Aimed at senior-level product leaders with internal audit or B2B software sales experience who can drive business strategy and execute with ownership, working in a remote-first environment with a focus on AI-native tools and collaboration with technical teams.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Fieldguide via Ashby
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 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 Goldman Sachs, Bessemer Venture Partners, 8VC, and Y Combinator.
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 we are building, seeking teammates who 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 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
You will be the Director/Senior Director of Fieldguide's internal audit product: own the P&L, set the strategy, and take it from first design partners to a repeatable, multi-million-dollar business.
Internal audit teams carry the same capacity problem as external auditors, often with smaller budgets: rising SOX and regulatory scope, new risk areas like AI, cyber and third parties, and a shrinking talent pool. Much of their work (walkthroughs, controls testing, evidence requests, workpapers, issue tracking) looks like the work Fieldguide's agents already execute for audit firms. This role takes that engine to a new buyer: Chief Audit Executives and internal audit leaders at corporations, plus the firms that deliver co-sourced and outsourced internal audit for them.
This is not a product management or a sales role. You will make the calls a founder makes: which internal audit workflows to attack first, which companies are the first customers, what to build next and what to kill. You will have a dedicated pod of engineers, designers and internal audit subject-matter experts, and the full weight of Fieldguide's platform, brand and firm relationships behind you.
What You'll Do
- Find the wedge. Spend real time inside internal audit functions with CAEs, audit directors, SOX program leads and staff auditors. Identify the high-volume, high-pain work (SOX controls testing, walkthroughs, evidence collection, risk assessments, operational audits) where an agent can do the job end to end, and decide which problem we win first.
- Build the product with the pod. Partner with engineering, and design leads and our internal audit SMEs to define what ships, in what order, and what "good enough" means for work that lands in front of audit committees and external auditors. Write the spec when needed; sit in the eval reviews.
- Land design partners, then customers. Help close the first 5–10 internal audit teams. Turn them into referenceable deployments with measurable hours saved, coverage gained and quality improved.
- Partner with GTM. Work with Sales, Marketing and Customer Success to shape how the product is positioned, sold and expanded: into corporate IA teams directly and through co-sourcing firms already on Fieldguide. Bring the customer insight and proof points they need, and help build a playbook they can run without you.
- Know the landscape. Understand where incumbent GRC and audit-management tools stop, and position Fieldguide as the system that does the work, not just tracks it.
- Build the team. Hire the first dedicated GTM, deployment and IA SME roles for the line as it scales.
- Know when to double down or stop. Run tight experiments, read the signal honestly, and bring the company a clear recommendation.
Who You Are
- 8+ years of experience, including at least one stint taking a product or business from zero to one: as a founder, a GM of a new line, or the first operator on a new product at a high-growth company.
- Real P&L or revenue ownership, with numbers you can talk through.
- Strong commercial instinct: you have sold complex B2B software to senior, skeptical buyers and closed deals yourself.
- Enough technical depth to work as a peer with AI engineers: you understand what agents can and can't do today, and how evals and human review fit in.
- Clear, structured writing. You turn ambiguity into a crisp memo and a plan people can act on.
Bonus Points
- Background in internal audit, SOX, risk or controls: as a practitioner or leader in a corporate IA function, in a Big Four or Top 100 firm's risk advisory or internal audit practice, or selling into CAEs. CIA or CPA a plus.
- Experience at a vertical SaaS, GRC or AI-native company between Series B and pre-IPO.
- Management consulting, investment or strategy background paired with hands-on operating experience.
More About Fieldguide
Fieldguide is a values-based company. Our values are:
- Fearless: Inspire and break down seemingly impossible walls.
- Fast: Launch fast with excellence, iterate to perfection.
- Lovable: Deliver happiness and 11 star experiences.
- Owners: Execute and run the business with ownership.
- Win-win: Create mutual value and earn trust for life.
- Inclusive: Scale the best ideas with inclusive teams.
Benefits
- Competitive compensation packages with meaningful ownership
- Flexible PTO
- 401k
- Wellness benefits, including a bundle of free therapy sessions
- Technology and Work from Home reimbursement
Source: Fieldguide careers (Ashby)