Head of Applied Intelligence

Fieldguide is establishing a new state of trust for global commerce and capital markets through automating and streamlining the work of assurance and audit practitioners specifically within cybersecurity, privacy, and financial audit. Put simply, we build software for the people who enable trust between businesses.

We’re based in San Francisco, CA, but built as a remote-first company that enables you to do your best work from anywhere. We're 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 an early stage start-up employee, you’ll have the opportunity to build out the future of business trust. We make audit practitioners’ lives easier by bringing together 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 Applied Intelligence is responsible for turning agents into real operating leverage inside CPA firms, beginning with Risk Advisory and Financial Audit.

This role owns:

• Leading structured agent pilots and converting them into scaled deployments

• Designing and delivering custom agents aligned to firm methodologies

• Building and scaling an agent-first operating model across Advisory and Audit

This is an operating role accountable for embedding agents into live engagements and reshaping how work gets done.

Design and execute structured pilots inside strategic accounts that prove agent value in real workflows.

• Identify high-leverage use cases across audit and advisory engagements

• Define pilot scope, workflow integration, and rollout plans

• Lead cross-functional execution with CSMs and Agent Architects

• Convert successful pilots into broader firm-wide deployments

Own agent customization as a core capability.

• Conduct deep discovery of firm methodologies, documentation standards, and engagement models

• Translate firm-specific approaches into tailored agent behavior and outputs

• Partner with Agent Architects to configure logic, structure, and output formats

• Oversee validation and go-live within live engagements

• Develop scalable customization frameworks that preserve depth while enabling reuse

Drive structural workflow transformation across Advisory and Audit practices.

• Map current-state engagement workflows

• Redesign workflows for active agent participation across planning, testing, documentation, review, and reporting

• Redefine human-agent role allocation within engagement teams

• Build structured rollout plans tied to recurring engagement cycles

• Establish maturity stages for agent integration within firms

Ensure agents become embedded in real engagement teams, not layered on top.

• Develop structured rollout and change plans

• Align firm leadership around expectations and operating shifts

• Design enablement programs for partners, managers, and staff

• Identify and resolve adoption friction points

• Partner closely with CSMs to integrate agent strategy into account plans

Create the systems that make transformation repeatable.

• Standardize frameworks for pilot design, customization, workflow redesign, and rollout

• Build scalable playbooks that extend across firms

• Establish adoption tracking and feedback loops

• Partner with Product and Engineering to inform roadmap based on field learnings

Build and scale a team of “Advisory Engineers” and “Audit Engineers” — AI-native domain experts who combine deep practice knowledge with the ability to design, customize, and operationalize agents.

• Hire and develop AI-native SMEs across Risk Advisory and Financial Audit

• Train them to translate firm methodologies into agent logic and workflows

• Embed them into pilot execution, customization, and workflow redesign efforts

• Establish them as the frontline operators driving agent-first transformation inside client engagements

• Create clear operating standards, playbooks, and career paths for this new function

• 10+ years of experience across product, consulting, operations, or professional services, with exposure to technology-driven transformation

• Experience working on AI-enabled products, workflow automation, or data-driven platforms

• A strong ability to analyze complex business processes and reimagine how they should work in a modern, AI-native environment

• Experience leading or contributing to change management initiatives, helping teams adopt new tools, processes, and ways of working

• Excellent written and verbal communication skills, with a track record of collaborating across product, engineering, design, and business stakeholders

• Comfort operating in ambiguous, fast-moving environments, where you help define both the product and the process as you go

• A technical, business, accounting, or related degree, or equivalent professional experience

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.