Proposal Writer Contract Jobs in Wisconsin (NOW HIRING)

Candidate Authenticity Statement

We recognize that AI tools are increasingly used in professional settings. However, during our assessment and interview process, we ask candidates to complete all responses independently, without the use of AI-generated assistance.

This ensures we can accurately assess your individual skills, communication style, and problem-solving approach. Submissions or responses that appear AI-generated may be considered misaligned with our evaluation standards.

Remote-First with In-Person Training

This position is remote following successful completion of onboarding. New hires are required to attend two weeks of in-person training at our Carrollton, TX corporate office to ensure a smooth and successful transition into the role.

POSITION SUMMARY

The Proposal Writer II is responsible for identifying, qualifying, developing, and submitting persuasive, compliant responses to government Requests for Proposals (RFPs), Requests for Information (RFIs), Requests for Qualifications (RFQs), Invitations for Bid (IFBs), and related public-sector solicitations. This role combines government opportunity sourcing with hands‑on proposal writing and serves as a key contributor throughout the department’s full proposal lifecycle, from opportunity discovery and bid/no-bid support through content organization, quality review, electronic submission, and post-submission follow-up activities as assigned.

The ideal candidate is an accomplished proposal writer who understands state, local, and education (SLED) procurement, can interpret complex government solicitation requirements (RFPs), and can translate technical, operational, and business information into clear, RFP‑compliant, client‑centered, evaluator‑focused responses. The Proposal Writer II works across sales, operations, legal, compliance, finance, and information security to produce accurate, differentiated, and compelling government proposals under firm government solicitation requirements (RFP) deadlines.

PRINCIPAL DUTIES & RESPONSIBILITIES Government RFP Sourcing & Pre-Qualification

• Partner with the Lead Proposal Writer to source and monitor government contracting opportunities through public procurement portals, bid-notification platforms, agency websites, and other market‑intelligence resources.
• Conduct targeted opportunity searches using relevant commodity codes, NAICS codes, NIGP codes, service categories, keywords, and agency‑specific filters.
• Review daily and weekly bid alerts to identify relevant RFPs, RFIs, RFQs, IFBs, pre‑solicitations, and related public‑sector opportunities, while supporting maintenance of an accurate opportunity pipeline.
• Perform preliminary solicitation analysis, including scope of work, eligibility requirements, mandatory qualifications, evaluation criteria, submission instructions, due dates, contract terms, estimated value, and potential barriers to entry.
• Report sourced opportunities and associated activity to the Lead Proposal Writer to support pipeline visibility and metrics related to opportunities reviewed, bids pursued, and proposals submitted.

Proposal Writing & Content Development

• Write original, company‑persuasive proposals that address each government entity’s objectives, requirements, scope, program, evaluation criteria, and desired outcomes.
• Develop compliant responses to government‑issued RFPs, including executive summaries, cover letters, technical and management responses, implementation and transition plans, service descriptions, resumes, experience statements, and value propositions.
• Translate complex operational, technical, compliance, security, financial, and product information into clear, concise language for public‑sector evaluators.
• Tailor approved content to each opportunity and clearly communicate organizational capabilities, differentiators, benefits, outcomes, and risk‑mitigation strategies.
• Edit contributor content for clarity, consistency, responsiveness, readability, grammar, and persuasive impact.

Solicitation (RFP) Analysis, Compliance & Submission

• Analyze complete government solicitations, including attachments, addenda, questionnaires, pricing forms, contract terms, and submission instructions.
• Develop compliance matrices, requirement trackers, content plans, and proposal schedules to ensure all required components are addressed.
• Identify mandatory requirements, exceptions, ambiguities, risks, and information gaps; coordinate with the territory salesperson and internal resources to prepare clarification questions for the issuing agency.
• Ensure responses comply with solicitation requirements, including page limits, formatting, section titles, file‑naming conventions, signatures, forms, and delivery instructions.
• Coordinate cross‑functional input and obtain timely, approved content and required management approvals.
• Prepare, validate, and submit final proposal files in accordance with the government entity’s instructions.
• Maintain complete proposal records, including addenda acknowledgments, submission confirmations, final files, and supporting documentation.

Proposal Quality, Content Management & Process Improvement

• Perform final quality‑control reviews of assigned written proposals from start‑to‑finish for compliance, accuracy, consistency, readability, and presentation.
• Maintain the proposal content library, including approved narratives, resumes, case studies, references, certifications, security documentation, implementation materials, and standard attachments.
• Partner with content owners to validate information and retire outdated, duplicative, or unsupported material.
• Use proposal automation and related tools to support drafting, research, content retrieval, and quality review while protecting confidential information and maintaining accountability for accuracy.
• Prepare, validate, and submit final proposal files in accordance with solicitation requirements.
• Maintain complete proposal records, including addenda acknowledgments, submission confirmations, final files, and supporting documentation.

Post-Submission & Stakeholder Support

• Support responses to government clarification requests, deficiency notices, oral presentation requests, best‑and‑final offers, negotiations, and finalist activities.
• Assist with presentation messaging, speaker notes, demonstration scripts, and other finalist materials when required.
• Monitor award notices and procurement outcomes; maintain accurate opportunity status information and support debrief requests or public‑record follow‑up as appropriate.
• Communicate professionally with internal stakeholders, procurement contacts, brokers, consultants, partners, and subcontractors while following solicitation communication restrictions.

KNOWLEDGE, SKILLS, AND ABILITIES REQUIRED Government Proposal Development Skills

• Advanced government proposal writing, editing, proofreading, and document-development skills. (Advanced)
• Strong knowledge of the end‑to‑end proposal lifecycle, public‑sector procurement practices, and compliance‑driven response development. (Advanced)
• Ability to analyze complex solicitations and translate requirements into actionable writing, compliance, and submission plans. (Advanced)
• Ability to develop compelling win themes, value propositions, differentiators, proof points, and evaluator‑focused narratives. (Advanced)
• Strong research and opportunity‑sourcing skills, including experience using government bid portals, agency websites, and public procurement records. (Advanced)

Technical Proficiency & Documentation Management Skills

• Expert proficiency in Microsoft Word and PowerPoint, with strong working knowledge of Excel, Adobe Acrobat Pro, Google Workspace, Salesforce or comparable CRM systems, and proposal automation platforms such as Loopio. (Expert)
• Exceptional attention to detail, organization, time management, version control, and document accuracy. (Advanced)
• Ability to manage multiple concurrent proposals, deadlines, and shifting priorities in a matrixed environment. (Advanced)
• Exceptional editing and proofreading skills to ensure clarity, conciseness, and alignment with solicitation requirements. (Advanced)
• Ability to create templates, checklists, and organizational tools to streamline the proposal creation process. (Advanced)

Interpersonal & Communication Skills

• Strong knowledge of proposal development processes and best practices. (Advanced)
• Strong verbal and written communication skills, with the ability to collaborate effectively across multidisciplinary teams and diverse stakeholders. (Advanced)
• Confidence to ask precise questions, address incomplete or unsupported content, and drive assignments to completion. (Advanced)
• Professional judgment, discretion, and a client‑focused demeanor when handling confidential, proprietary, procurement‑sensitive, or personally identifiable information. (Advanced)
• Ability to work independently, adapt to changing priorities, exercise sound judgment, and remain composed in a deadline‑driven work environment. (Advanced)

Time Flexibility

• Willingness to work after hours or on weekends as needed to meet proposal deadlines. (Advanced)

Work Location and Transition

• This position will initially work onsite at the corporate office to complete onboarding, training, and role‑specific development.
• Following successful completion of the onsite training period and demonstrated proficiency, the employee may transition to a remote‑work arrangement, subject to manager approval and company policy.
• Remote‑work eligibility depends on consistent performance, reliable attendance, effective communication, independent workload management, and compliance with departmental expectations.

Remote Work Responsibilities

• Maintain a professional, secure, and distraction‑minimized workspace with reliable internet access and the equipment necessary to perform assigned duties.
• Remain accessible and responsive during established business hours and participate fully in virtual meetings, working sessions, training, and team activities.
• Protect confidential, proprietary, procurement‑sensitive, and personally identifiable information in accordance with company security, privacy, and remote‑work requirements.
• Report to the corporate office for meetings, training, collaboration, or other business needs when requested.

CREDENTIALS & EXPERIENCE Education

• Bachelor’s degree ideally in Business, Marketing, Creative Writing, Communications, English, Journalism, or related.

Experience

• Minimum of 8 years of professional government proposal writing experience required; 10 years or more is strongly preferred. Candidates must provide relevant government proposal writing work samples.
• Demonstrated experience writing and submitting government proposals required, with a strong concentration in SLED (state, local, and education) government opportunities preferred.
• Experience sourcing SLED government contracting opportunities and using public procurement portals, bid‑notification platforms, or market‑intelligence tools desired.
• Deep experience independently writing complex RFP responses, not solely coordinating or assembling contributor content required.
• Experience with proposal automation software, content libraries, and electronic procurement portals required.
• Experience developing proposals within the third‑party administration, Flexible Spending Account, employee benefits, or broader healthcare industry is preferred.
• APMP certification or formal proposal‑management training preferred.

Note: The salary range for this position is between $75,000.00 - $80,000.00 annually with added bonus potential. BENEFITS

• Medical Insurance
• Vision Insurance
• Dental Insurance
• 401(k) Matching
• Flexible Spending Accounts
• Health Savings Accounts
• Disability & Life Insurance
• Employee Assistance Program
• LegalShield
• ID Shield
• Commuter Reimbursement Plan
• Tuition Reimbursement
• Bonus Pay - This position falls under our “Corporate Bonus Plan” which entitles you to a potential bonus payout of up to 10% of your annual salary as an annual bonus, if offered employment.

ADDITIONAL BENEFITS INCLUDE

• Wellable membership
• Telescope Health (telehealth) through Accresa
• Intellect (mental health) application
• Employee engagement activities, including voluntary events, raffles, book club, and more!