Customer Success Director
Stuut
Chicago, IL · $220k–$300k a year · Posted September 28, 2026
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Where Chicago, IL ranks
Where Chicago, IL placed in our monthly rankings, month by month. Each month stays online at its own address.
November 2026
- #1Best cities for government pay after cost of living$146k · of 18
- #1Cities with the most jobs that do not need a four-year degree in the Midwest684 jobs · of 51
- #1Cities with the most jobs that do not need a four-year degree in the Great Lakes684 jobs · of 36
- #1Best cities for software and engineering jobs in the Midwest1,140 openings · of 59
- #1Best cities for software and engineering jobs in the Great Lakes1,140 openings · of 48
- #1Best all-round cities for mid-career professionals in the Midwest80 / 100 · of 20
Rankings about customer success jobs
- Best cities for customer success jobs #1 New York (367 openings)
- Employers with the most customer success jobs #1 Gallagher (167 roles)
Customer Success jobs · Top Customer Success employers · All rankings
How AI is used in this kind of work
AI use among sales managers is little observed so far. Measured exposure for sales managers: 4% (little observed).
Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.
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About the job
ABOUT STUUT
Stuut is the AI coworker that runs order-to-cash for the world’s leading enterprises. Across order management, credit, collections, payments, cash application, disputes and deductions, Stuut does the work end to end and keeps going until the cash hits the bank.
Over 150 companies, spanning the mid-market to the Fortune 50, including Honeywell, ZoomInfo and PerkinElmer, use Stuut to unlock up to 40% more cash flow and cut DSO by 47%. More than $3 billion has moved through the platform to date.
Founded in New York by Tarek Alaruri and Ben Winter, Stuut has raised $93 million from Insight Partners, Andreessen Horowitz, M12, Microsoft’s Venture Fund, and others. Learn more at stuut.ai http://stuut.ai.
The Customer Success Director will own a book of accounts post-sale through renewal and expansion. You are the primary relationship owner: driving adoption, protecting retention, and finding expansion paths tied to the customer's AR outcomes (DSO reduction, cash application accuracy, dispute cycle time)
RESPONSIBILITIES
- Own onboarding through steady-state for an assigned account portfolio.
- Drive product adoption against each customer's stated business outcomes, not feature checklists.
- Run QBRs: outcomes delivered, ROI, expansion opportunities.
- Own renewal forecasting and GRR for your book; flag churn risk early with a clear reason and remediation plan.
- Identify and pursue expansion (upsell, cross-sell across Stuut products) in partnership with Sales.
- Escalate technical or implementation issues to FDE/Support with clear context; stay accountable for resolution from the customer's side.
- Maintain accurate account health data in Vitally.
WHAT SUCCESS LOOKS LIKE
- GRR and NRR targets met for your book (org target: NRR >110%).
- Onboarding velocity and time-to-value hit target.
- Clean, current account records; no surprises in forecast.
REQUIREMENTS
- 4+ years in Customer Success or Account Management at a B2B SaaS company, ideally fintech or finance-workflow software.
- Track record owning renewal/expansion numbers, not just satisfaction scores.
- Comfortable with ambiguity: this is a growth-stage company building CS process as it scales.
- Financial/AR domain fluency a plus, not required.
- Excellent written and verbal communication; comfortable running exec-level QBRs.
US Compensation
- Top-of-market salary and equity package
- Benefits (for U.S.-based full-time employees)
- Medical, dental & vision insurance coverage for you
- 401(k) & Match
- Equity
- Flexible PTO
- Parental Leave
Stuut is an equal opportunity employer committed to building a team with diverse backgrounds, perspectives, and experiences. We do not discriminate based on race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, genetic information, or any other characteristic protected by applicable law.
We are also committed to providing reasonable accommodations throughout the application and interview process. If you need any accommodations, please do not hesitate to reach out.