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Hightower loses newly hired president but it brims with 'Signature' talent -- Penny Phillips, Randy Bullard and Gurinder Ahluwahlia -- and it promises a 'near-future,' replacement

Roberto Stewart is out at the Chicago rollup, which is multitasking a revamp and a sale through Goldman Sachs under pressure from investors, waiting for an overdue payout on tied-up cash..

3 min read
By Brooke Southall June 30, 2026
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Penny Phillips also came aboard in April and could be a logical replacement.
  • Hightower president Roberto Stewart departs after brief tenure.
  • Centralized wealth platform Hightower One remains a strategic priority.
  • Firm promises a near-future replacement for the president role.
  • Key internal talent like Penny Phillips and Randy Bullard are potential successors.
AI generated

Roberto Stewart was hired in April to help unify the fragmented Hightower Advisors by building out its centralized wealth platform, Hightower One, but now a replacement will take on that “priority.” 

Roberto Stewart: Cuts career short at Hightower. 

The president of Hightower Advisors chose a quick parachute for undisclosed “personal reasons,” but apparently will stick around to help his as-yet-unnamed replacement. See: Thomas H. Lee puts Hightower rollup back on the market, with 'Goldman Sachs' as sherpa, after building in a softer, more organic side but two voracious RIA giant buyers are giving it a hard pass -- for now

 “The Hightower One platform remains a strategic priority for the firm, with continued focus on advancing the centralized capabilities available to Advisors, including investment management, account opening, and back-office operations," it responded to RIABiz in an email. 

Hightower adds that the priority means that it will have a designated leader – soon.

“Hightower plans to announce a replacement for the role in the near future,” the spokeswoman adds.

Randy Bullard won the job to build Hightower’s first centralized investment platform but winning RIAs may be bigger challenge
Related· Sep 5, 2025

Randy Bullard won the job to build Hightower’s first centralized investment platform but winning RIAs may be bigger challenge

Unusual circumstances

Whatever the circumstances of his departure, Stewart's hire was a head scratcher from the start, a consulting source who asked not to be identified says.

The Fort Lauderdale, Fla.-based executive's insurance-centric experience and his assignment at Hightower never seemed to align. 

Stewart was given a few months to build a unified managed household platform, a task that normally could take up to 18 months to accomplish, the person says.

Talent pool

Penny Phillips, who came aboard at the same time as Stewart and lives in New York City, where Hightower CEO Larry Restieri works, could be a logical choice to take the job, the source says, though she may need an operating officer. 

Thomas H. Lee puts Hightower rollup back on the market, with 'Goldman Sachs'  as sherpa, after building in a softer, more organic side but two voracious RIA giant buyers are giving it a hard pass -- for now
Related· Jun 11, 2026

Thomas H. Lee puts Hightower rollup back on the market, with 'Goldman Sachs' as sherpa, after building in a softer, more organic side but two voracious RIA giant buyers are giving it a hard pass -- for now

Randy Bullard: Could have an inside track at Hightower.

The other potential replacement – at least short-term is Gurinder Ahluwahlia, who previously held the president's role on an interim basis and is employed by Hightower's owner, Thomas H. Lee.

Door open?

Hightower's relationship with Stewart remains cordial.

“He remains deeply committed to Hightower and will work closely with the leadership team over the coming months to support a smooth transition,” a spokesperson told Citywire. 

“We are grateful for his leadership and contributions and wish him and his family the very best.”

Asked whether Stewart might return if his personal circumstances normalize, Hightower “kindly declines to comment,” it responded. 

 WealthManagement.com broke the story on Monday (June 29).

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Keith Girard contributed to the editing of this article.


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