Remote Chief Technology Officer Jobs (NOW HIRING)

Join Our Innovative Team at Mile 2!
Are you into solving tough problems and building cool tech? Do you thrive in a team where your ideas are heard and your creativity is encouraged? If you're nodding along, Mile 2 might be the place for you.
We're all about creating advanced solutions that really make a difference for our government partners. Our team uses the latest technologies to make a tangible impact, creating seamless integrations between human expertise and machine capabilities to tackle complex challenges.
Our core values guide everything we do: Supported Autonomy: We trust you to take initiative and make decisions, but we've always got your back. Humble Expertise: We respect everyone's knowledge and skills, creating an environment where we can all learn and get better together. Success is a Team Effort: We believe that we can only achieve great things when we work as a team. Tangible Results: We're motivated by the desire to create real, measurable impacts through our work.
When you join us, you'll work on meaningful projects that challenge you and help you grow. We offer a supportive and inclusive environment, competitive benefits, and plenty of opportunities to advance your career. If you're ready to level up your career and be part of something special, check out our current openings and apply today.
About Mile 2
Mile 2 is a small, mission-driven government contractor dedicated to advancing the state of the art in human-machine teaming for the U.S. Department of War. We build custom software that fuses rigorous user-centered design with cutting-edge engineering - creating systems where humans and intelligent machines collaborate more effectively, intelligently, and safely.
Our work directly supports warfighters and defense analysts at the DoW agencies. We are small by design: lean, deeply technical, and oriented toward impact over headcount. The person who joins as our CTO will help shape not just our technology roadmap, but the capability of the entire organization.
Position Overview
The Chief Technology Officer is a senior leadership role responsible for Mile 2's technical vision, engineering execution, and innovation strategy. You will serve as the company's senior-most technologist, reporting directly to the CEO, and will be deeply engaged both in high-level strategy and hands-on technical decisions.
You will set the standards for a talented technical team to deliver solutions that operate at the intersection of AI, human factors, and mission-critical software. You will be expected to represent Mile 2's technical capabilities to government customers, partners, and in proposal efforts.
As a member of the executive team, the CTO will align technical strategy with company growth objectives, drive enterprise technical maturity, support scalable delivery models, guide productization and reusable capability development, and partner with executive leadership on long-term business strategy.
The ideal candidate is technically exceptional, strategically minded, operationally grounded, growth-aware, mission-focused, and execution-oriented - capable of engaging effectively with engineers, operators, executives, acquisition officials, proposal teams, and mission customers.
Key Responsibilities
Technical Leadership & Vision

• Define and own Mile 2's technology strategy, roadmap, and architecture standards across all programs and internal initiatives.
• Champion human-machine teaming principles throughout the software development lifecycle - ensuring technology decisions are grounded in how real users think, decide, and act.
• Evaluate and guide adoption of emerging technologies including AI/ML, large language models, computer vision, and autonomous systems in the context of DoW use cases.
• Maintain sufficient technical depth and credibility to review architectures, guide technical tradeoffs, mentor engineering leadership, and engage deeply in solution strategy when required.
• Lead the strategic technical direction for integrated systems, specifically overseeing the convergence of custom software with hardware and embedded electronics for mission-critical environments.
• Provide executive oversight for the full product development lifecycle of both cloud-native applications and edge-computing devices.
• Establish and govern enterprise architecture standards, ensuring consistency, interoperability, and reuse across all programs and product lines.
• Define and steward reusable technical frameworks, shared capabilities, and a productization strategy that evolves one-off program work into sustainable mission systems.
• Align the capability roadmap with corporate growth priorities and prioritize technical investments (IRAD/R&D, infrastructure, tooling) against business outcomes.

Engineering Excellence

• Establish and enforce engineering best practices: code quality, DevSecOps pipelines, testing frameworks, and documentation standards appropriate for classified and unclassified environments.
• Oversee technical delivery across active contracts, ensuring teams meet performance, schedule, and quality requirements.
• Drive technical risk identification and mitigation across the portfolio.
• Establish enterprise technical governance and standardize engineering processes and frameworks to improve delivery consistency across programs.
• Reduce duplicate technical efforts and increase technical reuse across programs and business units.
• Strengthen transition-to-production pathways and support scalable sustainment models for fielded systems.
• Scale the engineering organization in step with company growth, maturing operations, hiring pipelines, and leadership bench depth.

Customer & Business Development

• Serve as a trusted technical advisor to DoW customers - translating complex mission problems into actionable software solutions.
• Partner with Growth to lead technical volumes in proposal efforts, including architecting technical approaches and estimating level of effort.
• Represent Mile 2's capabilities at customer briefings, conferences, and inter-agency engagements.
• Build and sustain relationships with DoW program offices, research labs (DARPA, AFRL), and key industry partners.
• Shape Mile 2's technical growth strategy and align IRAD/R&D investments with emerging market and mission opportunities.
• Support strategic capture efforts as a senior technical voice - developing scalable service offerings and improving technical differentiation in competitive pursuits.
• Drive successful transition of SBIR, OTA, and prototype efforts into programs of record and enduring mission capabilities.

Human-Machine Teaming & UX

• Integrate user-centered design and human factors engineering into the core of MileTwo's software development process.
• Oversee UI/UX research activities - user interviews, usability testing, cognitive task analysis - and ensure findings directly shape system design.
• Ensure that AI and automation features augment rather than replace operator decision-making, in line with DoW responsible AI principles.
• Drive adoption of iterative, design-led development practices across engineering and product teams.
• Advance Mile 2's leadership in operational AI, trusted and explainable AI, and human-centered decision support systems for mission environments.

Technical Steering Group (TSG) Leadership

• Lead and mature Mile 2's Technical Steering Group (TSG), aligning technical direction across business units and domains.
• Improve collaboration between AI/ML, platform engineering, CSE/HMT, mission applications, and delivery teams.
• Drive enterprise technical alignment and reduce siloed development efforts.
• Ensure TSG efforts support growth, delivery, capability evolution, and operational scale.

Requirements
Required

• Active Secret clearance (TS/SCI preferred); must be able to obtain and maintain clearance appropriate to contract requirements.
• 10+ years of progressive software engineering experience, with at least 3 years in a technical leadership role (CTO, VP Engineering, Chief Architect, or equivalent).
• Proven track record leading engineering teams across diverse disciplines, including software, firmware, and electronic systems integration.
• Demonstrated experience delivering open-standards-based software solutions for DoW or other federal government customers.
• Deep proficiency in modern software engineering practices: open standards and open-architecture design, cloud-native development (GCP), containerization (Docker/Kubernetes), CI/CD pipelines, and agile/DevSecOps methodologies.
• Hands-on experience with AI/ML integration in production systems - NLP, computer vision, decision-support, or reinforcement learning applications.
• Strong command of user-centered design principles and experience working alongside UI/UX researchers and designers.
• Excellent written and verbal communication skills; ability to present complex technical topics to both technical and non-technical audiences including senior government officials.
• Experience supporting capture and proposal strategy, technical solutioning, customer engagement, and technical growth planning.
• Experience scaling engineering organizations, maturing technical operations, standardizing delivery frameworks, and operationalizing technical governance.
• Demonstrated experience transitioning R&D, SBIR, or prototype technologies into scalable operational environments.
• Experience with edge/disconnected environments, DDIL operations, secure mission systems, and/or operational deployment realities.

Preferred

• Experience with cognitive systems engineering, human-machine teaming, human factors engineering, or human-autonomy interaction research.
• Familiarity with DoW acquisition frameworks: JCIDS, DAS, Software Acquisition Pathway (SWP), or Other Transaction Authority (OTA).
• Experience with RDT&E programs, SBIR/STTR, or rapid prototyping efforts.
• Background in cognitive science, human factors, software engineering, or applied AI research.
• Prior military service or deep operational understanding of warfighter workflows.
• Experience growing and leading engineering organizations of 10-100 people.
• Familiarity with DoW zero trust architecture, RMF/ATO processes, and cross-domain solutions.
• Zero Trust Architecture and modern platform engineering (Kubernetes, service mesh, GitOps).
• Experience delivering secure cloud mission systems and supporting edge/disconnected operations.
• Familiarity with AI governance and explainable AI frameworks.
• Experience scaling small-to-mid-size GovCon organizations.

Success Metrics - First 12-18 Months
Success in the role will be measured against demonstrable progress in the following areas:

• Improved engineering consistency and delivery maturity across programs.
• Reusable capability development and visible productization progress.
• Improved proposal technical quality and capture support outcomes.
• Operational scalability and a measurable reduction in technical fragmentation.
• Successful prototype-to-production transitions on identified programs.
• Cross-functional alignment delivered through active TSG leadership.
• Technical roadmap execution against agreed business objectives.

Our Approach to AI in Hiring
At Mile 2, applications are reviewed by real people-not filtered out by bots. Authenticity matters more than keyword tricks.
We know you're probably using AI tools to help draft or polish your resumes, and that's fine! We're using AI to write this blurb about AI! But we expect you to make it your own. Resumes that feel copy-pasted I -repetitive, oddly phrased, "too perfect" matches to our job description- may hurt your chances. Adding personal touches and real examples of your work will make your application stronger.
We look forward to meeting the real you!
A Note About Our Application Process
Please answer our screener questions honestly and thoroughly (rather than writing "see resume"). These are reviewed by real people-not bots-and play an important role in our selection process. Thoughtful responses will strengthen your application.