AI Support Lead for Enterprise & Automation

PointFive, Inc.; New York (NY); Hybrid; USD 130,000 - 175,000; Full time

Benefits offered by this job

Equity

Generous PTO

401K

Meal & commuter benefits

Health, dental, vision

Job summary

PointFive, Inc. is hiring its first Technical Support Lead to own enterprise support end-to-end. You will design an agentic solution, measure success, and escalate to Engineering when needed, all while building a self-serve knowledge base.

The role is based in NYC hybrid, with a focus on transforming how customers are supported using AI-driven tools and integrated APIs. You will shape support strategies and partner with Product and Engineering to reduce friction for enterprise clients.

Qualifications

• Shipped AI agents or LLM-powered tools with real users.
• Hands-on experience integrating and debugging APIs, webhooks, and data sources.
• 3 - 5 years customer-facing technical experience (support, solutions, or forward deployed engineering)
• Hands-on experience running technical support day to day, owning issues end to end from first response to resolution.
• Built evals to measure agent quality before and after shipping.
• Clear, concise writing for both customers and engineers.
• Ability to operate in a startup environment: adaptable, self-directed, and resourceful.

Responsibilities

• Design and build an agentic solution to resolve customer tickets end to end, from first response through diagnosis and resolution.
• Define what success looks like and build the measurement layer to track it (time to first response, time to resolution, CSAT).
• Work the escalations your agents can't solve yet, then teach the system to handle them next time.
• Partner with Engineering and Product on recurring issues, routing confirmed bugs to Engineering's coding agents with the context needed to fix them.
• Turn resolved tickets into self-serve documentation customers can use on their own.
• Feed support trends back into the product roadmap.

Skills

Shipped AI agents

API integration

Customer-facing tech experience

Issue triage & escalation

Documentation writing

Startup adaptability

Tools

Pylon

Intercom Fin

Zendesk AI

Job description

PointFive, Inc. is hiring its first Technical Support Lead to own enterprise support end-to-end. You will design an agentic solution, measure success, and escalate to Engineering when needed, all while building a self-serve knowledge base.

The role is based in NYC hybrid, with a focus on transforming how customers are supported using AI-driven tools and integrated APIs. You will shape support strategies and partner with Product and Engineering to reduce friction for enterprise clients.