Senior Manager, Proposal Strategy & Operations

About the Role

TimelyCare is seeking a Sr. Manager, Proposal Strategy & Operations to own and scale the company's proposal function, including RFPs, RFIs, RFQs, and other complex or strategic customer responses. This role will lead the full proposal lifecycle - from intake, qualification, and response strategy through content development, cross-functional review, submission, and outcome reporting. Reporting to the Vice President of Product Marketing, this individual will serve as the central point of accountability for proposal operations and will partner closely with Sales, Product Marketing, Product, Care, Customer Success, Legal, Security, Finance, and other subject matter experts. The Manager will improve how TimelyCare prioritizes opportunities, develops differentiated responses, manages institutional knowledge, and measures proposal performance. The ideal candidate combines exceptional proposal writing and project management skills with the ability to build scalable processes, influence cross-functional stakeholders, and translate complex healthcare and technology capabilities into clear, compelling customer value.

What You'll Do

Proposal Strategy & Execution

• Own the end-to-end proposal lifecycle for RFPs, RFIs, RFQs, and other strategic customer responses, from intake and qualification through submission and post-response follow-up.
• Lead solicitation analysis, response strategy, proposal kickoffs, writing, reviews, approvals, and final submission.
• Develop differentiated, customer-focused narratives that clearly connect institutional needs to TimelyCare's capabilities, outcomes, and value.
• Lead or support writing of executive summaries, strategic sections, and high-value or complex responses.
• Ensure every submission is compliant, accurate, persuasive, professionally presented, and delivered on time, or early.
• Coordinate contributors across Sales, Product Marketing, Product, Clinical, Customer Success, Legal, Security, Finance, Implementation, and other teams, and project manage proposals to completion.
• Clarify owners, deadlines, escalation paths, and approval requirements; proactively resolve gaps or risks that could affect submission quality or timing.
• Conduct an annual audit of both process and responses for continuous improvement.

Proposal Operations & Content Governance

• Build, document, and continuously improve proposal workflows, SOPs, templates, review processes, and service-level expectations.
• Own proposal content libraries, answer banks, approved claims, proof points, case studies, references, attachments, and reusable assets.
• Establish content owners, refresh cadences, version controls, and quality standards to ensure information remains current and reliable.
• Design and govern AI-enabled workflows that accelerate content development while maintaining security, accuracy, compliance, and human oversight.
• Leverage AI and insights from a database of prior RFPs, including competitor responses and market trends, to strengthen proposal strategy, identify differentiators, and inform more compelling responses.
• Direct contract or overflow proposal resources during peak periods, as applicable.

Systems, Reporting, and Optimization

• Maintain accurate RFP and proposal data in Salesforce and proposal-management systems.
• Track proposal volume, status, workload, turnaround time, outcomes, win rates, no-bid rationale, and pipeline influence.
• Lead proposal debriefs and partner with Sales and Revenue Operations on win/loss analysis.
• Translate performance insights into recommendations that improve qualification, messaging, content, process, and resource allocation.

What You Bring

• Bachelor's degree in Marketing, Business, Communications, English, Healthcare Administration, or related field.
• 7+ years of experience in proposal management, bid management, or complex B2B proposal development, including demonstrated ownership of end-to-end RFP or proposal processes.
• Experience in public-sector, higher education, K12, healthcare technology, or other complex B2B procurement processes.
• Demonstrated experience leading complex, deadline-driven proposals involving multiple business, technical, legal, and executive stakeholders.
• Excellent writing, editing, proofreading, and project management skills.
• Demonstrated ability to convert technical, clinical, operational, or product information into clear customer value.
• Experience maintaining proposal content libraries and proposal management tools.
• Experience managing proposal data, reporting, and workflows in Salesforce and proposal or knowledge-management platforms.
• Experience leveraging RFP and proposal platforms (e.g., Responsive, Inventive, Loopio) and opportunity intelligence tools (e.g., Starbridge, GovSpend, BidPrime) to improve efficiency and identify opportunities.
• Experience leveraging AI tools to improve proposal development and workflow efficiency preferred.
• Strong judgment and comfort making prioritization and go/no-go recommendations.
• APMP certification or equivalent proposal-management training is preferred.

Who You Are

• Collaborative and relationship-oriented with the ability to influence without direct authority.
• Comfortable exercising judgment, establishing boundaries, and pushing back constructively when an opportunity, timeline, or requested approach creates unnecessary risk.
• Calm and decisive under deadline pressure, without relying on last-minute heroics.
• Able to move between strategic thinking, detailed editing, process design, and hands-on execution.
• Exceptionally organized and detail-oriented.
• A persuasive, precise writer and editor who can simplify complex clinical, technical, and operational information without sacrificing accuracy.
• Curious, process-minded, and always looking for ways to improve.
• Passionate about TimelyCare's mission and delivering an exceptional customer experience.

Benefits + Perks

• Paid Company Holidays + No work on your birthday!
• Flexible PTO + Volunteer Time Off (VTO) as an organization to give back to the community
• Variable bonus eligibility on a quarterly basis
• Company-sponsored Health Insurance (Medical, Dental, Vision) + Pet Insurance
• Company-paid group Life Insurance + Company-paid Short Term Disability
• Concierge benefit support services
• 401(k) with employer match
• Free access to TimelyCare virtual medical and mental health support
• Mission-Driven Purpose with a Supportive Team Culture

Pay

The salary range for this opportunity is $135,000-$145,000 per year, depending on education and experience. This is the base pay. You will be eligible for a discretionary bonus in addition to the base pay, to be discussed during the interview process.