Senior SMB Digital Success Lead, Commercial

Accountabilities:: Own the Commercial SMB business end to end, including customer accounts, cases, outreach, retention, adoption, and expansion activities. Serve as the central point of contact for the SMB segment across Sales, Support, Partners, and other internal teams. Build and continuously improve a proactive success model that identifies customer risks early and drives onboarding, adoption, retention, and expansion across the SMB portfolio. Own the SMB onboarding experience, including curriculum design, delivery methods, performance outcomes, and ongoing optimization based on customer behavior, case trends, and AI-agent signals. Lead the rollout of AI agents and digital workflows for SMB customers, partnering with AI teams to define requirements, design solutions, test functionality, and drive adoption. Determine which customer interactions and success processes should be automated and where human intervention provides greater value. Work with Sales, Marketing, and RevOps to identify expansion and Mid-Market opportunities, develop adoption campaigns, and establish segmentation and customer coverage strategies. Partner with leadership and AI Operations to define success metrics, establish operating standards, and execute initiatives designed to exceed business targets. Act as the voice of the SMB customer, translating frontline insights into product, process, enablement, and customer experience improvements. Document and share effective workflows, playbooks, processes, and lessons learned so successful approaches can scale across the broader Commercial Success organization. Monitor customer engagement, case patterns, and AI-agent performance to identify opportunities for operational improvement and stronger 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, tuning, deploying, and managing AI agents and AI-powered workflows, rather than simply using AI tools. Strong understanding of how to identify processes suitable for automation while recognizing situations where human engagement is essential. Proven program ownership and process-design capabilities, including the ability to transform undocumented or reactive customer motions into structured, measurable, and scalable programs. Experience designing customer success systems capable of serving a large SMB customer base while maintaining consistent and proactive engagement. Strong cross-functional influence skills and experience working with teams such as AI, RevOps, Marketing, Support, Sales, and Operations without direct authority. Ability to operate effectively in ambiguous, fast-changing environments and take ownership of initiatives from concept through execution. Strong analytical, organizational, and problem-solving abilities, with the capacity to turn customer behavior and operational signals into actionable improvements. Excellent communication and stakeholder-management skills, with the credibility to represent an entire customer segment across multiple functions. Experience developing documentation, workflows, playbooks, and scalable operating processes. Previous experience in commercial entertainment or FinTech is preferred but not required. Customer-focused mindset with strong commercial awareness and enthusiasm for applying AI and technology to improve customer experiences and business outcomes. Benefits: Competitive annual compensation based on location: US Zone 1: $121,500–$167,000 for locations including San Francisco, Los Angeles, Seattle, New York City, Boston, San Diego, and Washington, DC. US Zone 2: $115,500–$159,000 for locations including Austin, Chicago, Miami, and California outside Zone 1. US Zone 3: $103,000–$142,000 for all other US locations. Compensation ranges are based on geographic market benchmarks and exclude any applicable bonus, commission, benefits, or equity. Fully remote work with the ability to work from anywhere in the United States or Canada. Unlimited paid time off. Health and dental benefits. Up to $1,500 USD toward home-office IT equipment and setup. Up to 2% matching contribution toward a 401(k) or RRSP. Learning and professional development opportunities. Up to $50 USD toward internet or cell phone services. Opportunity to work alongside creative problem-solvers in a fast-growing technology environment. Opportunity to have significant impact by helping establish a scalable, AI-enabled customer success model. Inclusive and respectful workplace committed to creating a safe environment for people from diverse backgrounds, identities, and experiences.