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About the Role
Pylon is seeking a Head of Customer Success to lead and scale the post-sales organization. This strategic role involves growing the team, driving customer adoption of agentic support, and establishing Pylon as a thought leader in the AI-driven customer success space.
Responsibilities
- Own NRR, GRR, and churn, including weekly forecasting to the board.
- Drive cross-sell and upsell initiatives to meet quarterly expansion goals.
- Manage the commercial system, including goal setting, pipeline reviews, renewal motions, deal approvals, and compensation design.
- Lead the deployment and usage of Agentic Support across the customer base.
- Oversee the customer migration to usage-based billing, driving adoption and successful transitions.
- Develop and implement strategies for AI's impact on the customer success role.
- Scale the Customer Success organization across multiple offices, including hiring and developing managers.
- Design customer segments (Enterprise, Mid-Market, Scaled) and manage capacity planning.
- Own the Sales to CS relationship, including qualification criteria and customer expectations.
- Lead dogfooding and Championship programs, ensuring internal mastery of Pylon workflows.
- Utilize Pylon daily to shape product development.
- Represent Pylon externally through speaking, writing, and community engagement.
Requirements
- Ability to manage strategic and hands-on tasks fluidly.
- Proven track record of owning and exceeding NRR, GRR, and expansion targets at scale.
- Experience leading managers and developing talent within a Customer Success organization.
- Experience scaling systems that are already functional.
- Enthusiasm for managing a large account base.
- Demonstrated interest or experience in public speaking, writing, or building in the customer success domain.
- Proficiency with AI agents in personal workflows and ability to credibly demo Pylon's capabilities.
- Strong point of view on agentic customer success.
Skills
- Customer Success Management
- Revenue Operations (NRR, GRR, Churn)
- Sales Operations
- Team Leadership
- Manager Development
- AI/Agentic Support
- Usage-Based Billing
- Cross-selling and Upselling
- Forecasting
- Public Speaking
- Content Creation
- Community Engagement
Location
- San Francisco
- Remote (for EMEA team experience)
- London
- NYC
Work Type
- Full-time
- Onsite (San Francisco)
Experience Level
- 5+ years in post-sales
- 2+ years leading customer success organizations
- Managing managers in an org of 15+ people
Benefits
- Fully covered medical, dental, and vision insurance
- 401(k) retirement plan
- Commuter benefits
- Parental leave
- 14 company holidays + unlimited PTO
- Annual offsite
- Lunch, dinner, and snacks at the office
- Fitness stipend
About the Company
- Pylon is the only agentic support platform, purpose-built for B2B companies.
- Pylon enables humans and agents to collaborate on customer work, investigating, resolving, and acting on every signal across every channel.
- Pylon enriches interactions with deep account-level context, automates low-impact customer work, and surfaces answers proactively.
- Backed by a16z, BCV, General Catalyst, and Y Combinator.
- Over 1,500 companies, including Linear, Cognition, Modal Labs, and Incident.io, use Pylon.
- Featured on the Enterprise Tech 30 List.