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HilltopSecurities Hired Three From Sycamore Advisors

The Dallas-based firm added staff as the Indiana-based Sycamore Advisors winds down operations.

Updated on Sept. 21, 2026 in People

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HilltopSecurities has hired three former Sycamore Advisors employees following the Indiana-based firm's decision to wind down operations this August. AI Illustration. Upload story photo >

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HilltopSecurities hired Diana Hamilton, Ching Yin, and Susan Rehfeldt on August 26, 2026. The move follows a decision to wind down Sycamore Advisors LLC, which founder Diana Hamilton led for over 22 years.

Why it matters

The transition occurred because the regulatory environment has become increasingly complex and burdensome for smaller firms, prompting Diana Hamilton to seek a reduction in administrative demands.

HilltopSecurities advised on $36.6 billion in par amount deals in 2025, maintaining a third-place industry ranking. The firm added three new employees to its roster following the winding down of Sycamore Advisors LLC.

The players

HilltopSecurities

This is a Dallas-based financial firm that provides municipal advisory services and recently celebrated its 80th anniversary.

Diana Hamilton

She is the founder of Sycamore Advisors LLC and served as the Indiana public finance director between 1997 and 2003.

Sycamore Advisors LLC

This firm provided public finance advisory services across Indiana and Illinois before beginning its wind-down process.

The details

HilltopSecurities did not acquire Sycamore Advisors LLC as a business entity, instead opting to hire its employees individually. The shift allows the staff to continue their work while avoiding the growing administrative complexities facing boutique advisory firms.

Timeline

  1. Diana Hamilton served as Indiana public finance director from 1997 to 2003.

  2. HilltopSecurities ranked third among municipal advisors in 2025.

  3. HilltopSecurities marked its 80th anniversary in April 2026.

  4. The new employees officially joined HilltopSecurities on August 26, 2026.

Market Landscape

This move highlights the ongoing consolidation trend in municipal financial advisory services as smaller firms struggle with rising regulatory overhead. By absorbing seasoned talent rather than acquiring entities, larger firms like HilltopSecurities are effectively increasing their market share.

Clients previously served by Sycamore Advisors in Indiana and Illinois will now access services through HilltopSecurities. This transition ensures continuity for ongoing public finance projects managed by the hired staff.

The takeaway

Smaller advisory firms often face significant hurdles in managing modern regulatory requirements independently. Professionals in this sector are increasingly opting to join larger, established platforms to alleviate these administrative burdens.

Further reading

For more on industry personnel movements, read the latest coverage on People.

Source note: This article includes information reported by Bond Buyer.

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Are increasing federal regulations making it too difficult for small businesses to operate profitably?