Senior Associate, Proposal Project Manager

Accountabilities: Proposal leadership and planning: Lead assigned proposal initiatives from initial intake through final submission, assessing requirements, complexity, timelines, deliverables, resource needs, dependencies, and review expectations. Project planning and governance: Develop and maintain comprehensive project plans outlining milestones, critical paths, responsibilities, approvals, deadlines, and communication protocols. Cross-functional coordination: Mobilize and coordinate stakeholders across Sales, Underwriting, Product, Legal, Compliance, Technology, Operations, and other business functions to support successful proposal delivery. Meetings and decision-making: Facilitate kickoff meetings, working sessions, project reviews, and stakeholder discussions to establish alignment, clarify responsibilities, resolve questions, and maintain momentum. Progress monitoring and risk management: Track project status, dependencies, resource constraints, and deadlines; anticipate risks, develop mitigation and recovery plans, and escalate issues requiring leadership decisions. Stakeholder communication: Provide clear, concise updates on progress, outstanding deliverables, risks, decisions, and required actions while maintaining accountability across teams. Proposal writer partnership: Work closely with proposal writers to coordinate content development, gather information and supporting materials, manage review cycles, and resolve feedback efficiently. Submission readiness and compliance: Oversee final reviews, approvals, documentation, and submission activities to ensure responses are complete, accurate, compliant, and delivered on time. Quality and process governance: Maintain project records, approvals, and submission documentation in accordance with established standards, workflows, and proposal-management practices. Technology and workflow optimization: Leverage proposal-management platforms, collaboration tools, automation, and AI-enabled capabilities to improve planning, tracking, productivity, and consistency. Continuous improvement: Identify process inefficiencies, contribute to standardized methodologies and templates, capture lessons learned, and support operational excellence across proposal management. Requirements Education: Bachelor's degree or equivalent professional experience. Relevant experience: At least 5 years of progressive experience in proposal management, RFP project management, project management, business operations, sales enablement, or a related field, including independently leading complex, deadline-driven initiatives. Proposal and industry expertise: Demonstrated experience managing RFPs, RFIs, DDQs, security questionnaires, proposals, or comparable client-facing deliverables within group benefits, insurance, healthcare, financial services, or another highly regulated industry. Proposal governance: Knowledge of formal proposal-development methodologies, governance practices, review processes, and the requirements of complex or strategically significant submissions involving senior stakeholders. Project management skills: Proven ability to manage multiple complex projects simultaneously, including integrated project plans, milestones, critical paths, dependencies, deliverables, review cycles, risks, and escalation plans. Risk and issue management: Experience anticipating project challenges, developing mitigation strategies, resolving obstacles, adjusting plans, and maintaining progress against demanding deadlines. Stakeholder leadership: Strong facilitation and relationship-management skills, with the ability to influence without direct authority, establish accountability, and drive alignment and decisions across organizational boundaries. Business judgment: Ability to prioritize competing demands, navigate ambiguity, respond to changing requirements, and make sound decisions aligned with project objectives and business outcomes. Communication: Excellent written and verbal communication skills, including the ability to communicate project status, risks, decisions, and action items effectively to stakeholders at all levels. Organization and attention to detail: Strong planning and documentation skills, with the ability to balance detailed execution with a strategic view of project goals, dependencies, and potential risks. Adaptability and professionalism: Demonstrated composure, flexibility, accountability, and follow-through in a fast-paced, deadline-driven environment. Technology proficiency: Experience with proposal-management platforms, project-management tools, workflow and collaboration technologies, document-management systems, and Microsoft Office applications. Preferred qualifications Experience supporting group benefits or employee benefits proposals and working with brokers, consultants, Sales, Underwriting, Product, Legal, Compliance, Technology, and other business partners. Experience applying artificial intelligence, automation, or emerging technologies to proposal management or business workflows. Familiarity with project-management methodologies, tools, controls, and best practices. Experience contributing to process improvement, operational transformation, or the implementation of standardized workflows. Core competencies Project leadership, execution, and strategic prioritization. Business acumen, sound judgment, and effective problem-solving. Stakeholder management, cross-functional collaboration, and influence without authority. Risk, issue, dependency, and deliverable management. Proposal governance, decision facilitation, and executive-level communication. Accountability, adaptability, resilience, and attention to detail. Operational excellence, process improvement, and technology enablement. Benefits Annual base salary: $75,000–$85,000, depending on experience, skills, qualifications, and job location. Annual discretionary bonus: Eligible for consideration under the employer's discretionary bonus program. Potential incentive compensation: Additional participation in an incentive program may be available, subject to applicable eligibility criteria. Remote work: Fully remote position open to candidates in any U.S. state. Comprehensive employee benefits: Access to a broad benefits package designed to support employee well-being and financial security. Leave programs: Access to employee leave benefits. Family support: Adoption assistance programs. Financial wellness: Student loan repayment programs. Professional development: Opportunities to develop project management, stakeholder leadership, and technology-enabled proposal execution skills. Collaborative environment: Opportunity to work with multidisciplinary teams on complex proposals and business initiatives within the group benefits sector.