Controller

Location: Remote (US)
Reports to: Chief Financial Officer

About ZestyAI

ZestyAI is the leading property and climate risk analytics platform for the P&C insurance industry. Our AI-powered models provide property-level insights into the risks that drive the majority of losses including wildfire hail and water damage. Using proprietary data from aerial imagery property characteristics permits and environmental signals we help insurers price accurately underwrite smarter and reduce losses creating a stronger and more resilient insurance market. As climate events grow more frequent and complex legacy models can no longer keep pace. ZestyAI replaces outdated assumptions with dynamic property-specific intelligence. Our next wave of innovation leverages agentic and generative AI to accelerate decision-making across the insurance value chain.

The Opportunity

We are hiring a Controller to build and lead a modern automation-first accounting function at a rapidly growing AI company.

This is a rare opportunity to design the financial control environment of an AI-native platform company from the ground up.

We are intentionally building a flat highly capable finance team where senior leaders operate as high-impact individual contributors and leverage automation outsourced partners and AI agents to maximize efficiency. You will work directly with the CFO to:

• Professionalize accounting policies and monthly close process
• Design scalable accounting processes and infrastructure
• Implement scale-appropriate financial controls
• Drive automation across close reporting and compliance
• Build a finance function that scales to $100M without unnecessary headcount

If you are a technically strong Controller who is curious self-directed and already experimenting with AI in your current finance workflows this role puts you at the forefront of how AI reshapes will not be constrained by legacy systems or bureaucracy. You will be empowered to build.

What Youll Do

Own the Accounting Function

• Lead the monthly quarterly and annual multi-entity close process; produce accurate consolidated GAAP financial statements (P&L Balance Sheet Cash Flow)
• Managing outsourced bookkeeping
• Develop accounting policies SOPs and internal controls
• Manage/oversee AP AR payroll accounting reconciliations
• Maintain reconciliations schedules and documentation at audit-ready standards

Revenue & Contract Accounting

• Own revenue recognition policy and execution (including complex data licensing and multi-element contracts)
• Partner with Go-To-Market and Legal to ensure contract structures align with accounting treatment
• Maintain deferred revenue schedules and ensure billing collections and reporting are clean and reconciled

Controls Risk & Audit

• Design and implement scalable internal controls
• Prepare the company for financial audits and future diligence
• Partner cross-functionally to ensure control maturity aligns with growth
• Build documentation and workflows that support compliance and enterprise customer requirements

Automation & AI-Driven Finance

• Lead the accounting systems roadmap (ERP close tools bill pay spend management)
• Leverage automation to reduce manual journal entries and reconciliation work
• Identify and implement AI agents or workflows to assist with:
• Reconciliations
• Contract review
• Close checklists
• Policy drafting
• Variance analysis
• Establish an automation-first mindset across the finance function

You will have wide latitude to test implement and scale AI tooling inside finance.

Vendor & Outsourced Partner Oversight

• Manage outsourced bookkeeping tax payroll and other accounting support
• Establish clear service standards and quality expectations
• Ensure outsourced workflows integrate seamlessly with internal systems

Cash & Financial Discipline

• Oversee AP/AR workflows and improve billing and collections rigor
• Strengthen working capital management
• Support cash forecasting accuracy through clean accounting data

What Were Looking For

• 7 years of progressive accounting experience
• Strong US GAAP foundation including CPA and audit experience (either auditor-side or company-side)
• Experience in high growth recurring revenue software startup
• Experience managing revenue with enterprise contracts
• Familiarity with enterprise sales commission plans
• Proven experience operating in a lean or growth-stage environment
• Experience managing audits and building documentation discipline
• Demonstrated ability to improve processes and implement systems

Bonus Points For

• Experience in Insurtech fintech data platforms or AI-driven companies
• ERP implementation experience
• Hands-on experimentation with AI tools in accounting workflows
• Clear examples of automation initiatives you have personally driven

Who You Are

• Curious and self-directed
• Comfortable building in ambiguity
• Energized by improving systems rather than maintaining legacy processes
• Highly accountable and detail-oriented
• Excited by AIs role in reshaping finance operations
• Motivated by impact and ownership not title hierarchy

Youve likely already found ways to use AI in reconciliations policy writing close management or analysis and youre eager to go further.

Why Join ZestyAI

• Join a recognized AI and Insurtech leader reshaping risk analytics
• Work directly with executive leadership in a high-impact role
• Build a modern accounting function designed for scale
• Operate in a flat team with significant ownership
• Be at the forefront of AI adoption in finance operations

This is a career-defining opportunity for a Controller who wants to build not just maintain.