Controller (Remote)

Zesty.ai • Chicago, IL

7h • Remote

About The Position

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 ZestyAI replaces outdated assumptions with dynamic, property-specific intelligence.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.
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 accounting. You will not be constrained by legacy systems or bureaucracy. You will be empowered to build.

Requirements

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

Nice To Haves

• 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
• You’ve likely already found ways to use AI in reconciliations, policy writing, close management, or analysis — and you’re eager to go further.

Responsibilities

• 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
• 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
• 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
• 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
• Manage outsourced bookkeeping, tax, payroll, and other accounting support
• Establish clear service standards and quality expectations
• Ensure outsourced workflows integrate seamlessly with internal systems
• Oversee AP/AR workflows and improve billing and collections rigor
• Strengthen working capital management
• Support cash forecasting accuracy through clean accounting data

Benefits

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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed