# Sr. Manager/Director, Customer Success

**Company:** [Permitflow](https://hotfix.jobs/companies/permitflow)
**Location:** New York, NY
**Role:** Customer Success
**Salary:** $150k – $250k/yr
**Experience:** 8+ years
**Skills:** Customer Success, bi dashboards, customer health metrics, data-driven decision-making, internal communication, presentations, Coaching
**Posted:** 2026-07-30

> Lead and scale a team of 7 midmarket Customer Success Managers at PermitFlow. Own gross/net retention, adoption, expansion, and renewal while driving operational excellence, customer escalations, and cross-functional partnerships in a high-growth AI construction tech startup.

## Job Description

## What You'll Do
- Lead, mentor, and develop a team of 7 midmarket Customer Success Managers, fostering a high-performance, customer-centric culture.
- Own gross and net retention for the midmarket segment including adoption, expansion, and renewal.
- Set and refine the midmarket coverage model, segmentation, and engagement cadence as the book scales.
- Partner with CSMs to identify at-risk customers and deploy proactive success plans.
- Lead customer escalations and executive communications, ensuring fast resolution and strong outcomes.
- Ensure the team delivers measurable outcomes that align with both customer objectives and PermitFlow's business goals.
- Partner cross-functionally with leaders across Sales, Product, and Operations to improve the customer experience.
- Act as a champion of customer insights to inform strategic decisions and prioritization.

## Requirements
- 4+ years of experience in a people leadership position in Customer Success, including experience managing a team carrying a retention or revenue number.
- 8+ years of experience in Customer Success, with time spent in a midmarket segment.
- Strong analytical skills and comfort with BI dashboards, customer health metrics, and data-driven decision-making.
- Adept at producing clear documentation, thoughtful analysis, concise internal communication, polished presentations, and direct, effective coaching.
- Experience in startup or high-growth environments, with a builder's mindset and bias toward action.

## What We Offer (Full-Time Roles Only)
- Competitive salary and meaningful equity in a high-growth company.
- 100% company-paid base medical, dental, and vision coverage for employees + healthcare FSA.
- 401(k) savings plan.
- Unlimited PTO and paid family leave.
- Home office & equipment stipend.
- Daily in-office lunch and dinner provided.
- Commuter benefits (pre-tax transit and parking).

## Similar roles

- [Senior Manager/Director, Customer Success](https://hotfix.jobs/jobs/d116a912-e9af-404f-974b-741da5aa1383) - Permitflow - New York, NY - $150k – $250k/yr
- [Director of Partner Solutions](https://hotfix.jobs/jobs/fa8d9bf5-16ab-4e1e-b7e7-9d188d8080c6) - Ascertain - Remote - $150k – $195k/yr
- [Director of Customer Service, Enablement and AI](https://hotfix.jobs/jobs/8aeba7e4-50d2-43a9-a0d5-e83f04c69dd2) - Skylight - Remote - $150k – $185k/yr
- [Director of Customer Experience](https://hotfix.jobs/jobs/4e502fd5-985f-4c5d-965e-bc9f59ae0b3d) - Lightning AI - New York, NY - $155k – $220k/yr
- [Head of Customer Marketing](https://hotfix.jobs/jobs/21afc287-68e3-4321-ade5-a7f4f3c868e3) - Launchdarkly - Remote - $145k – $235k/yr

**Apply:** https://hotfix.jobs/jobs/acdc6892-9878-484c-b2e9-87ad10409612
**Canonical:** https://hotfix.jobs/jobs/acdc6892-9878-484c-b2e9-87ad10409612