Strategic Proposal & Presentation Enablement Manager

Overview

Via Benefits, a WTW business, helps employers guide eligible retirees and other populations to individual health insurance coverage through personalized enrollment support, ongoing advocacy, and reimbursement account administration. We are looking for a Strategic Proposal & Presentation Enablement Manager to help bring our story to life and support growth across Retiree Solutions, Active/Individual Coverage Health Reimbursement Arrangement (ICHRA) Solutions, Access, and Public Sector Solutions.

In this hands-on role, you will shape the client experience by reviewing, creating, and formatting client and finalist presentations; applying WTW and Via Benefits branding standards; and turning complex information into clear, polished slides. You will also coordinate proposals from intake through submission, develop compelling client-centered messaging, manage reusable content, and use approved AI tools to improve speed, consistency, and quality.

Location: Remote – Open to Candidates within the US

What You’ll Do

• Bring client and finalist presentations to life by shaping storylines, simplifying complex information, formatting slides, refining speaker notes, and applying WTW and Via Benefits branding standards.

• Lead the coordination of RFPs, RFIs, renewals, standard proposals, and other priority pursuits from intake and planning through final submission.

• Review solicitation documents to identify requirements, deadlines, submission instructions, risks, gaps, and questions, then turn them into clear workplans and assignments.

• Partner with sales and solution leaders to develop win strategies, executive summaries, proposal narratives, and messaging tailored to each prospect’s priorities.

• Deliver submission-ready materials by consolidating edits and confirming completeness, accuracy, terminology, branding, formatting, compliance, and overall quality.

• Keep pursuits moving by managing timelines, review cycles, stakeholder responsibilities, approvals, collaboration workspaces, document ownership, and version control.

• Use Microsoft Copilot, Loopio, and other approved tools to analyze requirements, strengthen first drafts, retrieve approved content, identify gaps, and increase reuse while maintaining human review and confidentiality.

• Keep proposal content, presentation assets, prompts, templates, and knowledge resources current and easy to use across Loopio, Teams, and SharePoint.

• Bring together input from Sales, Solution Architecture, Client Management, Operations, Product, Marketing, Legal, Finance, and subject-matter experts to ensure content is accurate, current, and aligned.

• Help continuously improve proposal processes, templates, review checklists, ownership models, and handoffs by applying lessons learned from completed pursuits.

Required Experience and Skills

• 5-8+ years of relevant experience in proposals, presentations, sales enablement, business development, communications, consulting, or a related professional-services environment.
• Exceptional writing, editing, synthesis, storytelling, presentation-development, and document-quality skills.
• Advanced PowerPoint and Microsoft 365 skills, with the ability to create polished, brand-compliant presentations and manage collaborative workspaces.
• Strong project-management skills and a track record of coordinating multiple high-priority deliverables, stakeholders, reviews, and deadlines.
• Sound judgment and the ability to translate technical information for executive, employer, advisor, and participant audiences.
• A practical, client-focused approach to balancing speed, quality, and risk in a fast-paced environment.
• Experience using Microsoft Copilot or another enterprise AI platform to support analysis, drafting, content review, or meeting preparation.

Preferred Experience

• Experience supporting employee benefits, retiree health, health care, exchange, or technology-enabled service solutions.
• Familiarity with Loopio or a comparable proposal-management platform, including AI-assisted drafting, approved-content retrieval, library maintenance, tagging, and response reuse.
• Familiarity with SharePoint, Teams, content-management systems, and document-governance practices.

How You Work

• You communicate clearly and persuasively and take pride in the details.
• You build strong partnerships and are comfortable coordinating and influencing across functions.
• You pair strategic thinking with practical business judgment and a continuous-improvement mindset.
• You stay organized, adapt quickly, and maintain quality while managing competing priorities.

What Success Looks Like

• Proposals and presentations are accurate, complete, delivered on time, and aligned with client, brand, formatting, compliance, and quality expectations.
• Clear ownership, practical timelines, organized workspaces, and approved content make review and production cycles faster and easier for everyone involved.
• Client-facing materials are concise, visually effective, on brand, and tailored to what matters most to each prospect.
• Approved AI tools improve efficiency while maintaining source validation, human review, confidentiality, and required approvals.
• Current content in Loopio and SharePoint is easy to find, reuse, and maintain with minimal duplication.
• Cross-functional partners experience fewer missed edits, version-control issues, and avoidable rework.

If you enjoy combining hands-on presentation development, proposal coordination, strategic writing, content governance, and practical AI enablement, this role offers an opportunity to help Via Benefits respond more efficiently and communicate its value with clarity and impact.

Note: Employment-based non-immigrant visa sponsorship and/or assistance is not offered for this specific job opportunity

This position will remain posted for a minimum of three business days from the date posted or until sufficient/appropriate candidate slate has been identified.

Compensation and Benefits

Base salary range and benefits information for this position are being included in accordance with requirements of various state/local pay transparency legislation. Please note that salaries may vary for different individuals in the same role based on several factors, including but not limited to location of the role, individual competencies, education/professional certifications, qualifications/experience, performance in the role.

Compensation

The base salary compensation range being offered for this role is $85,000-$95,000 USD annually. This role is also eligible for an annual short-term incentive bonus.

Company Benefits

WTW provides a competitive benefit package which includes the following (eligibility requirements apply):

• Health and Welfare Benefits: Mental health/emotional wellbeing (including Employee Assistance Program), medical (including prescription drug coverage and fertility benefits), dental, vision, Health Savings Account, Commuter Accounts, Health Care and Dependent Care Flexible Spending Accounts, company-paid life insurance, supplemental life insurance, AD&D, group accident, group critical illness, group legal, identify theft protection, wellbeing program, adoption assistance, surrogacy assistance, auto/home insurance, pet insurance and other work/life resources
• Leave Benefits: Paid holidays, annual paid time off (includes state/local paid leave where required), company-paid disability (short-term and long-term disability), other leaves (e.g., bereavement, FMLA, ADA, jury duty, military leave, and Parental and Adoption Leave),  Paid Time Off (only included for Washington roles)
• Retirement Benefits: Qualified contributory pension plan (if eligible) and 401(k) plan with annual nonelective company contribution. Non-qualified retirement plans available to senior level colleagues who satisfy the plans’ eligibility requirements 

Pursuant to the San Francisco Fair Chance Ordinance and Los Angeles County Fair Chance Ordinance for Employers, we will consider for employment qualified applicants with arrest and conviction records.

EOE, including disability/vets

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