Remote opportunity at
FieldguideHead of Deployed Engineering
The Head of Deployed Engineering is a full-time, remote leadership role at Fieldguide, a San Francisco-headquartered company that builds software for audit, advisory and tax practitioners…
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About This Role
The Head of Deployed Engineering is a full-time, remote leadership role at Fieldguide, a San Francisco-headquartered company that builds software for audit, advisory and tax practitioners at large CPA firms. The company aims to strengthen trust in global commerce and capital markets by automating and streamlining practitioners' work. The role leads forward deployed engineers who work alongside practitioners at the largest audit firms, building prototype agents on real workflows and…
Job Description
The Head of Deployed Engineering is a full-time, remote leadership role at Fieldguide, a San Francisco-headquartered company that builds software for audit, advisory and tax practitioners at large CPA firms. The company aims to strengthen trust in global commerce and capital markets by automating and streamlining practitioners' work.
The role leads forward deployed engineers who work alongside practitioners at the largest audit firms, building prototype agents on real workflows and shipping production code. One open challenge involves generating citations that can be checked against spreadsheet-heavy evidence files, because auditors need to trace each conclusion back to its underlying support.
The position starts as a player-coach role. The leader stays hands-on, taking charge of major customer deployments that may involve single-tenant or government cloud infrastructure, regulated information, and audit methods that vary by firm. Over time the focus shifts toward building the team, including hiring, coaching and growing engineers, and turning field work into repeatable playbooks and reusable platform features.
The role reports to the company's CTO and co-founder and works closely with Product, Engineering and Customer leadership. It suits an experienced technical leader who still writes production software, is comfortable with senior enterprise stakeholders, and can judge when to build for a single customer versus the broader platform.
Responsibilities
- Lead high-stakes customer deployments personally, from scoping through production
- Write production code for agents, integrations and internal tools
- Serve as the senior technical voice for partners, CIOs and audit leaders
- Recruit, coach and grow a team of forward deployed engineers
- Create repeatable deployment playbooks, tools and metrics that shorten time to value
- Spot patterns across deployments and help turn them into reusable features with Product and Engineering
Requirements
- Eight or more years of leadership experience in forward deployed, deployment, solutions or customer engineering
- Recent hands-on experience writing production software
- Experience leading or mentoring engineers and enthusiasm for building a team from an early stage
- Comfort presenting to senior enterprise stakeholders in regulated or complex environments
- Sound judgment on single-customer versus platform work, and willingness to push back on scope
- Interest in bringing AI agents into high-stakes professional work
Qualifications
- Experience at a Big 4 firm such as Deloitte, PwC, EY or KPMG, or at 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
Core Skills
Benefits
- Competitive compensation packages with meaningful ownership
- Flexible PTO
- 401k
- Wellness benefits starting on the first day
- Technology and work-from-home reimbursement
- Flexible work schedules
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Is this job remote?
Yes. The posting lists the location as remote and the position as full-time.
Does the posting list a salary?
No. The posting does not specify a salary.
What experience is required?
The posting asks for at least eight years of leadership experience in forward deployed, deployment, solutions or customer engineering, plus recent hands-on software work.
Who does this role report to?
It reports to the CTO and co-founder and works closely with Product, Engineering and Customer leadership.
Sample Interview Questions
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