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Is This the Most Sought After Job in Wealth Management?

Those who have been chief of staff at Dynasty Financial Partners – shadowing and keeping CEO Shirl Penney on schedule – have consistently become executives and directors at the firm.

Pay and perks are important but a job with great potential can trump others in a flash. That’s exactly why Brendan Bell chose to become the chief of staff at Dynasty Financial Partners. He saw what those before him have gone on to do.

Since Dynasty was founded in 2010, chiefs of staff have regularly moved on to become executives and directors at the service provider to a network of 47 RIAs. These RIAs manage more than $40 billion in assets, in aggregate, including more than $18 billion in assets on its turnkey asset management platform, or TAMP.

Justin Weinkle, who Dynasty named chief financial officer earlier this week, was a summer analyst in 2012 and then joined the company full-time as chief of staff from 2013 to 2015. After only four years, including stints as senior vice president of Finance, head of strategic analysis, and director of M&A, Weinkle is now in a powerful position at a company that plans to double in size.

Dynasty’s chief administrative officer, Austin Philbin, was also CEO Shirl Penney’s right-hand man prior to becoming a managing director and executive.

Following 10 years in the Navy as a pilot and air-to-air combat flight instructor, Benjamin Bines attended Harvard Business School and then became chief of staff. Now, he’s the senior vice president of Network Development at Dynasty.

Jason Pinkham, managing director of Relationship Management & Transition at Dynasty, joined the firm in 2010 to become chief of staff after spending years in operations for the Pittsburgh Pirates and Major League Baseball.

“The chief of staff role at Dynasty is essentially an 18-24-month crash course in all things related to our business, with the underlying job description of affording Shirl leverage in every way imaginable,” said Bell, the current chief of staff.

Much of the chief of staff’s daily duties are akin to an administrative assistant. Bell manages Penney’s calendar and sometimes wild travel schedule. In addition to popping back and forth between New York and Dynasty’s new headquarters in St. Petersburg, Fla., Penney makes frequent appearances on the industry conference circuit.

Bell is also a stand-in for his boss; his eyes and ears because even Penney can’t make two meetings at once.

“It is a position that I would say is not unique to Dynasty but is one that attracted me to the firm in the first place,” Weinkle said.

Eventually, the chief of staff becomes more efficient. The mundane duties get done more quickly, freeing up time for opportunities to learn through “osmosis,” while taking on projects of interest. 

“The success story of Justin working his way from chief of staff to CFO is exactly how Shirl intends the role to work, and I certainly hope to emulate that path in some way,” said Bell, who acknowledges that he is unsure of where the role will ultimately lead.

To his knowledge, Weinkle said Dynasty has never posted a chief of staff opening on LinkedIn or any other job site. Most candidates are people Shirl knew previously or they were stand-outs in Dynasty’s summer analyst program. The chief of staff is often someone Shirl thinks will be a good long-term employee but who lacks the skillset for a given job opening at the time.

“Several” assistants to Penney didn’t work out in the past because they weren’t able to keep up with him and the chief of staff role was created in part to remedy that, Weinkle said. 

“I’ll just say it requires a much higher level of traditional execution capacity,” Weinkle said. “You have to be someone who puts their ego aside for a couple years.”