Senior Manager, Enterprise Customer Success

About the role

Lead and develop a team focused on supporting Dutchie's most significant retail and cannabis commerce partners. This role requires a strategic thinker and meticulous executor to refine and scale customer success operations. You will be instrumental in elevating the enterprise customer success function through process innovation and team empowerment.

Key facts

What you'll do

• Guide and develop a group of Enterprise Customer Success Managers, focusing on high-value accounts.
• Identify successful strategies and behaviors from top performers and formalize them into repeatable processes for the entire team.
• Train the team on creating executive-level presentations and using data to drive consultative recommendations.
• Enhance the team's skills in strategic account management, executive communication, and navigating complex organizational structures.
• Design, implement, and refine scalable customer success workflows.
• Establish and manage a structured quarterly business review process to demonstrate value and identify growth opportunities.
• Define and monitor customer health metrics, focusing on predictive indicators of potential issues.
• Implement systematic account mapping and relationship management to ensure deep integration with partner ecosystems.
• Develop and execute proactive strategies to identify and mitigate customer churn risks.
• Collaborate with Sales to ensure smooth account transitions and coordinated strategies.
• Partner with Sales leadership to identify and pursue opportunities for account growth and cross-selling.
• Gather and communicate enterprise-level trends and product feedback to Product and UX teams.

Requirements

• A minimum of 8 years of experience in B2B SaaS customer success, account management, or strategic consulting.
• At least 3 years of direct experience managing enterprise-level customer success teams.
• A demonstrated history of successfully designing, launching, and ensuring adoption of new operational processes and team playbooks.
• Proven ability to create customer health scoring systems and use data analytics to forecast and prevent churn.
• Experience managing and growing a significant book of business, with a track record of team members managing books of at least $500k ARR.
• Exceptional organizational skills and a results-oriented approach to project management.
• Strong understanding of enterprise account mapping and managing relationships with multiple stakeholders at the executive level.
• Excellent written and verbal communication skills, with the ability to lead discussions and align diverse teams.
• Commercial understanding of renewal management, negotiation, and driving expansion revenue.

Nice to have

• Experience with Salesforce, customer success platforms like Gainsight, Totango, or ChurnZero, JIRA/Atlassian, and productivity suites such as Google Workspace or Microsoft 365.
• Previous management experience in retail technology, e-commerce, or the cannabis industry.
• A commitment to high-touch service and fostering a proactive, results-driven team culture.

Skills & tools

• Salesforce
• Customer Success Platforms (Gainsight, Totango, ChurnZero)
• JIRA/Atlassian
• Google Workspace/Microsoft 365

Practical notes

• Target starting salary range: $111,000 - $150,000.
• Comprehensive benefits package including medical, dental, and vision insurance.
• Stock options for all employees.
• Allowance for technology and professional development.
• Flexible paid time off policy.