Director of AI

Banyan Software•Washington, DC

16h•Remote

About The Position

Banyan Software is seeking a Director of AI to lead its AI Factory – Application Modernization Program. The AI Factory is Banyan’s centralized engine for modernizing legacy applications into modern platforms using AI-powered discovery and an integrated delivery model. This program aims to rewrite aging codebases (15-25 years old) into modern, cloud-native, mobile-first SaaS platforms within 15-25 weeks. The Director of AI will play a crucial role in shaping the evolution of Banyan's portfolio over the next decade, operating at the intersection of product strategy, field engineering, and platform operations. The role involves three key leadership pillars: the AI Factory Product Team, Forward Deployed Engineering, and Cloud Operations & Platform Automation. This is a full-time, remote (US-based preferred) position with up to 15% travel.

Requirements

10+ years of progressive software engineering experience, with at least 3 years spanning both technical delivery and program management.
Demonstrated experience leading application modernization, re-platforming, or digital transformation—ideally in a multi-product or multi-company environment.
Proven ability to embed with or lead cross-functional engineering teams without formal authority.
Hands-on proficiency with cloud-native architectures (AWS, Azure, or GCP), CI/CD tooling, infrastructure as code, and DevSecOps practices.
Experience building teams, processes, and playbooks from scratch in a high-growth or startup-like setting.
Strong executive communication skills with a track record of presenting to C-level stakeholders.
Entrepreneurial Ownership: Treat this program as your own business—identifying problems, proposing solutions, and executing without waiting for direction. Ability to articulate P&L-level thinking.
Influence Without Authority: Redirect technical direction through credibility, trust, and persuasion, earning followership by rolling up your sleeves and shipping alongside the team.
Hands-On Technical Depth: Currently write production code, architect cloud-native solutions, set up CI/CD pipelines, and debug complex integration issues.
Ambiguity Tolerance: Thrive without a playbook, then codify your learnings into one. Create clarity in undefined roles.
Resilience & Pivot Ability: Ability to handle project failures, change course rapidly, and discuss failure without defensiveness.
Cloud-Native & Modernization: Deep practical experience with re-platforming, microservices, cloud-native patterns (AWS/Azure), IaC, and DevSecOps. Ability to describe a specific migration.
AI-Assisted SDLC Fluency: Daily use of AI-assisted dev tools (Cursor, Claude Code, Copilot) and ability to train others. Understanding of AI acceleration and risks.
Structured Problem Decomposition: Approach complex, ambiguous problems with frameworks, breaking modernization challenges into workable components and thinking in hypotheses.
Technical-to-Business Translation: Translate AI and engineering concepts into business value and ROI. Experience presenting to executives on technical topics.
Change Management Execution: Drive change through to adoption, understanding resistance, skill gaps, and the politics of technical transformation.
Metrics & ROI Orientation: Define success in measurable terms: velocity, value delivered, and business impact.

Nice To Haves

Experience in forward-deployed engineering, professional services, or embedded consulting.
Background in private equity portfolio operations, multi-entity software, or vertical-market software.
Familiarity with AI-assisted dev tools (Cursor, Claude Code, GitHub Copilot, agent-based development).
Experience with legacy application assessment, strangler-fig patterns, or monolith-to-microservices transformations.
Agile coaching or program management background (CSM, SAFe, PMP, or equivalent).

Responsibilities

Own the strategic direction and delivery cadence of the core AI Factory product team, including developers, team lead, and AI-powered tooling.
Drive the product roadmap and continuously evolve factory capabilities based on field learnings.
Build, lead, and scale the Forward Deployed Engineer (FDE) team from the ground up.
Embed FDEs directly with OpCo engineering teams to drive modernization, upskill developers on AI-assisted workflows, and ensure clean knowledge transfer.
Recruit the first FDEs, author the engagement playbook, and run initial transformations as a player-coach.
Oversee the operational infrastructure underpinning every modernized application, including multi-cloud architecture, CI/CD automation, observability, security, and resiliency engineering.
Own the AI Factory’s end-to-end program lifecycle across its 9-phase modernization process.
Define and track program-level KPIs, velocity metrics, and business-value outcomes.
Translate technical progress into executive-ready language for OpCo CEOs and Banyan leadership.
Continuously refine the factory’s operating model based on field learnings.
Recruit, hire, and develop the FDE team; define the FDE role, career path, and engagement model.
Author the FDE playbook covering engagement kickoff, stakeholder alignment, technical assessment, embedded delivery, knowledge transfer, and OpCo handoff.
Personally lead early FDE engagements, embedding with operating company teams, earning trust through technical credibility, and driving adoption of AI-assisted workflows.
Manage and mentor direct reports across the FDE team and the supporting Project Manager / Scrum Master.
Build a culture of ownership, velocity, and craftsmanship.
Drive the MACROSS framework (Maintainability, Adaptability, Cost Accountability, Reliability, Observability, Scalability, Security) as the decision-making lens for every engagement.
Present to and align with OpCo CEOs, CTOs, and product leaders during kickoffs, weekly syncs, and milestone reviews.
Partner with Banyan’s VP of Engineering and executive leadership to shape the AI Factory’s strategic roadmap, investment priorities, and portfolio expansion plan.