Senior Customer Success Manager

About Toolio

At Toolio, we’re on a mission to help retailers navigate the complex, competitive, and ever-changing retail landscape so they can deliver what their customers want—when and where they want it. Merchandise planning is one of the most critical retail disciplines, yet it has long been dominated by manual, error-prone spreadsheets. As inventory risk continues to rise, accurate, agile planning has never been more important.

Toolio’s cloud-based merchandise planning platform helps next-generation retailers automate critical workflows, gain real-time insights, and make faster, data-driven merchandising decisions. Toolio is trusted by 100+ leading brands and retailers including Rothy’s, Knix, Filson, Tommy John, Peloton and more.

The Opportunity

We are hiring a Senior Customer Success Manager to own customer outcomes after go-live. This role is accountable for driving product adoption, measurable value, retention readiness, and long-term customer health across a portfolio of retail customers.

As a Senior CSM, you “own the journey” once a customer is live on Toolio. You will act as a trusted advisor to retail operators and functional leaders, ensuring customers fully adopt Toolio, realize ROI, and continuously mature their planning workflows. You will partner closely with Account Management (Sales), who owns renewals and commercial negotiations, to support expansion and long-term growth.

This is a senior, highly visible role that blends retail planning expertise, customer success leadership, and operational rigor.

You will report to Toolio’s VP of Customer Success and work closely with Customer Support, Sales, Product, and Engineering.

What You’ll Do

Own Post–Go-Live Customer Success

• Own the post–go-live customer lifecycle, including adoption, success planning, optimization, retention readiness, and ongoing value realization.
• Serve as the primary owner of customer health, outcomes, and satisfaction.
• Maintain clear success plans tied to customer goals, KPIs, and business outcomes.

Drive Adoption & Value Realization

• Monitor usage health, adoption trends, and engagement signals across accounts.
• Proactively identify risks (e.g., declining usage, stalled workflows, organizational changes) and drive mitigation plans.
• Coach customers on best practices across Toolio workflows, translating retail planning concepts into effective product usage, working in partnership with our Value Development team.
• Document and communicate ROI, impact metrics, and customer wins internally and externally.

Strategic Customer Engagement

• Own day-to-day relationships with customer operators and functional leaders.
• Lead regular operator check-ins with clear agendas, action items, and documented outcomes.
• Lead Monthly / Quarterly Business Reviews (MBR / QBRs) focused on adoption, KPIs, ROI, and future success plans.
• Partner with Account Managers in executive QBRs—CSM presents value and outcomes; AM frames future partnership and growth.

Partner with Customer Support

• Collaborate closely with Customer Support to ensure issues are resolved efficiently.
• Review open support tickets, escalate high-priority issues, and identify recurring themes impacting adoption.
• Feed insights back into success plans, enablement materials, and product feedback loops.

Customer Advocacy & Feedback

• Collect structured customer feedback and advocate internally as the voice of the customer.
• Contribute to customer advocacy efforts including case studies, references, referrals, and success stories.
• Share insights with Product and Engineering to inform roadmap and prioritization.

Cross-Functional Collaboration

• Partner with Account Managers on account strategy, renewal readiness, and expansion signal identification (CSM supports; AM owns the deal).
• Share customer health, usage insights, and risk signals cross-functionally.
• Maintain accurate CRM documentation and success reporting.

What We’re Looking For

Experience & Background

• 5+ years of experience in Customer Success, Consulting, or a related customer-facing role in a SaaS environment.
• Strong retail planning or merchandising background (e.g., merchandise planning, buying, allocation, inventory management, planning systems).
• Experience owning post–go-live customer relationships with accountability for adoption and retention.

Skills & Capabilities

• Deep understanding of customer health, adoption metrics, and value realization frameworks.
• Strong analytical and problem-solving skills, with comfort using usage data to drive action.
• Excellent written, verbal, and presentation skills—able to communicate clearly wi