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2026 Connect Money Next Generation Wealth Management Awards

Winners

Robert Howland: Modernizing a Legacy Firm While Deepening Client-Centered Advice

Company: 

Howland and Associates, LLC

SVP leads the shift to concierge-style wealth management

As SVP at Howland and Associates, LLC, Robert Howland has made a clear and lasting impact by helping evolve the business from a traditional investment advisory practice into a more comprehensive, concierge-style wealth management firm. He has been instrumental in integrating investment management with tax awareness and estate considerations, creating a more cohesive and personalized client experience. That holistic approach has strengthened long-term relationships, improved retention, and deepened multi-generational engagement with families the firm serves.

Robert has also driven meaningful operational improvements. He has supported the refinement of internal systems, reporting tools, and workflows to improve efficiency and consistency across the organization. These enhancements have reduced administrative friction and freed advisors to spend more time on strategy, communication, and portfolio oversight, reinforcing the firm’s disciplined, research-driven investment philosophy—especially during periods of market volatility when client guidance matters most.

Known for his ability to explain complex investment concepts in straightforward terms, Robert helps clients navigate key decisions with clarity, confidence, and transparency. He plays a central role in shaping customized portfolio strategies aligned with each client’s goals and risk tolerance, reinforcing the firm’s client-first ethos.

Beyond his direct client work, Robert fosters a collaborative, accountable culture. He mentors team members, contributes to strategic planning, and supports initiatives that promote sustainable growth. His leadership has helped position Howland and Associates for continued success while preserving the firm’s long-standing values.

Outside the office, Robert extends this commitment through community involvement, mentorship, and charitable engagement, supporting organizations focused on financial literacy, opportunity, and responsible decision-making. He also serves as a mentor to younger professionals, emphasizing ethics, risk management, and long-term thinking.

Recognized with honors such as the 5-Star Financial Planners Award and selection to the Florida Advisory Council, Robert embodies the next generation of wealth management—blending modern communication, thoughtful use of technology, and holistic planning with the discipline and integrity that underpin durable client relationships.

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Inside The Story

Robert Howland

About Joe Palmisano

Joe Palmisano is editorial director of Connect Money, where he oversees daily coverage of alternative assets, direct investments, financial advisory and the economy. He brings three decades of experience as a financial journalist, analyst and portfolio manager. Before joining Connect Money, Palmisano wrote for The Wall Street Journal, covering foreign exchange, global fixed-income and equity markets. He later served as a senior research analyst and portfolio manager, producing market analysis and managing foreign exchange and U.S. equity portfolios for FX Concepts. His work has also appeared in SFO Magazine and CMT Association publications. Palmisano earned a bachelor’s degree in finance from The American University and holds the Chartered Market Technician (CMT) designation and is a member of the CFA Institute.