AdvicePay finds its 'rockstar' leader after 14-month process where external candidate fizzled; now in-house candidate is ready to sizzle

AdvicePay exists because co-founders  Michael Kitces and Alan Moore found no product – forget PayPal – on the market that allowed XY Planning Network to bill for financial plans sold as a separate service.

But AdvicePay grew too fast and became too complex for Moore to handle as a part-time co-CEO, in addition to his duties at XY Planning and father of three in Montana's wide open spaces.  See: Alan Moore can't catch a break; AdvicePay CEO exits after seven months, adding job he hoped to escape back on top of XYPN role; search on for new AdvicePay president

So the search began for his replacement, and Kelsey Lewis ultimately fit the bill. What's more, she already lives in Bozeman! 

Finding an outside executive who had the skills, embraced the company's culture and was willing to relocate to Montana proved to be "a pain point we didn't know about," says Kitces.

Bozeman is a postage stamp-sized city of 56,000, located on the windswept Great Plains surrounded by mountain ranges in what's known as the “Valley of the Flowers.”

Insider connection

Skiers and outdoor types flock there, but financial industry types are as scarce as the bobcats and bears that sometimes wander through town. 

Lewis, 36, was working as AdvicePay's head of Customer Success when she got the call. Now, she's taking over as president, with CEO-like duties, according to Kitces.  

The company hit a critical mass that demanded its own CEO, Kitces told RIABiz in February a year ago. See: Alan Moore is the No. 2 busiest man in the RIA business and he just convinced the No. 1 busiest man to budget $200,000 to hire a 'rockstar' to replace him

“As a tech company, it’s reached that crossover point where there’s a clear product-market fit – crossing 8,000 [it's now 15,000] users, and that’s actually paying advisor users."

Kitces and Moore launched AdvicePay after discovering there was virtually no client visibility as a payment travels from client-to-advisor-to-broker-dealer and back to advisor over the course of 60 days.

"The whole 60 days the advisor is saying: 'Where is my money?' Now advisors can see everything," says Kitces.

Cultural fit

“The President's role is a big one with the growth of AdvicePay, fully accountable for the P&L and day-to-day execution across the entire business,” Kitces wrote today by email. 

“So Kelsey's first task in the role will be back-filling her replacement to lead Customer Success, if you know anyone who's looking!”

And there's no question she fits the culture, according to her company bio.  

"When she’s not at the forefront of building relationships, Kelsey enjoys skiing at Big Sky, leisurely floats along the Madison River and water-skiing adventures at the lake with her friends and family," it states. 

‘Rockstar' wanted

She will have big shoes to fill – even if they are her own, according to the AdvicePay release.

“Lewis worked with many of the industry’s largest RIAs and broker-dealers,” the company writes. 

"Her efforts helped AdvicePay achieve a 36% increase in transaction volume while maintaining a 100% enterprise customer retention rate.” See: Funded to the teeth by RIAs, Michael Kitces and Alan Moore now have a second big play--modernizing plan payments--and broker-dealers are beating down the door

The effort to replace Moore at AdvicePay came to RIABiz's attention last year, when the company wrote a help-wanted advertisement for the ages. 

It sought a “rockstar” – at a middling executive salary of about $200,000 – but also an eye-popping list of perks and benefits. 

It thought it had one in New Jersey executive Alex Sauickie, 52, who was hired last July, and allowed to commute from Jersey to Bozman. That lasted about eight months; he departed in March by mutual agreement. 

Bill Winterberg suffered a similar fate. He was hired as AdvicePay's first ever vice president of financial planning growth and lasted about 12 months before his position was eliminated. 

 Perking up

Lewis should avoid all those complications and reap a substantial list of perks that includes pet insurance (remember bobcats!), equity, $1800/year toward the cost of working with a financial planner, plus up to $500 toward the one-time upfront fee. 

Added to that are the following:

• $250/quarter to spend on yourself specific to our Core Value of “Be Well Being You”
• $500 donated to a non-profit organization of your choice when you volunteer 40 hours/year
• $2,000/year in Professional Development funds
• A sabbatical program that includes a cash bonus and extra time off at five, ten and 15 years
• Subsidized employer-sponsored childcare through its internal daycare program
• And a MacBook!

Asked why she joined AdvicePay, Lewis talked about her original hiring process in 2021 and what she was looking for – and looking to avoid.

“I sought out AdvicePay because of Alan [Moore] and what he was building from a cultural perspective – and talking about the customer experience,” she says. See: Alan Moore and Michael Kitces pledge 50-50 gender ratio at XYPN then digitally fill two crucial roles with women -- one hire using Indeed and the other by Twitter

“I've had a few not-as-good experiences.”

Solid experience

Asked whether her job as head of customer success prepares her for being president, Lewis says “yes.” 

In her previous role, she said she was actively engaged with all parts of the company to be sure customers succeeded – a practice she believes will pay off now.

Lewis earned her MBA from the University of Utah; before joining AdvicePay, she was director of business operations at Montana Mex, a Bozeman company that makes organic sauces, seasonings and oils. 

Before that, she was director of client experience at Wisetail Learning & Operation Solutions, an executive employee training company in Bozeman. 

Now, Lewis solves the next AdvicePay “pain point” – helping Moore, 37, find time to live his life in Bozeman and continue to grow both fast-growing young enterprises.