for decades. They built solid tools back in the day, but time (and tech) marched on. Many are now stuck with legacy architectures – imagine trying to bolt new features onto a platform that’s old enough to order a beer. Not easy. (There are a few well-known systems in particular that gets a lot of eye-rolls; I won’t name names, but if you know, you know.)

Bottom line: we’ve put our stake in the ground here.

I might have been a wide-eyed tourist at that first conference in 2022, but now I’d say I have resident status. And with each new TPA partner we onboard, our conviction grows that this is exactly where we’re meant to be.

The Road Ahead

Our journey with TPAs is just getting started. We constantly think about how to add more value and cover more ground in the retirement plan ecosystem. The vision is to expand into adjacent verticals that work closely with TPAs, in ways that strengthen TPAs’ work rather than compete with it.

What does that mean in practice? It means building features and integrations for the other professionals who collaborate with TPAs daily. For example:

• Plan Auditors: Annual plan audits involve a lot of document exchange. We see an opportunity to streamline that – maybe auto-generate complete audit packets or give auditors a secure, read-only portal to necessary data. If we can save both the auditor and the TPA hours of back-and-forth, that’s a win for everyone.

• ERISA Attorneys: These lawyers draft plan documents and help keep plans compliant. They often coordinate with TPAs on amendments and regulatory updates. We want to make that collaboration smoother – perhaps by integrating document updates and approvals into our system, so when an attorney makes a change, the TPA is instantly alerted and has the latest document.

• Financial Advisors: Advisors rely on TPAs for plan health reports and compliance updates. We envision giving advisors a dashboard (fed by TPA-curated data) where they can see key metrics about their plans on-demand. Imagine an advisor seeing up-to-date participation rates or testing results without having to ask the TPA for a report.

• Outsourced Service Providers: Outsourcing has been around for a while, but has exploded in the industry recently. Credentialed administrators are available in countries where cost of living is a tenth of what it is here in the US. Additionally, there are companies like Pinnacle and Aegis who outsource actuarial work. DB valuations and cross-testing are not for the faint of heart. For TPAs who want to focus on 401(k)s, such companies offer flexibility. We aim to streamline this process so it's easier for TPAs to collaborate with outsourced providers easily.

In pursuing these extensions, we’re careful about one thing: mission focus.

The goal isn’t to do everything for everyone, but to double down on what we do best (automation, data handling, workflow) in service of the retirement plan community. We’re not about to turn into auditors or lawyers or advisors. We’ll leave that to the pros. But if we can build bridges between TPAs and those allies through technology, we’ll gladly do it.

Looking ahead, we’re excited to apply AI to even more challenges – imagine predictive analytics catching issues early or AI assistants drafting routine documents, all while keeping TPAs firmly in the driver’s seat.

My Message to TPAs

To all the TPA professionals reading this: thank you for welcoming an outsider like me into your world, for candidly sharing your challenges, and for giving us a chance to help.

Stax.ai isn’t here to disrupt you – we’re here to uplift you. Trust is earned, and we’re committed to earning it by delivering solutions that make your life easier and your business stronger.

I often remind my team, “We’re not tourists in the TPA industry.” We’re not just passing through, grabbing some swag, and moving on to the next thing. This is our home now. We’ve traded the novelty of the new for the satisfaction of digging in and solving tough problems side by side with you, the experts.

This is baked into our culture.

From crashing that first conference to now, it’s been one heck of a ride. And the road ahead looks even brighter. We’re here to stay, and we’re here to serve. Together, let’s build the future of retirement plan administration - one innovation (and maybe one witty conference story) at a time.

Stax.ai 💙 you!