Director of Proposal Strategy and Operations

Job Summary

The Director, Proposal Strategy & Operations is a leadership role responsible for elevating HMA's proposals function into a high-performing, technology-forward engine for competitive growth. Reporting to the Chief Growth Officer, this leader sets the strategic direction for the proposals team, drives adoption of AI-enabled tools and modern workflows, evolves team capabilities around a newly streamlined proposal process, and identifies new opportunities to strengthen how HMA competes and wins. This role requires a collaborative and forward-thinking leader who brings both strategic vision and operational discipline, and who can build trust across a talented team while guiding the function through an exciting period of growth and evolution.

Work Performed and Job Requirements

• Strategic Leadership & Vision
  • Define and execute a multi-year strategy for the proposals function aligned to HMA's growth objectives and go-to-market priorities.
  • Serve as the senior proposals voice to executive leadership, advising on bid qualification, win strategy, competitive positioning, and resource investment.
  • Champion a culture of continuous improvement, accountability, and innovation across the proposals team.
  • Identify opportunities that HMA is not yet capitalizing on, including new content strategies, pursuit models, proposal formats, and service offerings, that would materially improve win rates.
  • Represent the proposals function in cross-functional leadership forums, shaping how growth opportunities are identified, prioritized, and pursued.

• Team Leadership & Development
  • Lead, coach, and develop a skilled proposals team, setting clear expectations, providing ongoing feedback, and creating a high-trust environment where people do their best work.
  • Align team roles and responsibilities to the current and evolving scope of the proposals function, ensuring each team member has clarity on how their work contributes to HMA's growth goals.
  • Actively invest in the professional development of team members, building individual capabilities and identifying opportunities for growth and advancement.
  • Manage performance with consistency and care, recognizing strong contributors and providing clear direction and support where improvement is needed.
  • Foster a team culture oriented toward winning, continuous learning, and collaboration with the broader growth organization. 

• Technology Adoption & Process Innovation
  • Lead the adoption and scaling of AI-enabled proposal tools, automation platforms, and intelligent content management systems (e.g., Loopio, RFPIO/Responsive, or comparable platforms).
  • Identify and eliminate manual, low-value processes across the proposal lifecycle, replacing them with scalable, SLA-driven workflows that improve both throughput and quality.
  • Expand the formats and presentation approaches used in proposals, including development of PowerPoint-based and simplified proposal formats that complement traditional written submissions and better capture evaluator attention.
  • Build and maintain a robust repository of reusable, high-quality content that enables the team to respond faster and more consistently without sacrificing differentiation.
  • Establish and maintain a performance measurement framework tracking win rates, cycle time, content reuse, team productivity, and quality to drive data-informed decisions.
  • Partner with IT and other functions to evaluate, procure, and implement emerging technologies that advance the proposals function's capabilities.
  • Continuously benchmark HMA's proposal operations against industry best practices, introducing innovations that strengthen competitive positioning.

• Integration of Acquisitions & Expanded Scope
  • Lead the integration of recently acquired organizations into HMA's proposal workflows, ensuring consistency in process, quality standards, and content strategy across the combined enterprise.
  • Develop scalable onboarding and integration frameworks that can be applied to future acquisitions, enabling the proposals team to absorb new business lines efficiently and without disruption to ongoing work.
  • Partner with growth, operations, and consulting leadership at acquired organizations to understand their existing proposal practices and identify opportunities to align and elevate them within HMA's approach.

• Operational Excellence & Quality Governance
  • Oversee end-to-end proposal operations across all opportunity types, ensuring submissions are compliant, differentiated, and competitively positioned.
  • Design and govern a tiered proposal support model that allocates team resources appropriately based on opportunity complexity and strategic importance.
  • Establish rigorous quality standards, review protocols, and content governance practices, ensuring consistency and excellence across all client-facing submissions.
  • Own the content management strategy, including reusable content libraries, knowledge management, and version control, in partnership with relevant stakeholders.
  • Ensure accurate, timely pipeline tracking and reporting in the CRM (Vantagepoint), leveraging data to inform resource planning and leadership reporting.

• Stakeholder Engagement & Cross-Functional Collaboration
  • Partner with consulting, business development, marketing, and finance leaders to align proposal strategies with HMA's broader go-to-market approach.
  • Lead bid qualification discussions with senior leadership to focus team resources on the highest-probability, highest-value opportunities.
  • Serve as an escalation point and trusted advisor on high-stakes proposals, ensuring appropriate executive engagement and strategic messaging.
  • Drive win/loss review discipline, translating competitive intelligence into actionable improvements in strategy, content, and process. 

• All other duties assigned. 

Education/Training

Bachelor's degree in business, communications, marketing, or a related discipline required; advanced degree preferred. APMP or Shipley certification is strongly preferred.

Experience

• Minimum of 10 years of progressive experience in proposal management, with a minimum of 3+ years in a senior leadership or director-level role overseeing a proposals function.
• Demonstrated experience leading teams through periods of growth and operational change, including building new capabilities and evolving team structures in response to shifting organizational needs.
• Proven track record implementing AI-enabled proposal tools, automation platforms, and scalable process improvements that measurably improved outcomes.
• Experience operating in a professional services, consulting, or healthcare advisory environment strongly preferred.
• Experience integrating acquired teams or organizations into existing proposal workflows is a plus.
• Track record of navigating complex organizational dynamics, building stakeholder credibility, and influencing outcomes across functions and levels

Knowledge, Skills, and Abilities

• Deep expertise in proposal lifecycle management, operations, and scalable process design
• Strong strategic leadership, including vision setting, change management, and team alignment
• Advanced stakeholder influence, executive communication, and cross-functional collaboration
• Proficiency in AI, data analytics, CRM systems, and proposal technologies to drive efficiency
• Ability to translate strategy into execution, leveraging data and performance metrics
• Skilled in developing high-quality, persuasive content across multiple formats
• Effective decision-making, problem-solving, and facilitation in complex environments
• Strong organizational, prioritization, and delivery capabilities under tight deadlines

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities

The contractor will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor’s legal duty to furnish information. 41 CFR 60-1.35(c)

People Leadership Competencies

• Coaching: Builds the capability of direct reports through clear guidance, steady feedback, and intentional development.
• Performance Leadership- Sets expectations, monitors progress and manages performance with fairness and consistency.