Head of Deployed Engineering

Fieldguide; Oregon; Hybrid; USD 210,000 - 270,000; Full time

Benefits offered by this job

Competitive compensation with equity

Flexible PTO

401k

Wellness benefits

Home office stipend

Flexible work schedules

Job summary

Fieldguide is hiring a Head of Deployed Engineering to lead and hands-on work in deploying our AI-enabled audit tools at major enterprise clients. You will directly deploy, code, and guide the team, while partnering with product and leadership to set strategy and deliver value.

The role blends technical depth with team-building and customer-facing leadership. You will start hands-on in customer deployments, writing production code, and solving hard problems.

Qualifications

• 8+ years of leadership experience in forward deployed, deployment, solutions or customer engineering.
• You still build. You've written production software recently and want to keep doing it.
• Experience leading or mentoring engineers, and excitement about building a team from an early stage.

Responsibilities

• Lead deployments for large enterprise customers from scoping through production.
• Write production code, build agents, integrations and tools with the team.
• Be the senior technical voice with customers and partners on AI agent integrations.
• Build the FDE team by hiring, coaching and growing engineers.
• Make deployment repeatable by turning learnings into playbooks, tools and metrics.
• Turn field deployments into reusable platform features.

Skills

Leadership experience

Hands-on software development

Mentoring engineers

Stakeholder communication

AI agent familiarity

Job description

About Us

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.

About the Role

Our forward deployed engineers (FDEs) work alongside practitioners at the world's largest audit firms. They build prototype agents on those firms' real workflows and ship production code. One current problem is producing verifiable citations from dense Excel workbooks, because an auditor has to trace every conclusion back to the exact evidence. Our Head of Deployed Engineering role will start as a player-coach role where you will need to be hands on as we build and scale this effort. At the start, you'll be working directly in customer deployments, writing production code and solving the hardest technical problems yourself. You'll also build and lead the team around you. As the team grows, your focus will move toward leadership, but you'll always be close to the work. You'll report to our CTO/co-founder and work closely and with Product, Engineering and Customer leadership.

What You'll Do

As a player:

• Lead important deployments yourself. Own technical delivery for some of our largest enterprise customers, from scoping through production. This includes single-tenant and government-cloud environments, regulated data, and audit methods that differ from firm to firm.
• Write production code. Build agents, integrations and tools alongside the team, and handle the hardest technical problems directly.
• Be the senior technical voice with customers. Act as a trusted advisor to partners, CIOs and audit leaders on how AI agents fit their practice.

As a coach:

• Build the FDE team. Hire, coach and grow strong engineers who can both build and work directly with customers. Set the bar through your own work first.
• Make deployment repeatable. Turn what you learn from hands-on work into playbooks, tools and metrics that speed up time-to-value as we grow upmarket.
• Turn field work into product. Spot patterns across deployments and work with Product and Engineering so solutions built for one customer become reusable platform features.

What We're Looking For

• 8+ years of leadership experience in forward deployed, deployment, solutions or customer engineering. That might mean FDE leadership at Palantir or a similar company, a Field CTO role, or leading technical work with large enterprise customers.
• You still build. You've written production software recently and want to keep doing it. This role isn't a fit for someone looking for a manage-only role.
• 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, and the ability to push back on scope when it matters.
• Excitement about bringing AI agents into high-stakes professional work.

Bonus Points

• 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.

More about Fieldguide

Fieldguide is a values-based company. Our values are:

• Fearless - Inspire & break down seemingly impossible walls
• Fast - Launch fast with excellence, iterate to perfection
• Lovable - Deliver happiness & 11 star experiences
• Owners - Execute & run the business with ownership
• Win-win - Create mutual value & earn trust for life
• Inclusive - Scale the best ideas with inclusive teams

Some of our benefits include

• Competitive compensation packages with meaningful ownership
• Flexible PTO
• 401k
• Wellness benefits starting on your first day
• Technology & Work from Home reimbursement
• Flexible work schedules