Dwight Taylor-Peay Sr
@dwighttaylor-peaysr
I lead insurer distribution growth as a senior sales director and revenue coach.
United StatesWhat I'm looking for
I’m a strategic sales executive and revenue leader with 27+ years across insurance, financial services, mortgage lending, and commercial finance. I’ve built and scaled distribution models in regulated environments, pairing technology and data with field-tested sales leadership.
For the past decade, I’ve owned and operated a high-performing P&C, Life & Health, and Commercial Lines agency, driving 31% year-over-year growth through targeted, demographic-based marketing. I’ve managed a remote agent team covering the full book of business, daily servicing, and campaign execution to meet annual agency goals.
I’m known for recruiting and developing high-output sales teams and coaching them into consultative, conversation-based selling. I design executive-level training and use CRM-driven pipeline management (Salesforce) to improve visibility, follow-up, and performance—while staying grounded in regulatory compliance and multi-state licensing.
I also bring InsurTech and digital distribution experience, deploying AI and automation tools (Gamma, Grok, ChatGPT) to strengthen customer marketing strategies and pipeline execution. I’ve partnered through Rocket Mortgage, originating home financing and closing just under $1M monthly in purchase and refinance volume, and I’m eager to bridge traditional carrier operations with InsurTech platforms in a Director or District Manager role.
Experience
Work history, roles, and key accomplishments
Owned and operated a P&C, Life & Health, and Commercial Lines agency, driving 31% year-over-year growth via targeted demographic-based marketing. Supervised a remote agent team and used AI/automation tools alongside Salesforce CRM to manage customer marketing, follow-ups, and pipeline visibility.
Led business-market implementation of FiOS across Maryland, Virginia, and DC by building and managing a commercial client pipeline. Translated technical capabilities into revenue-generating business solutions for the region.
Built carrier-side underwriting and policy knowledge across personal lines and developed a consultative sales approach. Applied that foundation later in agency ownership.
Commercial Finance Officer
Privately-Held Commercial Finance Brokerage
Jan 2006 - Jan 2009 (3 years)
Built and managed a $20M commercial finance loan book, personally generating revenue behind the portfolio. Structured financing solutions including amusement park project financing, international letters of credit, and working capital loans for business owners.
Branch Manager, Mortgage Lending
Household Finance Corporation (HFC)
Jan 2004 - Jan 2006 (2 years)
Led a mortgage lending branch closing an average of $1.7M monthly in mortgage and personal loans, ranking among top-performing branches nationally. Recruited, trained, and managed a loan origination team in a highly regulated lending environment.
Education
Degrees, certifications, and relevant coursework
Coppin State University
Bachelor of Science in English Studies, English Studies
1998 - 2004
Grade: GPA: 3.4
Activities and societies: Dean's List; recognition for extended finals research paper.
Earned a Bachelor of Science in English Studies from Coppin State University (1998–2004), with recognition for an extended finals research paper.
Tech stack
Software and tools used professionally
Availability
Location
United StatesAuthorized to work in
Job categories
Skills
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