Founding Director of Technology
Entrepreneurial Leadership | Ownership Mindset | Remote-First
This Is Not a Job. It’s a Founder Opportunity.
We are a Disabled Veteran-Owned Small Business (SDVOSB) and AI-enabled systems integration professional services firm in the early stages of growth, building a progressive organization designed around technology leadership, security, autonomy, and long-term value creation.
We are seeking a Founding Director of Technology who thinks like an entrepreneur—not an employee. This role is intended for a technology leader who wants to design secure systems, architectures, and innovation strategy from zero, influence company direction, and participate in a contributor-based ownership model rather than a traditional hierarchy.
There is no initial salary by design. This is a low-risk, flexible founder role, intended to be built alongside existing professional work. As the company grows, ownership, equity participation, and compensation pathways will be structured based on contribution, impact, and clearly defined milestones.
Role Structure & Legal Status
This is a founder-level, equity-based leadership role and not a traditional W-2 employment position at inception.
The Founding Director of Technology will initially participate under an advisory/executive services arrangement, designed to comply with applicable labor, employment, and federal contracting laws.
Participation is strategic and architectural in nature:
- No promise of wages for services rendered
- No fixed schedules or timekeeping requirements
- No employee-style supervision or billable labor
- Clear separation from contract-charged activities
Ownership & Equity Framework
Ownership participation is earned through contribution and impact, with equity structured around clearly defined technical, operational, and business milestones, vesting schedules, and governance protections.
Equity mechanisms (e.g., profits interest, phantom equity, or future conversion structures) will be discussed transparently with finalists and aligned with company structure and compliance requirements.
How We Work
- Remote-first, outcome-driven environment
- Four-day workweek (long-term vision toward three-day workweeks)
- High autonomy, high accountability
- No micromanagement, no time clocks
What You Will Build
As a founding executive reporting directly to the CEO and participating in early leadership governance, you will architect and lead the technology and security foundation of the company, including:
- Enterprise technology and systems architecture
- AI-enabled systems integration strategy
- Secure data, automation, and analytics platforms
- Cybersecurity architecture aligned with NIST frameworks
- CMMC readiness strategy and technical controls (Level 1–3 alignment)
- Identity, access, and data protection controls appropriate for federal work
- Human-in-the-loop AI frameworks emphasizing accountability and auditability
- Secure, scalable, and audit-ready technology environments
- Technology standards aligned with federal, defense, and regulated clients
You won’t inherit insecure legacy systems—you’ll define a secure, compliant technology blueprint.
Cybersecurity & Compliance Scope
While this role is not an ISSO or compliance officer position, the Founding Director of Technology is expected to:
- Establish security-by-design principles across all systems
- Align internal technology practices with NIST 800-53 / 800-171 expectations
- Lead CMMC preparedness efforts in coordination with legal, operations, and external assessors
- Ensure AI-enabled systems are explainable, governed, and defensible
- Support secure environments suitable for future DoD and federal prime contracts
Ideal Founder Profile
- 10+ years of technology or systems leadership experience
- Prior experience at the Director, CIO, CTO, or equivalent leadership level
- Strong understanding of AI-enabled systems, automation, and data platforms
- Working knowledge of cybersecurity frameworks (NIST, CMMC, Zero Trust concepts)
- Experience in regulated, enterprise, or government-adjacent environments preferred
- Entrepreneurial mindset: builder, architect, systems thinker
Selection Process
This opportunity is not about chasing a title or climbing a ladder. It’s about building something secure, responsible, and future-ready—from the ground up.
The screening process will consist of three phases.
Phase 1: Candidates must submit their resume or CV to jbolden@cbridgeautomation.com
Phase 2: Only the most qualified candidates will be selected to complete an online character-based assessment.
Phase 3: The two finalists will participate in an in-person panel interview.
If you’re curious, let’s talk. No pressure. No obligation. Just an honest conversation about whether this founder journey makes sense for you.