Senior Proposal Leader

This is a fully remote position, open to applicants in United States.

📋 Description

• Oversee the complete development process of intricate, high-stakes RFPs, RFIs, proposals, and finalist engagements.

• Evaluate solicitation requirements, customer priorities, evaluation criteria, competitive dynamics, and business goals to formulate pursuit strategies.

• Create winning themes, value propositions, executive summaries, response strategies, and distinctive, customer-centric messaging.

• Organize proposal kickoffs, strategy meetings, review sessions, and finalist preparations.

• Take ownership of proposal workplans from initial intake and kickoff through drafting, review, approval, submission, and closeout.

• Manage multiple simultaneous pursuits and coordinate assignments, dependencies, reviews, approvals, and stakeholder contributions.

• Identify delivery risks, resource constraints, content deficiencies, and decision bottlenecks; escalate issues and propose solutions.

• Maintain accurate project records, status updates, and closeout documentation.

• Act as the primary proposal partner among producers, subject matter experts, business leaders, Marketing/Design, Legal, Risk Management, and other contributors.

• Convert technical and expert input into clear, accessible, customer-focused content while ensuring accuracy and compliance.

• Assist with high-value finalist presentations, including story flow, presentation strategy, content development, speaker preparation, and rehearsal coordination.

• Conduct senior-level reviews for responsiveness, strategic alignment, writing quality, consistency, brand standards, and compliance.

• Manage Loopio and other proposal-management tools, enhancing templates, boilerplate, response frameworks, and content libraries.

• Mentor, coach, onboard, and provide peer review and support to proposal team members.

• Assist with workload visibility, resource planning, special projects, and capability development.

• Participate in post-submission reviews and utilize metrics, win/loss insights, feedback, and operational data to enhance performance.

• Advocate for proposal technology, Microsoft 365, workflow tools, AI-enabled capabilities, and automation within approved governance standards.

• Stay updated on proposal best practices, market trends, and emerging tools.

⛳️ Requirements

• 7+ years of experience in proposal management, RFP/RFI development, pursuit strategy, business-development support, or a related field, with a focus on leading complex or high-value pursuits.

• Proven experience managing proposals from inception to completion and coordinating multidisciplinary contributors under tight deadlines.

• Outstanding writing, editing, facilitation, communication, and stakeholder management skills.

• Demonstrated experience in mentoring, coaching, onboarding, or providing senior-level guidance to proposal professionals.

• Strong project management, prioritization, resource planning, and organizational skills.

• Familiarity with proposal/content management platforms and Microsoft 365; ability to quickly adapt to workflow, CRM, collaboration, and AI-enabled tools.

• Bachelor’s degree in Business, Communications, Marketing, English, or a related field, or equivalent relevant experience.

• Experience in insurance, employee benefits, financial services, professional services, HR technology, healthcare, or another complex regulated/service environment.

• Proficiency with Loopio, SharePoint, Salesforce or CRM platforms, and structured workflow/project management tools.

• Experience in supporting finalist presentations, public-sector or formal procurement responses, and compliance-heavy pursuits.

• APMP certification or other relevant proposal/project management certification.

• Experience in content governance, reusable libraries, proposal templates, process design, reporting, or technology adoption.

🏝️ Benefits

• Health Benefits: Medical/Rx, Dental, Vision, Life Insurance, Disability Insurance.

• Financial Benefits: ESPP; 401k; Student Loan Assistance; Tuition Reimbursement.

• Mental Health & Wellness: Free Mental Health & Enhanced Advocacy Services.

• Paid Time Off.

• Holidays.

• Preferred Partner Discounts.