VP of Customer Success

Company Overview

We’ve partnered with a fast-growing B2B SaaS company that creates an all-in-one commerce platform for retail operators within the regulated cannabis market. Their product suite encompasses various solutions including POS, Payments, eCommerce & Delivery, CRM, Loyalty & Marketing, Inventory, and Business Intelligence. The company has recently undergone an organizational refresh and is focused on efficiently scaling into the SMB and multi-store operator segments.

Role Overview

We’re seeking a strategic and operationally strong VP of Customer Success to lead the combined Customer Experience organization, which includes Customer Success, Technical Support, and Implementation teams. This leader will report directly to the CEO and will be an integral part of the executive team, responsible for overseeing the post-sales experience from onboarding through renewals and expansions.

Responsibilities

• Lead the Customer Success, Technical Support, and Implementation teams (approximately 20 total, including 3 Directors).
• Own and enhance key metrics such as Net Revenue Retention (NRR), churn, Customer Satisfaction (CSAT), and Net Promoter Score (NPS).
• Design and implement scalable processes for onboarding, renewals, and customer expansion.
• Drive cross-functional alignment across Sales, Product, and Marketing to ensure a seamless customer journey.
• Transform the Support team from a reactive unit to a proactive, insights-driven organization.
• Establish tiered Service Level Agreements (SLAs), escalation frameworks, and feedback loops between Customer Experience and Product.
• Develop playbooks, reporting systems, and leadership structures to support the company’s growth phase.
• Champion customer advocacy and retention through measurable outcomes and storytelling.

Requirements

• 12+ years of progressive experience leading Customer Success, Technical Support, or Professional Services in B2B SaaS.
• 5+ years in an executive leadership role (VP or above) managing multi-functional, customer-facing teams.
• Proven success in enhancing retention and expansion at scale.
• Strong operational insight with a history of designing organizations and systems that can scale.
• Executive presence with excellent communication and influencing skills.
• In-depth knowledge of customer lifecycle management, onboarding frameworks, and renewal processes.
• Familiarity with SaaS tools such as Salesforce, Gainsight, HubSpot, Intercom, or Zendesk.

Benefits

• Competitive Salary + Bonus.
• Comprehensive health, dental, and vision coverage.
• Flexible, remote-first work environment.
• Generous PTO and a professional development stipend.
• Opportunity to shape the customer experience at one of the fastest-growing technology companies in the cannabis sector.