Heather Calabrese
Cromwell,CT
Summary
Director of Strategic Partnerships with expertise in consultant relations, relationship management, and enterprise collaboration. Successfully leads cross-functional initiatives, translates client needs into strategic solutions, and drives meaningful business outcomes. Strong reputation for leadership, executive presence, and stakeholder engagement in complex, high-visibility environments.
Overview
19
19
years of professional experience
Work History
Lead Director, Strategic Partnerships
Aetna
Hartford, CT
02.2024 - Current
- Lead consultant-focused thought leadership initiatives, educational programs, and executive leadership meetings that strengthen relationships, elevate market presence, and expand strategic influence.
- Build, deepen, and maintain high-impact relationships with national and regional benefit consulting firms, brokers, and key industry experts to strengthen Aetna’s market presence and expand strategic influence.
- Represent the consultant perspective internally, translating market feedback into actionable insights that inform business strategy, product innovation, and competitive positioning.
- Serve as a trusted liaison between internal business leaders and external consulting partners, facilitating executive-level collaboration and advancing key strategic initiatives.
- Partner closely with cross-functional teams, including Sales, Underwriting, Proposals, Marketing, Product, Clinical, Legal, and Government Affairs, to ensure consultant-facing materials, insights, and messaging are accurate, timely, and strategically aligned.
- Monitor industry dynamics, competitive trends, regulatory activity, and consultant feedback to guide strategic planning and support product and market innovation.
Lead Director, Account Management & Client Success
CVS Health
Hartford, CT
05.2022 - 02.2024
- Led team of senior account managers, responsible for driving retention, satisfaction, adoption and growth within Retail Health.
- Drove revenue through long-term partnerships and key account growth.
- Developed comprehensive account management strategies, which resulted in increased sales and maximized profitability.
- Collaborated with cross-functional teams to design and implement customer retention strategies, strengthening client relationships.
- Guided and coached team members through performance evaluations, fostering individual growth and enhancing overall team success.
- Worked with and influenced executive leadership on critical business decisions.
- Reviewed KPIs to identify opportunities for improving operational performance and informed strategic adjustments.
- Partnered with product development on client feedback to deliver new product enhancements.
Senior Account Manager
CVS Health
Hartford, CT
06.2020 - 04.2022
- Managed a portfolio of 30+ large-employer clients and exceeded annual revenue targets across a $60M+ book of business.
- Led the full customer lifecycle—including implementation, adoption, expansion, and renewal—to maximize retention and satisfaction.
- Maintained 95%+ client satisfaction through proactive engagement, ensuring strong client relationships and retention.
- Drove adoption of CVS Health products and services, enhancing client value and contributing to portfolio growth.
Strategic Planning Manager
CVS Health
Hartford, CT
09.2018 - 06.2020
- Advised Vice President of Product Development and senior leadership on strategic initiatives.
- Collaborated on financial planning, budgeting, forecasting, and staffing with Finance to enhance resource allocation.
- Facilitated project progression and ensured timely deliverables to prevent delays.
- Researched, benchmarked, and analyzed data to inform product and service recommendations for the Transformation team.
- Led organizational performance and talent development processes.
- Developed executive communications and presentation materials, including content for external broker/consultant conferences and industry events.
Meeting & Conference Manager
Aetna
Hartford, CT
04.2012 - 09.2018
- Subject matter expert and trusted advisor on Aetna's highest-level meetings, including Board of Directors, Annual Shareholders, customer advisory boards and executive committee offsite meetings.
- Collaborated with Office of the Chairman and CEO to develop strategic event agendas that aligned with organizational objectives.
- Led enterprise conference management team, coordinating with meeting partners to execute successful events.
- Implemented best in class co-sourcing model with meeting suppliers to meet business objectives during peak meeting periods, reducing meeting and FTE costs by 22%.
- Analyzed meeting data for monthly business reviews, identifying trends in spend and savings to inform future planning.
Senior Planner, Meetings & Events
Aetna
Hartford, CT
05.2007 - 04.2012
- Planned and executed national and international meetings, events, and incentive programs, managing budgets up to $1.5M.
- Led end-to-end event management, including supplier sourcing, contract negotiations, logistics, registration, and onsite operations.
- Consulted with business leaders to design meetings and events that aligned with strategic goals and objectives, ensuring stakeholder engagement.
- Managed RFI/RFP processes and vendor relationships, achieving cost savings and enhancing operational efficiency.
- Developed and managed event registration platforms and reporting tools, leveraging Cvent and other event technologies.
- Created meeting intelligence reporting to enhance policy compliance, increase spend visibility, and support ongoing cost optimization.
Education
Master of Business Administration -
University of Arizona
Global Campus01-2024
Bachelor of Arts - Public Relations
University of Connecticut
Storrs, CT01-2005
Skills
- Executive Relationship Management
- Strategic Partnership Development
- Cross-Functional Leadership
- Business Strategy & Execution
- Data-Driven Decision Making
- Client & Consultant Engagement
- Enterprise Stakeholder Management
- Executive Communications
- Market Growth & Business Development
- Customer Experience Enhancement
- Operational Excellence
- Innovation & Solution Development
IT Experience
- Microsoft Suite
- SalesForce
- SharePoint
Timeline
Lead Director, Strategic Partnerships
Aetna
02.2024 - Current
Lead Director, Account Management & Client Success
CVS Health
05.2022 - 02.2024
Senior Account Manager
CVS Health
06.2020 - 04.2022
Strategic Planning Manager
CVS Health
09.2018 - 06.2020
Meeting & Conference Manager
Aetna
04.2012 - 09.2018
Senior Planner, Meetings & Events
Aetna
05.2007 - 04.2012
Master of Business Administration -
University of Arizona
Bachelor of Arts - Public Relations
University of Connecticut