Billing Operations Lead

We're transforming the grocery industry

At the company, we invite the world to share love through food because we believe everyone should have access to the food they love and more time to enjoy it together. Where others see a simple need for grocery delivery, we see exciting complexity and endless opportunity to serve the varied needs of our community. We work to deliver an essential service that customers rely on to get their groceries and household goods, while also offering safe and flexible earnings opportunities to the company Personal Shoppers.

The company has become a lifeline for millions of people, and we’re building the team to help push our shopping cart forward. If you’re ready to do the best work of your life, come join our table.

The company is a Flex First team

There’s no one-size fits all approach to how we do our best work. Our employees have the flexibility to choose where they do their best work—whether it’s from home, an office, or your favorite coffee shop—while staying connected and building community through regular in-person events. Learn more about our flexible approach to where we work.

Why this role is on the menu

The Billing Operations Lead oversees and optimizes the end-to-end billing lifecycle across all the company Marketplace retailers, ensuring accurate invoicing, compliance with financial controls, and timely month-end close. This role serves as the operational and strategic anchor for the billing team, partnering closely with Finance, BD, Financial Systems, Legal, Product, and Engineering to drive accuracy, scalability, and continuous improvement.

The ideal candidate brings deep billing operations experience, strong analytical ability, and a bias for operational excellence — someone equally comfortable mentoring junior team members as they are collaborating with cross-functional stakeholders to scope system enhancements and automation opportunities.

What you'll cook up in your first year

• Billing portfolios across strategic retail partners and multiple revenue streams are owned and operating accurately, with day-to-day billing operations executed with a focus on revenue recognition inputs and timely month-end close.

• Billing policies, SOPs, and quality standards are developed and maintained, with discrepancies and escalations resolved in close partnership with Finance Systems, BD, and Revenue.

• Dashboards, reporting, and KPIs that track billing health are built in collaboration with Finance Systems, enabling continuous improvement and proactive identification of issues.

• Billing system enhancements, integrations, and automation opportunities are scoped and delivered in partnership with Product and Engineering, reducing manual workload and improving operational scalability.

• Internal controls, audit requirements, and contractual billing terms are enforced, with junior team members mentored and billing operations scaled to support the company's growth.

The secret ingredients we're looking for

Must-have pantry staples (Minimum Qualifications)

• Bachelor’s degree in Accounting, Finance, Information Systems, or related field, or equivalent practical experience.

• 5+ years of experience in Billing Operations, Order-to-Cash, or Accounts Receivable within technology, ecommerce, marketplace, or subscription/SaaS environments.

• 2+ years leading cross-functional billing or quote-to-cash projects as an individual contributor, from requirements through UAT and launch.

• Hands-on experience with Salesforce CPQ and at least one billing platform (e.g., Zuora, Chargebee, Stripe Billing) plus one ERP (e.g., NetSuite, SAP, Oracle).

• Proficiency in Excel (pivot tables, lookups) and basic SQL for reconciliations and data analysis.

• Working knowledge of billing controls, SOX requirements, and revenue considerations (e.g., ASC 606) as they apply to invoicing, credits, and adjustments.

Optional garnishes (Preferred Qualifications)

• Demonstrated success leveraging data modeling tools such as Alteryx to automate billing processes.

• Aptitude and demonstrated success leveraging AI solutions to improve billing processes.

#LI-Remote

The company provides highly market-competitive compensation and benefits in each location where our employees work. This role is remote and the base pay range for a successful candidate is dependent on their permanent work location. Please review our Flex First remote work policy here . Currently, we are only hiring in the following provinces: Ontario, Alberta, British Columbia, and Nova Scotia.

Offers may vary based on many factors, such as candidate experience and skills required for the role. Additionally, this role is eligible for a new hire equity grant as well as annual refresh grants. Please read more about our benefits offerings here .

For Canadian based candidates, the base pay ranges for a successful candidate are listed below.

CAN

$95,000 — $100,000 CAD