319 Proposal Manager jobs in Kentucky Jobs Near Me

Category: Program Delivery

reqId: P-100259

Posted Date: 08/30/2026

Work Environment: Hybrid

Exempt

widget: Full Time

Location: Baltimore, Maryland, United States

None

Up to 10% Travel

Job Requirements

VP of Solutions Engineering, Federal

At Fearless, the VP of Solutions Engineering, Federal, is a critical player-coach who drives technical strategy and proposal excellence across our business development pipeline. This leadership role balances strategic oversight with hands-on execution, responsible for both leading the solutioning function and actively driving complex pursuits. As a functional leader, you will manage solutioning coverage across all active bids, mentor and grow a dispersed network of Solution Owners, and shape Fearless' solutioning methodologies and technical standards. Simultaneously, you will directly lead technical discovery and author high-impact solution designs for customer opportunities, ensuring every bid reflects disciplined architecture, coherent technical narratives, and achievable delivery commitments.

The Impact You Will Create:

Impact on the Organization

• Drives Technical Strategy: Sets and executes technical direction, ensuring solutions align with business goals and market needs.
• Enhances Proposal Excellence: Leads and improves the quality, coherence, and competitiveness of proposals, increasing win rates and business growth.
• Builds Solutioning Capacity: Mentors and expands a network of Solution Owners, strengthening internal expertise and coverage for federal bids.
• Standardizes Methodologies: Shapes and enforces solutioning standards and technical practices, promoting consistency and high-quality deliverables across teams.
• Fosters Innovation: Identifies areas for technical improvement and innovation, helping Fearless stay ahead in the federal digital services market.

Impact on Customers

• Delivers High-Impact Solutions: Leads technical discovery and authors solution designs that directly address customer missions and requirements.
• Ensures Quality and Reliability: Guarantees disciplined architecture and achievable delivery commitments, reducing risk for customers.
• Strengthens Relationships: Engages directly with customers, building trust and understanding to tailor solutions to their unique needs.
• Improves Customer Outcomes: By maintaining high standards and technical accuracy, ensures that solutions are effective, sustainable, and aligned with customer objectives.

Overall, the VP of Solutions Engineering, Federal, acts as a catalyst for organizational excellence and customer satisfaction by combining strategic leadership with hands-on technical expertise.

Your Responsibilities in This Role:

Doing Solutioning Work (i.e. being a technical Solutionist): 70% of role to start

• Lead technical discovery, customer engagement, and pre-sale capture activities to uncover needs and shape solution recommendations aligned to client missions.
• Own final proposal quality including solution coherence, technical accuracy, pricing basis of estimates, recruiting requirements, and oral presentation readiness.
• Directly author technical solution content and fill coverage gaps on proposals when no dedicated Solution Owner is available.
• Independently pitch technical solutions to current and prospective federal customers to support account growth and relationship development. Build customer relationships within the account(s) and own the solution narrative and pitch end to end within their domain or agency.
• Be an internal and external entrepreneur to drive and build out the solution(s) owned. Drive Fearless' thought leadership and methodologies around the solution, and represent Fearless in industry and customer events to drive messaging and amplification.
• Understand existing Fearless technical architecture and program delivery in the solution(s) owned to identify areas of deficiency and areas for innovation and growth.

How we’ll measure success of Doing Solutioning Work:

• Number of needs solutioned
• Collaboration Rating from Account Leads and Account Executives in your portfolio
• Proposal win rate on those solutions

Leading Solutioning Work (i.e. Strategy, Leadership, & Management): 30% of role to start

• Set solutioning strategy for all active Federal bids, ensuring appropriate technical leadership for every opportunity. Proactively drive and directly fill coverage gaps when no Solution Owner exists.
• Define and maintain solution standards, templates, and practices to ensure consistency and quality across all proposals.
• Coach Solution Owners on pricing strategy, solution structure, recruiting requirements, and competitive positioning to strengthen proposal outcomes.
• Build and sustain the Solution Owner network inside Federal by strategizing the market and upcoming solutions needed, identifying skill gaps, proposing creative solves for Fearless coverage, and/or recruiting talent to expand solutioning capacity.
• Build and manage internal systems and processes to drive specific ISV Partnership management across the organization, including certifications, training, sales logs, etc, so that ISVs can be utilized in solutioning across the accounts.

How we’ll measure success of Leading Solutioning Work:

• Year 1: Developing a plan to build solutioning capacity in your portfolio long term
• Packaged solutions in your portfolio that are being actively sold elsewhere
• Progressed partner qualifications for ISVs assigned

Skills and Qualifications We Require at Fearless:

• Minimum of 10 years of experience in solutions architecture, technical consulting, digital transformation, or related leadership roles supporting federal digital services.
• Bachelor’s degree in Computer Science, Engineering, Information Systems, Business, or a related field, or equivalent combination of education and experience.
• Demonstrated experience leading technical solution design for complex federal proposals across multiple domains and technical disciplines.
• Proven ability to translate customer missions, business objectives, and technical requirements into coherent, achievable solution architectures.
• Experience developing pricing strategies, staffing plans, technical Basis of Estimates (BOEs), and other proposal artifacts for competitive government bids.
• Strong understanding of the federal procurement lifecycle and experience supporting proposal development from opportunity shaping through award.
• Experience leading customer discovery sessions and collaborating with customers to identify needs, validate assumptions, and shape solution strategies prior to proposal submission.
• Proven ability to lead cross-functional teams and drive solution development across Business Development, Delivery, Engineering, Recruiting, and Finance without direct reporting authority.
• Experience presenting technical solutions to executive stakeholders, customers, and evaluation panels, including participation in oral presentations or technical demonstrations.
• Demonstrated ability to manage multiple concurrent pursuits while maintaining high-quality deliverables and meeting aggressive proposal deadlines.
• Excellent written and verbal communication skills, including the ability to communicate complex technical concepts to both technical and non-technical audiences.

Preferred Experience

• Experience coaching or mentoring solution architects, technical leaders, or proposal teams on solution development best practices.
• Experience defining or improving solutioning methodologies, templates, reusable assets, and standards across an organization.
• Familiarity with cloud modernization, digital services, AI/ML, data platforms, cybersecurity, and scaled Agile delivery models in government settings.
• Experience supporting large, complex federal pursuits (e.g., $10M+ opportunities or multi-award IDIQ/task order competitions).
• Experience partnering with recruiting organizations to develop staffing strategies and key personnel plans for competitive proposals.
• Existing relationships or experience supporting agencies such as CMS, HHS, GSA, VA, DHS, SEC, or other federal civilian organizations.
• Familiarity with Shipley, APMP, or other proposal management and capture methodologies.

Fearless Skills and Competencies

Analytical Thinking: The ability to observe and interpret information, break down complex problems into parts, identify patterns/relationships and draw logical conclusions to develop effective solutions.

Synthetic Thinking: The ability to combine different ideas, information, or concepts to create a new, complex understanding or solution by integrating disparate elements into a new, meaningful whole.

Adaptability: Comfort with change, flexibility in the face of shifting demands and resilience to setbacks.

Ownership & Accountability: Committed to taking responsibility for outcomes, ensuring that all commitments are met with a focus on enhancing service delivery.

Consultative Advising: Identifies and articulates client challenges, scopes projects and aligns recommendations to business goals and client expectations.

Communicating with Influence: Capable of crafting and delivering clear, persuasive messages that integrate data insights and structured narratives, tailored to the strategic needs of diverse audiences to drive effective decision-making.

Managing Priorities & Client Alignment: Skillfully negotiates and manages conflicting priorities to strategically align decisions, enhancing service delivery and client satisfaction.

Environmental & Customer Awareness: Maintains awareness of agency and other external dynamics, power structures within client environments as well as regulatory trends and contract requirements that influence service delivery and company expansion/growth.

Complex Solution & Definition Positioning: Translates business requirements into technical solution requirements, coordinating technical expertise, sizing, scoping and defining delivery and deployment approach timelines, identifying required resources, coordinating demonstrations of proof of concept supporting internal deal acceptance

Solution Presentation & Facilitation: Clearly presents and leads discussions on technical IT solutions for government customers, translating complex concepts into accessible language. Engages stakeholders, builds trust, and aligns solutions to mission, regulatory, and technical needs ensuring solutions solve customer challenges.

Physical Requirements:

• Ability to sit for extended periods while working on a computer or during meetings.
• Must be able to travel occasionally to client sites or company meetings.
• Ability to communicate effectively via phone, email, and in-person, requiring clear speech, listening, and written communication skills.
• Ability to move within an office environment, including reaching for files, using office equipment, and occasional light lifting (up to 10 pounds).

Life at Fearless

We’re a digital integration consultancy on a mission to build a better tomorrow. At Fearless, we combine technology, people, and organizational development to solve meaningful problems. Through iterative development, we deliver smart, user-friendly solutions that make tech work better—for everyone.

But great tech is just part of the story. What really makes us Fearless is our Purple Culture.

What Makes Us Purple?
Being Purple means you:

• Are valued as a whole person—not just a job title
• Get matched with work that plays to your strengths and passions
• Are supported by coaches, not micromanagers
• Have the autonomy and clarity to make decisions and drive impact
• Join a community that celebrates equity, curiosity, and innovation
• Do work that matters—every day

We believe in flexibility, growth, and balance. Our benefits and culture are designed to support you in doing your best work—while making space for what matters to you outside of it.

We’re proud to be an equal opportunity employer. At Fearless, we’re building a workplace that welcomes and respects everyone—across race, gender, age, religion, identity, background, and ability.

Compensation at Fearless
Fearless is committed to providing a competitive compensation package that will meet your current and future needs. Our philosophy is aimed at rewarding team member contributions, supporting long-term financial growth and security, and overall well-being.

We believe in paying people fairly, so we've established a compensation model aimed to ensure everyone at Fearless — regardless of race, ethnicity, gender, sexual orientation, disability, religion, age, nationality, or willingness/ability to negotiate — is consistently paid fairly based on alignment to the needs and requirements of the role.

The salary range for this position is:

Minimum Salary: $152,037

Salary Midpoint: $203,729

Maximum Salary: $264,848

• This position is eligible for a discretionary bonus based on individual and company performance criteria.

Benefits at Fearless

At Fearless, we take care of our team—because when you're supported, you can do your best work. We offer a flexible, family-friendly environment with benefits designed to support your health, growth, and life outside of work.

For Full-Time Team Members (Starting Day One):

• Flexible, life-friendly schedules
• 100% coverage for our medical HSA plan + HSA contributions
• Dental & vision covered 100% for you and your dependents
• Competitive premiums for HMO/PPO and dependent coverage
• 401(k) with 4% match & immediate vesting
• Paid Parental Leave and 12 weeks paid FMLA
• Generous PTO, 11 Federal Holidays, a Birthday Holiday, and Sick Leave
• Up to 15 days for Jury Duty and Bereavement Leave
• Education, wellness, and tech allowances
• Referral bonus: $6K–$12K for each successful referral
• Pet insurance & discount plans
• Employee Assistance Program (EAP)
• Legal support, life insurance, disability coverage
• Performance-Based Bonuses: We believe your impact should be recognized. Our bonus program rewards both shared company success and individual contributions. Learn more about our bonus incentives here. This role is also eligible for a performance based commissions program.

Reasonable Accommodations
Fearless is committed to providing reasonable accommodations for applicants and candidates with disabilities. If a reasonable accommodation is needed to participate in the job application or interview process, please contact the Human Resources Department at hr@fearless.tech.

So, What’s Next?

We’ve refined our hiring approach to make sure every team member is a great fit for Fearless—and that we’re a great fit for you, too. If there’s alignment, we’ll reach out to kick off the interview process. Depending on the role or project, your experience may vary slightly, but it typically includes:

1. Introductory Interview

You'll connect with a recruiter to:

• Build rapport and get to know each other
• Review your experience and skills
• Talk through salary expectations and role details
• Set expectations for the rest of the process

2. Technical Assessment

We'll invite you to complete a role-specific assessment to see your skills in action. This helps us keep our hiring process fair and consistent. You can learn more about what to expect here.

3. Skills + Business Fit Interview

This is where we dig deeper to:

• Review findings from any technical assessments
• Walk through situational and values-based questions
• Explore how your approach aligns with Fearless culture and project needs

Some roles may also include customer interviews based on specific project requirements in addition to background check and security clearance requirements.

Where You Can Build with Fearless

At Fearless, we strive to build a powerful and diverse team. We are currently licensed and set up to hire talented individuals residing in the following 16 states:
Alabama, California, Delaware, District of Columbia, Florida, Georgia, Maryland, New Jersey, New York, North Carolina, Pennsylvania, South Carolina, Tennessee, Texas, and Virginia.

#LI-Hybrid