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Trustmark

Voluntary benefits and self-funded health plans

Proposal Services Manager

Full-TimeUpdated on 10/23/2026
$62.9k - $90.9k/yr+ Bonus
Junior, Mid
Bachelor's
Lake Forest, IL, USA
Hybrid
Project & Program ManagementProposal Management

About the job

Requirements
  • A bachelor's degree with 2–4 years of related experience, or a high school diploma or GED with 4–6 years of related experience.
  • People management experience.
  • Proficiency in Microsoft Office products and Adobe Writer.
  • Insurance product experience from a Sales or Underwriting background.
  • At least 3 years of experience with Life/Health Insurance.
  • Strong documentation skills.
Responsibilities
  • Lead workforce planning and team development by monitoring demand and capacity trends, determining staffing requirements, recruiting and onboarding talent, and fostering a high-performance culture focused on continuous improvement, employee development, accountability, and operational excellence.
  • Establish, monitor, and report operational performance metrics for submission and RFP activities, including turnaround times, quality standards, productivity measures, and year-over-year trend analysis, to drive business insights and process improvements.
  • Analyze and report on year-to-year trends and create and distribute activity reports to appropriate teams.
  • Develop, maintain, and enforce operational standards, procedures, job aids, and documentation to support consistency, scalability, knowledge transfer, and continuous process improvement across the team.
  • Direct proposal workflow, quality assurance, and audit functions to ensure timely, accurate, and compliant delivery of customer-facing submissions; develop and maintain auditing methodologies, quality control processes, and best-practice standards; and serve as a key liaison between Sales, Underwriting, and other business partners throughout the proposal and quote lifecycle.
  • Monitor and manage the workflow of proposal requests and underwriting offers, review and evaluate requests and output quality, create and update auditing and quality-control documentation, audit team cases, review best practices in key areas, and liaise between Sales and Underwriting teams as needed to complete proposals and underwriting offers.
  • Work with team subject-matter experts across the organization to create and maintain online and manual tools for proposal and rate creation, as well as training documents used by the Proposal and Submission teams.
  • Provide strategic oversight of AI-enabled submission technologies, including monitoring large language model performance, validating output accuracy, analyzing usage trends, and refining model inputs and governance practices to align with business objectives, compliance requirements, and customer needs.
  • Provide strategic oversight of the transition from Salesforce to Dynamics, including current Salesforce and Client Central processes for the Proposal and Submission teams.
  • Determine staffing requirements, interview and hire team members, work with others to train them, develop and mentor them through bi-weekly one-on-ones, create and maintain a positive team environment, and hold the team accountable for performance.
  • Lead the RFP Submission Team, overseeing AI-enabled submission tools, governance processes, and quality-audit functions to ensure accurate translation of information into business-ready, customer-facing deliverables.
  • Manage the Proposal Unit responsible for comprehensive responses to external customer requests, including RFPs, product proposals, pricing and rate requests, questionnaires, and third-party portal submissions.
  • Perform other duties as assigned.
Desired Qualifications
  • Insurance product experience from a Sales or Underwriting background.
  • At least 3 years of experience with Life/Health Insurance.
  • Strong documentation skills.

About the company

Trustmark provides employee benefits services nationwide, focusing on voluntary benefits, self-funded health plan design and administration, and wellness programs. Its products include Trustmark Voluntary Benefits (life, hospital, accident, disability, and critical illness) with employee education and communications support; Trustmark Small Business Benefits offering level-funded or self-funded health plans for small to mid-size employers with simplified underwriting; and HealthFitness wellness and prevention programs. It differentiates itself by combining national scale with personalized service and long-term relationships, giving smaller employers access to benefits typically available to large companies, along with education resources to improve understanding and utilization. Its goal is to help people and businesses thrive by providing practical benefit options, comprehensive plan administration, and wellness programs.

Company Size

1,001-5,000

Company Stage

N/A

Total Funding

N/A

Headquarters

Lake Forest, Illinois

Founded

1991

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Simplify Jobs

Simplify's Take

What believers are saying

  • Erik Braun joined March 16, 2026 after scaling Kuvare premiums from $46 million.
  • June 18, 2026 expansion added Critical HealthEvents, Hospital StayPay, and Life + Care.
  • Healthcare Highways and Vori Health broaden Trustmark Small Business Benefits' provider network.

What critics are saying

  • Phil Goss retires after 18 years; Braun must preserve finance discipline through 2026.
  • Expanded state launches raise compliance and filing complexity across Washington, Hawaii, and Oregon.
  • If digital enrollment lags, brokers migrate employers to Sun Life and Unum in 2027.

What makes Trustmark unique

  • Mutual ownership lets Trustmark reinvest profits into benefits and carrier relationships.
  • June 2026 product expansion spans Washington, Hawaii, and Oregon with bundled protection.
  • Enroll For Life integrates digital enrollment with voluntary benefits, reducing employer friction.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Life Insurance
  • Health Savings Account/Flexible Spending Account
  • 401(k) Retirement Plan
  • Wellness Program

Company News

Business Wire
Mar 16th, 2026
Erik Braun joins Trustmark as CFO after growing Kuvare premiums from $46M to $7B

Trustmark Mutual Holding Company has appointed Erik Braun as Chief Financial Officer and Treasurer, effective immediately. Braun succeeds Phil Goss, who is retiring after 18 years with the company and will remain through end-2026 to support the transition. Braun brings over 20 years of finance experience in insurance and financial services. He joins from Kuvare Holdings, where he spent nine years, serving as Corporate Controller before becoming CFO in 2024. At Kuvare, he helped grow premiums from $46 million to over $7 billion through acquisitions and integration of multiple carriers. Goss joined Trustmark in 2008 and became CFO in 2010. Under his leadership, the company received an upgraded AM Best rating to A (Excellent) in 2023.

Associated Press
Jan 20th, 2026
Trustmark appoints Nancy Harris and Terry Shaw to board of directors

Trustmark Mutual Holding Company has appointed Nancy Harris and Terry Shaw to its board of directors. Harris is the retired Executive Vice President and Managing Director of North America at Sage Group PLC, where she oversaw a $1 billion revenue business with 2,500 employees across the US and Canada. She currently serves on the board of Intapp, Inc. Shaw is the retired President and CEO of AdventHealth, one of America's largest faith-based healthcare organisations. During his eight-year tenure as CEO, he helped double the organisation's annual revenue and expand its workforce to 97,000 employees. Trustmark Chairman David Weick said the appointments would bring valuable strategic vision and expertise to the board as the company navigates technological change and evolving customer expectations.

Yahoo Finance
Sep 4th, 2025
Erich Sternberg Joins Trustmark as President of Voluntary Benefits and Chief Strategy Officer

Erich Sternberg joins Trustmark as President of Voluntary Benefits and Chief Strategy Officer.

Business Wire
Mar 3rd, 2025
Trustmark Mutual Holding Company Names John Anderson President & CEO, Completing Planned Leadership Transition

Anderson succeeds Kevin Slawin, who has retired after more than six years as Trustmark CEO.

Business Wire
Nov 7th, 2024
Trustmark Acquires Enroll For Life[TM] Technology Platform

Trustmark has successfully partnered with iOpt LLC and used this technology on select permanent life case enrollments since 2022.