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Skip Schweiss
Skip Schweiss

Skip Schweiss Joins Sierra Group of Companies as Its First CEO

Schweiss, who spent 12 years at TD Ameritrade before leaving in 2020, will join Sierra on Oct. 1.

Skip Schweiss, a former TD Ameritrade executive and volunteer president for the Financial Planning Association, will be joining the Sierra Group of Companies as the first chief executive officer in its more than three-decade history.

The Sierra Group of Companies includes Sierra Investment Management, as well as Ocean Park Asset Management and Wright Fund Management (the latter of which manages Sierra Mutual Funds). Schweiss will take on the CEO role effective Oct. 1, according to a statement from Sierra Investment Management. Sierra co-founder Ken Sleeper said the organization was “delighted” to have Schweiss come on board.

“Skip understands the advisor business and the unique challenges advisors face at a level few others do,” Sleeper said. “Given his experience, expertise and network, we have no doubt that his addition will allow us to better meet the needs of investors and advisors as we continue to grow.”

Both Sleeper and co-founder David Wright will be involved in the investment management side of Sierra, while Schweiss will focus on “the continued growth of the enterprise,” according to the statement. Sierra has operated since 1987, with an investment approach designed to limit downside risk and work with clients favoring “a conservative approach.” Sierra Investment Management’s investors are usually conservative in their risk profiles, retirees and have a minimum of $1 million in assets that can be invested (in total, the Sierra Group manages or advises on more than $9 billion in client assets).

Wright said Sierra was “proud” to support Schweiss’ ongoing volunteer role as FPA’s president (Schweiss is scheduled to remain in the position until the end of this year). In an interview with WealthManagement.com, FPA CEO Pat Mahoney said the organization was “really proud” of Schweiss and commended him on his new role. Schweiss said he’d known Sierra’s co-founders for more than 30 years and had seen them develop a singular firm combining a “rules-based investing approach” with client service. 

“I’m joining Sierra at a time when the firm is experiencing significant growth, especially within the financial advisor community with the Sierra Mutual Fund and Ocean Park Asset Management offerings,” he said. “Sierra is trusted by advisors and seeks to keep investors out of trouble through challenging market cycles.”

Besides his work with the FPA, Schweiss spent 12 years at TD Ameritrade, serving as the president of TD Ameritrade Trust Company and the managing director for advisor advocacy (he left the company in 2020). Prior to his time with TD Ameritrade, Schweiss worked at Fiserv Investment Support Services for 20 years, including a role as executive vice president of Fiserv Trust Company before TD Ameritrade acquired it in 2008.

“I can’t think of anyone better than Skip to help us show advisors and investors the value and utility of the Sierra approach,” Sleeper said.

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