Senior Associate, Proposal Project Manager

Location Designation: Fully Remote 

Business Unit Overview

Group Benefit Solutions delivers comprehensive insurance and absence management solutions for mid-size and large companies. Our work fosters a healthier, happier and more secure workforce, contributing to New York Life’s legacy of being there when we’re needed most. Here, you’ll design, implement and support these solutions directly impacting customers’ lives. At our core, we provide financial security and peace of mind to people through our absence, accident, disability, voluntary benefits and life insurance solutions.

Role Overview

The Proposal Project Manager leads the end-to-end planning, coordination, and project execution of complex Requests for Proposal (RFPs), Requests for Information (RFIs), due diligence questionnaires (DDQs), security questionnaires, and related proposal initiatives supporting Group Benefits opportunities.

Serving as the project-management lead for assigned pursuits, this role establishes and drives the proposal execution strategy, mobilizes cross-functional resources, manages critical-path activities and dependencies, mitigates risks, and ensures the timely delivery of accurate, compliant, and high-quality submissions.

The Proposal Project Manager operates with a high degree of autonomy and judgment, partnering closely with Proposal Writers and business stakeholders to translate proposal requirements into actionable project plans, facilitate decision-making, and maintain alignment throughout the proposal lifecycle.

What You’ll Do

Proposal Leadership & Project Initiation

• Lead assigned proposal pursuits from intake through final submission, serving as the project-management lead and primary coordinator of execution activities.

• Analyze solicitation materials to identify requirements, deliverables, timelines, risks, dependencies, resource needs, and review requirements.

• Assess pursuit complexity and develop an appropriate project-management approach, governance model, operating cadence, and communication strategy.

• Translate proposal requirements into comprehensive project plans that define deliverables, milestones, ownership, dependencies, reviews, approvals, and deadlines.

• Engage Proposal Writers, subject matter experts, and business stakeholders to establish alignment on strategy, priorities, roles, and execution expectations.

• Leverage proposal-management technology, workflow tools, automation, and AI-enabled capabilities to support efficient planning and execution.

Project Management & Cross-Functional Coordination

• Manage proposal project plans throughout the lifecycle, ensuring visibility into deliverables, milestones, dependencies, risks, resource needs, and deadlines.

• Lead kickoff meetings, working sessions, and project reviews to drive alignment, decision-making, and execution.

• Coordinate resources across Sales, Underwriting, Product, Legal, Compliance, Technology, Operations, and other business functions.

• Establish clear ownership and expectations for deliverables while facilitating collaboration across stakeholders.

• Monitor progress, address barriers, prioritize competing demands, and adjust plans as business needs evolve.

• Provide timely, concise communication regarding project status, risks, decisions, and required actions.

Stakeholder Engagement & Risk Management

• Influence stakeholders without direct authority to secure commitments, resolve obstacles, and maintain project momentum.

• Anticipate and manage risks, competing priorities, resource constraints, and execution challenges that may impact quality or deadlines.

• Develop mitigation strategies and recovery plans when projects encounter delays or changing requirements.

• Escalate issues when leadership involvement or business decisions are required, presenting impacts, recommendations, and options.

• Foster strong cross-functional partnerships that support efficient collaboration and timely decision-making.

Proposal Writer Partnership

• Partner closely with Proposal Writers to support the successful development and delivery of proposal content.

• Provide project structure, scheduling, governance, stakeholder coordination, and workflow management that enable effective content development.

• Coordinate collection of information, supporting materials, data, and subject matter expertise required for proposal responses.

• Manage review and approval cycles and facilitate timely resolution of feedback, questions, and outstanding items.

• Maintain ownership of execution processes, allowing Proposal Writers to focus on messaging, positioning, strategy, and content quality.

Submission Management & Governance

• Oversee review, approval, and submission processes to ensure all requirements are satisfied and deliverables are completed on time.

• Monitor proposal readiness and identify outstanding risks, gaps, decisions, or dependencies requiring resolution.

• Maintain accurate project records, documentation, approvals, and submission materials in accordance with established standards.

• Ensure adherence to proposal-management processes, governance requirements, quality standards, and documentation practices.

• Coordinate final readiness reviews and submission activities to ensure complete, compliant, and timely delivery.

Continuous Improvement & Operational Excellence

• Identify opportunities to improve proposal-management processes, governance, collaboration, scalability, and execution efficiency.

• Contribute to the development and enhancement of project-management methodologies, templates, workflows, tools, and best practices.

• Capture lessons learned and apply insights to strengthen future proposal execution.

• Promote effective use of technology, automation, and AI-enabled capabilities to improve visibility, productivity, and consistency.

• Share expertise and support continuous improvement initiatives across the broader RFP organization.

What You’ll Bring

Required Qualifications

• Bachelor's degree or equivalent experience.

• 5+ years of progressive experience in proposal management, RFP project management, project management, business operations, sales enablement, or a related field, including demonstrated success independently leading complex, deadline-driven initiatives.

• Demonstrated experience managing RFPs, RFIs, DDQs, security questionnaires, proposals, and other complex client-facing deliverables within Group Benefits, insurance, healthcare, financial services, or another highly regulated environment.

• Knowledge of formal proposal-development methodologies, proposal governance practices, and review processes, with experience leading complex and strategically significant proposal initiatives involving senior stakeholders.

• Demonstrated ability to independently lead multiple complex projects involving cross-functional stakeholders, competing priorities, interdependencies, and demanding deadlines, including development and management of integrated project plans, milestones, critical paths, dependencies, deliverables, review cycles, risks, and escalation plans.

• Proven ability to anticipate project risks, develop mitigation strategies, resolve issues, maintain project momentum, and drive projects to successful completion.

• Strong stakeholder-management and facilitation skills, including the ability to establish accountability, influence without direct authority, lead complex meetings and working sessions, and drive alignment, decisions, ownership, and results across organizational boundaries.

• Strong business judgment and decision-making skills, with the ability to effectively prioritize competing demands and navigate ambiguity, changing requirements, and evolving business priorities.

• Excellent written and verbal communication skills, including the ability to clearly communicate project status, risks, decisions, and required actions to stakeholders at all levels of the organization. Strong organizational skills and attention to detail, balanced with the ability to maintain a strategic view of project objectives, risks, dependencies, and business outcomes.

• Demonstrated adaptability, professionalism, and composure in a fast-paced, deadline-driven environment.

• Experience with proposal-management platforms, project-management tools, workflow and collaboration technologies, document-management systems, and proficiency with 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 AI, automation, or emerging technologies to proposal-management or business-process workflows.

• Knowledge of project-management methodologies, tools, controls, and best practices.

• Experience contributing to process improvement, operational transformation, or implementation of standardized ways of working.

Core Competencies

• Project Leadership and Execution

• Strategic Planning and Prioritization

• Business Acumen and Judgment

• Stakeholder Management and Influence

• Cross-Functional Leadership

• Influence Without Authority

• Risk, Issue and Dependency Management

• Decision Facilitation and Problem Solving

• Proposal Governance and Deliverable Management

• Communication and Executive-Level Visibility

• Accountability and Follow-Through

• Adaptability and Resilience