Senior Manager, Enterprise Customer Success

About This Job

As the Senior Manager of Enterprise Customer Success, you will lead, mentor, and scale a high-performing team of Enterprise Customer Success Managers (CSMs) dedicated to our highest-impact retail and cannabis commerce partners. You are not just a people manager; you are a master of process, a strategic operational architect, and a relentless executor who knows how to "get shit done".

Your mission is to level up our enterprise CS function. You will build, implement, and standardize scalable customer journeys, establish a rigorous Quarterly Business Review (QBR) operating cadence, and empower your team to turn complex retail operations into thriving, high-revenue accounts. We need a leader who can codify excellence—taking what our very best CSMs do in critical situations and replicating it across the entire team to ensure ultimate consistency. If you are incredibly organized, deeply process-driven, and know how to map enterprise accounts to drive massive value, we want you at the helm.

What You'll Do…

Team Leadership & Performance Elevation

• Coach & Mentor: Manage and upscale a team of high-touch Enterprise CSMs.
• Replicate Best Practices: Identify the strategies, playbooks, and behaviors of top- performing CSMs and turn them into standardized best practices to ensure consistency across the entire organization.
• Deck Building & Storytelling: Directly train and level up the team in executive-level deck building, teaching them how to use data to tell a compelling story that drives consultative recommendations.
• Skill Development: Elevate the team’s capabilities in strategic selling, executive presence, and navigating complex, multi-stakeholder enterprise environments.

Process Design & Operational Excellence

• Process Architecture: Build, implement, and continuously refine scalable, consistent CS processes from scratch to optimize customer-facing workflows and ensure internal operational agility.
• QBR Operating Cadence: Establish, standardize, and enforce a rigorous, high-impact Quarterly Business Review (QBR) framework that demonstrates clear ROI and uncovers growth levers.
• Account Health & Leading Indicators: Define, measure, and monitor comprehensive customer health metrics. Move beyond lagging data to identify early, leading indicators of potential churn.
• Account Mapping & Risk Mitigation: Drive a disciplined approach to account mapping and relationship management, ensuring CSMs are deeply embedded in partner ecosystems. Implement proactive risk mitigation protocols and playbooks to catch and save churn risks early.

Cross-Functional Collaboration & Commercial Alignment

• Sales & CS Partnership: ensure seamless handoffs, coordinated account mapping, and maximum conversion.
• Revenue & Expansion: Partner with Sales leadership to identify, track, and execute account expansion and cross-sell opportunities across our entire technology suite.
• Product Feedback Loop: Act as an internal champion, synthesizing high-level enterprise trends and product feedback into actionable insights for our Product and UX teams.

What You Bring...

• 8+ years of experience in B2B SaaS Customer Success, Account Management, or Strategic Consulting.
• 3+ years of direct people management experience, specifically leading enterprise-level CS teams.
• Process Implementation History: A proven track record of successfully designing, launching, and driving strict adoption of new internal operational processes and team playbooks.
• Data & Health Tracking Savvy: Demonstrated success in establishing customer health scoring systems and utilizing data analytics to forecast and prevent churn.
• Book Management: Proven track record of managing and growing a multi-million dollar ARR book of business (with individual team members previously managing $500k+ ARR books).

Key Competencies

• Hyper-Organization & Execution: A master of multi-tasking and project management who loves details, thrives in fast-paced environments, and consistently delivers results.
• Strategic Relationship Management: Deep understanding of enterprise account mapping, multi-stakeholder navigation, and building C-suite alignment.
• Master Communicator: Exceptional written and verbal communication skills; ability to command a room, resolve conflicts with poise, and align cross-functional teams.
• Commercial Acumen: Strong background in renewal management, commercial negotiations, and driving expansion revenue.

It’s a Bonus if You…

• The Tech Stack: Advanced proficiency with Salesforce (for book management/forecasting), CS Health Management platforms (Gainsight, Totango, ChurnZero, etc.), JIRA/Atlassian (for product alignment), and productivity suites (Google Workspace/Microsoft 365).
• Industry Savvy: Prior management experience in retail tech, e-commerce optimization, or the cannabis commerce ecosystem is a massive plus.
• The "White Glove" Benchmark: A dedication to high-touch, premium service and the ability to instill a "whatever it takes" mindset into a growing team.

You’ll Get…

We are targeting a starting salary of $111,000 - $150,000 based on the intended level for this role.

In addition to cash compensation, our total rewards package includes:

• Full medical benefits including dental and vision plans to ensure you always have the best care.
• Equity packages in the form of stock options to all employees.
• Technology (hardware, software, reading materials, etc..) allowance
• Flexible vacation and sick days