About Smokeball
Join an award-winning legal tech company that’s transforming how law firms work by boosting their organization, productivity, and profitability with software they actually love. Smokeball is a global, community-driven company united by a love for the law and a mission to help small and midsize firms thrive. We’re passionate about what we do and our clients know it! If you’re looking for a company that truly cares about its clients and its people, you’re in the right place. 

The Role

• Job Title: Commercial Finance Manager
• Department: Finance
• Reports To: VP of Finance
• Manages: Order to Cash Analyst, Collections Analyst
• Location: Chicago, IL- This is a hybrid role, 2 days per week in office

We are seeking an experienced Finance Leader who can design, refine, and execute scalable systems and processes within our Order-to-Cash (O2C) cycle. This role is not about chasing invoices, it’s about building a robust framework that ensures accuracy, efficiency, and reliability across financial operations. You will lead a small team focused on invoicing, billing inquiries, and past-due resolution, while driving systemic improvements that improve cash collection on recurring revenue streams.

Key Responsibilities

Architect and enforce commercial controls: Develop and communicate policies for commercial transactions that balance deal velocity with strong internal controls.

Optimize invoicing processes: Ensure all orders are invoiceable, resolve exceptions, and enforce cutoff timelines to meet close requirements.

Drive systemic improvements: Partner with Sales, Client Success, and Systems teams to identify root causes of billing issues and implement long-term fixes.

Establish monitoring cadences: Track stalled invoices, blockers, and escalations; implement controls for credit memos, credit holds, refunds, and corrections.

Enhance data integrity: Collaborate across departments to improve data hygiene and reduce defects impacting invoicing and collections.

Manage risk and compliance: Review receivable write-offs, enforce collection processes, and escalate accounts past due for suspension.

Standardize commercial terms: Work with Sales and Client Success to reduce DSO and improve contract consistency across customer cohorts.

Leverage technology: Utilize ERP, CRM, and middleware tools to automate workflows and improve reporting accuracy.

Commission and accrual management: Calculate attainment, post accruals, and manage payout processes.

Qualifications

• Strategic mindset: Ability to distinguish between edge-case transactional issues and systemic process gaps.
• Leadership experience: Proven ability to lead teams and influence cross-functional stakeholders.
• Process design expertise: Skilled in building scalable systems, policies, and controls that align with growth objectives.
• Technical proficiency: Healthy familiarity with NetSuite, Stripe, LeapFin, and CRM/ERP systems.
• Analytical capability: Strong understanding of internal controls, risk mitigation, and financial systems optimization.
• Experience: Minimum of 10 years in finance or accounting with deep knowledge of O2C cycles; MBA or CPA preferred.
• Communication skills: Ability to articulate complex issues and gain buy-in for change initiatives.
• Automation and improvement: Demonstrated success in process improvement and leveraging technology for efficiency.

What You Bring

• Excellent analytical, problem-solving, and decision-making skills.
• Strong leadership and team management abilities.
• Exceptional communication and interpersonal skills.
• Ability to articulate how business operations impact invoicing and cash collections
• Ability to work effectively in a fast-paced, dynamic environment.
• Ability to challenge status quo and influence peers to improve business processes.
• Familiarity with subscription and usage billing models.
• Knowledge of applicable accounting standards and practices.

Compensation 

$140,000 - 150,000 base salary, plus thirdly bonus

The Team

Your Manager

Ben Pomeroy: Hi, I am Ben and I’ve worked at Smokeball for three years. I oversee the North American Finance team and help tell the financial story of the company each month as well as guide the strategic decision making with in our region. Our team consists of 6 employees that are passionate about helping the company grow commercially and actively partner across the business to drive business decisions. I am a big believer in empowering staff to make decisions and bring their ideas to the table to assist the company. When I am not working, I enjoy playing with my kids, reading and golfing.

Teammate

Art Garza: Hi, I’m Art! I’ve been with Smokeball for six years now and I’ve enjoyed my experience so much since joining the company. The finance team started off very small, with me being here in the US and the CFO, Mick Campbell, in Australia. Since then, we have doubled the finance team and are looking to add more teammates to help meet the demands of our clients. With our growing client base come new challenges – which we all get energy from! We have a collaborative team environment which not only aids in the business’ growth, but also for our own personal development.

Life at Smokeball 

• Great Culture: We’ve been named a 'Best Place to Work' five years in a row. For us, caring is not optional and we have an ongoing commitment to building a workplace where our people feel valued and collaboration flourishes. 
• Work-Life Balance: 20 vacation days, 7 sick days, 3 reboot days, 11 paid holidays, birthday off, volunteer time, and more!  
• Career Growth: Smokeball believes in investing in our own people and promoting from within. Our own President started at Smokeball as an Account Manager! 
• Benefits: Excellent medical, dental, and vision coverage. 401(k) match, monthly wellness stipend, generous parental leave. 
• The Office: The kitchen is stocked with breakfast items, snacks, and beverages, and we have plenty of games to help you relax (ping-pong, billiards, pinball). We also offer weekly catered lunch and free monthly massages provided by a licensed massage therapist!  

Want to Know More? 

Why do we do what we do? Where did the name ‘Smokeball’ come from? What are our values? Learn more here! 

Smokeball values diversity & inclusion and is proud to be an Equal Employment Opportunity employer. Smokeball considers all individuals seeking employment without regard to race, color, religion, national origin, age, sex, marital status, ancestry, physical or mental disability, veteran status, gender identity, sexual orientation, or any other legally protected characteristic.  

If you’re excited about this role, we encourage you to apply even if your experience doesn’t check every box.