[All remote jobs](https://jobicy.com/jobs.md)[![Wrapbook logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2024/03/4daf69c7-221.jpeg)](https://jobicy.com/company/wrapbook.md)[Wrapbook](https://jobicy.com/company/wrapbook.md) # Senior SMB Digital Success Lead, Commercial Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/wrapbook.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md), [Canada](https://jobicy.com/job-region/canada.md)SalaryUSD 121,500–167k / yrDepartment[Customer Support & Success](https://jobicy.com/categories/supporting.md)EmploymentFull TimeExperienceSeniorPublished26 Oct 2026Apply before25 Nov 2026Listing views32Application actions1Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Wrapbook is seeking a senior customer success leader to own the Commercial SMB segment end to end across onboarding, adoption, retention, and expansion. The role designs a proactive, scalable customer-success model using AI-assisted engagement, agents, and workflow automation. It serves as the central point of contact across Sales, Support, Marketing, RevOps, AI, and partner teams while bringing customer insights back to product and operations. The successful candidate will combine customer-success ownership, AI-agent building experience, program design, and strong cross-functional influence. This is a remote full-time role for candidates located in the United States or Canada. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 4/5EasyHard ### Pace & Pressure 4/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a high-ownership senior role responsible for defining and scaling an undocumented SMB success motion rather than operating an established program. It requires both strategic customer-success leadership and hands-on capability building, including AI-agent design, testing, and adoption. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Market rate$144,250US market range (per year)$120k–$175k0$192.50k AI insightThe employer discloses a yearly base-pay range of $121,500–$167,000 USD, with a midpoint of $144,250. This range is credible for a senior, remote North American customer-success leadership role with AI workflow and cross-functional program ownership. Estimated US market compensation is $120,000–$175,000 USD per year; actual compensation may vary by location, experience, and total-rewards structure. ## Core skills Skills and capabilities most closely associated with this opportunity. [Customer Success](https://jobicy.com/jobs?search_keywords=Customer%20Success.md)[SMB Account Management](https://jobicy.com/jobs?search_keywords=SMB%20Account%20Management.md)[Customer Onboarding](https://jobicy.com/jobs?search_keywords=Customer%20Onboarding.md)[Retention Strategy](https://jobicy.com/jobs?search_keywords=Retention%20Strategy.md)[Account Expansion](https://jobicy.com/jobs?search_keywords=Account%20Expansion.md)[AI Agent Development](https://jobicy.com/jobs?search_keywords=AI%20Agent%20Development.md)[Workflow Automation](https://jobicy.com/jobs?search_keywords=Workflow%20Automation.md)[Program Management](https://jobicy.com/jobs?search_keywords=Program%20Management.md)[Process Design](https://jobicy.com/jobs?search_keywords=Process%20Design.md)[Customer Adoption](https://jobicy.com/jobs?search_keywords=Customer%20Adoption.md)[Cross-functional Collaboration](https://jobicy.com/jobs?search_keywords=Cross-functional%20Collaboration.md)[RevOps](https://jobicy.com/jobs?search_keywords=RevOps.md)[Customer Journey Mapping](https://jobicy.com/jobs?search_keywords=Customer%20Journey%20Mapping.md)[Stakeholder Management](https://jobicy.com/jobs?search_keywords=Stakeholder%20Management.md) Sample interview questionsHow would you build a proactive customer-success model for an SMB segment with a large account base?I would first segment customers by lifecycle stage, value, product usage, support volume, and risk indicators. I would define measurable health signals, then deploy automated onboarding, education, and intervention workflows with clear human-escalation paths. I would review retention, activation, time-to-value, and expansion outcomes regularly to refine the model. Describe how you have built or improved an AI agent or workflow for customer success. I start with a narrowly defined customer or operational problem and map the current workflow, inputs, decisions, and success criteria. I partner with technical stakeholders to create requirements, test the agent against real scenarios, monitor accuracy and customer impact, and iterate based on exceptions. I ensure that sensitive, complex, or high-risk cases have a clear human handoff. How would you identify early churn risk across the Commercial SMB portfolio? I would combine behavioral and operational indicators such as low product adoption, incomplete onboarding, declining engagement, repeated support issues, unresolved cases, payment-related signals, and changes in account activity. These indicators should be weighted into a practical health framework that triggers targeted outreach or automated guidance. I would validate that the signals predict churn by comparing them with historical retention outcomes. How do you influence Sales, Support, Marketing, and RevOps when you do not directly manage them? I create alignment around shared customer and business outcomes, use data to make problems visible, and translate customer evidence into actionable requests for each team. I establish clear ownership, decision points, and feedback loops so collaboration does not depend on informal follow-up. Consistently delivering useful insights and documenting results builds trust and influence over time. What metrics would you use to evaluate SMB onboarding and customer-success performance? I would track time to first value, onboarding completion, activation of key features, support-case volume and resolution trends, product adoption, customer health, retention, expansion, and customer sentiment. I would also measure the effectiveness of AI-assisted workflows through containment, escalation quality, accuracy, and impact on customer outcomes. The metrics should be segmented to reveal where particular cohorts are getting stuck. Opportunity details ## About this role. About Us: Wrapbook is the AI platform for production finance. We’re building a system of action that puts finance teams in control of their whole production, from payroll, to spend, to accounting. Built for feature films, TV, and commercials, Wrapbook is trusted by teams at Netflix, Paramount, Anonymous Content, and more. With backing from Andreessen Horowitz, Bessemer Venture Partners, and Jeffrey Katzenberg’s WndrCo, our team of 350+ is using AI to transform how finance teams work and empower them to do more with less. 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. This is a remote position open to candidates located in the United States or Canada. We are unable to sponsor or take over sponsorship of employment visas or work permits for this position. Applicants must be currently authorized to work in the country from which they will perform the work. Why Join Us At Wrapbook, creativity meets technology — and not just in the product. In addition to a competitive salary and all the benefits you can expect from a fast-growing technology company, you’ll get access to a team of creative problem solvers and the chance to see your contributions make large impacts. Benefits include: * 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 set up 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 Our Pledge to Fostering an Inclusive and Safe Workplace: Wrapbook pledges to be a harassment- and discrimination-free space for everyone, regardless of age, disability, ethnicity, gender identity or expression, nationality, neurotype, personal appearance, political affiliation, professional background, race, religion, or sexual identity or orientation. Apply Now Have we got your attention? Submit your application today and a member of our Talent team will be in touch with you shortly! #LI-Remote Show more [Apply now >](https://jobicy.com/jobs/157185-senior-smb-digital-success-lead-commercial.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. 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