Senior Manager, Enterprise Customer Success

Remote from: 🌐 Anywhere
Salary, yearly, USD: 111,000 - 150,000
Department: Customer Success
Employment type: Full Time,
Job posted: 22 Jul 2026
Apply before: 22 Aug 2026
Experience level: Senior
Views / Applies: 20 / 2

A technology platform that powers dispensary operations, while providing consumers with safe and easy access to cannabis

Computer Software
2017

AI Summary

Dutchie is seeking a Senior Manager of Enterprise Customer Success to lead and scale a high-performing team dedicated to top-tier retail and cannabis commerce partners. The role involves building scalable customer journeys, establishing rigorous QBR processes, and replicating best practices across the team. The ideal candidate is a process-driven leader with strong executive presence and experience in enterprise account management. This position offers the opportunity to shape the customer success function at a leading cannabis technology company. The role is based in the US and requires a mix of strategic thinking and hands-on execution.

Role DNA

Job Complexity

Easy Hard

Pace & Pressure

Relaxed Fast-paced

Autonomy Level

Guided Full Ownership

Communication Load

Independent Highly Collaborative

AI Insight The role demands advanced skills in team leadership, process design, and cross-functional collaboration, typical for senior management, but it is not the highest executive level, hence a difficulty of 4.

Salary Analysis

AI Insight The offered salary range of $111,000 - $150,000 is competitive for a Senior Manager, Enterprise Customer Success role in the US market. The median of $130,500 aligns well with industry standards for tech companies, especially considering the cannabis sector's growth. This compensation is attractive for candidates with experience in scaling customer success operations.

Core Skills Required

Customer Success Enterprise Account Management Team Leadership Process Improvement QBR Data Analysis Cross-functional Collaboration SaaS Strategic Planning Customer Retention

Cover Letter Sample

Dear Hiring Team,

I am writing to express my strong interest in the Senior Manager, Enterprise Customer Success position at Dutchie. With over 8 years of experience in customer success leadership, I have a proven track record of building scalable processes, driving revenue retention, and mentoring high-performing teams. My background in enterprise account management and cross-functional collaboration aligns perfectly with the needs of this role. I am excited about the opportunity to contribute to Dutchie's mission of powering the cannabis industry through technology. I look forward to discussing how my skills can support your team's goals.

Sample Interview Questions

Describe your experience in building and standardizing customer success processes from scratch. Can you give a specific example?

In my previous role, I implemented a QBR cadence for our enterprise accounts, standardizing the agenda, metrics, and follow-up actions. This led to a 20% increase in upsell revenue and a 15% decrease in churn. I documented the process in a playbook that was adopted across the team.

How do you identify and replicate best practices from top-performing CSMs across a team?

I regularly shadow top performers, analyze their strategies, and conduct debrief sessions. I then codify their approaches into templates and training modules. For example, I created a 'Power Playbook' for executive deck storytelling that improved overall team effectiveness.

How do you balance strategic leadership with hands-on execution in a fast-paced environment?

I prioritize setting clear goals and processes so the team can execute effectively. I stay involved in key escalations and QBRs to maintain a pulse, but I focus my time on coaching and scaling. For instance, I implemented a weekly 15-minute standup to align on priorities without micromanaging.

Describe a time you turned around a high-risk customer account. What steps did you take?

I identified a key account with declining usage and disengaged stakeholders. I held a crisis meeting, mapped the account to re-engage the executive sponsor, and created a 90-day success plan with measurable milestones. We regained trust and expanded the contract by 30%.

How do you foster a culture of continuous improvement within your team?

I encourage experimentation and regular feedback loops. For example, I implemented a 'retrospective' after each QBR to discuss what worked and what didn't. I also recognize team members who suggest process improvements and share their ideas company-wide.

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.

Apply now >