Head of Finance - Chicago - Hyprwork

Description

Job Title: Head of Finance
Location: Remote (with occasional in-person strategy meetups)
Reports to: COO, Fractional CFO
Salary: Flexible Base (tied to experience) + Performance Bonus
About Us
We're a fast-scaling 9-figure direct-response eCommerce health brand built around performance, speed, and data. Our team is lean, aggressive, and focused on results, not vanity metrics.
We thrive on clarity, accountability, and creative excellence.
The Role
We are hiring a Head of Finance who can take full ownership of the financial engine that underpins revenue growth, operational efficiency, liquidity, and profitability across the entire portfolio.
You will be responsible for all financial operations across the business. This includes managing the finance team, owning financial reporting, improving profitability levers, strengthening internal controls, overseeing tax and compliance, and building systems that make our marketing, operations, and leadership teams faster and more informed.
You are expected to combine hands-on execution with strategic leadership. You will identify bottlenecks, prioritise financial initiatives that unlock growth, and create a financial roadmap that supports an aggressive scaling agenda.
What You'll Be Responsible For
Leadership & Team Ownership

• Lead, manage, and develop the finance team across all brands.
• Build a world-class finance function with clear processes, accountability, and reporting cadence.

Financial Strategy & Performance

• Own P&L performance across the portfolio, ensuring margin optimisation and cost discipline.
• Build scalable reporting systems for revenue, cash flow, inventory planning, and marketing spend allocation.
• Partner closely with the CEO/CFO to shape financial strategy, capital allocation, and risk management.

Financial Operations

• Oversee production of monthly management accounts, dashboards, KPIs, and variance analyses.
• Maintain full accuracy of revenue reporting, COGS, fulfilment fees, marketing spend, subscription metrics, and performance by brand.
• Drive improvements in gross margin, contribution margin, and EBITDA through data-driven insights.

Cash Flow, Liquidity & Working Capital

• Manage cash cycles, payment terms, 3PL billing, freight spend, and supplier relationships.
• Ensure adequate liquidity to support inventory, growth, and major scaling initiatives.

Controls, Compliance & Governance

• Implement robust financial controls, processes, and audit trails across all companies.
• Oversee VAT, sales tax, corporate filings, intercompany structures, transfer pricing and compliance requirements.
• Ensure clean books, reconciliations, and audit readiness at all times.

Commercial & Operational Partnership

• Support marketing with financial insights into CAC, LTV, MER, channel profitability, and testing economics.
• Partner with operations on supply chain cost optimisation, inventory turns, purchasing decisions.
• Support leadership with scenario modelling, sensitivity analyses.

Systems & Automation

• Improve financial systems, dashboards, and reporting tools.
• Implement automation to reduce manual work, minimise error, and increase team velocity.

Reporting

• Deliver weekly and monthly reporting on performance, risks, opportunities, and upcoming priorities.

Requirements

• Proven finance leadership experience in a DTC brand, ecommerce company, or subscription business.
• Strong understanding of ecommerce unit economics, CAC/LTV modelling, MER analysis, and margin improvement levers.
• Experience managing finance teams and running structured financial reporting processes.
• Ability to translate commercial objectives into actionable financial plans.
• High sense of ownership for accuracy, compliance, and financial performance.
• Ability to move quickly, maintain high standards, and thrive in a fast-growth environment.
• Comfortable balancing hands-on execution with strategic oversight.

Preferred Experience

• Experience with Shopify, subscription billing platforms, inventory and fulfilment systems.
• Familiarity with multi-entity structures, intercompany flows, VAT/sales tax, transfer pricing and international expansion.
• Experience supporting multiple brands simultaneously.
• Experience with rapid growth environments where speed and iteration matter.
• Ability to build dashboards, automation tools, or financial systems.

What Success Looks Like
After 30 Days

• Full audit of all financial processes, systems, reporting structures, and brand profitability.
• Identification of major inefficiencies, risks, and opportunities.
• Cleaned-up reporting cadence with accurate dashboards and structured weekly finance updates.

After 60 Days

• Improved financial clarity across the leadership team.
• Reporting stabilised and producing meaningful insights.
• Tighter margin controls and improved visibility into CAC/LTV, MER, and brand-level performance.

After 90 Days

• Stronger controls implemented, reduced variance between forecast and actuals, improved cash visibility.
• Key financial roles hired and a finance team operating with rhythm and accountability.
• Fully structured month-end close process, automated where possible.

After 180 Days

• Material improvement in gross margin, contribution margin, cash flow stability, and profitability.
• Streamlined financial operations supporting new brand launches, new markets and larger marketing budgets.
• A mature financial infrastructure built for scale.