Director of Finance

About Gray Swan

Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs along with building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.

We're a team of approximately 50 people, well-funded, growing quickly. Our work directly influences how the world deploys AI agents and systems at scale..

Learn more about how we work.

The Role

We’re looking for our first Director of Finance to build and scale the financial foundation of Gray Swan as we enter our next phase of growth.

Reporting directly to executive leadership, this is a highly visible role that combines strategic finance with operational execution. You’ll own the company’s financial planning processes while building the systems, reporting, and operational rigor needed to support a rapidly scaling business.

This is not a role where you’ll simply oversee the work of others. We’re looking for a working director—someone equally comfortable owning the monthly close process, building complex financial models, implementing systems, preparing board materials, and partnering with leadership on strategic investments.

If you enjoy building from scratch, solving complex business problems, and operating with high ownership in a fast-moving startup, we’d love to talk.

What You’ll Do:

Finance Operations

• Own the monthly close process, partnering closely with external accounting partners to ensure accurate, timely financial reporting.

• Oversee the order-to-cash process, including invoicing, customer payments, collections, and revenue operations.

• Review and approve employee expense reports, ensuring policy compliance and operational efficiency.

• Manage revenue recognition in accordance with GAAP and ensure accurate financial reporting.

• Oversee day-to-day cash management, liquidity planning, and runway forecasting.

• Develop financial reporting, KPI dashboards, and executive reporting that provide visibility into company performance.

Financial Planning and Analysis

• Lead the annual budgeting process and rolling forecasts across all departments.

• Build sophisticated financial models supporting hiring plans, infrastructure investments (including GPU spend), product initiatives, and strategic company investments.

• Develop scenario analyses and long-range planning models that inform executive decision-making.

• Partner with leadership on pricing, resource allocation, investment prioritization, and business planning.

• Prepare financial reporting, analyses, and narratives for executive leadership, investors, and Board meetings.

• Deliver actionable recommendations on growth opportunities, operating efficiency, margin improvement, and capital allocation.

Systems & Process

• Evaluate, select, and lead implementation of a scalable ERP and financial systems stack.

• Build finance processes that scale with company growth while improving reporting accuracy and operational efficiency.

• Identify opportunities to automate workflows and leverage AI to improve forecasting, reporting, and financial operations.

• Establish internal controls, financial policies, and operational best practices appropriate for a high-growth startup.

Cross-Functional Partnership

• Partner closely with Accounting, Operations, and leadership on company-wide initiatives.

• Serve as the primary finance business partner across the organization, translating financial insights into actionable business decisions.

• Balance hands-on execution with strategic leadership, operating comfortably as both an individual contributor and functional leader.

• Support fundraising, investor diligence, strategic planning, and special projects as the company scales.

Who You Are:

• 8+ years of experience in strategic finance, FP&A, corporate finance, investment banking, consulting, or finance leadership roles within high-growth technology companies.

• Experience building or scaling finance functions in startup or rapidly growing environments.

• Strong understanding of accounting fundamentals, monthly close processes, revenue recognition, budgeting, forecasting, and cash management.

• Exceptional financial modeling skills with experience building investment analyses, scenario planning, operating models, and board-level reporting.

• Experience partnering directly with executive leadership to influence strategic decisions.

• Comfortable owning both finance strategy and day-to-day operational execution.

• Experience evaluating and implementing ERP systems or other finance technology platforms.

• Strong executive communication skills with the ability to simplify complex financial information for diverse audiences.

• Highly organized with exceptional attention to detail and a bias toward action.

• Curious about AI and excited to leverage modern AI tools to improve financial planning and operational decision-making.

• Thrives in ambiguity and enjoys building processes where none currently exist.

Bonus Points If You Have:

• CPA, MBA, or advanced degree in Finance, Accounting, Economics, or Business.

• Experience at a Series A or Series B SaaS startup.

• Experience implementing NetSuite, Sage Intacct, Oracle, Workday, Adaptive Planning, Rippling, or similar ERP/FP&A platforms.

• Experience supporting venture fundraising, investor relations, and Board reporting.

• Deep understanding of SaaS metrics including ARR, burn multiple, CAC, gross margin, and cash runway.

• Experience partnering closely with engineering organizations or evaluating infrastructure investments.

• Experience building finance organizations from the ground up.

If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.

What Success Looks Like:

• Established a predictable monthly close process and executive financial reporting cadence.

• Built a scalable budgeting and forecasting process used across every department.

• Improved visibility into cash flow, runway, revenue, and company performance.

• Implemented stronger operational processes across invoicing, collections, expense management, and financial controls.

• Delivered investment analyses that influence hiring, infrastructure, product, and go-to-market decisions.

• Evaluated and began implementing the ERP and financial systems needed to support Gray Swan’s next stage of growth.

• Become a trusted strategic advisor to leadership while remaining deeply involved in day-to-day finance execution.

What We Offer:

We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data.

Compensation: $170,000 - $260,000 plus performance based bonus and meaningful equity package

Benefits:

• 401k with up to 4% matching

• 28 days annual leave (vacation + holidays)

• Health, dental, and vision coverage

• Catered lunches (Pittsburgh office)

• Flexible work arrangements

• Visa sponsorship available for exceptional candidates

How to Apply

Submit your resume, link to your portfolio, and answer the questions on the application.