Our Leadership Team

Flávia brings deep expertise in regulatory compliance, risk assessment, and mortgage operations to Dovetail Mortgage. She began her career in post-closing mortgage quality assurance before spending 12 years as a real estate attorney representing lenders, banks, and investors. She later managed Massachusetts branch operations for two national banks, overseeing production, compliance, and team performance.

Flávia implements and oversees federal, state, and local regulatory compliance programs, including RESPA, ECOA, and TILA, ensuring adherence to industry standards while maintaining a strong culture of transparency and accountability. She defines internal policies and procedures, advises loan originators on compliance and marketing regulations, and maintains state licensing and audit readiness for mortgage operations.

As Founder of Dovetail Mortgage, Flávia leads the company’s strategic growth plan with a continued focus on customer experience, operational excellence, and forward-thinking innovation.

Robert brings 30 years of experience in residential lending, with comprehensive expertise across bank lending, non-bank lending, and mortgage brokerages. He has extensive knowledge of all mortgage products and a deep understanding of underwriting guidelines, income calculation, and loan structuring. He previously served as a Branch Manager and was a President’s Club honoree for a leading national lender.

As Dovetail Mortgage’s Chief Experience Officer, Robert is responsible for aligning the company’s customer experience with its internal operational standards to ensure consistency, excellence, and efficiency at every stage of the loan process. He mentors and trains Loan Originators on guidelines, scenario structuring, and income analysis while also acting as an elevated Sales Manager — helping team members set goals, track KPIs, and drive sustainable production growth.

His leadership bridges sales performance, operational precision, and client satisfaction, ensuring every transaction reflects Dovetail’s commitment to service, expertise, and execution.

Diana delivers a decade of experience in real estate transactions as a broker and investor. In the past 4 years, she contributed to the success of an innovative start-up with her expertise in low cost operations and social media marketing.

Ryan is skilled in preparing loans for seamless underwriting by evaluating them for accuracy, completion and compliance with industry guidelines. He leads the Dovetail Processing Team ensuring loan packages are processed timely and efficiently while ensuring the underwriting process is effectively communicated with borrowers.

Recognized as a Boston Magazine Top Mortgage Professional, Brittany brings over a decade of banking experience and has guided hundreds of families through the home financing process. In her expanded role as Chief Deal Architect, she serves as the strategic front line for Dovetail’s production team — structuring loan scenarios, analyzing income, aligning deals with the right lenders, and supporting Loan Originators with complex files. She also collaborates on sales strategy, lender relationships, and team education while continuing to originate loans. Brittany combines deep product knowledge, relationship-building expertise, and creative problem-solving to ensure every transaction is structured for success from the start.

Kristy Sassone brings a strong background in Business and Marketing, along with years of hands-on experience in residential mortgage lending. Since becoming licensed in 2021, she has helped a wide range of clients—from first-time homebuyers to seasoned homeowners—find the right loan solutions with speed and clarity. She specializes in Conventional, FHA, VA, and Non-Conforming loan programs, and stays current with evolving guidelines to best serve her clients. Kristy was named a Top Loan Originator in Plymouth and Barnstable Counties and recognized as one of the Top 5 Loan Officers on the South Shore. She is committed to building lasting relationships through transparency, responsiveness, and a truly client-first approach.

Michael brings over 20 years of experience in Residential Development and Real Estate Sales and has a proven track record in the dynamic financial and housing industries. Currently, he is focused on residential mortgage lending, specializing in FHA loans, VA loans, and their associated entitlements, as well as Conventional, Jumbo, Rehabilitation, and Construction loans. He also has extensive experience in Non-Conforming financing, including DSCR financing and Bank Statement loans. Whether working with first-time homebuyers, those refinancing, or experienced property owners, he is dedicated to guiding clients through every step of the home loan process. His commitment lies in building long-lasting relationships based on integrity, transparency, and trust.

With over 20 years in the mortgage industry, Jay is dedicated to exceeding client expectations and building lifelong relationships. Specializing in customized loans for each client’s needs, Jay combines deep knowledge of New England and national lending markets with a unique perspective from a background in real estate. Known for professionalism, responsiveness, and a commitment to client satisfaction, he strives to make the mortgage process smooth and accessible, especially for first-time homebuyers. Offering a wide range of mortgage products and competitive rates, he is there to guide clients from application to closing, living by the motto: “30 MINUTE CALL BACK 7 DAYS A WEEK .”

Rob Caramante is a trusted Loan Originator at Dovetail Mortgage, where he has built a stellar reputation as a top producer in the industry. Known for his unwavering dedication to excellence, Rob consistently earns referrals and repeat business from satisfied clients and an exceptionally loyal network of Realtors. Rob’s approach to lending is rooted in providing dependable, seamless service. His clients appreciate his commitment to “getting the job done with no last-minute surprises,” ensuring a smooth and stress-free process from application to closing. With his deep understanding of the mortgage landscape and a keen ability to tailor solutions to individual needs, Rob has become a go-to professional for borrowers seeking clarity, confidence, and success in their home financing journey.

Lance brings over 28 years of real estate expertise to his role as a Loan Officer at Dovetail Mortgage. With 15 years as a licensed real estate agent in Massachusetts and New Hampshire and extensive experience as a professional house flipper, he offers a well-rounded perspective on the buying, selling, and investment process. Prior to joining Dovetail, he spent 13 years as a Branch Manager for a mortgage company, earning multiple accolades, including Presidents Club honors. Lance’s deep understanding of real estate, from construction and renovations to financing and investing, makes him a valuable resource for homebuyers, investors, and builders alike. As a member of the Northeast Association of Realtors and the Northern Worcester County Landlord Association, he stays actively involved in the industry and up to date on market trends.

Outside of real estate, Lance is a former professional chef who traveled the country competing in cooking competitions, even making appearances on the Food Network! Whether you’re a first-time homebuyer, an experienced investor, or planning a renovation project, Lance is dedicated to finding the right financing solutions to help you succeed.

With over 20 years of mortgage origination experience, Jeff is a trusted loan specialist dedicated to helping clients buy, sell, refinance, or build with confidence. He provides personalized guidance in a constantly changing market, ensuring a smooth loan process with clear communication and on-time closings.

Jeff lives in Middleboro with his family and shares a special bond with his daughter, to whom he donated a kidney in 2022. Known for his integrity and 5-star service, he is committed to helping families make smart, lasting financial decisions through real estate.

Johanna Lynch combines her strong analytical skills and passion for helping others in her role as a Loan Officer. With a background in mathematics and education, including a Master’s in Special Education, Johanna excels at guiding clients through the mortgage process with clarity and care. Her decade of experience teaching high school math sharpened her problem-solving and communication skills, which she now applies to finding personalized solutions for her clients. As a licensed Realtor and active community leader in Medford, Johanna offers a unique, well-rounded perspective to help families achieve their homeownership goals

Kathy brings compassion, expertise, and a customer-first mindset to her role as a Loan Officer. With a background as a Global Channel Manager in software sales and experience as an educator and union leader, Kathy has honed her skills in problem-solving, advocacy, and delivering tailored solutions. Her hands-on experience with building, buying, and selling homes, combined with her dedication to clear communication and respect for her clients, makes her an invaluable partner in achieving homeownership dreams. Kathy’s ability to blend analytics with genuine care ensures every client finds the perfect fit for their needs. Just like crafting a perfect meal, Kathy skillfully brings the right ingredients together to guide her clients to success—whether they’re buying their first home or their next.

Brandon brings his extensive experience in real estate where he acted as a real estate broker helping buyers find their dream homes. Born and raised in Dorchester, MA, Brandon is knowledgeable in the Boston market and understands his client’s needs. He joined Dovetail in 2023 to help borrowers navigate and provide clarity to the mortgage loan process. He is licensed in Massachusetts.

Shiv is passionate about providing the best experience to customers. With over six years of experience in the hospitality and customer service industry, his skills include problem-solving, mentoring, and cultivating strong client relationships. He aims to use his customer service skills to create a seamless experience for borrowers. Shiv joined Dovetail in 2022 and is licensed in Florida.

John brings grit, hustle and heart to everything he does, Born and raised in Boston, he developed a strong work ethic and determination that continue to shape his approach today. Now calling Sarasota home, John blends that Boston tenacity with Gulf Coast creativity and a deep sense of community. With a background in hospitality, John has a natural ability to build trust, simplify complex processes, and keep the mortgage experience as smooth and stress-free as possible. His positive, down-to-earth approach quickly puts clients at ease. John is passionate about helping people achieve their homeownership goals and is committed to guiding clients every step of the way.

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Our Leadership Team

Flávia da Silva-Benson, Esq.

Robert Benson

Diana Morselli

Ryan Lambert

Brittany Finnemore

Kristy Sassone

Michael Doherty

Jay Holmes

Robert Caramante

Lance Ela

Jeff Drew

Johanna Lynch

Kathleen Taris

Brandon Wahlberg

Shiv Makavana

John Larsen

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