Medical Billing jobs in Work From Home, Canada

CSC Generation is the AI-native holding company re-engineering omnichannel retail. We acquire iconic brands and transform them with Genesis, our operating platform combining a Data Fabric, Automation Engine, proprietary tools, and shared services to modernize operations, elevate customer experience, and expand margins. With $1B+ in revenue across 13 brands, our portfolio includes Sur La Table, Backcountry, One Kings Lane, and others that serve as real-world innovation labs.

Reports to: Corporate Controller

Location: Remote US / Remote Canada

About the Role

CSC Generation is building an AI-native accounting function from the ground up — software agents, automated reconciliations, and compressed close cycles are the mandate, not an aspiration. As Director of Accounting, AI-Operations, you will own all aspects of accounting operations across a portfolio of 13 brands while designing and deploying the intelligent workflows that replace manual processes.

We are open to two profiles: a Senior Manager ready to step into a Controller seat and prove themselves through AI-driven execution, or an experienced Controller who is genuinely deep on AI and can demonstrate it. Either way, you will be building automations — not just overseeing them. In your first year, success means a measurably faster close, fewer manual reconciliation touchpoints, and an accounting center of excellence that other portfolio companies adopt.

This is a lean team. You will own a lot, move fast, and make decisions with full end-to-end responsibility.

What You'll Do

Own the Accounting Foundation

• Own all aspects of accounting operations — monthly close, reconciliations, and monthly financial reporting across multiple portfolio companies.
• Manage the general ledger, ensuring accuracy, consistency, and compliance with GAAP and ASC 606.
• Oversee revenue recognition, contract setup, and billing integrations (Stripe and similar platforms).
• Operate at the corporate holding company level with the ability to get into the weeds with individual portfolio company general ledger systems and processes.

Build Intelligent Workflows and an Accounting Center of Excellence

• Design and deploy AI agents for A/R, A/P, and General Ledger reconciliations — eliminating manual touchpoints and compressing close timelines.
• Evaluate and implement automation tools that improve close speed, accuracy, and financial visibility.

Cross-Functional and Portfolio Support

• Support tax compliance activities as needed.
• Support annual audits and the annual budget process as needed.
• Backfill portfolio-company accounting positions as needed, providing hands-on coverage where the business requires it.

Required Qualifications

• CPA or equivalent experience managing audit processes and ASC 606 compliance.
• 5–8 years of progressive accounting experience in PE-backed or high-growth companies.
• Proven ownership of a financial close process — you have led it, improved it, and taken full accountability for results.
• Hands-on AI experience you can speak to concretely: you have built automations, deployed agents, or materially accelerated workflows using AI tools.
• Track record of implementing and optimizing accounting systems, integrations, and workflow automations.
• Strong communicator who works fluidly across engineering, finance, and go-to-market teams.
• Comfortable operating in ambiguity and high growth, where you are often setting the process before you follow it.

Why Join

The people who do best here are builders. They take ownership, move fast, and want to see the direct impact of their work.

• Executive Access: Work directly with the Corporate Controller and C-suite leadership, shaping how accounting operates across a $1B+ portfolio.
• Build the Playbook: Define what an AI-native accounting function looks like — your automations and workflows will become the standard across 13 brands.
• Portfolio-Wide Ownership: Set strategy for accounting operations at the holding company level with direct line-of-sight into every brand.
• Competitive Benefits (US): Paid time off policies, 401(k) match, medical/dental/vision and a variety of supplemental policies, and employee discounts across our portfolio of brands.
• Competitive Benefits (Canada): Paid time off policies, RRSP match, medical, dental, and vision coverage, a variety of supplemental benefit options, and employee discounts across our portfolio of brands.

Interview Process

Interview process is subject to change. Any updates will be communicated promptly and clearly.

CSC Generation is an equal opportunity employer. We do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other characteristic protected by law.

The CSC Generation family of brands is committed to providing reasonable accommodations for qualified individuals with disabilities in our job application procedures. If you need assistance or accommodation due to a disability, please contact hrbenefits@cscshared.com.

For Ontario applicants, please note that this posting is for an existing vacancy.

For US-based candidates, this posting is intended for candidates that reside in the following states:
AZ, DE, FL, GA, IN, LA, MI, MS, MO, NV, NC, OK, PA, TN, TX, UT, WV, WI, and WY.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.