Cara Westover
Charlotte,NC
Summary
Executive operations and strategy leader with 15+ years driving organizational transformation in high-growth healthcare and digital health environments. Proven Chief of Staff and Interim Clinical Operations Director skilled in orchestrating executive decision-making, aligning priorities, and translating strategy into scalable execution. Adept at leading cross-functional teams across clinical, product, operations, and data domains. Combines clinical credibility (LMFT) with revenue-oriented B2B business development experience, enabling strong executive partnership, strategic clarity, and operational excellence.
Overview
20
20
years of professional experience
1
1
Certification
Work History
Consultant — Acting Interim Clinical Operations Director & Chief of Staff
Westover Collective Consulting
12.2024 - 08.2025
- Client: Backpack Healthcare
- Served as strategic advisor to the CEO and CCO, establishing executive operating rhythms, alignment frameworks, and structured decision workflows.
- Directed enterprise EHR transition achieving 95%+ documentation compliance and full adoption across 70+ clinicians.
- Increased clinician utilization from 65% to 86% through staffing model redesign, automated reporting, and performance governance.
- Improved NPS by 20 points by standardizing client engagement workflows and enhancing organization-wide quality practices.
- Validated and operationalized AI-enabled clinical tools with product and engineering teams to improve safety and workflow integration.
- Implemented measurement-based care systems improving visibility into client risk and outcomes across service lines.
- Built scalable onboarding and training infrastructure supporting 3,000+ clinician development hours.
- Synthesized complex operational challenges into executive-ready recommendations, enabling faster strategic decision-making.
- Supported operational strategy contributing to a $750K annual district contract.
Senior Manager, Therapy Services
Headspace
10.2020 - 07.2024
- Directed national clinical workforce operations by managing 10 clinical managers and indirectly supporting 150+ clinicians across all 50 states.
- Shaped national care delivery strategy with executive, clinical, and product leaders to support scalable virtual therapy operations.
- Oversaw clinical operations impacting tens of thousands of virtual therapy sessions annually.
- Increased provider utilization by 30% through staffing model redesign and performance accountability systems.
- Maintained 90%+ client continuity during major organizational restructuring and market shifts.
- Built operational frameworks, documentation standards, and quality systems supporting consistent care delivery.
- Provided clinical strategy insights influencing $1.5M+ in employer contracts.
Program Leadership & Quality Operations
Breathe Life Healing Center | La Ventana Behavioral Health | Center for Discovery
01.2012 - 01.2018
- Developed treatment pathways, program structures, and crisis management protocols supporting retention and quality outcomes.
- Led teams through CARF & Joint Commission audit readiness, achieving 100% compliance.
- Supported multidisciplinary collaboration across multiple levels of care.
Earlier Career: Business Development & B2B
Verifi | Bushman Products | Integrated Marketing
01.2006 - 01.2010
- Experience in B2B sales, marketing, and GTM execution across consulting and creative industries.
- Led business development and marketing initiatives supporting enterprise pipeline growth.
- Managed national trade show strategy, campaigns, and ROI analysis.
- Developed messaging, positioning, and stakeholder engagement strategies aligned with revenue goals.
- Led cross-functional teams to develop strategic solutions for client challenges.
- Conducted comprehensive market analysis to inform client decision-making processes.
Education
M.A. - Clinical Psychology (Marriage & Family Therapy)
The Chicago School of Professional Psychology
B.F.A. - Fine Arts
School of Visual Arts
New YorkSkills
- Epic
- Cerner
- TherapyNotes
- Simple Practice
- Tableau
- Looker
- Advanced Excel
- Asana
- Mondaycom
- AI/ML Clinical Tools
- Project & Operations Management Systems
Certification
- LMFT: California #114151
- North Carolina #10558
Executive Highlights
- Increased clinician utilization from 65% to 86% through redesigned staffing models and accountability systems.
- Led enterprise EHR transition achieving 95%+ adoption and documentation compliance across 70+ clinicians.
- Directed 10 managers and indirectly supported 150+ clinicians across all 50 states at Headspace.
- Improved client experience (NPS) by 20 points through workflow standardization and quality enhancements.
- Built scalable onboarding and training ecosystem delivering 3,000+ clinician development hours.
- Influenced revenue growth through operational leadership supporting a $750K district contract and $1.5M+ in employer partnerships.
Core Competencies
- Chief of Staff Operations
- Executive Partnership
- Strategic Planning
- Operating Rhythms
- Cross-Functional Alignment
- Workforce Optimization
- KPI & Accountability Systems
- Organizational Design
- Change Management
- EHR Implementation
- Quality & Compliance
- AI/ML Workflow Integration
- Stakeholder Management
- GTM Strategy
- Business Development
Timeline
Consultant — Acting Interim Clinical Operations Director & Chief of Staff
Westover Collective Consulting
12.2024 - 08.2025
Senior Manager, Therapy Services
Headspace
10.2020 - 07.2024
Program Leadership & Quality Operations
Breathe Life Healing Center | La Ventana Behavioral Health | Center for Discovery
01.2012 - 01.2018
Earlier Career: Business Development & B2B
Verifi | Bushman Products | Integrated Marketing
01.2006 - 01.2010
B.F.A. - Fine Arts
School of Visual Arts
M.A. - Clinical Psychology (Marriage & Family Therapy)
The Chicago School of Professional Psychology