Head of Customer Success

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. Design and build the Customer Success organization across Onboarding, Customer Success, and Support .

Posted 10/22/2026full-timeNew York City • New York • United StatesLead💰 $170,000 - $210,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in building and managing Customer Success organizations, with a focus on onboarding, retention, and customer satisfaction. Proficient in developing scalable processes, playbooks, and leveraging AI tools to enhance customer engagement and operational efficiency.

Highest-signal resume keywords

Customer Success ManagementTeam LeadershipOnboarding ExperienceRetention ImprovementAI and Automation Tools

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Data MigrationProduct ConfigurationCustomer TrainingPlaybook DevelopmentDashboard Creation

Soft Skills

Clear CommunicationCoachingTeam Building

Tools & Technologies

HubSpotPylonIntercomLinearClaudeZapier

Industry Keywords

B2B SaaSVertical SaaSCustomer SegmentationAccount ManagementRenewal-Risk Monitoring

About the role

Key responsibilities & impact

Design and build the Customer Success organization across Onboarding, Customer Success, and Support
Grow the team from 5 to 10 people after the Series A
Define team structure, roles, customer segments, account loads, and specialization sequence
Hire, onboard, coach, and establish career paths for the team
Define handoffs from Sales through Onboarding, Customer Success, and Support
Improve the path from signed contract to go-live through kickoff, data migration, configuration, training, and launch
Create repeatable onboarding playbooks, migration templates, and import tooling
Define successful go-live criteria
Establish post-launch account management, segmentation, health scores, adoption plays, and renewal-risk monitoring
Own retention, run save plays for at-risk accounts, and partner with Sales on expansion
Develop customer references and case studies
Build dedicated Support with ticket triage, SLAs, escalation paths, and afternoon/evening coverage
Use AI and automation to reduce repetitive support work
Bring structured customer feedback and priorities to Product and Engineering
Build CS reporting and manage the team using data
Serve as the final escalation point for serious customer issues
Carry a personal customer book during the first 90 days before transitioning to full-time management
Report to the CEO and co-founder

Requirements

What you’ll need

6+ years in customer success, onboarding/implementation, or support at a B2B SaaS company
At least 3 years managing a team
Experience building or rebuilding a CS function at a Seed to Series B startup
Track record of improving retention and time-to-value for SMB customers at high account volume
Hands-on technical onboarding experience, including data migrations, product configuration, and customer training
Ability to build scalable playbooks, dashboards, and processes while remaining customer-facing
Clear, warm communication with non-technical small-business owners
Experience using AI and automation tools such as Claude and Zapier
Vertical SaaS experience, especially in education, enrichment, fitness, or appointment- and lesson-based businesses (nice to have)
Experience with payments or billing products (nice to have)
Familiarity with HubSpot, Pylon, Intercom, or Linear (nice to have)
Willingness to work in the New York City office in person 4 days a week
Expected availability for 50–60-hour weeks, some late nights, and occasional weekends

Benefits

Comp & perks

Annual target bonus of 15–20% of base salary
Meaningful stock option grant with 4-year vesting and a 1-year cliff
Work with a mission-driven product supporting small-business owners, educators, and local communities
Industry conferences and networking opportunities
Customer Success team-building events