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.