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Permitflow logo

Sr. Manager/Director, Customer Success (Midmarket)

PermitflowConstruction Tech company
New York, United StatesDirector
Accel logo
Accel
Kleiner Perkins logo
Kleiner Perkins
Felicis
Initialized Capital logo
Initialized Capital
Altos Ventures
Y Combinator logo
Y Combinator
Sales & Account Management

About the role

TL;DR

Lead and scale the midmarket Customer Success team to drive retention and advocacy.

  • PermitFlow is seeking an experienced Sr Manager/Director, Customer Success to lead, grow, and scale our midmarket Customer Success team.
  • Reporting directly to the VP, Customer Success, you'll own team performance, operational excellence, and the execution of success strategies that drive retention and advocacy across our midmarket book.
  • Key Responsibilities 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.
  • 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.
  • Experience in startup or high-growth environments, with a builder's mindset and bias toward action.
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Required skills

Customer SuccessSalesforceHubSpotRevenue OperationsCoachingMentoringExcelPowerPoint

Domain expertise

productivity

Benefits & perks

Competitive salary and meaningful equity, 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)

Tech stack

PythonJavaScriptTypeScriptSQLNode.jsReactAWSGoogle CloudAzureDockerKubernetesCI/CDGitJiraConfluenceSalesforceHubSpotExcelPowerPointGoogle AnalyticsGA4Looker StudioWorkdayGreenhouseLeverMarketo

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