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Head of AI-Native Engineering (Senior Director) at Stampli · Trevo
We are looking for a Head of AI-Native Engineering at the Senior Director level: a technology and innovation leader who will identify, build, and scale the next generation of AI-driven capabilities across our software development lifecycle.
This is not a traditional R&D management role. It is a high-impact builder role for someone who can challenge the status quo, identify opportunities before they become obvious, and turn ambitious ideas into meaningful technological and organizational transformation.
Working closely and directly with the VP of R&D, you will have a broad mandate and strong organizational backing to experiment, build new capabilities from the ground up, and rethink how software gets built at Stampli. You will be expected to move from ideas to execution, prove what works, and scale successful approaches across the R&D organization.
You will build and lead a team responsible for developing the tools, infrastructure, workflows, and organizational capabilities required to make AI-native software development a scalable and measurable reality at Stampli.
What you'll do
Lead Our AI Transformation: You will transition the organization from AI assisted coding/reviewing toward an outcome-based workflow. The objective is to replace traditional, coordination-heavy processes with precise specifications and externalized behavioral scenarios, allowing AI agents to build and test software autonomously, as a black box.
Build and Lead the Team: Build and lead a team responsible for developing and scaling the tools, infrastructure, workflows, and capabilities required for AI-native software development.
Own Coding Agents and AI Tools: Evaluate and select coding agents and AI tools, define how they are used across R&D, and create shared context across repositories—including instructions, skills, and MCP servers.
Design Agentic Development Workflows: Define the end-to-end flow from idea to production, including how work and responsibilities are divided between developers and AI agents.
Reimagine the SDLC: Rethink how software is designed, developed, tested, deployed, and maintained, and translate that vision into practical, scalable ways of working.
Shape AI-Ready CI/CD: Define the requirements for faster and more reliable delivery pipelines, including quality gates designed for AI-generated code. Partner closely with DevOps, which will implement and own the pipelines.
Enable Parallel Development at Scale: Establish isolated development environments that can be provisioned quickly, enabling developers and AI agents to work safely and efficiently in parallel.
Build From Zero to Scale: Identify high-impact opportunities, validate ideas quickly, and turn successful experiments into scalable capabilities adopted across the organization.
Turn Innovation Into Impact: Lead POCs and strategic technology initiatives from initial concept through development, implementation, adoption, and measurable organizational impact.
Transform Processes and Team Structures: Adapt development processes, team rituals, roles, and team composition to support AI-native ways of working. Identify areas of inefficiency, time waste and any opportunity to improve productivity; then plan, execute and monitor solutions.
Measure Adoption and Impact: Define success metrics, track tool adoption, organizational impact, performance, and cost, and report transparently on progress and results.
Establish AI Governance: Define AI usage policies and agent permissions in close partnership with Security, ensuring innovation is implemented responsibly and at scale.
Own What You Build: Maintain end-to-end ownership of the tools and capabilities developed by you and your team—from experimentation and implementation through rollout, adoption, and ongoing evolution.
Shape the Technology Vision: Define a forward-looking technology vision, challenge existing assumptions, and explore emerging technologies, architectures, and new possibilities.
Elevate Our Culture of Innovation: Build on Stampli’s existing culture by expanding experimentation, continuous learning, ownership, and entrepreneurial thinking across R&D.
What You Will Bring
Significant experience as a technology leader in a product company, such as a Founder, Co-Founder, CTO, Entrepreneur in Residence, or senior technology leader.
Proven experience building and leading high-performing technical teams.
A track record of identifying opportunities and turning early-stage ideas into real products, systems, or organizational capabilities.
Experience leading AI adoption, major technological change, or organization-wide innovation.
Strong technical depth and credibility, with the ability to engage deeply in software architecture, infrastructure, development practices, CI/CD, and AI-assisted development.
Hands-on familiarity with coding agents, AI development tools, agentic workflows, or the infrastructure required to deploy them effectively across an R&D organization.
An AI-native mindset and the ability to rethink how software should be built and how R&D organizations should operate in the AI era.
A builder mentality, with the ability to move quickly from exploration and experimentation to implementation and measurable impact.
An entrepreneurial mindset and the initiative to take action without waiting for a predefined roadmap.
Strategic thinking, with the ability to anticipate future technological shifts while translating them into decisions and actions today.
The ability to challenge senior leaders, influence across teams, and build alignment without relying solely on direct authority.
Strong execution capabilities and the determination to drive complex initiatives from concept through adoption at scale.
Why Join Stampli?
Stampli is revolutionizing financial operations with AI, far ahead of competitors. For nearly a decade, our AI assistant, Billy, has set the industry standard—processing $100B+ in invoices annually and saving millions of labor hours for 1,600+ customers. More than automation, Billy transforms finance teams by freeing them from manual work.
Our explosive growth places us among the top tech companies at our stage, with exceptionally low churn. After conquering the Accounts Payable space, we are now revolutionizing the entire procure-to-pay (P2P) lifecycle with our new platform, which “connects every dot from request to reconciliation.”
What sets us apart? We adapt to our customers—not the other way around—integrating with 70+ ERPs in weeks, not months. Our customer-first approach extends to our award-winning workplace culture and vibrant global offices. We have earned multiple Comparably awards, including Best Company Outlook, Work-Life Balance, Compensation, Happiness, and Perks & Benefits.
At Stampli, we build exceptional products with exceptional people. Join our dynamic team and grow your career in an environment that champions creativity, collaboration, ownership, and meaningful innovation.