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.
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!
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Skills Required
- 3+ years of experience in customer success or a similar customer-facing role
- Track record of owning customer retention and expansion outcomes
- Experience building, tuning, and operating AI agents and workflows
- Strong program ownership and process design experience
- Ability to design scalable systems serving an entire SMB customer base
- Cross-functional influence without authority and comfort with ambiguity
- Experience in commercial entertainment or FinTech
What We Do
Employers in media production and the entertainment industry are constantly hiring. Freelance employees move between projects and could get onboarded 30 or more times in a single year. And yet, much of the industry uses physical paperwork with no easy way to track payments, often struggling with compliance (due to ever-changing laws and union rules), and has few automation processes in place when it comes time to send payroll reports to their accountants. Wrapbook is an intuitive payroll and insurance solution for those balancing multiple projects. With digital solutions, simplified compliance, and comprehensive reporting, we take the stress away so employers and project-based workers can focus on the big picture. Commercial producers, filmmakers, and anyone creating media deserve robust solutions to meet their unique demands. With Wrapbook, you only have to ask for documents from cast and crew once. Our platform lets you move all the onboarding forms associated with any crew from a project to any future ones, giving you back hours. By swapping out paper timecards with digital ones, approving payroll is now a piece of cake. Crew can log into Wrapbook from any device to enter their hours and expenses. Providing producers with the right tools to onboard crew and process payments helps them put routine work on auto-pilot. That way, they can focus on more compelling tasks. Let us tackle paperwork, payroll, and insurance, so you can continue creating the work that matters.
