Senior SMB Digital Success Lead, Commercial

Accountabilities:

• • Own the Commercial SMB customer portfolio end to end, including accounts, cases, customer outreach, retention, adoption, and expansion initiatives.

  • Serve as the primary point of contact across Sales, Support, Partners, and other internal teams for the SMB segment.

  • Design and continuously improve a proactive customer success model that accelerates onboarding, increases adoption, identifies risks early, and supports retention across the SMB customer base.

  • Own the SMB onboarding experience, including curriculum, delivery model, performance outcomes, and continuous improvements based on customer behavior, case trends, and agent signals.

  • Lead the rollout of AI-powered agents and workflows for SMB customers, partnering with AI teams to define requirements, build and test solutions, monitor performance, and drive adoption.

  • Determine which customer success activities should be automated and where human engagement remains essential.

  • Collaborate with Sales, Marketing, and RevOps to identify expansion and Mid-Market opportunities, develop adoption campaigns, and establish appropriate customer segmentation and coverage models.

  • Partner with leadership and AI Operations to define success metrics, establish performance expectations, and execute initiatives designed to exceed business targets.

  • Act as the voice of the SMB customer, bringing insights about customer needs, product opportunities, process improvements, and enablement gaps to the relevant internal teams.

  • Document successful workflows, playbooks, processes, and learnings to help scale effective approaches across the broader Commercial Success organization.

  • Continuously evaluate customer data, case queues, AI-agent signals, and engagement patterns to identify opportunities for process optimization and improved customer outcomes.

  Requirements:

  • 3+ years of experience in customer success, account management, or a comparable customer-facing role, with demonstrated ownership of retention and expansion outcomes.

  • Hands-on experience building, configuring, tuning, and operating AI agents and AI-powered workflows, beyond simply using generative AI tools.

  • Strong understanding of when customer success processes can be automated and when human intervention is necessary.

  • Demonstrated program ownership and process-design capabilities, with the ability to turn undocumented or reactive processes into structured, measurable, scalable operating models.

  • Experience designing systems and customer engagement models that can effectively serve a large SMB customer base while maintaining consistent service quality.

  • Strong cross-functional collaboration skills, particularly when working with teams such as AI, RevOps, Marketing, Support, Sales, and Operations.

  • Ability to influence stakeholders and drive initiatives without direct authority over the teams responsible for execution.

  • Strong organizational, analytical, and problem-solving skills, with the ability to identify patterns in customer behavior and translate them into actionable improvements.

  • Comfortable operating in ambiguous, fast-changing environments where priorities, processes, and responsibilities may evolve.

  • Strong communication skills and the credibility to represent the needs of an entire customer segment across multiple internal teams.

  • Experience creating documentation, workflows, playbooks, and scalable operating processes.

  • Previous experience in commercial entertainment, production technology, or FinTech is preferred but not required.

  • A customer-first mindset combined with strong commercial awareness and an interest in using technology and AI to improve customer outcomes.

  Benefits:

  • Annual compensation of approximately CA$103,000–CA$142,000 for candidates based in Canada, excluding any applicable bonus, commission, benefits, or equity.

  • Fully remote work with the ability to work from anywhere in Canada or the United States.

  • Unlimited paid time off.

  • Health and dental benefits.

  • Up to CA$2,025 toward home-office IT equipment and setup.

  • Up to 2% RRSP matching.

  • Learning and development opportunities.

  • Up to CA$67.50 toward internet or cell phone services.

  • Opportunity to work with a team of creative problem-solvers in a fast-growing technology environment.

  • Opportunity to make a significant impact by helping shape a scalable, AI-enabled customer success model.

  • Inclusive and harassment- and discrimination-free workplace committed to respecting diverse backgrounds, identities, experiences, and perspectives.