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Proposal Manager/Writer (Part-Time Employee or Independent Contractor)

August 1, 2026

Company Overview Akiak Enterprise Services, LLC is a tribally owned Alaska Native organization that provides strategic management, technology, and operational support services to a portfolio of government-focused businesses within the Akiak Holdings family of companies. The company specializes in areas such as digital transformation, cybersecurity, AI/ML, grant management, and federal contracting support. Rooted in Yup’ik values and culture, Akiak Enterprise Services is committed to delivering innovative solutions to federal clients while promoting sustainable economic growth and community advancement for the Akiak Native Community. We are seeking a highly skilled Proposal Manager/Writer (Part-Time Employee or Independent Contractor) with deep experience developing government contract proposals, grant applications, and IT technical proposals. This role is ideal for a strategic thinker who can translate complex requirements into persuasive, compliant, and technically accurate proposal content. The position offers flexible hours and remote work options while supporting mission‑critical growth initiatives. The Proposal Manager/Writer leads and/or supports the development of federal and state proposals, including coordination, drafting, and compliance review, consistent with established direction and approval authorities. The role may require judgment within established guidelines in interpreting solicitations, preparing responses, and meeting submission deadlines. A minimum of 5 years of experience writing federal, state, local, and nonprofit proposals is required, along with demonstrated success supporting IT‑focused bids (e.g., cybersecurity, cloud services, software development, managed services). Key Responsibilities Proposal Management <ul> <li>Manage and/or support the proposal lifecycle, including planning, drafting, and submission activities as prime contractor and as subcontractor to an external prime contractor. </li> </ul> <ul> <li>Lead proposal submission efforts for assigned responses. </li> </ul> <ul> <li>Support company’s President in pipeline development. </li> </ul> <ul> <li>Develop proposal response compliance matrices and outlines in coordination with internal and external proposal teams. </li> </ul> Content Development <ul> <li>Draft and edit technical RFI responses and proposal narratives, and grant applications. </li> </ul> <ul> <li>Leverage approved tools (including AI-assisted tools, where permitted) to support response content drafting and editing. </li> </ul> <ul> <li>Use approved templates for final RFI, RFQ, and RFP response submissions. </li> </ul> <ul> <li>Coordinate with internal stakeholders to gather required inputs and ensure timely submission. </li> </ul> <ul> <li>Escalate risks, gaps, or compliance issues to leadership as appropriate. </li> </ul> Scope Clarification <ul> <li>Primary focus: Proposal writing and management (approximately 70–80%) </li> </ul> <ul> <li>Secondary focus: process support, compliance review, and administrative coordination (20–30%) </li> </ul> Requirements: <ul> <li>College Degree in Business Sciences, Information Technology, or another related field. </li> </ul> <ul> <li>Minimum of at least 5 years of Govcon proposal writing and/or end-to-end proposal management experience. </li> </ul> <ul> <li>Must be proficient in editing content provided by other technical writers. </li> </ul> <ul> <li>Strong written and verbal communication skills to translate research, statistics, goals, and objectives into compelling stories that keep the reader’s attention and can explain the outcome of a program or process. </li> </ul> <ul> <li>Must be highly analytical to meticulously assess complex opportunities, identify potential challenges, and develop persuasive proposals that align with business priorities. </li> </ul> <ul> <li>Must be able to successfully work cross functionally with internal and external stakeholders including Finance, HR, and Contracts to develop complete proposal packages for submission. </li> </ul> <ul> <li>You must be a U.S. Citizen </li> </ul> Preferred Qualifications: <ul> <li>Experience managing and creating submissions for GSA schedule, RFI, and RFQ responses. </li> </ul> <ul> <li>Experience using AI tools (e.g.Copilot) to develop proposal content. </li> </ul> <ul> <li>Mid to Senior level understanding of federal government contracting and grants process. </li> </ul> This opportunity may be filled in one of the following capacities based on candidate qualifications and business needs: Option 1: Part-Time Employee (Exempt) <ul> <li>Part-time, salaried (exempt) position</li> <li>Eligible for company employment in accordance with organizational policies</li> <li>Works as part of an internal team supporting proposal development and submission</li> <li>This part-time role has the potential to convert to a full-time position based on business needs.</li> </ul> Option 2: Independent Contractor (1099) <ul> <li>Engagement as an independent contractor (individual or company)</li> <li>Contractor will provide proposal development and writing services under a mutually agreed contract</li> <li>Contractor retains discretion over methods, schedule, and means of performing the work, consistent with deliverable requirements and deadlines</li> <li>Contractor is responsible for all applicable taxes, insurance, and business expenses</li> </ul> Individuals engaged as independent contractors will not be treated as employees and will not be eligible for employee benefits. Teleworking: The company has a hybrid remote policy for all employees and is dependent upon the type of position. This position may be assigned to support a federal contract, or to work in office. The Company’s teleworking eligibility may not apply if the employee is supporting a federal services contract. In this instance, the employee may be subject to federal telework policies. Employee Non-Disclosure: The employee must sign and attest to the Company’s non-disclosure statement. The employee is responsible for reporting to the Company’s Compliance, Risk and Ethics Officer any conflicts of interest, and/or provide notification of outside employment, or when release of confidential business is shared with external parties. Equal Opportunity Employer The Akiak Family of Companies will attempt to provide equal opportunity to all qualified employees and applicants for employment, with the exception of those situations affected by the Tribal Preference policy. All aspects of employment will be governed on the basis of merit, competence, and qualifications and will not be influenced by race, color, religion, sex, age, national origin, disability or any other basis prohibited by law. Contract ‑Mandated U.S. Citizenship Because this position supports a federal contract that restricts performance to U.S. citizens, you will be required to provide proof of U.S. citizenship (e.g., a U.S. passport or passport card; a U.S. birth certificate with a government-issued photo ID; or a Certificate of Naturalization or Citizenship).This request is solely to confirm contract eligibility and is separate from Form I‑9. For the I‑9, you may present any acceptable document(s) of your choosing; we do not request or require specific I‑9 documents. We will complete EVerify‑ within 3 business days of your start date in accordance with federal requirements.

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...