Proposal Manager

Courtesy Products, Inc.; Florida; Hybrid; USD 90,000 - 130,000; Full time

Benefits offered by this job

Medical, Dental & Vision Insurance

401(k) Retirement Plan with Company In

Paid Time Off (PTO)

Tuition Reimbursement

Paid Training

Career Advancement Opportunities

Life Insurance & AD&D Coverage

Voluntary Benefits including Short-/L0

Job summary

TKC Holdings, Inc.—comprising Trinity Services Group, Keefe Group, and Courtesy Products—seeks a seniorProposal Leader to drive complex RFP/RFI responses from kickoff to archive. You will own planning, scheduling, and compliance while guiding cross-functional teams and communicating with Sales to deliver defensible, client-specific proposals.

Your role requires expert writing, editing, and project management, plus experience with AI-assisted drafting and standard proposal templates.

Qualifications

• Bachelor's degree in Business, Communications, or English related discipline preferred; seven to 10 years of related proposal development experience, including managing multiple complex proposals, or equivalent combination of education and experience.
• Self-motivated, goal-oriented, organized, detail-oriented multi-tasker who excels in a rapid development environment, with exceptional communication skills.
• Ability to work independently and lead cross-functional contributors to meet deadlines.
• Excellent project management and time management skills, with the ability to work under pressure and manage multiple projects simultaneously.
• Excellent writing, editing, and reading comprehension skills, including the ability to interpret RFP requirements and evaluation criteria.
• Exceptional organizational skills and attention to detail, preparing materials with a high degree of accuracy.
• Proficient in Adobe InDesign, Adobe Acrobat and Microsoft Word.
• Excellent working knowledge of SharePoint, Microsoft Copilot, Microsoft Teams (or equivalent) and Salesforce.
• Working knowledge of the Apple computer platform.
• Work independently and in a team, providing constructive feedback and direction to support team goals.

Responsibilities

• Lead the proposal process from RFP receipt through submission and archive, owning the plan, schedule, compliance, and final quality of each response.
• Review and analyze RFPs, RFIs, and addenda to identify requirements, evaluation criteria, due dates, ship dates, upload instructions, and special requirements.
• Participate in Sales’ proposal kickoff calls and communicate with Sales throughout the project to ensure the best possible response, including custom content based on client knowledge.
• Create the proposal outline with a matrix of findings and assignments; assign sections and information requests to Sales, Operations, Finance, Menu Development, HR, Legal, and Risk, and follow up until complete.
• Apply Trinity proposal templates and library content, tailoring the level of detail to the size and type of facility; contribute new information to the proposal templates and libraries as necessary.
• Set internal deadlines, track progress, and escalate risks and missing inputs early.
• Monitor and review upload sites, client Q&A, and addenda, and communicate changes to Sales and Operations.
• Work with subject matter experts to turn detailed information into accurate, defensible proposal language.
• Write, edit, proofread, and format the proposal draft, tailoring content to the client, facility type, and incumbent or new-business status.
• Use approved AI tools for drafting and for RFP-to-proposal compliance and gap analysis against requirements and evaluation criteria; verify all output and clear any operational content derived from AI with an SME before it is used.
• Direct the final quality review: ensure all RFP requirements are satisfied and confirm signatures and attachments.
• Prepare final bid packages and submittal letters, oversee electronic submission files, and coordinate printing and shipping with the Print Center; print and ship proposals in emergencies.
• Archive the total proposal archive and related PDFs using established procedures.
• Train and mentor Proposal Specialists as needed.
• Develop business relationships among internal associates to ensure effective proposal generation.
• Assist with client presentations and Best and Final Offers; conduct post-submission lessons learned.
• Maintain the strict confidentiality of sensitive information.

Skills

Writing proficiency

Editing

Communication skills

Project management

Time management

Cross-functional leadership

Attention to detail

Independent work

AI drafting tools

Education

Bachelor's degree in Business/Communications/English

7–10 years proposal development experience

Tools

Adobe InDesign

Adobe Acrobat

Microsoft Word

SharePoint

Microsoft Copilot

Microsoft Teams

Salesforce

Job description

Work Location

Hybrid

Overview

TKC Holdings, Inc.—comprised of Trinity Services Group, Keefe Group, and Courtesy Products - is a mid market respected leader in the corrections and hospitality industries for more than 40 years. With thousands of team members across the country, we continue a tradition of innovation, integrity, and success. TKC is committed to delivering excellent products and services, exceeding customer expectations, and empowering the career development of every team member.

We are proud to be a military and veteran-friendly employer.

BENEFITS:

We care about our employees and offer benefits that support your health, finances, and career growth.

• Medical, Dental & Vision Insurance
• 401(k) Retirement Plan with Company Match
• Paid Time Off (PTO)
• Tuition Reimbursement
• Paid Training
• Career Advancement Opportunities
• Life Insurance & AD&D Coverage
• Voluntary Benefits including Short-Term Disability, Long-Term Disability, Critical Illness, Accident Coverage, and more.

Benefits

We care about our employees and offer benefits that support your health, finances, and career growth.

• Medical, Dental & Vision Insurance
• 401(k) Retirement Plan with Company Match
• Paid Time Off (PTO)
• Tuition Reimbursement
• Paid Training
• Career Advancement Opportunities
• Life Insurance & AD&D Coverage
• Voluntary Benefits including Short-Term Disability, Long-Term Disability, Critical Illness, Accident Coverage, and more.

About This Position

Lead the development and submission of complex RFP/RFI responses from solicitation through archive. Own the plan, schedule, compliance, and quality; direct contributors across departments; and communicate with Sales throughout to deliver the best possible response.

Essential Functions, Duties, and Responsibilities

• Lead the proposal process from RFP receipt through submission and archive, owning the plan, schedule, compliance, and final quality of each response.
• Review and analyze RFPs, RFIs, and addenda to identify requirements, evaluation criteria, due dates, ship dates, upload instructions, and special requirements (bonds, audited financials, notarized forms).
• Participate in Sales’ proposal kickoff calls and communicate with Sales throughout the project to ensure the best possible response, including custom content based on knowledge of the client and incumbent or new-business status.
• Create the proposal outline with a matrix of findings and assignments; assign sections and information requests to Sales, Operations, Finance, Menu Development, HR, Legal, and Risk, and follow up until complete.
• Apply Trinity proposal templates and library content, tailoring the level of detail to the size and type of facility; contribute new information to the proposal templates and libraries as necessary.
• Set internal deadlines, track progress, and escalated risks and missing inputs early.
• Monitor and review upload sites, client Q&A, and addenda, and communicate changes to Sales and Operations.
• Work with subject matter experts (SMEs) to turn detailed information into accurate, defensible proposal language.
• Write, edit, proofread, and format the proposal draft, tailoring content to the client, facility type, and incumbent or new-business status.
• Use approved AI tools for drafting and for RFP-to-proposal compliance and gap analysis against requirements and evaluation criteria; verify all output and clear any operational content derived from AI with an SME before it is used.
• Direct the final quality review: review the final proposal for compliance, technical issues, and errors, ensuring all RFP requirements and evaluation criteria are satisfied, and confirm signatures, required forms, attachments, addenda, and confidential markings.
• Prepare final bid packages and submittal letters, oversee electronic submission files, and coordinate printing and shipping with the Print Center; be able to print and ship proposals in an emergency with provided equipment.
• Archive the total proposal archive, the final low-resolution PDF, and the final low-resolution redacted PDF using established procedures.
• Train and mentor Proposal Specialists as needed.
• Develop business relationships among internal associates to ensure effective proposal generation.
• Assist with client presentations and Best and Final Offers as requested; conduct post-submission lessons learned.
• Maintain the strict confidentiality of sensitive information.
• Other duties as assigned.

What You'll Need

• Bachelor's Degree in Business, Communications, or English related discipline preferred; seven to 10 years of related proposal development experience, including managing multiple complex proposals, or equivalent combination of education and experience.
• Self-motivated, goal-oriented, organized, detail-oriented multi-tasker who excels in a rapid development environment, with exceptional communication skills.
• Ability to work independently and lead cross-functional contributors to meet deadlines.
• Excellent project management and time management skills, with the ability to work under pressure and manage multiple projects simultaneously.
• Excellent writing, editing, and reading comprehension skills, including the ability to interpret RFP requirements and evaluation criteria.
• Exceptional organizational skills and attention to detail, preparing materials with a high degree of accuracy.
• Proficient in Adobe InDesign, Adobe Acrobat and Microsoft Word.
• Excellent working knowledge of SharePoint, Microsoft Copilot, Microsoft Teams (or equivalent) and Salesforce.
• Working knowledge of the Apple computer platform.
• Work independently and in a team, providing constructive feedback and direction to support team goals.
• Ability to direct and motivate contributors across departments.
• Sound judgment in identifying compliance risks, unsupported claims, and gaps, and in escalating them to Sales, Operations, or Legal.
• Multi-task and prioritize across multiple proposals, strictly adhering to deadlines.
• Communicate with all levels of the organization and work well with a variety of personalities.
• Adapt to change, solve problems proactively, and complete tasks under stressful situations with efficiency and accuracy.

EEO Statement

Equal Employment Employer as to all protected groups, including protected veterans and individuals with disabilities.

We maintain a drug-free workplace.

A copy of our Privacy Policy and CA Employee Privacy Notice can be found here: https://tkcholdings.com/privacy-policy-108