Senior Proposal Manager

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

Benefits offered by this job

Medical, Dental, Vision

401(k) retirement benefits

Paid time off

Life and disability insurance

Job summary

eSimplicity is seeking a Senior Proposal Manager to join our Proposal Operations team. You will lead the full lifecycle of federal proposals, collaborating with capture, business development, and solution architecture to craft compelling, compliant responses.

The role requires proactive leadership, sharp judgment, and the ability to drive multiple complex proposals to successful completion. Our team leverages AI tools to baseline content, perform compliance checks, and produce high-impact

Qualifications

• Bachelor's degree in English, Communications, IT, or a related field.
• Extensive Federal pre-RFP and proposal development/management experience (10+ years).
• Proven history supporting large, complex Federal proposals and leading prime IT system development proposals >$50M.
• Strong Federal proposal writing and editing skills and ability to create original content using interviews, research and AI tools.
• Ability to organize material, lead cross-functional teams, and manage multiple concurrent proposals to meet deadlines.

Responsibilities

• Lead the full proposal lifecycle for active RFPs/RFQs, ensuring timely execution and milestones.
• Track amendments and update materials to reflect requirements.
• Review solicitation requirements, instructions, and evaluation criteria for compliance.
• Create and distribute schedules, outlines, compliance matrices, and storyboards.
• Coordinate with capture, business development, and solution architecture leads to articulate technical and management solutions.
• Lead reviews and debriefs to drive continuous improvement and ensure clear win themes and discriminators.

Skills

Proposal management

Federal contracting

Leadership

MS Word

PowerPoint

Excel

SharePoint

Adobe Acrobat

Illustrator

AI-assisted writing

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.