Senior SMB Digital Success Lead

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About the role

  • 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

Job type

Full Time

Experience level

Senior

Salary

$103,000 - $167,000 per year

Degree requirement

No Education Requirement

Location requirements

RemoteUnited States

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