Director of Finance

About Us
We’re a fast-growing, purpose-driven B2B financial services company built on integrity, accountability, and continuous growth. We have developed our own proprietary health and life insurance products for employers, currently scaling rapidly across the country. Our leadership team brings proven expertise from multiple sectors of finance, and every team member plays a direct role in expanding both our clients’ success and our company’s vision.

The Role
First Gen Financial is looking for a process-driven Finance leader or a strong up-and-coming leader ready to step into this scope, to own and scale our finance function. We are not looking for someone to simply inherit an existing finance department, we're looking for someone to help build it. As First Gen Financial continues to scale, new products, entities, revenue streams, and operational complexities will require new financial systems, controls, reporting structures, and processes. This role is ideal for someone who thrives in building infrastructure from the ground up and wants the opportunity to become the long-term finance leader of a rapidly growing company.This is a player-coach role, not a pure oversight seat. We need someone who is still hands-on with the data, the models, and the close, while also building the systems and processes that let Finance operate at scale.

This role sits at the center of a fast-moving, broker-distributed benefits business spanning MEC wellness plans, life insurance, and supplemental benefits.

Key Responsibilities

• Own weekly, biweekly, and monthly billing and reconciliation reporting across multiple payroll and enrollment data sources
• Stand up finance processes, infrastructure and tools from scratch, you're not waiting on someone else to build the system, you're building it.
• Build and maintain quarterly financial projections and hold the function accountable to them
• Manage product- and SKU-level profitability, including margin analysis across plan types and client segments
• Maintain float accounting for premiums in transit. Tracking cash collected vs. fees accrued.
• Run accrual-based accounting practices and ensure books reflect true period performance, not just cash movement
• Operate across multiple ERP/finance systems and data sources, with the ability to integrate and normalize data from disparate platforms (payroll registers, portal enrollment data, broker commission feeds)
• Own commission systems and billing logic specific to insurance/benefits distribution, schedules, reconciliation, and dispute resolution
• Partner with Operations and Business Engineering on reconciliation infrastructure between payroll, billing, and enrollment systems
• Build the reporting cadence and dashboards that give the CEO/COO real-time visibility into the financial health of the business

What You’ll Do Day-to-Day

• Work with our Third Party Administrator to ensure billing and collections are running smoothly and on time.
• Oversee the finance manager and their responsibilities.
• Run daily AR aging reports and prioritize outreach on outstanding balances
• Validate Reconciliation of carrier bills against internal enrollment data and build systems to flag discrepancies for resolution
• Communicate with clients via phone and email to resolve escalated billing questions and collect due amounts professionally
• Coordinate retroactive adjustments, adds, terms, and COBRA billing with carriers and internal teams
• Prepare weekly AP disbursement runs and obtain appropriate approvals
• Maintain organized billing files and support audit requests from carriers, partners, or compliance teams
• Track KPIs including days sales outstanding (DSO), collection rates, and reconciliation accuracy

What Success Looks Like

Within 90 days:

• Fully ramped on current billing, payroll, and commission data flows across all active carriers and payroll platforms
• Daily/weekly reporting cadence operating in a standardized fashion
• Clear map of current finance tooling gaps and a prioritized build plan

Within 6 Months:

• Quarterly projection process live and being held to
• Metric Dashboard with data integrity project complete
• At least one major finance tool stood up and in production use
• Commission reconciliation process tightened and documented

Within 12 Months:

• Product/SKU-level profitability reporting fully operational and used in strategic decisions
• Float and accrual accounting fully systematized

Requirements

• 8–10+ years of progressive finance experience, with real depth in insurance or healthcare , billing practices and commission structures specifically
• Demonstrated experience standing up finance tools, and processes from the ground up, not just operating within existing systems
• Comfort working across multiple ERP platforms and reconciling data across systems that weren't built to talk to each other
• Strong grasp of accrual accounting and float/cash-in-transit accounting
• Experience with product/SKU-level profitability and margin analysis
• A bias toward being hands-on: you'll be in the data, not just reviewing someone else's output
• Comfort operating in a remote-first, fast-scaling environment with ambiguity and shifting priorities
• CPA (Preferred)

Who You Are
You’re precise by nature and relentless by habit. You’re proactive & a self-starter. You don’t let finance sit stagnant. You are working in the business and cross departments to get things done day over day! You chase it down, document it, and fix it. You understand that in the insurance space, accuracy isn’t just good practice; it’s a compliance obligation and a client trust issue.

You embody First Gen’s core values:

• Ironclad Integrity
• 24-Carat Accountability
• Catalyst
• Wholehearted