SEAN WINCHESTER
Middle Island,NY
Summary
Senior Managing Director with proven results in strategic planning and financial management. Directed business transformations delivering measurable performance improvements. Led growth initiatives, streamlined operations, and increased profitability. Built high-performance teams to improve customer satisfaction and corporate value.
Overview
34
34
years of professional experience
Work History
Senior Managing Director | CRE Relationship Manager & Team Leader
WEBSTER BANK
01.2022 - Current
- Manage a nearly $2B CRE mortgage portfolio and approximately $200M in deposits; lead $100M–$200M in annual loan originations.
- Drove annual portfolio and deposit growth of 3%–5% through targeted business development, enhanced client retention, and effective cross-selling.
- Led CRE client relationships, developed lending strategies, managed portfolio performance, and fostered team development.
- Structured acquisition, construction, bridge, permanent, refinance, and recapitalization transactions; coordinated treasury management and derivatives solutions to optimize client offerings.
- Oversee credit quality and risk management; coach and develop relationship managers.
- Led Webster Bank commercial banking strategies across lending, deposits, and client growth.
- Built executive relationships with corporate clients, community leaders, and internal stakeholders.
- Reviewed market trends to shape Webster Bank business development priorities and outreach.
- Negotiated client solutions involving treasury services, lending structures, and pricing terms.
Senior Managing Director | CRE Relationship Manager & Team Leader
STERLING NATIONAL BANK
01.2020 - 01.2022
- Led CRE relationship management, developed lending strategy, enhanced client coverage, and nurtured team growth.
- Developed lending and deposit opportunities; partnered with credit, risk, treasury management, and derivatives teams to deliver client solutions.
- Managed portfolio performance and strengthened client relationships during merger with Webster Bank.
- Executed merger with Webster Bank in 2022
Managing Director | CRE Relationship Manager
STERLING NATIONAL BANK
07.2017 - 01.2020
- Generated CRE lending, deposit, treasury management, and derivatives opportunities with real estate owners, developers, and investors.
- Managed client relationships while supporting loan origination and credit structuring to facilitate portfolio growth.
- Established Sterling's mortgage and deposit book by leveraging existing client relationships and developing new clients.
Vice President | Director | Long Island Market Relationship Manager
CAPITAL ONE, N.A.
01.2009 - 12.2017
- Led relationship development, loan origination, credit structuring, and portfolio management to drive growth across Long Island.
- Expanded client opportunities in CRE lending, deposits, and treasury management by evaluating borrower financials and credit risk.
- Managed $1B CRE portfolio, enhancing service delivery for institutional, middle-market, and family-office clients.
Vice President | Underwriter & Relationship Manager
CAPITAL ONE, N.A.
12.2006 - 01.2009
- Facilitated CRE underwriting, borrower financial analysis, credit assessment, and relationship management to structure loans effectively.
- Drove revenue by cultivating successful client relations.
- Shaped strategic plans for Capital One customer experience and product growth.
- Directed governance reviews for Capital One compliance, policy, and control processes.
- Analyzed financial data to support Capital One business decisions and planning.
Vice President | Underwriter & Relationship Manager
NORTH FORK BANK
01.2005 - 12.2006
- - Helped underwrite and manage CRE relationships by reviewing borrower strength, property cash flow, collateral, repayment capacity, and transaction structure to support sound credit decisions.
- - Monitored credit performance and covenant compliance, flagged emerging risk, and supported credit analysis and loan approvals to reduce potential defaults.
- - Assisted with integration efforts during Capital One’s acquisition of North Fork Bank, supporting smooth transition and alignment of operational processes.
Assistant Vice President | Loan Servicing Team Leader
DIME SAVINGS BANK OF WILLIAMSBURGH
01.1993 - 01.2005
- Led 25-member loan servicing team, enhancing operations, developing staff, ensuring quality control, and maintaining regulatory compliance.
- Managed CRE loan administration, conducting annual credit reviews, monitoring portfolio performance, and addressing delinquencies and criticized credits.
- Executed workouts including deeds-in-lieu, foreclosures, note sales, modifications, and restructurings; ensured servicing controls and facilitated audits and regulatory examinations.
Education
Information Technology
The Age of AI — Risk Management Association
Fairfield, CT04-2024
M.S. - Real Estate Investments
New York University
New York, NY05-2003
Certificate - Community Bank Management
National School of Banking, Fairfield University
Fairfield, CT01-1999
B.B.A. - Accounting
Howard University
Washington, DC05-1993
Skills
- Credit lending and structuring
- Portfolio management
- Transaction structuring
- Treasury management
- Relationship management
- Relationship management
Accomplishments
- Secured approval for a $90M multifamily portfolio refinance, right-sizing bank exposure, updating the guarantor structure, and generating substantial derivative income; the CEO highlighted the transaction during a quarterly investor call.
- Helped retain top-tier, nine-figure deposit relationships by partnering with Treasury Management to facilitate participation in the IntraFi Cash Service (ICS) network.
AWARDS & COMMUNITY LEADERSHIP
Long Island Business Person of the Year — Long Island Business News, 2025 | SEISMIC Champion — Webster Bank, 2026 | Sales Council Champion — Webster Bank, 2025
Affiliations
Chair, Webster Bank United Way Campaign, 2025; Vice Chair, 2024 | Board Member, Long Island Housing Partnership, 2014–2017 | Member, Long Island Builders Associates; A Better Long Island; Long Island Associates
CORE EXPERTISE
CRE Lending & Originations | Relationship Management | Business Development | Portfolio & Credit Risk Management | Loan Structuring & Underwriting | Deposit Growth | Treasury Management | Derivatives | Construction, Bridge & Permanent Financing | Refinancing & Recapitalization | Loan Workouts | Team Leadership
Timeline
Senior Managing Director | CRE Relationship Manager & Team Leader
WEBSTER BANK
01.2022 - Current
Senior Managing Director | CRE Relationship Manager & Team Leader
STERLING NATIONAL BANK
01.2020 - 01.2022
Managing Director | CRE Relationship Manager
STERLING NATIONAL BANK
07.2017 - 01.2020
Vice President | Director | Long Island Market Relationship Manager
CAPITAL ONE, N.A.
01.2009 - 12.2017
Vice President | Underwriter & Relationship Manager
CAPITAL ONE, N.A.
12.2006 - 01.2009
Vice President | Underwriter & Relationship Manager
NORTH FORK BANK
01.2005 - 12.2006
Assistant Vice President | Loan Servicing Team Leader
DIME SAVINGS BANK OF WILLIAMSBURGH
01.1993 - 01.2005
Information Technology
The Age of AI — Risk Management Association
M.S. - Real Estate Investments
New York University
Certificate - Community Bank Management
National School of Banking, Fairfield University
B.B.A. - Accounting
Howard University