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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 for Connect Money, where he brings nearly three decades experience of market insights as a financial journalist, analyst and senior portfolio manager for leading financial publications, advisory firms, and hedge funds. In his role as Editorial Director, Joe is responsible for the selection of content and creation of daily business news covering the financial markets, including Alternative Assets, Direct Investment and Financial Advisory services. Before joining Connect Money, Joe was a financial journalist for the Wall Street Journal, regularly publishing feature stories and trend pieces on the foreign exchange, global fixed income and equity markets. Joe parlayed his experience as a financial journalist into roles as a Senior Research Analyst and Portfolio Manager, writing daily and weekly market analysis and managing a FX and US equity portfolio. Joe was also a contributing writer for industry magazines and publications, including SFO Magazine and the CMT Association. Joe earned a B.S.B.A. in Finance from The American University. He holds the Chartered Market Technician (CMT) designation and is a member of the CFA Institute.