About this role.
This Customer Success Manager role at Dutchie focuses on owning customer health, retention, and churn risk for SMB dispensary customers. Working within a pod structure alongside Account Managers, the CSM proactively monitors account signals, identifies at-risk accounts early, and creates save plans to ensure successful renewals. The role is highly collaborative, requiring coordination with Support, Implementation, Solutions, Engineering, and Product teams. Candidates should have 3–5 years of SaaS customer success or account management experience, with a strong emphasis on churn management and proactive engagement.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
3/5Pace & Pressure
4/5Autonomy Level
4/5Communication Load
5/5Salary analysis
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Core skills
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Customer Success Manager position at Dutchie. With over four years of experience in SaaS customer success, I have a proven track record of reducing churn and driving retention through proactive relationship management. I thrive in collaborative, pod-based environments and am skilled at aligning cross-functional teams to resolve customer issues quickly. I would welcome the opportunity to contribute to Dutchie's mission of supporting the cannabis industry through technology.
Thank you for your consideration.
Sample interview questions
In my previous role, I monitored usage metrics and engagement signals to identify at-risk accounts early. I would then create save plans, involve the Account Manager for renewal discussions, and track progress to ensure we resolved issues before cancellation.
I use a risk scoring system based on severity and impact. I first address accounts with the highest revenue impact or imminent renewal dates, while keeping clear documentation for all others. I also proactively set up alerts to catch issues early.
I start by understanding their business goals and current pain points. I schedule onboarding check-ins, provide best practices, and ensure they know I am their advocate within the company. Consistency and responsiveness are key to building trust.
I once had a customer experiencing a recurring technical issue. I logged the issue with support, escalated to product with clear impact metrics, and kept the customer informed throughout. I also arranged a workaround to minimize disruption, which helped renew their contract.
I am passionate about the positive impact cannabis businesses have on local communities, and Dutchie is a leader in this space. The pod-based model is exciting because it emphasizes shared success and proactive customer health, which aligns perfectly with my strengths.
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 an SMB Customer Success Manager (CSM) at Dutchie, you’ll be part of an Account Team — partnered with Account Managers in a pod structure — focused on making sure our dispensary customers are successful as a business. Account health, retention, and churn risk ownership are at the core of what we do. In Dutchie’s model, Account Managers own the commercial relationship — renewals, pricing, and expansion — while CSMs own the churn lifecycle and customer health: identifying risk early, building save plans, and setting Account Managers up to win renewals well before the selling motion begins. CSMs pull context together across our internal teams (Support, Implementation, Solutions, Engineering, and Product) so customers always have someone keeping track of feedback, open requests, and high-priority issues. The focus is proactive risk mitigation, not reactive support — CSMs are not a ticket queue, and we protect that line deliberately.
What You’ll Do…
- Operate as part of an Account Team pod, partnering closely with Account Managers on account strategy — you own customer health and the churn lifecycle; they own renewals and commercial growth.
- Own the renewal runway: monitor accounts in the 90-day renewal window, flag at-risk accounts early, and have save plans in motion so Account Managers enter renewal conversations with no surprises.
- Manage churn risk end to end — triage, mitigation strategy, and resolution — partnering cross-functionally to remove blockers.
- Proactively monitor account health signals (engagement, product usage, billing indicators) and act on them before they become escalations.
- Pull context together across Product, Support, Sales, Solutions, and Implementation so customer feedback, open requests, and high-priority issues never go unanswered.
- Act as a strategic resource for customers — sourcing answers, guiding best practices, and finding paths (features, early-access programs, alternative solutions) when customers are stuck on a problem.
- Contribute to process improvements and team initiatives as we build out our pod operating model.
- Meet or exceed team KPIs: same-day customer response, quarterly engagement on every account, and pod-level net revenue retention.
What You Bring…
- 3–5 years of experience in Customer Success, Account Management, or a related client-facing role (SaaS or technology industry preferred).
- Experience managing churn risk and retention motions — you’ve owned saves, not just flagged them.
- Comfort operating in a shared-accountability model where your performance is measured alongside a team (pod-level metrics), with growing autonomy in commercial conversations.
- Strong technical aptitude and problem-solving skills; able to source or solution answers independently.
- Excellent communication, organizational, and prioritization abilities — you can run multiple active risk situations without dropping threads.
- Experience collaborating with cross-functional teams (Product, Support, Sales, Implementation).
- Proactive, ownership-driven approach with a focus on continuous improvement.
- Knowledge of the cannabis industry is a plus, but not required
You’ll Get…
We are targeting a starting salary of $55,000 – $75,000 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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