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Senior SMB Digital Success Lead, Commercial

Wrapbook· Client Operations
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Remote$121.5k - $167kFull-timePosted 3w ago

About the role

Senior SMB Digital Success Lead to build and own the Commercial SMB customer success model, focusing on onboarding, adoption, risk prevention, and expansion at scale for Wrapbook’s SMB segment. Remote position for USA & Canada.

Responsibilities

  • - Own the Commercial SMB business (accounts, cases, outreach, and retention) as the single owner and point of contact across Sales, Support, and Partners.
  • - Build a success model that catches risk early and drives onboarding, adoption, and expansion across the whole SMB base through AI-assisted engagement.
  • - Own SMB onboarding fully: curriculum, delivery, and results; iterate based on case queue and agent signals.
  • - Lead the agent rollout for SMB; collaborate with AI team to design, build, test, and drive adoption of AI agents and SMB app; own every agent touching SMB from requirements through adoption.
  • - Work with Sales, Marketing, and RevOps to grow the SMB portfolio; surface expansion and Mid-Market opportunities; shape adoption campaigns and alignment on segmentation and coverage.
  • - Partner with leadership and AI Ops to define success metrics and exceed targets.
  • - Be the voice of the SMB customer; bring product, process, and enablement insights from the front line to relevant teams.
  • - Help scale best practices across Commercial Success by documenting workflows, wins, and playbooks.

Qualifications

  • - 3+ years in customer success or a similar customer-facing role with a track record of retention and expansion outcomes.
  • - Real AI building skills: built, tuned, and ran AI agents and workflows; know what to automate and what requires a human.
  • - Strong program ownership and process design; ability to turn reactive motions into measurable ones.
  • - Comfortable designing scalable systems for the entire SMB base with consistent, proactive support.
  • - Cross-functional influence without authority (AI, RevOps, Marketing, Support); ability to be the single point of contact for a segment.
  • - Prior experience in commercial entertainment or FinTech is preferred but not required.

Skills

Required:Customer success ownershipAI agent design and deploymentProgram design and process ownership

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 home
  • - Up to 2% matching RRSP / 401K
  • - Learning and Development opportunities
  • - Up to $50 USD / $67.50 CAD towards Internet/Cell phone service
Last updated Oct 21, 2026. Interested? Apply on the company site.

About Wrapbook

Control all your spend in one AI‑powered system

The AI platform for production payroll, accounting, and AP. Save time and decrease risk with smarter workflows and concierge paymaster support.

production payrollproduction accountingaccounts payabledata insightsonboardingpayroll
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