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VP of Engineering

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Remote from
USA
Salary
USD 200k–250k / yr
Employment
Full Time
Experience
Director
Published
Apply before
26 Nov 2026
Listing views
35
Application actions
1
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AI Summary

The role, at a glance.

Oddball is seeking a VP of Engineering to lead and scale an engineering organization of more than 100 professionals delivering federal digital modernization programs. The role sets technical strategy, engineering standards, career frameworks, talent practices, and adoption of AI-enabled development tools across a multi-program portfolio. This executive will partner with program leaders and government clients while remaining capable of contributing directly to architecture, technical problem-solving, and solutioning. Success requires substantial federal contracting leadership experience, strong cloud modernization and DevSecOps knowledge, and the ability to translate commercial product practices to public-sector delivery.

Role DNA

A quick view of the complexity, pace, ownership and collaboration implied by the job description.

Job Complexity

5/5
EasyHard

Pace & Pressure

5/5
RelaxedFast-paced

Autonomy Level

5/5
GuidedFull ownership

Communication Load

5/5
IndependentCollaborative
AI insightThis is a senior executive role with portfolio-wide accountability for technical quality, organizational development, delivery outcomes, and growth support. It requires balancing hands-on technical judgment with leadership across complex federal programs and stakeholder groups.

Salary analysis

Estimated compensation compared with the broader US market for similar roles.

Estimated job median (per year)Market rate
$225,000
US market range (per year)$210k–$300k
AI insightThe yearly pay period is inferred from the job context; it was not explicitly stated by the employer. The employer discloses a US wage range of $200,000–$250,000 annually; the annual cadence is inferred from the compensation magnitude and senior full-time US executive role. The stated midpoint is $225,000 per year. A reasonable estimated US market range for a VP of Engineering with federal delivery expertise is $210,000–$300,000 annually, depending on organization size, clearance requirements, and scope.

Core skills

Skills and capabilities most closely associated with this opportunity.

Sample interview questions
How would you create consistent engineering standards across more than 100 engineers working on multiple federal programs?

I would establish a lightweight engineering operating model with shared architecture principles, secure delivery baselines, communities of practice, and measurable quality indicators. Standards should provide clear guardrails while allowing program teams to make context-specific implementation decisions.

Describe how you would adapt commercial product engineering practices for federal delivery environments.

I would retain outcome-focused product discovery, iterative delivery, automated testing, observability, and user feedback loops, then adapt them to federal security, procurement, compliance, and authorization constraints. The goal is to improve speed and quality without treating governance as an afterthought.

How do you assess and develop Tech Leads who need to grow both technically and managerially?

I set explicit expectations for technical judgment, communication, delivery leadership, and people development, then use regular coaching, peer learning, targeted stretch assignments, and feedback from teams and program partners. A transparent career ladder makes advancement criteria consistent and actionable.

What is your approach to introducing agentic AI tools into engineering teams responsibly?

I would begin with controlled, high-value use cases, define security and data-handling guardrails, measure impact on quality and developer productivity, and provide training for engineers. Adoption should be evidence-driven and compatible with client, compliance, and software supply-chain requirements.

How would you handle a program that is delivering on schedule but accumulating significant technical debt?

I would make the debt visible through architecture and operational risk assessments, quantify its impact on delivery and security, and partner with program leadership to prioritize remediation. I would then build debt reduction into the roadmap through incremental work, clear ownership, and outcome-based tracking.

This analysis is generated from the job description. Salary estimates, role characteristics and sample answers are guidance, not employer-provided facts.
Opportunity details

About this role.

Oddball believes that the best products are built when companies understand and value the things they are working on. We value learning and growth and the ability to make a big impact at a small company. We believe that we can make big changes happen and improve the daily lives of millions of people by bringing quality software to the federal space.

We’re looking for a VP of Engineering to lead and scale Oddball’s engineering practice across our federal digital modernization portfolio — someone who brings proven practices from commercial and product-focused organizations and knows how to adapt them to the realities of federal delivery.

What you’ll be doing:

  • Set and drive technical standards, best practices, and engineering consistency across 100+ engineers spanning multiple federal programs — including how teams adopt and build with agentic AI tools
  • Own engineering talent decisions — identifying and promoting top performers, developing those with growth potential, and maintaining a high bar across the organization
  • Partner with Program Managers, Tech Leads and VPs to ensure programs are delivering high-quality, technically sound solutions
  • Roll up your sleeves when it matters — dig into architecture, solve a hard technical problem, or prototype an idea to move it forward
  • Build and own the engineering career ladder — defining skill levels, growth paths, mentorship structures, certifications, continuing education and promotion criteria
  • Coach and support Tech Leads in both technical and managerial dimensions
  • Drive technical strategy across the portfolio, identifying opportunities to improve performance, tooling, and delivery
  • Stay current on emerging technology including AI/ML, cloud platform engineering, and developer productivity — and turn it into practical advantages for our clients
  • Contribute to growth and capture efforts — solutioning, proposal reviews, and technical viability assessments
  • Provide thought leadership internally and externally, representing Oddball’s engineering capabilities to clients and at industry events

What you’ll bring:

  • Deep experience leading engineering organizations with meaningful time in a federal contracting environment
  • Commercial, product, or industry experience outside government is strongly preferred — and a clear sense of how to bring those lessons into federal delivery
  • Hands-on technical credibility — you spend most of your time guiding and enabling, but you can still go deep when the situation calls for it
  • Track record of building technical culture, career development programs, and high-performing engineering teams
  • Strong understanding of Agile delivery, DevSecOps, and cloud modernization in federal contexts
  • A collaborative leadership style — you build alignment and empower teams rather than dictate a single way of working
  • Experience building partnerships and driving technical change with government clients
  • Exceptional communication skills — you can translate complex technical concepts for both engineers and non-technical stakeholders

Requirements:

  • Applicants must be authorized to work in the United States. In alignment with federal contract requirements, certain roles may also require U.S. citizenship and the ability to obtain and maintain a federal background investigation and a security clearance.

Education:

  • Bachelor’s degree

Benefits:

  • Fully remote
  • Annual stipend
  • Comprehensive Benefits Package
  • Company Match 401(k) plan
  • Flexible PTO, Paid Holidays

Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities:

Oddball is an Equal Opportunity Employer and does not discriminate against applicants based on race, religion, color, disability, medical condition, legally protected genetic information, national origin, gender, sexual orientation, marital status, gender identity or expression, sex (including pregnancy, childbirth or related medical conditions), age, veteran status or other legally protected characteristics. Any applicant with a mental or physical disability who requires an accommodation during the application process should contact an Oddball HR representative to request such an accommodation by emailing hr@oddball.io.

The contractor will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by the employer, or (c) consistent with the contractor’s legal duty to furnish information. 41 CFR 60-1.35(c)

At Oddball, we may use AI-assisted tools as part of our recruitment process to help review applications, verify applicant information, and identify potentially fraudulent submissions. These tools support our recruiting team in maintaining a fair and secure hiring process. AI-generated findings are reviewed by our recruiting team and are not used as the sole basis for hiring decisions.

Compensation:

At Oddball, it’s important each employee is compensated competitively and fairly. In alignment with state legal requirements. A range for the included position is listed below. Be advised, actual offer details are determined by job category, job location, and candidate skill level.

United States Wage Range: $200,000 – $250,000

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