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Meet the Team

The Penta Wealth Management team is a group of experienced wealth management professionals whose shared mission is to help clients achieve their financial planning goals.

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Jonathan Penta, CEPA®

Founder & Managing Director
Senior Wealth Advisor

Jonathan is the Founder & Managing Director of Penta Wealth Management, leading the firm's comprehensive wealth management services. With 23 years of experience in financial services, Jonathan provides expert guidance to a select group of high-net-worth individuals, families, and business owners, helping them navigate the complexities of wealth management. His firm employs a proprietary 5-step consultative process, ensuring each client receives personalized strategies tailored to their unique financial goals and values.

Jonathan is a leader in financial planning, investment strategy integration, and business exit planning. He specializes in building fully customized investment strategies centered around clients' financial plan goals and objectives. As a Certified Exit Planning Advisor (CEPA®), Jonathan helps business owners and CEOs plan for successful exits, maximize business value, and integrate business planning with personal financial goals.

Jonathan's understanding of both personal and business financial planning, from early-career professionals to business owners preparing for exit, makes him highly sought-after for comprehensive wealth management services. His expertise in retirement income planning, portfolio construction, and value acceleration for businesses adds a unique perspective to financial decision-making, all delivered with genuine care and authenticity.

Wealth Management Approach

At Penta Wealth Management, Jonathan and his team utilize a detailed consultative process that includes:

  • Developing and implementing comprehensive wealth management plans
  • Providing expert guidance on investment strategy and portfolio construction
  • Offering specialized services in retirement income planning and business exit planning
  • Educating clients on making informed decisions in today’s complex financial landscape
  • Coordinating with clients’ existing advisors to streamline and optimize financial decision-making

Areas Of Expertise

  • Financial planning with integrated investment strategies
  • Expert portfolio construction, asset allocation, and investment planning
  • Building fully customized investment strategies
  • Retirement income planning and preparation
  • Business exit planning and value acceleration
  • Tax mitigation strategies and estate planning

Business Owner Services

  • Assessing and improving owner readiness for exit
  • Analyzing the impact of business sale on overall financial plans
  • Maximizing business value through Value Acceleration methodology
  • Accelerating business growth and maximizing profitability
  • Increasing net cash flow to the owner
  • Improving business efficiency

Professional Experience

  • Founder & Managing Director – Penta Wealth Management (2019-Present)
  • Senior Vice President, Wealth Advisor – UBS Financial Services (12 years)
  • Senior Vice President, Wealth Advisor – Morgan Stanley (7 years)

Education

  • Boston College, Carroll School of Management – Bachelor of Science, Finance

Professional Certifications

  • Certified Exit Planning Advisor (CEPA®)

Personal Life and Community Involvement

Jonathan resides in Wellesley, MA, with his wife, Paula, and their three children, Nicolas, Michael, and Juliana. The Penta family enjoys an active lifestyle, including traveling, fitness, and skiing. Jonathan is also a dedicated community member, contributing his time as a youth soccer coach.
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Mark H. Fiskio

Managing Director / Senior Wealth Advisor

With nearly 40 years of experience in financial services, Mark is a Senior Wealth Advisor specializing in portfolio construction, asset allocation, and client portfolio management. He is also an architect of the firm’s Rules Based Investing® philosophy—a disciplined framework designed to align portfolios with clients’ goals through consistent, data-driven decision-making. Mark’s career began in 1983 at Shearson-Lehman American Express. He later served as Vice President in the Investment Services Group at Donaldson, Lufkin & Jenrette and First Vice President of Investments at Advest. At Merrill Lynch, he built a partnership network of more than 190 advisors as a Senior Portfolio Manager, helping them deliver customized investment strategies to their clients. Mark holds a B.A. in Economics from Connecticut College.

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Anthony Lima

Director of Client Service & Operations

As Director of Client Service & Operations, Anthony is responsible for providing exceptional service for all client inquiries and requests, and ensures every Penta Wealth Management client receives a concierge-level experience that goes far beyond standard account management. Anthony manages all aspects of client operations—from account openings, money movement, and transfers to portfolio rebalancing, trade execution, and administrative support. He oversees the firm’s entire client service model and communication schedule, ensuring clients receive consistent, proactive attention at every stage of their financial journey. Before joining Penta Wealth Management, Anthony held leadership roles in operations and client service, including Vice President of Operations and Client Service and Associate Director of Operations within the investment management industry. Earlier, he spent a decade as Head of Operations for State Street Global Markets’ Currency Management Team. Anthony holds a B.S. in Economics from Northeastern University.

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Glenn Caldicott, CIMA®, AAMS®

Chief Investment Officer / Portfolio Manager / Senior Financial Advisor

As Chief Investment Officer and Portfolio Manager, Glenn leads the investment research, portfolio analytics, and manager due diligence processes for Penta Wealth Management. A Certified Investment Management Analyst (CIMA®) and Accredited Asset Management Specialist (AAMS®), Glenn brings deep expertise in asset allocation, portfolio construction, and risk management. Glenn is the original creator of proprietary investment strategies, including The Insider Portfolio® and Rules Based Investing®, which combine quantitative discipline with fundamental insights to drive long-term consistency and performance. His experience spans portfolio management, institutional trading, and investment research across leading firms such as Providence Capitol, L.F. Rothschild, Advest, and Merrill Lynch. Glenn began his career in New York City in 1983 and went on to manage multi-billion-dollar portfolios and later oversee nine Rules Based Investing® portfolios totaling over $800 million in assets at Merrill Lynch. He earned his Bachelor of Science in Finance and Investments from Babson College, where he was a two-sport athlete in soccer and hockey.

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John P. Shreenan

Senior Vice President / Wealth Advisor

John serves as a Senior Vice President and Wealth Advisor, managing client relationships and helping individuals and families integrate financial planning with personalized investment strategies. Known for his thoughtful, goal-oriented approach, John partners with clients to ensure their investment portfolios remain aligned with their broader financial objectives. With extensive experience in wealth and financial planning, John has held advisory roles at Merrill Lynch, TIAA, and Garrett Nagle & Co., where he served as Vice President of Portfolio Management and Corporate Development. His background combines strategic insight with hands-on relationship management, enabling him to deliver the exceptional client experience that distinguishes Penta Wealth Management. John is a Registered Investment Advisor (RIA) and is fully licensed in Life and Health Insurance. He earned a B.S. in Marketing and Finance from Bentley University.

Schedule a Consultation with the PWM Team

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Penta Wealth Management is proud to announce that we have been named as one of the Top Wealth Management Services Providers of 2023 by Banking CIO Outlook. The list recognizes the top firms who are at the forefront of delivering wealth management services and was determined using market research focused on peer/client recommendations and best practices. We are honored by this acknowledgment and proud of our team’s commitment to excellence.

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