Strategic Finance Manager at Letter AI – Chicago, Illinois

Strategic Finance ManagerFinanceChicago (3 Days In-Office)Full-time
About Letter AILetter AI is the world's first unified revenue acceleration platform powered natively by generative AI. Our platform empowers sales teams at customers like Lenovo and Redpanda to ramp up faster with AI-powered training and coaching, instantly find and personalize collateral for customers, and engage their buyers with the industry's first AI Sales Room.We recently raised a $40M Series B led by Battery Ventures, with participation from existing investors including Y Combinator, Lightbank, Northwestern Mutual Future Ventures, Stage 2 Capital, and Formus. The round comes just four months after announcing our Series A, signaling a shift we're seeing in real time: revenue teams are not asking for more tools, they are asking for better outcomes, and Letter AI is delivering.We 10Xed our revenue last year and are building the foundation for the next phase of growth.
The RoleWe are looking for our first Finance & Strategic Finance hire, a highly analytical operator who can own the financial backbone of the business while driving forward-looking strategic initiatives.This is not a traditional accounting role. While you will own our ERP system (Campfire AI) and ensure financial accuracy and discipline, the majority of your time will be spent partnering with leadership on strategic finance, planning, and growth initiatives.You should be equally comfortable closing the books as you are building a board deck, modeling a new pricing strategy, or evaluating a major investment decision.The ideal candidate is a former CPA who has transitioned into a strategic finance role, someone who understands the fundamentals deeply, but is energized by using finance to drive decisions, not just report on them.You will play a critical role in helping us scale from our current stage into a durable, high-growth business.
Your key responsibilities will include:ERP Ownership & Financial Operations

• Own and operate our ERP system (Campfire AI), ensuring clean, accurate, and timely financial data
• Manage core accounting workflows including close processes, reconciliations, and financial reporting
• Build scalable financial processes and controls to support rapid growth
• Partner with external accounting and tax partners as needed

Strategic Finance & Planning (Core Focus)

• Own company-wide financial planning, including budgeting, forecasting, and long-range planning
• Build and maintain operating models that support growth, hiring, and investment decisions
• Partner with GTM, Product, and Leadership teams to evaluate new initiatives and drive ROI-based decision making
• Analyze key business drivers including ARR growth, CAC, payback, expansion, and retention

Board & Investor Reporting

• Prepare board materials and investor updates, including performance insights and forward-looking analysis
• Translate complex financial data into clear, actionable narratives for executive stakeholders

Finance Infrastructure & Scale

• Build the finance function from the ground up, including systems, reporting, and internal processes
• Identify opportunities to automate and streamline workflows using AI and modern finance tools
• Establish KPIs and reporting frameworks that become the financial source of truth for the company

Cross-Functional Partnership

• Act as a strategic partner to leadership across Sales, Marketing, and Customer Success
• Support pricing strategy, deal structuring, and major customer or partnership decisions
• Help drive operational rigor across the business through data and financial insights

Qualifications for the role include:The Ideal Background

• 5–7 years of experience across accounting, finance, or strategic finance roles
• Background in accounting (CPA strongly preferred), with a clear transition into strategic finance

Startup Experience

• Experience working at a high-growth startup or in a fast-paced, ambiguous environment
• Comfortable building from scratch and operating without a fully built-out finance team

Technical & Analytical Strength

• Strong financial modeling and analytical skills, with the ability to connect data to business outcomes
• Experience working with modern ERP systems (experience with Campfire AI is a plus, not required)
• Advanced proficiency in Excel/Google Sheets; familiarity with BI tools is a plus

Operator Mindset

• Ability to zoom in and out, from detailed accounting workflows to high-level strategy
• Strong ownership mentality with a bias toward action and execution

AI-Native Approach

• Comfortable leveraging AI tools (e.g., ChatGPT, Claude, Copilot) to increase efficiency across financial analysis and operations

As a part of the team at this early stage, you will not only receive a competitive salary and benefits, but also a meaningful equity stake in the company.
How We OperateAt Letter AI, we want you to be unapologetically you while operating with our core principles in mind:Customer-obsessed: Make your customers unreasonably happy and everything else will fall into place. Ambitious yet practical: Set big goals, but stay grounded with disciplined execution and ruthless prioritization. Direct yet kind: Never hold back from speaking your mind, but do so in a way that is kind to your colleagues. Driven yet humble: Push for excellence and deliver fast, but keep your humility.