Senior Proposal Specialist

Accountabilities

• Manage the complete lifecycle of RFPs, RFIs, and customer-facing proposal requests, from initial intake and kickoff through coordination, review, approval, and final submission.

• Partner with Sales and Solutions teams to understand customer needs, evaluation criteria, submission instructions, deadlines, and response objectives.

• Build project plans, workback schedules, milestones, and clear ownership assignments to ensure timely and accurate deliverables.

• Coordinate cross-functional contributors and subject-matter experts by setting deadlines, facilitating working sessions, following up on outstanding items, and communicating project status and risks.

• Assemble, format, edit, and quality-check responses to ensure accuracy, completeness, consistency, readability, and compliance with customer instructions.

• Manage review and approval cycles, consolidate stakeholder feedback, and coordinate final submissions.

• Use approved proposal content libraries, previous responses, product documentation, and trusted internal resources to develop high-quality first drafts.

• Interpret customer questions, identify relevant source material, and tailor existing content to the specific requirements and context of each opportunity.

• Leverage approved AI tools and productivity solutions to accelerate research, content discovery, drafting, and response workflows, while validating outputs against authoritative sources.

• Identify missing information, outdated content, conflicting answers, and knowledge gaps, coordinating with the appropriate experts to resolve them.

• Project-manage information security assessments, compliance questionnaires, vendor assessments, and other customer due diligence requests from intake to completion.

• Act as the central coordinator for security and compliance requests, assigning questions to relevant owners, tracking progress, consolidating responses, and managing deadlines.

• Maintain accurate tracking of active requests, submission deadlines, response history, and upcoming deliverables to provide visibility into workload and project status.

• Identify and implement opportunities to improve proposal workflows, project tracking, templates, content reuse, and quality-control practices.

• Build effective working relationships across Sales, Solutions, Marketing, Product, Clinical, Legal, Information Security, Compliance, and other internal teams.

Requirements:

• At least 4 years of experience in proposal management, project management, sales operations, or a related role involving complex, deadline-driven deliverables.

• Experience supporting large and complex RFPs in healthcare, health technology, or enterprise SaaS environments.

• Excellent organizational skills and attention to detail, with the ability to manage competing priorities, track deadlines, and follow through on deliverables.

• Demonstrated experience coordinating cross-functional contributors and managing multiple projects or requests simultaneously.

• Strong writing, editing, and communication skills, including the ability to synthesize information from multiple sources into clear, accurate, well-structured responses.

• Experience using existing documentation, proposal content libraries, previous responses, and other source materials to create and tailor first drafts.

• Strong stakeholder management skills, with the ability to clarify requirements, obtain input, drive accountability, and escalate risks when necessary.

• Sound judgment and critical-thinking skills, including the ability to identify information gaps, inconsistencies, and content requiring subject-matter expert validation.

• Ability to quickly understand technical and business concepts and coordinate effectively with both technical and non-technical stakeholders.

• Proactive, self-directed working style, with the ability to work independently while collaborating across a matrixed organization.

• Adaptability and resilience in a fast-paced environment with evolving priorities and processes.

• Proficiency with proposal response management software such as Responsive (formerly RFPIO), as well as Google Workspace and Microsoft Office.

• Preferred qualifications:

  • Experience maintaining a centralized proposal content library, knowledge repository, or reusable response database.

  • Familiarity with information security, privacy, compliance, or technical due diligence processes.

  • Experience using AI tools to research source material, develop first drafts, improve content reuse, or streamline response workflows.

  • Familiarity with tools such as Slack, Salesforce, Adobe, and Monday.com.

  Benefits:

  • Annual base salary range of $90,000–$105,000.

  • Bonus included as part of the total compensation and benefits package.

  • Fully remote opportunity within the United States.

  • Approximately 5% travel, including potential onsite onboarding and occasional in-person team meetings in Boston, Massachusetts.

  • Medical, dental, and vision insurance.

  • Life and disability insurance.

  • Employee Assistance Program.

  • 401(k) retirement plan with company match.

  • Flexible Spending Accounts (FSA) and Health Savings Accounts (HSA).

  • Flexible time off and company holidays.

  • Up to 14 weeks of paid parental leave.

  • Pet insurance.

  • Location restriction: This role is not available to candidates residing in Alaska, California, Colorado, Hawaii, New York, or Washington.

  • Individual compensation is determined by factors such as location, qualifications, experience, skills, and internal alignment.