Vice President Finance

TruckerCloud is the leading telematics data platform for commercial auto insurance. We connect to roughly 200 telematics and ELD providers and deliver clean, standardized fleet data to insurance carriers and MGAs, who use it to underwrite, price, and manage risk. We're a venture-backed company growing quickly, and we're building the finance function that will carry us through the next stage.

The role This is the first senior finance hire at TruckerCloud, reporting directly to the CEO. You'll build the finance, accounting, and operating foundation from the ground up. That means designing the systems and processes, running them, and making sure the CEO and board can trust the numbers.

This is a hands-on seat. In year one, you'll spend as much time building the general ledger, cleaning up billing, and running the close as you will on planning and board work.

What you'll own Planning and reporting

• Build the annual budget and planning process, starting with the 2027 plan, including scenario models and a headcount plan.
• Set up FP&A and management reporting: monthly business reviews, KPI dashboards, and results against plan by function.
• Own the board and investor package, produced on a consistent quarterly cadence.
• Run a rolling 13-week cash forecast and manage liquidity.

Accounting and billing

• Design the chart of accounts and reporting structure, and lead the ledger migration.
• Run a monthly close that is reconciled and finished within 10 business days.
• Own AR, AP, usage-based billing, and collections.
• Write revenue recognition policies for usage-based and non-standard contracts, and work with the outside accountants on them.
• Manage the outsourced bookkeeping partner.

Pricing and profitability

• Build customer- and product-level profitability, including cost to serve, and report it straight from the ledger.
• Set list pricing by product and a discount approval framework.
• Analyze gross and net retention by segment, and work with sales and customer success on an expansion motion.
• Model pricing scenarios as the business evolves.

HR, compliance, and operations

• Oversee HR operations and compliance in the US and internationally, with support from a PEO.
• Support international entity setup and payroll, including our team in Chile.
• Own the cap table and equity administration.
• Maintain the compliance calendar across entities.

What we're looking for

• 10+ years in finance and accounting, including senior leadership at a venture-backed SaaS, data, or usage-based business.
• You've built finance functions before: systems selection, ledger design, and the first reliable close.
• Strong technical accounting, especially revenue recognition for usage-based or hybrid pricing.
• Experience preparing board materials and working with institutional investors.
• Comfortable running multi-entity and international operations.
• Prefers building and doing over managing a large team.