Head of Deployed Engineering

San Francisco, CA or Remote (USA) · 8+ years experience · Full-time · Remote · Posted Oct 14, 2026

At a glance

Fieldguide is establishing a new state of trust for global commerce and capital markets through automating and streamlining the work of advisory, audit, and tax practitioners at the world's largest CPA firms. Put simply, we build software for the people who enable trust between businesses.
We’re headquartered in San Francisco, CA and backed by top investors including Growth Equity at Goldman Sachs Alternatives, Bessemer Venture Partners, 8VC, Floodgate, Y Combinator, DNX Ventures, Global Founders Capital, Justin Kan, Elad Gil, and more.
We value diversity — in backgrounds and in experiences. We need people from all backgrounds and walks of life to help build the future of audit and advisory. Fieldguide’s team is inclusive, driven, humble and supportive. We are deliberate and self-reflective about the kind of team and culture that we are building, seeking teammates that are not only strong in their own aptitudes but care deeply about supporting each other's growth.
As a growth stage startup employee, you’ll have the opportunity to build out the future of business trust. We make audit practitioners’ lives easier by eliminating up to 50% of their work and giving them better work-life balance. If you share our values and enthusiasm for building a great culture and product, you will find a home at Fieldguide.

The Head of Deployed Engineering role starts as a player-coach position where you will be hands-on building and scaling the forward deployed engineering effort.
You will work directly in customer deployments, write production code, solve hard technical problems, and build and lead the team around you.
Reporting to the CTO/co-founder, your focus will eventually transition toward leadership while staying close to the work and collaborating with Product, Engineering, and Customer leadership.

Lead important deployments yourself and own technical delivery for some of the largest enterprise customers from scoping through production.
Handle single-tenant and government-cloud environments, regulated data, and differing audit methods.
Write production code to build agents, integrations, and tools alongside the team and handle the hardest technical problems directly.
Act as a trusted advisor and senior technical voice with partners, CIOs, and audit leaders on how AI agents fit their practice.
Build the FDE team by hiring, coaching, and growing strong engineers who can both build and work directly with customers.
Make deployment repeatable by turning lessons from hands-on work into playbooks, tools, and metrics to speed up time-to-value.
Turn field work into product by spotting patterns across deployments and collaborating with Product and Engineering to make solutions reusable platform features.

8+ years of leadership experience in forward deployed, deployment, solutions, or customer engineering.
Demonstrated ability to still build, with recent production software writing experience.
Experience leading or mentoring engineers and excitement about building a team from an early stage.
Comfort in front of senior enterprise stakeholders, especially in regulated or complex environments.
Good judgment about building for one customer versus the platform, with the ability to push back on scope when it matters.
Excitement about bringing AI agents into high-stakes professional work.

Experience at a Big 4 firm (Deloitte, PwC, EY, KPMG) or a major consulting firm such as Accenture, McKinsey, BCG, or Bain.
Knowledge of audit, accounting, risk, or compliance.
Experience deploying LLM or agent-based systems in production.