Build the foundation before you add the tool

This is the latest installment of our Partner Interview Series, where Gabe sits down with the people who help advisors and sales teams run their business, and gets into where AI fits into that today.

Next up is Kate Guillen, founder and CEO of Simplicity Ops, an operations consultancy that helps RIAs build the systems, workflows, and CRM foundations that let everything else — including AI — actually work. Kate started in an admin and ops role at a broker-dealer before moving to an RIA, and she founded Simplicity Ops in 2019 to share what she'd learned with other advisors. She's based in the San Diego area, where she recently moved onto a 7-acre avocado ranch with her family.

Give us some background on Simplicity Ops. Who do you work with, and what's the focus?

I think it starts at the origin. I've been working in the investment management industry since 2013, supporting financial advisors in an admin and ops capacity. I got a job at a broker-dealer when I was 24. I didn't know the difference between a stock and a bond — I just had some really strong administrative skills, and a friend of a friend introduced me to her husband, who was a stockbroker there, and he hired me because he needed admin help. The first day I showed up, he looked at me and said, listen, I'm not going to teach you anything — you're going to listen, ask questions, take notes, and learn. I thought, holy smokes, I've made a terrible decision, because I don't know anything and I need someone to teach me. But it was actually a fantastic introduction to the industry. I sat in on every meeting, every phone call, took notes. We didn't have things like ChatGPT back then, we had Investopedia, so I spent a lot of time teaching myself the difference between a stock and a bond and an IRA and a Roth, learning how to speak advisor.

About three years in, I left to join an RIA, which opened up a lot more freedom and flexibility around technology. I was working for a wonderful advisor — it was just him and me, managing about $150 million across 300 households, and pulling our hair out every day because we had no systems, no processes. Everything was reactive, stressful, fighting fires all day. It wasn't a lot of fun, and I knew I wasn't going to stick around feeling that level of stress. But I loved the advisor, his vision, his clients. So I had to figure out how to help him and help myself do it better.

He had a pretty snazzy tech stack that none of us were really using. Redtail was the industry-leading CRM at the time, and it was basically a really expensive Rolodex for us — contact info, maybe a note, but nowhere near the functionality it was capable of. I attended one of Redtail's Redtail University events and it blew my mind, all the CRM was capable of if somebody took the time to build it out. So I spent the next several years learning how to leverage the CRM as the hub of our business — the one-stop shop for contacts, tasks, sales pipeline, calendar — and delivering a proactive instead of reactive client experience, layering in workflows and other technologies to make his life and my life easier.

About three and a half years in, we'd hit some pretty lofty goals — grow AUM, increase profitability, better serve clients, leave our TAMP, bring portfolio management in-house, grow a team — and I looked up one day and realized we'd actually done all of it. We were happy. I wasn't hating my job anymore. He was leaving on time to go coach his kids' sports. I could take a vacation without a laptop. And I thought: this could be a really cool business idea, if I could share what I'd learned with other advisors who don't want to spend three and a half years making the same mistakes I made figuring it out. That's where Simplicity Ops came from.

What made you leave a job you'd finally gotten really good at, to go build something of your own?

I didn't want to work for somebody else's dream. I had my own dream, a big vision for myself and my life, and I knew I was going to hit a ceiling in that practice. I don't have a college degree, I don't have my CFP, and it was made very clear that to be a partner in that firm, I needed to be a revenue-producing advisor. I had no interest in going back to get a degree — I wanted to forge my own way. I talked to my boss about it, and he said he'd be sad to see me go but thought I had a really good idea, and offered to let me work part-time for him while I worked part-time on the side hustle. That was Christmas 2019. I got my first two clients in February 2020, and it was clear I was going to make more money on the side hustle than on my job, so I quit on March 5th, 2020. The world ended about five days later.

I thought, holy smokes, I've made a terrible decision. But between you and me, there was never a more apparent time that we needed an online system for managing an investment management practice than in 2020. When I'd joined that RIA, we were using paper and filing cabinets — that wasn't going to fly once everyone had to go virtual. Simplicity Ops really took off from there, because people recognized they needed an online system for running their business, to make sure things didn't slip through the cracks and that they could keep delivering a great client experience in a virtual world.

What size firms make up your sweet spot today?

Our bread and butter are firms managing north of $150 million in assets, with a team of three, four, five-plus between advisors and admin/ops folks. Having said that, our mission is to help as many advisors and their teams as possible run thriving businesses and live better lives, so we also have a service offering for smaller organizations under $150 million — maybe a solo shop or a solo plus an admin — that's more done-with-you than done-for-you. But predominantly, our best clients manage anywhere from $150 million to a couple billion in assets.

When you take on a new client, what does the process look like, and what are the common problems you run into?

I'll take it back a step before they even become a client. We work exclusively with advisors who use Redtail or Wealthbox, and recently we've added Slant into the mix. They get the highest adoption rates, and adoption is ultimately the key to success — we need everybody to adopt these systems. When we start an engagement, we go through an assessment: a deep dive into how well they're actually using their system.

The pain points we hear a lot: I'm the bottleneck of the operating system, everything relies on me, I can't delegate well, I can't take a vacation without a laptop, I'm worried about things slipping through the cracks, I'm losing sleep because things aren't documented, we do things differently every time, we're using maybe 10% of our CRM and our other technology, everything feels disjointed and clunky. We don't build the engagement around that emotion, though — we do the assessment to take a deep dive into the data behind it. How well are they actually using their CRM? Have they segmented their contacts? They'll tell us they manage 100 households and the CRM says 630. Where's the actual source of truth? Is it spreadsheets, or spread across too many systems? Do they have the regulatory-required information on file — dates of birth, social security numbers, addresses? Are they using the CRM as a task management system, or still tasking over DM, email, text, or shouting down the hall? Do they have a centralized firm calendar, a documented service model, a proactive system to make sure people are met with at the right cadence for their segment, workflows for the repetitive stuff — opening accounts, moving money, changing an address, running payroll, sending a newsletter? What does the prospect journey look like?

Once we've done that assessment, my team and I put our heads together and build a roadmap — here's what I'd do to organize the data better, structure contacts better, capitalize on the CRM's functionality, here's what other systems I'd use for notes and calendaring, here's templated emails, tasks, and workflows. Then we give them the option: go execute it yourself, or partner with a team that's done this hundreds of times and get there faster.

What's it like getting advisors to actually do this work?

It's hard, but I think one of the reasons we work so well with advisors is they like doing what they like to do, which is not what we like to do, and we like doing what they don't like to do. I had an advisor tell me that before working with us, he would've rather put a fork in his eye than write a workflow. We just love writing the systems, processes, and SOPs all day — it's a huge compliment to my team, because they make it fun and enjoyable. We're complete geeks about systematizing businesses, because we've watched what happens as a result of it.

If you'd asked me in 2020 what our goal was in partnering with advisors, I'd have said help them make more money, grow their business, grow assets. Now if you ask us, it's the complete opposite — it's to help them live a better life. They know the money follows; it's a result of the good work they do. And to do the good work, they need capacity, time to think and pour into themselves. Your business grows naturally and exponentially as long as you're doing those things first, and that's really hard to do when you're losing sleep, worried about dropped balls, dealing with employee turnover, or getting beaten to the punch because you don't have a proactive communication system in place.

Where do you think AI fits into all of this?

There is no silver bullet. Any AI tool needs a foundation to be effective. If you integrate AI into a messy, disorganized business, it's the same as bringing an employee into a chaotic business with no vision, no clarity, no systems, no processes — they end up sitting on Facebook all day. You have to have clarity and a vision for what the role entails, and the exact same thing is true of integrating an AI assistant. People miss that.

How do you think about a firm's tech stack — where do you start, and how does AI fit in?

We're big on the CRM being the source of truth for managing client relationships — contacts, tasks, sales pipeline, calendar, client experience, workflows, and SOPs. But the CRM can't be all the things; it's designed to be the database. There are some very necessary spokes that come off that hub to make the business run — portfolio management software, a financial planning tool — things the CRM just can't do.

We're not quick to recommend a bunch of technology — we actually do the opposite, and try to keep it very simple. But when we recognize a pain point on a team, that's where we go to the Kitces AdvisorTech Map to see what the options are and help evaluate who's best in class for that specific need. We take into account price point and budget, team size, complexity, whether they have a broker-dealer affiliation and what's been approved. We'll literally draw a T-chart of pros and cons. Note-taking is a big one we run into. For data gathering and form filling, is it PreciseFP, or does it need something custom? For calendaring, is it Calendly or GReminders? It depends on what else is in the stack, because we try not to integrate redundant technology, and we try to keep it as simple as possible — simplicity gets adoption, and simplicity scales. When you overcomplicate things, nobody's going to use it.

And if an advisor has to log in to three different places and remember what to click, it's not going to happen. The work has to get done for them.

It needs to happen for them, not to them. I think that's an important distinction.

Looking ahead to 2027, what's the biggest change you expect for the advisors you work with?

I think the way we operate is going to change. There's an oversaturation of tools right now, and I think we'll see combinations, mergers, acquisitions, or some of them will just phase out — which I'm hopeful makes decisions around technology easier. I'm really curious about the CRM space and how it's going to look. I've always talked about the CRM as being the hub, and I think more of the business — email, prospecting, calendar — is going to live in one place, so you can close out some tabs. That's the way it should be, and I think it's going to create a lot of efficiency. I'm curious to see how the established CRMs evolve, whether there are new players, and how we think about the CRM as the hub going forward. I think there's an opportunity to do it a whole lot better.

What would you tell advisors to do now to get ready for that?

Even in the CRMs we set up today, we're tracking all of those data points, but it's still a manual process to act on them. There's still too much manualness involved in delivering that experience. So what people need to be thinking about is consolidating tools, and selecting the tools that elevate their client experience, because that's what's going to differentiate people.

Favorite book, favorite tool, and how do you take your coffee?

Anything by Dr. Benjamin Hardy and Dan Sullivan — 10x Is Easier Than 2x, Who Not How, and The Gap and the Gain are fantastic. I cycle through them, I read them annually, I go back to them often.

My favorite tool right now is Slant. It's been really cool watching the pace at which they're innovating. At the end of the day, though, the people part of the business is the most important part, so for me it's about how we can spend more time doing the people stuff and better nurture relationships.

And I take my coffee black — iced black coffee, 365 days a year. I don't drink hot coffee. I drink coffee for the effect, not the taste. Just good old-fashioned drip coffee — and this is so gross — I drink the day-old pot over ice. I'm a one-cup-a-day gal, sensitive to caffeine, though I'm hoping to get into the tea game — I just ordered myself a nice teapot.

Kate's take on building the foundation before you add the tool — and her read on why AI needs to happen for advisors, not to them — is a good gut check no matter where you are in your tech stack. If you want to talk shop with her about getting your CRM and workflows in order, you can find her at Simplicity Ops or connect with her on LinkedIn.