GuidePoint Security provides trusted cybersecurity expertise, solutions and services that help organizations make better decisions and minimize risk. By taking a three-tiered, holistic approach for evaluating security posture and ecosystems, GuidePoint enables some of the nation’s top organizations, such as Fortune 500 companies and U.S. government agencies, to identify threats, optimize resources and integrate best-fit solutions that mitigate risk.
Senior Proposal Manager
General Description
We are looking for a skilled Senior Proposal Manager to own the cradle-to-grave proposal lifecycle for Federal opportunities, including RFPs, RFIs, RFQs, and sole- source justifications across DoD, Intelligence Community, and Civilian agencies. This role will drive compliant, competitive, and on-time proposal submissions while coordinating cross-functional teams spanning Sales, Pre-Sales Engineering, Legal, Contracts, and vendor partners.
About the Federal Region
GuidePoint Security is the trusted partner that defense and civilian government agencies rely on to lead their cybersecurity efforts and protect their organizations. We help solve their most complex security challenges, mature security architectures, and proactively reduce risk. Our purpose-built solutions ensure compliance, safeguard critical assets, and align security with organizational objectives. Backed by deep expertise, strong partnerships, and advanced technologies, we deliver scalable, adaptive capabilities that evolve with the threat landscape so Federal agencies can lead with confidence and protect what’s next.
Roles and Responsibilities
- Own the cradle-to-grave proposal lifecycle from opportunity qualification through submission, including compliance matrices, outlines, contributor coordination, reviews, and production.
- Manage multiple concurrent Federal proposals with competing deadlines, ensuring quality and compliance with solicitation requirements (FAR/DFARS).
- Develop and enforce proposal schedules, assign action items, and hold contributors accountable to deadlines.
- Conduct proposal kickoff meetings, color team reviews (Pink, Red, Gold), and lessons-learned sessions after award decisions.
- Build and maintain a library of reusable proposal content including past performance narratives, corporate capability statements, and boilerplate language.
- Analyze solicitation documents to identify requirements and evaluation criteria and develop win strategies in coordination with capture and sales teams.
- Support the go/no-go decision process by providing proposal-readiness assessments, risk identification, and resource availability inputs.
- Coordinate CLIN mapping and pricing volume assembly with Account Teams, vendors, and contracts staff — ensuring proposal pricing aligns with technical solutions.
- Edit, refine, and organize technical and management volume narratives provided by subject matter experts to ensure clarity, persuasiveness, and compliance. This role is not expected to write technical content from scratch but must be able to shape and strengthen contributor inputs into evaluator-ready language.
- Partner with Pre-Sales Technical teams to ensure technical solutions are accurately and compellingly represented in proposal narratives.
- Ensure all submissions meet formatting requirements, page limits, file naming conventions, and delivery instructions per the solicitation.
- Track proposal metrics including win rates, submission volumes, and cycle times to identify process improvements.
- Leverage AI tools to improve proposal efficiency, content quality, and turnaround times.
Required Experience and Education
- This role requires flexibility to work evenings and weekends as needed to meet proposal deadlines. Federal solicitation timelines are often compressed and non-negotiable. The expectation is that the Proposal Manager does what it takes to get a compliant, competitive submission out the door on time.
- 7+ years of Federal proposal management experience, including DoD and Civilian agencies.
- Bachelor’s degree or equivalent experience.
- Demonstrated track record managing complex, multi-volume Federal proposals (FAR Part 15, LPTA, Best Value, IDIQ task orders).
- Deep understanding of FAR/DFARS, Federal procurement processes, and compliance requirements.
- Experience with GWAC and BPA vehicles (e.g., SEWP, GSA MAS, CIO-SP3/4, ITES).
- Strong editing and content organization skills with the ability to refine SME- provided technical content into clear, evaluator-friendly language.
- Proficiency managing proposal schedules, compliance matrices, and color team review processes.
- Ability to manage multiple proposals simultaneously under tight deadlines.
- Proficiency with Google Drive, Egnyte, Salesforce, Microsoft Office Suite, and AI productivity tools.
- Embraces emerging technologies, including AI tools, to work smarter, solve problems, and drive better business outcomes.
Preferred Experience and Education
- APMP Foundation or Practitioner certification. GuidePoint Security offers a professional development support including APMP certification sponsorship.
- Experience in cybersecurity, IT services, or technology solutions proposals.
- Experience supporting proposals for value-added reseller (VAR) and professional services engagements.
- Active security clearance or the ability to obtain one.
Competencies
- Deadline-Driven: Thrives under pressure with a bias toward action and accountability.
- Detail-Oriented: Catches compliance gaps, formatting issues, and inconsistencies before they become problems.
- Cross-Functional Leadership: Coordinates contributors across Sales, Engineering, Legal, and Contracts without direct authority.
- Strategic Thinking: Understands win themes, competitive positioning, and evaluation criteria — not just document assembly.
- Clear Communication: Direct, precise, and professional in all written and verbal interactions.
Travel Requirements
- This is role supports REMOTE work; however the individual MUST be located in the National Capital Region.
Physical Requirements
- Sedentary work
- Substantial movement of the wrists, hands, and/or fingers for a minimum of 8 hours a day
- Required to have close visual acuity to view computer terminal and/or extensive reading for a minimum of 8 hours a day
- If you have additional physical requirements/changes, please discuss with HR first
“Applicants selected will be subject to a security investigation and must meet eligibility requirements for access to classified information.”
We use Greenhouse Software as our applicant tracking system and Zoom Scheduler for HR screen request scheduling. At times, your email may block our communication with you. Please be sure to check your SPAM folder so that you don't miss updates on your application.
Why GuidePoint?
GuidePoint Security is a rapidly growing, profitable, privately-held value added reseller that focuses exclusively on Information Security. Since its inception in 2011, GuidePoint has grown to over 1,300 employees, established strategic partnerships with leading security vendors, and serves as a trusted advisor to more than 6,200 customers.
Firmly-defined core values drive all aspects of the business, which have been paramount to the company’s success and establishment of an enjoyable workplace atmosphere. At GuidePoint, your colleagues are knowledgeable, skilled, and experienced and will seek to collaborate and provide mentorship and guidance at every opportunity.
This is a unique and rare opportunity to grow your career along with one of the fastest growing companies in the nation.
Some added perks….
- Remote workforce primarily (U.S. based only, some travel may be required for certain positions, working on-site may be required for Federal positions)
- Group Medical Insurance options: Zero Deductible PPO Plan (GuidePoint pays 90% of the premium for employees and 70% for family plans (spouse/children/family) or High Deductible Health Plan with HSA (GuidePoint pays 100% of the employees premiums and 75% for family plans (spouse/children/family). If you choose the High Deductible / HSA plan, GPS will contribute in 4 equal quarterly installments: ($850 per EE annually / $1750 per family annually (includes spouse/children/family options)
- Group Dental Insurance: GuidePoint pays 100% of the premium for employees and 75% of family plans
- 12 corporate holidays and a Flexible Time Off (FTO) program
- Healthy mobile phone and home internet allowance
- Eligibility for retirement plan after 2 months at open enrollment
- Pet Benefit Option
Skills Required
- 7+ years of Federal proposal management experience, including DoD and Civilian agencies
- Bachelor's degree or equivalent experience
- Experience managing complex, multi-volume Federal proposals, including FAR Part 15, LPTA, Best Value, and IDIQ task orders
- Deep understanding of FAR/DFARS, Federal procurement processes, and compliance requirements
- Experience with GWAC and BPA vehicles, such as SEWP, GSA MAS, CIO-SP3/4, or ITES
- Strong editing and content organization skills for refining technical subject matter expert content
- Proficiency managing proposal schedules, compliance matrices, and color-team review processes
- Ability to manage multiple proposals simultaneously under tight deadlines
- Proficiency with Google Drive, Egnyte, Salesforce, Microsoft Office Suite, and AI productivity tools
- Ability to work evenings and weekends as needed to meet proposal deadlines
- APMP Foundation or Practitioner certification
- Experience with cybersecurity, IT services, or technology solutions proposals
- Experience supporting value-added reseller and professional services proposals
- Active security clearance or ability to obtain one
- Must be located in the National Capital Region
GuidePoint Security Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about GuidePoint Security and has not been reviewed or approved by GuidePoint Security.
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Healthcare Strength — Company materials highlight fully covered employee premiums on a base medical plan, options including PPO and HSA, employer HSA contributions, and access to an EAP. These elements materially enhance the overall value of compensation for individuals.
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Flexible Benefits — A remote‑first model with telework/flex‑time and monthly phone/home‑internet stipends is emphasized. This flexibility and stipending increase the attractiveness of the total rewards across many roles.
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Leave & Time Off Breadth — Flexible Time Off, company holidays, and parental and other protected leaves are outlined in ESG materials and job postings. Such breadth supports work‑life balance and complements cash compensation.
GuidePoint Security Insights
What We Do
GuidePoint Security is an elite team of highly trained, top certified experts who cut through cyber chaos and confusion to put control back in your hands. We help you make the smartest, most informed decisions, choose and integrate products and services that are the best fit, and build the most effective cybersecurity posture. We provide organizations with holistic perspective on their cyber ecosystem to minimize gaps, vulnerabilities, and optimize resources, including: 1. Understanding the changing threat landscape, vulnerabilities, and gaps 2. New insights of how product decisions align with resource capacity 3. Insightful product comparisons and integration to save time, money, and mistakes
