Our Leadership Team

Our Team
Robert "Bobby" Benson

Robert Benson

Chief Experience officer (CxO)
NLMS# 42284

Robert has 24 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 da Silva-Benson, Esq.

Chief Legal Officer (CLO)
NMLS# 1115925

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 Good

Chief People Officer (CPO)
NMLS# 1000551

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 Morselli

President of Operations & Marketing
NMLS #2080541

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 Lambert

Director of Loan Processing
NLMS# 1369273

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.

Bob Raiche

Senior Loan Officer
NMLS #2096697

Bob has over 20 years of experience in high tech as a manager and senior executive and expert knowledge in real estate transactions both as an accomplished realtor and mortgage loan originator. Bob holds licenses in both MA and NH and has achieved Centurion status and won the Quality Service Award at Century 21. He is a certified instructor in MA for real estate pre-licensing and continuing education.  As a Senior Loan Officer for Dovetail, Bob’s main goal is to help guide his clients through the home buying process with care, efficiency and attention to detail.

Brandon Wheeler

Loan Officer - State of Florida
NNLS #2062835

Brandon comes from a background of sales and customer relations in both finance and digital marketing. His father was a Mortgage Broker for over 30 years and later owned and operated a Mortgage business, where Brandon spent a lot of time during his childhood and early adulthood.  He’s excited to follow in his father’s footsteps and become the best he can be, thanks to the 50+ years of knowledge, leadership and mentorship from the Dovetail team. 

Play Video

Join Our Team

To be a great place to work, we need great people to work with us. We believe that if we surround ourselves with empathetic and compassionate people we will accomplish the impossible! Are you new to the industry? No need to worry. We thrive on mentoring and aligning a career path for growth.

Find Out How

Apply Now

First Name

Last Name

Cell Phone


Fields marked * are required

Want to Learn More?

Our team of dedicated loan experts can answer any questions you may have regarding residential financing, whether you’re a first time home buyer, looking to refinance, or shopping for a second home. We are here to assist you.

First Name

Last Name

Cell Phone


Fields marked * are required