Senior Proposal Manager

eSimplicity Inc.; Columbia, Northern (MD, KY); Hybrid; USD 120,000 - 180,000; Full time

Benefits offered by this job

Medical, dental, vision

401(k) plan

Paid time off

Remote-friendly

Travel <5%

Job summary

eSimplicity Inc. seeks a Senior Proposal Manager to lead the full lifecycle of federal proposals. You will partner with capture, BD, and solution architecture to craft persuasive, compliant responses in a fast-paced environment.

The role emphasizes using AI tools, coordinating multi-disciplinary teams, and driving high-quality content and win themes. Remote-friendly with some travel, EST-aligned hours.

Qualifications

• Ten years of Federal pre-RFP and proposal development/management experience.
• Proven history supporting large, complex Federal proposals.
• Experience leading prime IT systems development proposals > $50M.

Responsibilities

• Lead full lifecycle proposals from RFP/RFQ to submission.
• Coordinate with capture managers and solution architects.
• Develop and maintain compliance matrices and outlines.
• Use AI tools to baseline content and run compliance checks.
• Prepare persuasive non-technical sections and review content.
• Lead reviews and post-mortems to improve processes.

Skills

Proposal leadership

Federal contracting

Team coordination

AI-assisted content creation

MS Word

PowerPoint

Excel

SharePoint

Adobe Acrobat

Education

Bachelor’s degree in English/Communications/IT

Tools

MS Word

PowerPoint

Excel

SharePoint

Adobe Acrobat

Illustrator

Job description

Description

About Us:

eSimplicity is a modern digital services company that partners with government agencies to improve the lives and protect the well‑being of all Americans, from veterans and service members to children, families, and seniors. Our engineers, designers, and strategists cut through complexity to create intuitive products and services that equip federal agencies with solutions to courageously transform today for a better tomorrow.

Position Overview

eSimplicity is seeking an experienced and dynamic Senior Proposal Manager to join our Proposal Operations team. If you are driven to make a meaningful impact through innovative proposal leadership and modern technology – and want to help government clients solve their toughest challenges – this is your opportunity to help our company grow while doing work that matters. This role shapes standout proposal responses that exceed basic compliance and influence broader business development strategy. You will partner with capture, business development, and solution architecture leads to develop and articulate technical and management solutions. The ideal candidate must be a proactive self‑starter who takes initiative, exercises sound judgment, and maintains momentum in a fluid environment.

Responsibilities:

Business Development/Pre-RFP:

• Work closely with Capture Managers to support pre-RFP planning including tracking milestones, creating templates, and scheduling strategy and solutioning sessions.
• Monitor targeted solicitations on SAM.gov, GovWin, GSA MAS, IDIQs, BPAs, etc.
• Support White Paper development for customer engagement.
• Assist with logistics and slide-deck development and preparation for customer meetings.
• Support RFI and Sources Sought responses to agencies/opportunities of interest.

Proposal Development/Management:

• Lead the full proposal lifecycle for active RFPs/RFQs, ensuring timely execution of action items and achievement of all milestones.
• Track amendments and update proposal materials accordingly.
• Review and interpret solicitation requirements, instructions, and evaluation criteria.
• Create and distribute proposal management artifacts (schedules, outlines, compliance matrices, kick-off slide decks, storyboards).
• Keep teams focused on producing compliant, compelling, competitive, and winning proposals.
• Communicate updates, activities, expectations, and timelines with internal leaders, proposal contributors, and external partners.
• Manage proposal activities and team responsibilities through daily stand-ups and regular meetings, adhering to schedules and deadlines.
• Plan, communicate, check progress, and take corrective action or elevate for all proposal volumes and artifacts to ensure all proposal development contributors including capture managers, solution architects, proposal writers, and program managers clearly understand and exceed expectation for their roles on the proposal.
• Use approved Artificial Intelligence (AI) tools and processes (e.g., baseline content, run compliance checks, etc.).
• Author non-technical sections (e.g., cover letters, past performance, resumes, etc.); proofread and draft content for clarity, consistency, and persuasiveness.
• Ensure templates and responses are compliant, compelling, accurate, and aligned with requirements.
• Lead Pink, Red, and Gold Team reviews by conducting In-Briefs with clear expectations and guiding reviewers to provide high impact, actionable feedback that ensures each draft becomes progressively more mature at every color cycle.
• Lead debriefs/retrospectives to capture lessons learned, drive continuous improvement, and integrate enhancements into current proposal processes.
• Ensure technical solution, win themes, discriminators, compliance, and clear understanding of the requirements are clearly reflected across all volumes.
• Support proposal orals teams by coordinating logistics, scheduling and attending sessions, and providing feedback to prepare participants.

Requirements

• Bachelor’s degree in English, Communications, IT, or a related field.
• Strong knowledge of the Federal Government contracting process.
• Minimum of ten (10) years Federal pre-RFP and proposal development/management experience.
• Proven history supporting large, complex Federal proposals.
• Demonstrated experience leading prime Federal IT systems development proposals greater than $50M.
• Strong Federal proposal writing and editing skills.
• Ability to create original content using interview, research, and AI tools.
• Ability to organize material, quickly assimilate information, and lead proposal teams.
• Demonstrated organizational and time management skills with the ability to manage multiple concurrent proposals while meeting deadlines and quality requirements.
• Ability to lead large multi-partner teams and adapt communication style to changing requirements and needs.
• Demonstrated ability to communicate effectively in both written and verbal formats.
• Demonstrated ability to produce accurate, thorough, and high-quality work with attention to detail.
• Demonstrated willingness and ability to learn new concepts, technologies, processes, and job-related skills.
• Expertise in MS Word, PowerPoint, Excel, SharePoint; and Adobe Acrobat and Illustrator.

Preferred Qualifications:

• Experience outside proposal management that enriches proposal capabilities (e.g., IT project roles, program management).
• Experience using Slack for communication and collaboration

Working Environment:

eSimplicity supports a remote work environment operating within the Eastern time zone so we can work with and respond to our government clients. Expected hours are 9:00 AM to 5:00 PM Eastern unless otherwise directed by your manager.

Occasional travel for training and project meetings. It is estimated to be less than 5% per year.

Benefits:

• eSimplicity offers a comprehensive benefits package, including medical, dental, and vision coverage, 401(k) retirement benefits, paid time off, paid holidays, life and disability insurance, and additional wellness and employee support programs. Eligibility may vary based on employment status and applicable plan terms.

Reasonable Accommodation:

eSimplicity is committed to providing reasonable accommodations to qualified individuals with disabilities during the application and hiring process. Applicants who need assistance or an accommodation should contact Human Resources.

Equal Employment Opportunity:

eSimplicity is an Equal Opportunity Employer, including disability and protected veteran status. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, protected veteran status, disability, or any other legally protected status.