Sales Enablement & Proposals Manager

Posted 2 Days Ago
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Hiring Remotely in Tampa, FL, USA
In-Office or Remote
79K-109K Annually
Senior level
Insurance • Software • Analytics
The Role
The Sales Enablement & Proposals Manager enhances sales effectiveness by executing enablement campaigns, managing RFP processes, and collaborating with Sales and Marketing.
Summary Generated by Built In

Healthesystems offers workplace flexibility with our Work-From-Home model, and a competitive compensation and benefits package including healthcare coverage, PTO, paid holidays, 401(k), company-provided life insurance/disability coverage, wellness options, and more.

Note:  we are unable to hire in every state 

The Sales Enablement & Proposals Manager is a senior individual contributor responsible for enabling sales effectiveness in complex B2B sales environments through high‑impact enablement campaigns and assets, disciplined RFP execution, and strong ownership of proposal workflows and tooling. This role supports a focused, relationship‑driven sales model and ensures sales teams are equipped with the right campaigns, content, and processes to move longer‑cycle, highly considered opportunities forward. The role partners closely with Sales, Marketing, and subject matter experts across the organization to translate strategy into clear, sales‑ready execution.

Key Responsibilities: “To simplify complexities for each customer.”

  1. Execute and operationalize sales enablement programs and campaigns within CRM and marketing automation platforms (e.g., HubSpot, Pardot/Salesforce), identifying opportunities to incorporate AI‑enabled tools and emerging technologies to enhance content delivery, personalization, and workflow efficiency, ensuring enablement assets are activated, accessible, and aligned to defined sales motions.
  2. Partner closely with Sales to deliver buyer‑aligned enablement support, translating established positioning, value propositions, and sales strategies into effective sales narratives, plays, and assets for the field.
  3. Ensure enablement and proposal materials remain current and on‑strategy, aligning to approved positioning, GTM priorities, and messaging while applying appropriate levels of customization.
  4. Support priority and late‑stage opportunities with tailored proposal and enablement materials, executing against deal strategy and buyer needs defined in partnership with Sales and leadership.
  5. Lead and manage the end‑to‑end RFP/RFI process and tooling, including intake, timelines, coordination with subject matter experts, quality control, and final submission.
  6. Maintain and continuously improve the RFP and proposal content library, including standard narratives, win themes, reusable responses, and best practices to drive consistency, speed, and differentiation.
  7. Administer and optimize proposal and enablement tools, workflows, and templates, ensuring ease of use, collaboration, and efficiency across Sales, Marketing, and Operations.
  8. Write, edit, and refine proposals, executive summaries, and enablement content, ensuring clarity, consistency, and compelling narrative flow while avoiding generic or overly templated language.
  9. Serve as a feedback conduit between Sales and Marketing, capturing insights on objections, content gaps, and asset usability, and sharing recommendations to inform ongoing enablement and automation improvements

Qualifications/Education/Certifications:

  • Bachelor’s degree in Marketing, Communications, Business, or a related field, or equivalent combination of education and experience.
  • 5-8+ years of relevant experience in sales enablement, proposal management, or related roles supporting large, relationship-driven accounts with extended B2B sales cycles where relationship continuity, credibility and tailored messaging are critical.
  • Experience working in highly regulated, services‑oriented, or healthcare‑adjacent environments preferred.

Knowledge, Skills and Abilities:

  • Direct, hands‑on experience owning RFP workflows and proposal tooling in a B2B environment.
  • Strong working knowledge of HubSpot or similar marketing automation and CRM platforms.
  • Familiarity with B2B sales pipelines, funnel stages, and opportunity progression, with the ability to apply this understanding to inform targeted enablement efforts and campaign effectiveness.
  • Exceptional written communication skills with the ability to translate complex offerings into clear, persuasive narratives.
  • Strong organizational and project management skills; able to manage multiple concurrent initiatives and deadlines.
  • High degree of business judgment and discretion when supporting priority opportunities.
  • Ability to collaborate effectively across Sales, Marketing, and subject matter experts.

Role-Based Competencies: 

  • Shows Drive & Initiative
  • Collaboration & Teamwork
  • Delivers Quality Results Timely
  • Communicates Effectively
  • Job Knowledge & Skills

Physical Demands/Working Conditions:

Duties are performed primarily in a home office setting utilizing computer equipment.  Travel to attend meetings and visit locations throughout the country may be required.  While performing the duties of this job, the employee is regularly required to sit and talk or hear.  The employee is frequently required to use hands.  The employee is occasionally required to stand and walk. *** Job descriptions will be reviewed and are subject to changes of business necessity.  Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Pay is based on several factors including but not limited to education, work experience, certifications, geographical cost of labor, etc.  In addition to base pay, Healthesystems offers a comprehensive benefits package including, health, dental, vision, disability and life insurance, wellness resources, recognition programs, 401k contribution, and PTO & Holiday pay (all subject to eligibility requirements). Applicable statutory benefits also provided, including the Colorado HFWA.  https://healthesystems.com/careers/

Anticipated Starting Pay Range
$79,000$108,570 USD

To facilitate working from home, and as a requirement for this role, candidates must provide their own reliable, high speed internet access with sufficient bandwidth to execute all job functions. Company laptop will be provided - (except for temporary internship roles)

Healthesystems California Prospective Employee Privacy Notice

Skills Required

  • Bachelor's degree in Marketing, Communications, Business, or related field
  • 5-8+ years of relevant experience in sales enablement or proposal management
  • Experience in regulated or healthcare-adjacent environments
  • Direct experience owning RFP workflows in a B2B environment
  • Strong working knowledge of HubSpot or similar platforms
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The Company
HQ: Tampa, FL
339 Employees
Year Founded: 2002

What We Do

Healthesystems is a specialty provider of innovative medical cost management solutions for the workers’ compensation industry. Our diverse suite of services includes a leading Pharmacy Benefit Management (PBM) program and Clinical Review Services as well as a revolutionary Ancillary Benefits Management (ABM) program for managing and adjudicating ancillary medical services. Leveraging powerful technology, clinical expertise and enhanced workflow automation tools, we provide clients with flexible programs that reduce the total cost of medical care while increasing the quality of care for injured workers. We are committed to developing new ideas to help our clients navigate the complex workers’ compensation industry while achieving measurable results such as improved pharmacy transaction efficiency, network penetration and drug utilization. Our services are tailored to each of our client’s needs to increase value and maximize results. Services include: A leading Pharmacy Benefit Management (PBM) program Comprehensive Clinical Review Services An unrivaled Ancillary Benefits Management (ABM) program Trending and Data Analytics tools Innovative Technology Solutions and Systems Integration Services

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