Head of Customer Success

Full time · Reports to Founder

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UpsellPlus helps Shopify brands increase their average order value and conversion rate through intelligent product recommendations and upsells.

More than 300 brands use our products across millions of orders. Our ideal customers are Shopify Plus and larger Shopify brands, particularly in beauty, health, supplements, food, apparel, and home.

We have strong products, demanding customers, and a customer success team of three. We are hiring a leader to turn that team into a measurable customer-retention and revenue operation.

Our current team provides onboarding, support, and ongoing assistance across our products. The next step is to build a complete customer success system around it.

We need every customer to have a clear owner, health status, onboarding journey, engagement cadence, and retention plan. We need to identify churn risk before a cancellation request arrives. We also need to connect customer activity to commercial outcomes: activation, adoption, retention, expansion, and net revenue retention.

This is a player-coach role. You will lead and develop the team, but you will also work directly with important customers, handle escalations, inspect the data, and build the operating system yourself.

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Within your first 90 days, you will:

• Establish trustworthy baselines for logo retention, gross revenue retention, net revenue retention, MRR churn, activation, onboarding time, response time, and customer health.
• Give every customer a documented segment, owner, health status, lifecycle stage, and next action.
• Implement a consistent onboarding process with clear activation milestones.
• Ensure eligible managed customers can launch within our existing 24-hour service commitment once required access and assets are available.
• Establish a proactive engagement cadence, including contact every 6–12 weeks based on account segment.
• Create a weekly at-risk account review with named owners and recovery actions.
• Create an accurate churn-reason system that distinguishes product, customer-fit, implementation, support, pricing, and involuntary churn.
• Introduce team quality reviews, coaching, role expectations, and individual scorecards.
• Reduce preventable gross MRR churn by at least 20% compared with the normalized prior 90-day baseline.
• Build a documented expansion process and begin producing attributable expansion opportunities from the existing customer base.

By day 30, we expect accurate baselines. By day 60, the new operating system should be running. By day 90, it should be producing measurable improvements.

“Setting up the system” is not the final result. The system must change customer behavior and revenue outcomes.

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Retention and customer economics

• Own gross revenue retention, net revenue retention, logo retention, and preventable churn.
• Establish targets once the initial data baseline has been validated.
• Maintain an accurate view of revenue at risk.
• Ensure every meaningful cancellation is reviewed and categorized.
• Identify the interventions most likely to improve retention.
• Report results and corrective actions, not just customer activity.

Onboarding and activation

• Define what successful activation means for each product and customer segment.
• Build an onboarding process that gets merchants to value quickly.
• Remove bottlenecks involving access, implementation, configuration, or unclear ownership.
• Track customers that stall before activation and intervene.
• Create appropriate high-touch and scaled onboarding paths.

Proactive customer success

• Segment customers based on value, potential, complexity, and risk.
• Create a clear contact cadence for each segment.
• Ensure strategic customers receive recommendations tied to AOV, conversion, adoption, and revenue.
• Introduce useful business reviews for appropriate accounts.
• Create playbooks for low adoption, declining performance, stakeholder change, renewal risk, and expansion.

Support operations

• Maintain fast live-chat coverage without allowing speed to replace quality.
• Establish response, resolution, escalation, and follow-up standards.
• Improve handoffs between shifts and teams.
• Identify recurring issues and remove their root causes.
• Build self-service resources where they materially improve customer outcomes.
• Ensure critical issues have clear ownership and customer communication.

Team leadership

• Lead, coach, and develop the existing customer success team.
• Define responsibilities and measurable scorecards for each role.
• Review conversations, calls, onboarding outcomes, account plans, and churn events.
• Address performance problems directly and promptly.
• Hire or restructure only when the operating data demonstrates a genuine need.
• Create a culture of ownership instead of escalation and dependency.

Customer expansion

• Identify customers that could obtain more value from additional products, features, or service levels.
• Build a consistent process for identifying and qualifying expansion opportunities.
• Coordinate with the founder or sales owner where commercial negotiation is required.
• Measure expansion MRR attributable to customer success.
• Avoid forcing inappropriate upsells that damage trust or retention.

Voice of the customer

• Convert customer feedback into structured product intelligence.
• Distinguish isolated requests from recurring, commercially important problems.
• Work directly with product and engineering on prioritization.
• Close the feedback loop with customers.
• Ensure product decisions are informed by customer evidence rather than anecdotes.

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• You have built or materially improved customer success at a SaaS company.
• You have owned retention or net revenue retention, not only satisfaction or ticket metrics.
• You have led and developed a small customer-facing team.
• You are comfortable working directly with demanding, commercially important customers.
• You can build operating systems without creating unnecessary bureaucracy.
• You understand onboarding, adoption, support, renewals, expansion, and churn as one connected lifecycle.
• You are analytical enough to find the truth in imperfect customer and revenue data.
• You can move between an executive customer conversation, a difficult coaching discussion, and a spreadsheet without losing effectiveness.
• You communicate directly, calmly, and clearly.
• You take responsibility for solving constraints within your control.

Shopify or ecommerce experience is strongly preferred. Experience with SMB or mid-market SaaS, usage-based products, app ecosystems, or conversion optimization is valuable.

This role is probably not for you if

• You want to manage from a distance rather than work directly with customers.
• Your idea of customer success is primarily responding to support tickets.
• You report NPS and activity metrics without connecting them to retention and revenue.
• You need a dedicated operations team before you can create reliable reporting.
• You treat low adoption or churn as someone else’s problem.
• You avoid difficult performance conversations.
• You build elaborate processes before validating that they improve customer outcomes.
• You explain missed targets without presenting a corrective plan.

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• Leaders remain close to the work.
• Ownership includes the result, not only the activity.
• Transparency and direct communication are expected.
• We prefer simple systems that people actually use.
• Progress matters more than ceremony.
• AI should improve team speed and customer intelligence while preserving judgment and human accountability.

Please submit your resume or LinkedIn profile and answer:

1. What retention, churn, or net revenue retention metric have you personally owned?
2. What was the starting point, what did you change, and what measurable result followed?
3. Describe a customer success system you built rather than inherited.
4. Tell us about a team member whose performance you materially improved, or a difficult personnel decision you had to make.
5. What would you inspect during your first 30 days at UpsellPlus?

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