Head of Customer Success (B2B SaaS)

Location: New York City, United States; hybrid, in person at the New York City office 4 days a week.

Base salary: $190,000–$240,000 plus a 15–20% performance-based bonus and 0.25%–0.5% equity. The detailed compensation section also lists a base salary of $170,000–$210,000 depending on experience, an annual 15–20% bonus, and a meaningful stock option grant with 4-year vesting and a 1-year cliff.

Company

hirify.global is an AI-native operating system for U.S. after-school businesses, including tutoring centers, music schools, sports academies, and dance studios. The platform combines scheduling, billing, payroll, marketing, CRM, communications, classroom management, and student and parent portals, using AI agents to automate manual work.

What you will do

• Own the entire post-sales function across onboarding, customer success, and support, including go-live volume, time to go-live, retention, and support quality.
• Grow the team from 5 to 10 people after the Series A and design roles, customer segments, account capacity, specialization, career paths, and handoffs across Sales, Onboarding, Customer Success, and Support.
• Improve onboarding through kickoff, data migration, configuration, training, repeatable playbooks, migration templates, import tooling, and clear go-live standards.
• Build account management with segmentation, health scores, adoption plays, renewal-risk detection, save plays, expansion collaboration, references, and case studies.
• Build dedicated support with ticket triage, SLAs, escalation to Engineering, afternoon and evening coverage, and AI-assisted automation for repetitive work.
• Bring customer feedback to Product and Engineering, build reporting, run the functions on data, and serve as the final escalation point. Carry a customer book during the first 90 days before moving into full-time management.

Requirements

• 6+ years in customer success, onboarding/implementation, or support at a B2B SaaS company, including at least 3 years managing a team.
• Experience building or rebuilding a Customer Success function at a Seed to Series B startup.
• A track record of improving retention and time-to-value for SMB customers at high account volume.
• Hands-on comfort with technical onboarding, including data migrations, product configuration, and customer training.
• Ability to build scalable playbooks, dashboards, and processes while continuing to speak with customers.
• Clear, warm communication with non-technical small-business owners.
• Current use of AI and automation tools such as Claude and Zapier to help a small team do more.

Nice to have

• Vertical SaaS experience, especially in education, enrichment, fitness, or other appointment- and lesson-based businesses.
• Experience with payments or billing products.
• Familiarity with HubSpot, Pylon, Intercom, or Linear.

Culture & Benefits

• Customer-focused environment with direct customer conversations, support calls, school visits, and industry conferences.
• Collaborative, low-ego decision-making with strong ownership of a mission-critical business function.
• Expected workload of 50–60 hours per week, with some late nights and occasional weekends.
• Hybrid work from the New York City office, in person 4 days per week.
• Performance-based annual bonus and stock options with 4-year vesting and a 1-year cliff.

Hiring process

• Introductory call with the hiring manager.
• Deep dive on a Customer Success organization built or rebuilt by the candidate.
• Case exercise covering the first 30, 60, and 90 days of structuring Onboarding, Customer Success, and Support.
• Customer role-play, followed by meetings with the founders and cross-functional colleagues.