Senior Manager, Enterprise Customer Success

About This Opportunity

Our talent team at Get A Job.ai is representing a well-funded cannabis technology platform serving dispensaries across North America. We're seeking a Senior Manager, Enterprise Customer Success to lead and scale their high-performing enterprise CS team. This is a remote position based in the USA.

This role is for a strategic operational leader who excels at building scalable processes from the ground up. You'll be responsible for establishing rigorous customer success frameworks, standardizing best practices across the team, and driving measurable impact for the organization's highest-value retail partners. If you're incredibly organized, process-driven, and know how to replicate excellence across an entire function, we want to speak with you.

Responsibilities

• Lead and develop a team of Enterprise Customer Success Managers supporting high-impact accounts, providing coaching, mentorship, and performance management
• Design and implement scalable customer success processes, workflows, and playbooks to ensure consistency and operational excellence across the enterprise CS function
• Establish a rigorous QBR operating cadence that demonstrates clear ROI, uncovers growth opportunities, and strengthens executive-level client relationships
• Build comprehensive customer health frameworks including leading indicators, account mapping protocols, and proactive risk mitigation strategies to prevent churn
• Replicate top performer behaviors by identifying and codifying the strategies of your best CSMs into standardized best practices for the entire team
• Train the team in executive storytelling and data-driven deck building to deliver compelling, consultative recommendations to C-suite stakeholders
• Partner cross-functionally with Sales, Product, and UX teams to ensure seamless handoffs, coordinate account expansion opportunities, and synthesize enterprise feedback
• Drive revenue growth by identifying and executing expansion and cross-sell opportunities across the technology suite
• Manage multi-million dollar ARR portfolios across your team while maintaining high retention and satisfaction rates

What We're Looking For

Required Experience and Skills:

• 8+ years of experience in B2B SaaS Customer Success, Account Management, or Strategic Consulting
• 3+ years of direct people management experience leading enterprise-level CS teams
• Proven track record of designing, launching, and driving adoption of new operational processes and team playbooks
• Demonstrated success establishing customer health scoring systems and utilizing data analytics to forecast and prevent churn
• Experience managing and growing multi-million dollar ARR portfolios (with team members managing $500k+ individual books)
• Exceptional organizational skills with ability to manage multiple priorities in fast-paced environments
• Deep expertise in enterprise account mapping, multi-stakeholder navigation, and C-suite relationship building
• Outstanding written and verbal communication skills with ability to command executive-level conversations
• Strong commercial acumen including renewal management, negotiations, and expansion revenue strategies

Bonus Qualifications:

• Advanced proficiency with Salesforce, CS health management platforms (Gainsight, Totango, ChurnZero), JIRA, and productivity suites
• Management experience in retail technology, e-commerce, or cannabis commerce sectors
• Track record of delivering high-touch, premium service and instilling a "whatever it takes" mindset in teams

How We Work With You

When you apply through Get A Job.ai, one of our experienced recruiters will review your qualifications and conduct an initial screening conversation. If there's a strong match, we'll submit your profile to our client for consideration. Throughout the interview process, we'll provide guidance and support to help you succeed.

Important: Please apply exclusively through Get A Job.ai. Do not attempt to contact the client directly, as this may disqualify your application.

Compensation and Benefits

Our client is targeting a starting salary of $111,000 - $150,000 based on experience and qualifications. The total rewards package also includes:

• Comprehensive medical, dental, and vision coverage
• Equity compensation in the form of stock options
• Technology allowance for hardware, software, and professional development materials
• Flexible vacation and sick time

Equal Employment Opportunity: Get A Job.ai is committed to providing equal employment opportunities to all applicants without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other characteristic protected by law.