Senior SMB Success Lead owning retention, onboarding, and expansion for Wrapbook’s AI production-finance platform. Building scalable AI-agent workflows for Commercial customers.
Responsibilities
Own the Commercial SMB business, including accounts, cases, outreach, and retention
Serve as the single point of contact across Sales, Support, and Partners
Build a proactive, AI-assisted success model driving onboarding, adoption, expansion, and early risk detection
Own SMB onboarding curriculum, delivery, outcomes, and continuous improvement
Lead the SMB AI-agent rollout with the AI team, including requirements, building, testing, and adoption
Partner with Sales, Marketing, and RevOps to grow the SMB portfolio and identify expansion and Mid-Market opportunities
Define success targets with leadership and AI Ops and execute plans to exceed them
Represent the SMB customer voice to product, process, and enablement teams
Document and share workflows, wins, and playbooks across Commercial Success
Requirements
3+ years in customer success or a similar customer-facing role
Track record of owning retention and expansion outcomes
Experience building, tuning, and running AI agents and workflows
Ability to determine what to automate and what needs a human
Strong program ownership and process design skills
Ability to design systems serving the entire SMB customer base at scale
Cross-functional influence across AI, RevOps, Marketing, and Support
Comfort with ambiguity
Prior experience in the commercial entertainment or FinTech sectors is preferred but not required
Currently authorized to work in the country from which you will perform the work
Wrapbook cannot sponsor or take over sponsorship of employment visas or work permits
Benefits
Unlimited Paid Time Off
Work from anywhere in Canada and USA
Health and Dental benefits
Up to $1,500 USD / $2,025 CAD towards IT setup for your home
Up to 2% matching RRSP / 401K
Learning and Development opportunities
Up to $50 USD / $67.50 CAD towards Internet/Cell phone service
Competitive salary
Inclusive and harassment- and discrimination-free workplace
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