Chief Technology Officer

Mile Two, LLC•Dayton, OH

About The Position

Mile 2 is seeking a Chief Technology Officer (CTO) to lead its technical vision, engineering execution, and innovation strategy. This senior leadership role reports directly to the CEO and involves both high-level strategy and hands-on technical decision-making. The CTO will set standards for a talented technical team, delivering solutions at the intersection of AI, human factors, and mission-critical software. Responsibilities include representing Mile 2’s technical capabilities to government customers and partners, aligning technical strategy with company growth, driving enterprise technical maturity, supporting scalable delivery models, guiding productization, and partnering 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 with a diverse range of stakeholders.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.
Evaluate and guide adoption of emerging technologies including AI/ML, large language models, computer vision, and autonomous systems.
Maintain sufficient technical depth and credibility to review architectures, guide technical tradeoffs, mentor engineering leadership, and engage deeply in solution strategy.
Lead the strategic technical direction for integrated systems, overseeing the convergence of custom software with hardware and embedded electronics.
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.
Define and steward reusable technical frameworks, shared capabilities, and a productization strategy.
Align the capability roadmap with corporate growth priorities and prioritize technical investments.
Establish and enforce engineering best practices: code quality, DevSecOps pipelines, testing frameworks, and documentation standards.
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.
Reduce duplicate technical efforts and increase technical reuse across programs and business units.
Strengthen transition-to-production pathways and support scalable sustainment models.
Scale the engineering organization in step with company growth, maturing operations, hiring pipelines, and leadership bench depth.
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.
Drive successful transition of SBIR, OTA, and prototype efforts into programs of record and enduring mission capabilities.
Integrate user-centered design and human factors engineering into the core of Mile 2’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.
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.
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.