Fieldguide provides an agentic AI-native platform that streamlines audit, advisory, and assurance engagements for regulated professional services firms.
ABOUT US 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. OVERVIEW As a Director of Solutions Engineering, reporting to the VP of Revenue, you will lead and scale our pre-sales technical function at Fieldguide. You will be a technical counterpart, who can hold their own on AI architecture, data residency, security, and platform integrations, to c-suite firm leaders (CIOs, CISOs, etc.). This role owns the demo motion, POC execution, technical close, and the playbook that gets every Solutions Engineer on the team to a consistent bar. You will work side by side with Sales, Product, Engineering, and Customer Success leadership. WHAT YOU’LL DO: - Pre-Sales Technical Strategy: Own the end-to-end pre-sales technical motion across discovery, demo, POC, security review, and technical close. Set the technical strategy for our top strategic deals and engage on the highest-leverage opportunities. - Demo and POC Excellence: Define what a great demo looks like at Fieldguide and raise the bar across the team. Own POC scoping, success criteria, exit criteria, and the operating cadence that converts POCs into closed deals rather than open-ended pilots. - AI and Architecture Depth on Enterprise Deals: Lead technical conversations with firm CIOs, CISOs, and architecture review boards on AI architecture, data residency, model governance, security, and integration patterns. Build the bench so this is not a one-person dependency. - SE Enablement and Playbook: Build the Solutions Engineering playbook, ramp plan, and certification program. Standardize the reusable assets (demo flows, reference architectures, security responses, technical objection handling) so every Solutions Engineer shows up at a consistent bar. - Team Leadership: Hire, develop, and coach the existing Solutions Engineering team. - Cross-Functional Partnership: Partner with Product and Engineering on roadmap influence, customer feedback synthesis, and competitive response. Partner with Customer Success on technical handoff and post-sales continuity. - Deal Coverage Model: Define when Solutions Engineers engage, at what stage, and at what intensity. Build the coverage model that gives AEs leverage without spreading SEs thin. - Competitive Technical Positioning: Own the technical battlecards, demo objection responses, and proof points across the competitive set (Auditboard, GRC platforms, low-cost emerging entrants). Make sure every Solutions Engineer can win the technical bake-off. - Continuous Improvement: Iterate on the playbook, ramp, and coverage model based on win/loss patterns, technical objections, and customer feedback. - Day to Day AI Integration: Use AI tools daily in your own work to build demos, personalize POC environments, generate technical content, and analyze patterns across deals. We expect you to set the standard for what AI-native Solutions Engineer work looks like at Fieldguide, and to pull your team there with you. WHO YOU ARE: - 8+ years in Sales Engineering, with at least 3 years in a leadership role at an enterprise SaaS or Vertical AI company. - Experience selling to or working within CPA firms, audit and advisory practices, or professional services. - Strong technical depth on modern AI architecture, cloud infrastructure, security, and data integration. You can hold a credible conversation with a firm CIO without needing backup. - Proven track record building Solutions Engineering teams, playbooks, and ramp programs from the ground up. - Operating rigor on demo standards, POC execution, and technical forecast accuracy. You measure your team and your motion. - Strong cross-functional muscle with Product and Engineering. You have influenced roadmaps while maintaining collaborative relationships. - Comfortable in the trenches. You will still run the most strategic demos and POCs. - Low ego, constant learner, coachable in real time. SUCCESS METRICS - Win rate and average deal size on SE-supported strategic deals. - Reduction in technical-cycle time from discovery to technical close. - POC-to-close conversion rate and time-in-POC. - SE team ramp time and quota attainment. - Adoption of the SE playbook and reusable assets across the team. - Roadmap influence: customer-driven product priorities sourced through SE feedback.