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Fieldguide is building software that automates and streamlines work for audit, advisory, and tax practitioners at the world's largest CPA firms. The company is backed by top-tier investors including Goldman Sachs Growth Equity, Bessemer Venture Partners, Y Combinator, and others.
The Head of Deployed Engineering role is a player-coach position that will evolve as the team scales. You will start hands-on, working directly in customer deployments, writing production code, and solving complex technical problems. One current focus is producing verifiable citations from dense Excel workbooks—enabling auditors to trace conclusions back to exact evidence.
As a player, you will:
- Lead important deployments for the largest enterprise customers, owning technical delivery from scoping through production, including single-tenant and government-cloud environments with regulated data
- Write production code, building agents, integrations, and tools alongside the team
- Serve as the senior technical voice with customers, acting as a trusted advisor to partners, CIOs, and audit leaders on AI agent deployment
As a coach, you will:
- Build and lead the Forward Deployed Engineering (FDE) team, hiring and growing engineers who can both build and work directly with customers
- Make deployment repeatable by turning hands-on learnings into playbooks, tools, and metrics that accelerate time-to-value
- Spot patterns across deployments and collaborate with Product and Engineering to turn field solutions into reusable platform features
You'll report to the CTO/co-founder and work closely with Product, Engineering, and Customer leadership. The role requires someone who remains deeply technical and hands-on while building and scaling a team.
REQUIREMENTS:
- 8+ years of leadership experience in forward deployed, deployment, solutions, or customer engineering roles (e.g., FDE leadership at Palantir, Field CTO roles, or leading technical work with large enterprise customers)
- Demonstrated ability to write production software recently; this is not a manage-only role
- Experience leading or mentoring engineers with excitement about building a team from early stage
- Comfort presenting to and advising senior enterprise stakeholders, especially in regulated or complex environments
- Strong judgment about building for individual customers versus platform solutions, with ability to push back on scope
- Enthusiasm for deploying AI agents in high-stakes professional work
BONUS:
- Experience at a Big 4 firm (Deloitte, PwC, EY, KPMG) or major consulting firm (Accenture, McKinsey, BCG, Bain)
- Knowledge of audit, accounting, risk, or compliance
- Production experience deploying LLM or agent-based systems
