• Lead development of pricing strategies for new business, renewals, and strategic client expansions • Analyze large volumes of healthcare data and build robust pricing models incorporating utilization, PMPM trends, network economics, and administrative cost assumptions • Translate clinical, network, and operational assumptions into clear, defensible financial models • Create and maintain benchmarks by line of business using historical utilization, cost, and performance trends to inform pricing assumptions and proposal strategy • Analyze historical trends to identify key cost and utilization drivers, variability, and risks across products, markets, and populations • Conduct scenario analysis, sensitivity testing, and margin evaluation to inform price‑to‑win decisions • Prepare and present pricing insights, financial rationale, and trade‑off analyses to executive stakeholders and health plan partners • Own the end‑to‑end pricing workflow for proposals, including intake, prioritization, modeling, review, and final submission • Coordinate closely with Sales, Growth, Product, Network, and Clinical teams to align technical, operational, and financial components • Create executive‑ready pricing summaries and recommendations for leadership review • Lead discussions with health plan partners by clearly explaining pricing assumptions, utilization drivers, and value propositions • Partner with Finance on performance tracking, variance analysis, and ongoing refinement of pricing assumptions • Contribute to continuous improvement of pricing tools, templates, benchmarking frameworks, and governance processes • Perform other duties as needed.

• Lead proposals, MSAs, and SOQs from initial kickoff and planning through final submission. • Analyze RFP requirements to create compliance matrix, propose template, team assignments, and production schedules. • Facilitate internal kickoff sessions, strategy discussions, and formal reviews with executive leadership. • Oversee content development, formatting, and graphics to ensure clear alignment with company win themes. • Work with technical staff and project managers to gather, refine, and translate complex data. • Maintain proactive communication across teams to unblock issues quickly and adhere strict deadlines. • Update and optimize the proposal boilerplate, resumes, project profiles, and content asset libraries, utilizing responsive platforms.

Role Description We’re looking for a Senior Proposal Manager to own our bid program end to end from the moment we receive an RFP to the day we submit, and through any follow-on BAFO or oral presentation support. - Own the win strategy and narrative for each bid alongside Sales leadership. - Write and edit substantial portions of every response. - Build the content infrastructure that makes each successive bid stronger than the last. - Work across Product, Engineering, Operations, Legal, Security, and Finance to extract credible inputs for responses. - Turn inputs into clear, persuasive, compliance-meeting proposal language. - Use AI tooling to accelerate drafting and content reuse. - Have judgment to know when AI output meets the bar and when it needs significant human intervention. Qualifications - 5+ years of proposal management or bid writing experience, with direct ownership of complex, long-form RFP responses. - Demonstrated experience in public-sector or regulated B2G technology procurement (govtech, infrastructure, SaaS sold to government agencies, or similar). - Strong writing and editing skills — ability to show proposals written, not just managed. - Experience coordinating multi-stakeholder input processes and holding contributors to deadlines without formal authority. - Hands-on familiarity with AI writing and productivity tools (ChatGPT, Claude, Copilot, or similar). - Exceptional organizational and project management skills; comfortable owning multiple concurrent workstreams under deadline pressure. Requirements - Manage the full bid lifecycle for 8-12 major municipal RFPs per year: kickoff, compliance matrix, schedule, review cycles, production, and on-time submission. - Build and maintain bid governance processes that create predictability and accountability across contributing teams. - Track and manage all RFP requirements, addenda, and clarifications; flag compliance risks early and resolve them before they become submission issues. - Own the go/no-go input process and maintain a bid calendar that gives leadership clear line-of-sight into upcoming pipeline. - Develop the win theme and narrative strategy for each bid in partnership with Sales. - Write and edit executive summaries, company overviews, approach narratives, implementation plans, and other long-form sections. - Conduct structured SME interviews and working sessions to extract technical, operational, and compliance content. - Review all contributed sections for consistency of voice, accuracy, and alignment with the win story. - Build and maintain a reusable proposal content library: baseline answers to common RFP questions, modular narrative blocks, case studies, client references, proof points, certifications, and past performance documentation. - Continuously improve library content based on evaluation feedback, new contract wins, and product and capability updates. - Develop and maintain standard templates for common response structures used in municipal technology procurement. - Use AI tools actively to accelerate first-draft generation, content adaptation, and library search. - Help establish and follow internal protocols around what proposal content and client data can appropriately be used with AI tooling. - Stay current on emerging AI capabilities relevant to proposal development. Benefits - Competitive salary. - Comprehensive health benefits. - Flexible work environment. - Opportunities for professional development. Company Description Trellint delivers comprehensive parking and curbside management solutions that make the curb easy to use and accessible to all. Our vision is to enhance the value of every curb. To accomplish this, we are leading the transformation of the industry with intelligent curbside management solutions that promote equitable access to the curb, conquer congestion, and improve safety.

• Coordinates all phases of PSI’s proposal process while maintaining the company’s win rate of 30% and higher. • Contributes to everything from RFP strategy to bid defense slide decks. • Partners with global teams of subject matter experts from various departments to rapidly produce winning proposals. • Prepares viable RFP calendars and ensures RFP milestones are met by all involved individuals in a timely manner. • Organizes, attends, and leads strategy calls for each RFP; prepares and distributes minutes/action items. • Develops draft budgets: reviews clients’ specifications, obtains quality feedback from various stakeholders within the company. • Works with the budgeting team to develop competitive budgets and obtaining missing costs. • Prepares vendor RFPs and obtaining vendor quotes. • Writes strategic proposals that meet our clients’ needs. • Provides support for bid defense meetings. • Maintains all RFPs in Salesforce and PSI’s CTMS.