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Amazing Lead Generation, Sales, Training and Mentoring

The Penso Agency provides YOU -yes YOU! an opportunity to partner with a company where growth and income are limitless.

71

Members

156+

Personal Growth

100%

5 Star Ratings

Timothy Penso

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Your Journey Starts Here


  • Financial Planning:
    Personalized strategies to help you manage, grow, and protect your wealth at every stage of life.
  • Debt Management:
    Solutions to help you manage, reduce, and eliminate debt, ensuring a stronger financial future.
  • Legacy Planning:
    Comprehensive strategies to protect your legacy and assets and ensure they are passed on according to your wishes

"Attitude does not start and end at work, but it is reflected in all aspects of our lives. From achieving personal and professional growth, to building impactful relationships – our people-first mentality is contagious."

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Experience The Penso Agency

Turnkey System

Discover our proven sales and business-building system that has helped hundreds of individuals just like you achieve sustainable growth and success.

Mentoring

Experience continuous mentorship and support through a combination of regular calls, webinars, and exclusive events designed to keep you on track and motivated.

Leads

Gain access to a diverse and proven lead generation system, exclusively available to The Penso agents, designed to support and accelerate the growth of your business.

Training

Jumpstart your career with fast-track, comprehensive training led by top experts from the Agency.

Ownership

Discover the benefits of our True Contractual Agency Ownership Program, a unique opportunity that puts you in control of your career and future.

Potential

Grow to your full potential with an agency that provides everything you need – the tools, the resources and the support!

MEET THE TEAM

We Work as A True Team and We Strive to Be A Positive Influence

Timothy Penso

Timothy Penso

Boston, MA based Managing Vice President & Elite Producer
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Chiara Cinquemani

Boston, MA based Field Underwriter & Top Producer
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Devon Fleming

Florida based Top Producer and Agency Owner
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Gabbie Savas

Director of Operations
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Grow With Us

Explore insights from our professionals on how they built their career from the ground up.

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© 2025 - The Penso Agency

Tim Penso

Tim Penso has been in the insurance industry since he was 20 years old.  While getting into the insurance industry wasn’t a childhood dream of his, becoming financially independent was. He hit Agency Owner only 6 months after starting with SFG, while Placing $1M in his first year, and has since mentored 3 agents to hit Agency Owner, as well!

Chiara Cinquemani

Chiara Cinquemani started with Symmetry at the Penso Agency at the young age of 22 years old and has achieved 4 commission raises, as well as the Top Producer title, within her first year and a half. As a recent college graduate when she started, she had no prior experience in the industry before coming to the Penso Agency, however, she saw the immense growth opportunities and was inspired to create the same success for herself that she saw others had found at Symmetry. She is currently working to build an agency of like-minded individuals, ready to do the same and experience the massive impact this industry has had on her life in the short time she has been here.

 

Devon Fleming

Devon Fleming has been working in the financial services industry for over 20 years,  originally working on Wall Street in Quantitative Analytics, Institutional Investment, and Investment Banking. Devon came to Symmetry Financial and has been with the Penso Agency since 2018.  With her high energy and ability to “constantly correct” she became a Top Producer and Subject Matter Expert in Advanced Markets. In 2024 Devon broke out as an Agency Owner and hasn’t looked back. She understands the need to follow the system and coupled with her strong determination to follow Tim’s lead, desires to implement new technology, making her a real candidate for reaching the top of the company.

 

Gabbie Savas

Gabbie Savas has a Bachelor’s degree from Appalachian State University and has held roles such  as HR Director and Bookkeeper. Gabbie has been working side by side with Tim and The Penso Agency, since 2019 and continues to wear multiple hats at the Penso Agency, including acting as Chief Operations Officer & onboarding Director. She is extremely skilled in the areas of bookkeeping, business operations, and staff management.