ERIN OVERSTREET
Harrisonburg,VA
Summary
Enterprise transformation leader with deep experience building and scaling complex organizations. Proven ability to design operating structures, strengthen execution, and lead cross-functional teams through sustained growth and change. Known for elevating client service, strengthening operational discipline, and creating enterprise-level products, insights platforms, and revenue ecosystems in highly data-driven environments. Recognized for developing strong leadership teams, raising performance standards, and empowering people to deliver exceptional results by aligning people, processes, and technology around clear, measurable outcomes.
Overview
2019
2019
years of professional experience
Work History
Senior Director of Digital Sales
Gray Media
01.2016 - 01.2019
- Led national digital sales strategy, market education, and revenue development across all digital product lines.
- Created scalable sales frameworks, pricing models, and adoption strategies that improved digital performance and sales alignment across markets.
Director of Digital Media & Sales Executive
WHSV-TV3, Gray Media
Harrisonburg, VA
01.2008 - 01.2016
- Oversaw digital advertising strategy, content integration, and collaboration across news, sales, and creative teams.
- Strengthened digital revenue performance and developed foundational expertise in integrated marketing, client strategy, and digital product development.
- Leveraged business-owner relationships built as a financial advisor into a successful transition into digital media leadership.
Financial Advisor
Stern & Heatwole Financial Group
Harrisonburg, VA
01.2005 - 01.2008
- Certified Financial Advisor holding Series 7, 66, licenses, along with life, health, disability licenses.
- Managed investment portfolios, risk strategies, and long-term financial planning for individual and business clients.
- Built a client network of business owners that led directly to a career transition into media and advertising.
Vice President, Gray Digital Media & Digital Sales
Gray Media
Remote
2019 - 2025
- Executive leader overseeing enterprise digital transformation, organizational scale, and revenue growth for Gray’s national digital agency.
- Built and led a 70+ person multi-disciplinary digital organization across Paid Media, Programmatic, Managed Platforms, QA, Creative, Data & Insights, Reporting, and Corporate Sales.
- Scaled digital operations by more than 2,000%, driving over 900% revenue growth, and elevating Gray into a nationally competitive digital agency in five short years.
- Architected enterprise workflows, operational frameworks, and leadership structures that standardized delivery across all markets.
- Strengthened execution quality, reduced operational friction, and improved campaign reliability, and speed to market.
- Led the development of a bespoke, fully integrated Order Management System (OMS), enabling seamless order entry, campaign execution, and automated reconciliation.
- Oversaw the creation of forecasting models, insights dashboards, and advanced permissioning systems adopted across the company.
- Partnered with senior executives across Sales, Finance, Product, and Operations to expand digital maturity and elevate strategic execution.
- Influenced enterprise planning, digital transformation initiatives, and nationwide product adoption.
Education
Bachelor of Arts -
James Madison University
Skills
- Executive leadership
- Organizational design
- Digital transformation execution
- Team development
- Strategic visioning
- Controls enhancement
- Stakeholder relations
- Product innovation
- Negotiation skills
- Financial oversight
- Ethical leadership
- Revenue growth
- data analysis
- Artificial intelligence integration
- Media relations
- Empowering leadership
Most Notable Community Leadership
- President, Board of Directors, Rockingham Harrisonburg SPCA, 2023 - Current
- Past President, Board of Directors, Big Brothers Big Sisters, 2016 - 2023
- Executive Board, Harrisonburg–Rockingham Chamber of Commerce, 2016 - 2023
- Big Sister, Big Brothers Big Sisters (Governor's Virginia Mentor of the Year Award, 2017), 2008 - Present
Timeline
Senior Director of Digital Sales
Gray Media
01.2016 - 01.2019
Director of Digital Media & Sales Executive
WHSV-TV3, Gray Media
01.2008 - 01.2016
Financial Advisor
Stern & Heatwole Financial Group
01.2005 - 01.2008
Vice President, Gray Digital Media & Digital Sales
Gray Media
2019 - 2025
Bachelor of Arts -
James Madison University