Senior SMB Digital Success Lead, Commercial

The Opportunity - SMB Digital Success Lead - (Remote - USA & Canada)

We're looking for a Sr. SMB Digital Success Lead to build how Wrapbook serves its Commercial SMB customers. You'll own the SMB business end to end and turn it into a proactive success model where onboarding is faster, risks are caught early, and customers get help when it matters — all starting from what customers actually do, at scale.

SMB is where our agent-first approach to Customer Success moves fastest — the segment where you can shape what proactive, AI-powered success looks like. If you'd rather design a model than inherit one, this is a rare shot to set the standard for how a whole segment gets served.

What you'll do:

• 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: the curriculum, how it's delivered, and the results. Keep improving it based on what the case queue and agent signals tell you about where customers get stuck.

• Lead the agent rollout for SMB. Work with the AI team to design the model and to build, test, and drive adoption of the AI agents and SMB app. Own every agent that touches 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 align on segmentation and coverage so every account gets the right level of service.

• Partner with your leader and AI Ops to define what good looks like and execute on the plan to exceed those targets.

• Be the voice of the SMB customer. Bring product, process, and enablement insights from the front line back to the teams who can act on them.

• Help scale what works across Commercial Success. Document and share workflows, wins, and playbooks so the approach can grow beyond SMB.

What you'll have:

• 3+ years in customer success or a similar customer-facing role, and a track record of owning retention and expansion outcomes.

• Real AI building skills, not just AI usage. You've built, tuned, and run AI agents and workflows, and you know what to automate and what needs a human.

• Strong program ownership and process design. You can own a deliverable others execute, and rebuild an undocumented, reactive motion into a measurable one.

• Comfort working at scale, designing systems that serve the entire SMB base well — so every customer gets consistent, proactive support.

• Cross-functional influence without authority (AI, RevOps, Marketing, Support), comfort with ambiguity, and the credibility to be the single point of contact for a whole segment.

• Prior experience in the commercial entertainment or FinTech sectors is preferred but not required.

Why Join Us

• Unlimited Paid Time Off

• Work from anywhere in Canada and USA

• Health and Dental benefits

• Up to 2% matching RRSP / 401K

• Learning and Development opportunities

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