HilltopSecurities expands Midwest advisory footprint with Sycamore hires

Sycamore Advisors LLC president Diana Hamilton
Sycamore Advisors LLC president Diana Hamilton is joining HilltopSecurities.
Diana Hamilton

HilltopSecurities has hired three of the employees, including the president, of boutique Indianapolis-based municipal advisory firm Sycamore Advisors LLC in a move that will expand the Texas firm's Midwest advisory footprint.

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The move comes as Sycamore president Diana Hamilton, a prominent public finance advisor who founded the Indiana firm more than 22 years ago, said the regulatory regime has become too burdensome for small firms.

"The regulatory environment has become increasingly complex and overwhelming for smaller firms," Hamilton said. "If you can't achieve a certain scale, it's not sustainable to operate."

The firm's three employees — Hamilton, Ching Yin and Susan Rehfeldt — officially joined Hilltop on Aug. 26. Peter Orr, who joined Sycamore in late 2024, did not make the move.

"We're looking for people who you can trust and whose clients love them," said David Medanich, Hilltop's head of public finance. "They have the relationships and they have a good business model," Medanich said of Sycamore.

Hamilton "has the same heart for the business that we do," he added.

Hilltop has several times expanded its footprint by hiring a firm's employees without acquiring the actual business, which makes for a simpler transaction, Medanich said.

Hamilton, who served as Indiana's public finance director from 1997 to 2003 before she founded Sycamore, is in the process of winding down the firm.

"I love the client work but I didn't want to spend my time doing administrative work," Hamilton said.

"It's bittersweet because I wanted to run a boutique MA shop with five to seven senior professionals, but in this regulatory environment I don't believe that's financially feasible," she said. "Look at the number of five-man shops left in the MA business — it's really few and far between."

Ahead of the deal, Hamilton said she did her homework on the Texas firm and heard nothing but glowing reviews from professionals across the public finance industry.

"I heard excellent feedback about their execution and integrity," she said, adding that Hilltop's pricing desk is an important resource as more clients are looking for that from their municipal advisors.

"Most important to me is my reputation and the integrity of the business," Hamilton added. "I felt it was important that I find a place that reflects that."

Hilltop, which is based in Dallas with offices across the country, operates as a municipal advisor and broker dealer and offers other public finance services, including investment management and post-issuance compliance. In April the firm marked its 80th anniversary.

Hilltop consistently ranks among the top three municipal advisors in recent years and ranked third among municipal advisors in 2025, advising on deals that totaled $36.6 billion par amount. It also ranked third in the first quarter of 2026 by par amount and second by 97 deals and second by transaction count. The firm is a leader in the advisory business in the Southwest region.

Sycamore, which operated as a WBE and DBE-certified firm, served issuers ranging from the cities of Indianapolis and Chicago, the Chicago Transit Authority, the state of Illinois, and New York's Metropolitan Transportation Authority.

As Indiana's head of public finance, Hamilton was named a "Sagamore of the Wabash" by former Governor Frank O'Bannon, Indiana's highest award for public service.


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