Our Leadership Team

Robert has 27 years of experience in residential lending with broad knowledge in bank lending, non-bank lending, and mortgage brokerages. He has extensive knowledge in all types of mortgage products with a keen understanding of underwriting guidelines. He was last branch manager and President’s Club honoree for a leading national lender.

Flávia brings her expertise in regulatory compliance and risk assessment. Flávia started her career in post closing mortgage quality assurance followed by 10 years representing lenders as a real estate attorney. She last managed branch offices in Massachusetts for two national banks.

Craig has 27 years of experience in mortgage lending and product knowledge as a loan originator, business owner and market leader. Craig’s talent lies in mentoring teams, business development, recruiting, and customer relations. He directs Dovetail’s culture, vision and values through mentoring, engagement and motivation.

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 Award recipient, Brittany is the trusted Mortgage Advisor you want by your side. With over a decade of experience in the banking industry, she has successfully guided hundreds of families through every aspect of the home buying process. Brittany’s professionalism and enthusiasm are the cornerstones of her ability to build lasting, loyal relationships with clients and referral partners. By combining her expertise with your trust, you can count on a smooth and stress-free transaction every step of the way.

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.

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.

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.

Justin brings over 20 years of lending experience, having worked as a Loan Officer with top lenders like Citizens Bank, Wells Fargo, and Countrywide Home Loans. A Brockton, MA native, Justin is passionate about helping clients achieve their dream of homeownership, especially those who thought it might be out of reach. He prides himself on transparent communication, personalized service, and making the mortgage process as smooth as possible.

Outside of work, he’s a dedicated father of two, a die-hard Boston sports fan, and a proud owner of two Cane Corsos—a true dog whisperer at heart! Justin is committed to providing the best possible experience for every client, making their journey toward homeownership as seamless and stress-free as possible.

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.

Melissa Ivy brings a strong foundation in credit knowledge and a heartfelt dedication to helping people achieve their homeownership dreams, guiding clients with clarity, care, and confidence every step of the way. She believes that every client deserves not just great service, but also clear guidance and education throughout the mortgage process. Her passion lies in making homeownership more accessible—especially for those who may need extra support navigating their finances. Melissa is a strong advocate for financial literacy and works closely with clients to ensure they feel confident, empowered, and ready to succeed. Whether you’re buying your first home or looking for expert guidance, Melissa is here to be a reliable partner and resource every step of the way.

John Larsen combines the determination and drive he developed growing up in Boston with the creativity and community-minded approach he brings to life in Sarasota, Florida. He is committed to helping clients navigate the mortgage process with ease, providing guidance that is both clear and supportive. With a background in hospitality, John knows how to build strong relationships and communicate effectively, ensuring every client feels informed and confident. His passion is helping homebuyers—especially those entering the process for the first time—feel empowered and prepared to reach their homeownership goals. Whether you’re purchasing a new home or exploring refinancing options, John serves as a reliable partner and resource throughout every step of the journey.

With over 20 years of experience in capital markets—including roles in investment banking, a Big 4 accounting firm, and private equity—Charles brings deep expertise in mortgage products, securitization, and secondary markets. He began his career in mortgage-backed securities risk management and has since specialized in portfolio hedging and trading strategies. Charles is dedicated to understanding each client’s unique needs and finding the best mortgage solution to match

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.

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Our Leadership Team

Robert Benson

Flávia da Silva-Benson, Esq.

Craig Good

Diana Morselli

Ryan Lambert

Brittany Finnemore

Kristy Sassone

Michael Doherty

Jay Holmes

Robert Caramante

Jeff Drew

Lance Ela

Michael Mularczyk

Johanna Lynch

Kathleen Taris

Melissa Ivy

John Larsen

Charles Li, CFA

Brandon Wahlberg

Shiv Makavana

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