Dig Insights is a tech-enabled research company that helps our clients - global consumer brands - move beyond consumer-centric to decision-centric. Our clients can then go-to-market with innovations that shift consumer decisions in their favor.

Our work is supported by the technologies that we leverage and create. This includes Upsiide, our proprietary innovation insights platform. Upsiide is a SaaS platform that reinvents how enterprise companies screen, optimize, and build a business case for innovation.

Our clients span verticals including CPG, QSR, retail, technology, financial services, and telecommunications. Our work is led by a team of over 250 strategists, insights leaders and data scientists. We work for a global client base out of offices in Toronto, Chicago, and London.

Our success is due to our strong commitment to our clients, and the creativity and dedication of our entire team. Since the beginning, we have been focused on building the smartest consumer insights company and that means hiring people who are bright, creative, resourceful, and kind. People who succeed at Dig are curious, question established norms and are passionate about helping our clients to move their businesses forward. If you want to join a team that takes themselves just seriously enough to produce great work, we’d love to welcome you.

As we continue to grow, both geographically and in our expertise we are looking for people who want to join a high-growth and highly collaborative company.

About this role:

Reporting to the Accounts Receivable Manager and partnering closely with Dig’s client-facing teams, the AR Specialist owns end-to-end billing and collections for an assigned portfolio of customer accounts. This role is responsible for issuing accurate invoices on time, ensuring required billing documentation (POs, vendor onboarding materials, portal submissions) is in place, and proactively following up with customer AP teams to drive timely payment.

Dig operates with a unique mix of SaaS and professional services . Success in this role comes from being organized, persistent, and comfortable navigating enterprise and mid-market AP workflows – independently and in a remote environment.

What you’ll be responsible for:

Billing execution

• Prepare and issue accurate invoices on schedule for SaaS subscriptions and professional services, aligned to customer agreements (Order Forms, Statements of Work, Purchase Orders).
• Validate billing requirements prior to invoicing (billing contacts, PO compliance, legal entity details, required backup documentation).
• Submit invoices through customer portals or procurement / AP systems when required and track acceptance / receipt confirmations.

Collections and AR ownership

• Own collections for assigned accounts, including a consistent follow-up cadence, clear documentation of status, and proactive escalation of risks/blockers.
• Monitor AR aging and customer payment behaviour; identifying risk and delayed payments early and drive resolution through to payment.
• Investigate and resolve payment issues (invoice rejections, missing PO, onboarding gaps, statement mismatches, short payment) by coordinating with customer AP and internal stakeholders.
• Assist with cash receipt tracking and basic reconciliation support (e.g., identifying remittances, resolving unmatched items).

Client onboarding and billing enablement

• Support customer onboarding activities that enable billing and payment (vendor setup forms, banking letters, portal onboarding).
• Collect, verify, and maintain required contracting and billing documentation and customer-specific invoicing instructions.

Process hygiene and continuous improvement

• Maintain clean records in Dig’s systems so account status is visible and auditable (notes, disputes, commitments, documentation).
• Identify recurring order-to-cash friction points and suggest practical improvements to templates, checklists, and workflow.
• Support with ad-hoc process and workflow improvements in partnership with the AR Manager / Finance.

Experience, skills, and requirements:

• 3-5+ years in billing and accounts receivable, with direct responsibility for invoicing and collections.
• Experience working with mid-market to enterprise customers , including customer portals, procurement/AP processes, and PO-driven environments.
• Strong organization and follow-through: able to independently manage a portfolio of accounts, competing priorities, and deadlines with minimal oversight.
• Confident communicator - comfortable engaging with customer AP teams and internal stakeholders to resolve issues quickly and professionally.
• Advanced Excel proficiency (e.g., XLOOKUP, SUMIFS, pivot tables) and strong general systems aptitude.
• Experience with ERP/CRM and billing/payment tools (experience with NetSuite, HubSpot, Maxio, Stripe is an asset).
• Bachelor’s degree or diploma in Business Administration, Accounting, Finance, or related field, is an asset.

Working style

• Comfortable working independently in a hybrid environment , with strong written communication, disciplined task tracking, and proactive stakeholder updates.
• Takes ownership, escalates appropriately, and brings solutions.

Work Perks:

• Hybrid working policy that provides flexibility to work remotely or from one of our office locations. Please note that this role includes certain responsibilities that require a regular in‑office presence at our downtown Toronto office.
• Unlimited vacation policy
• Reimbursement for health and wellness classes/memberships, and continuous learning
• Medical Insurance
• In-person and virtual social events such as poker night, paint night, trivia night and more

To find out more about us visit us at www.diginsights.com & www.upsiide.com

Our culture is built on 5 core values: Energy, Excellence, Evolution, Equality and Empathy. We believe that our success is dependent on the diverse talents, skills, and ideas of its staff. We are committed to creating an inclusive work environment and encourage applications from all qualified candidates including those in the BIPOC and LGBTQ communities, and from people with disabilities.

We thank you for your interest in Dig Insights, however, only candidates who are chosen for an interview will be contacted.