About this role.
Dutchie is seeking a Senior Manager to lead and develop an enterprise Customer Success team serving high-impact retail and cannabis-commerce partners. The role owns scalable CS process design, including QBR standards, customer-health scoring, account mapping, churn-risk mitigation, and executive-level storytelling. It also requires close partnership with Sales, Product, and UX to drive renewals, expansion, and actionable product feedback. Candidates need substantial B2B SaaS customer success or account-management experience, direct enterprise-team leadership, and demonstrated ownership of multi-million-dollar ARR portfolios. This is a commercially oriented people-management role with high expectations for operational rigor and execution.
Role DNA
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Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
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Core skills
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Sample interview questions
I begin by identifying the repeatable behaviors of top performers through call reviews, account plans, QBR materials, and outcome data. I convert those behaviors into practical playbooks, templates, training sessions, and manager coaching routines, then monitor adoption through leading indicators and customer outcomes.
I would combine product adoption and usage depth, support trends, executive engagement, renewal timing, commercial risk, sentiment, implementation milestones, and relationship coverage. The model should use both quantitative signals and structured CSM judgment, with clear intervention thresholds and ownership for recovery plans.
A strong QBR starts with the customer’s stated business objectives and uses relevant data to demonstrate realized value, adoption progress, risks, and future opportunities. I coach CSMs to make the conversation executive-ready, agree on measurable next steps, and document owners and dates so the QBR drives action rather than becoming a reporting exercise.
I establish shared account plans, clear handoff rules, and recurring pipeline reviews centered on verified customer value and readiness. Customer Success should surface needs and outcomes, while Sales leads the commercial motion; both teams remain aligned on timing, messaging, and the customer’s success criteria.
I would describe a situation where health signals and stakeholder feedback identified risk before the renewal deadline. I would explain how I built an executive account map, diagnosed root causes with internal partners, created a time-bound recovery plan, communicated transparently with the customer, and tracked progress through renewal and adoption results.
About Dutchie
Founded in 2017, Dutchie is a comprehensive technology platform powering dispensary operations, while providing consumers with safe and easy access to cannabis. Dutchie aims to further support the positive societal change the cannabis industry brings to the world through wellness benefits, social justice, and empowering local communities through tax revenue. Powering thousands of dispensaries across 40+ markets throughout the United States and Canada, Dutchie is the leading technology company in the cannabis space and was named in Fast Company’s 10 Most Innovative Companies in North America and listed two years in a row on LinkedIn’s Top 50 Startups.
Dutchie has raised over $600M in funding to date, backed by D1 Capital Partners, Tiger Global, Dragoneer, DFJ Growth, Thrive Capital, Howard Schultz, Snoop Dogg’s Casa Verde Capital, Gron Ventures, members of the founding team at DoorDash, Kevin Durant’s Thirty Five Ventures, and other notable angel investors.
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
At Dutchie, we’re committed to providing an environment of mutual respect where equal employment opportunities are available to all applicants and teammates 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. Dutchie believes that diversity and inclusion among our teammates is critical to our success, and we seek to recruit, develop and retain the most talented people from a diverse candidate pool.
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