AI-Driven Technical Support Lead for Enterprise

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

Benefits offered by this job

Health, dental, vision

Equity

401K

Meal & commuter benefits

Job summary

PointFive is seeking a Technical Support Lead to own enterprise support for our AI-driven platform. This role centers on designing an agentic solution to triage, diagnose, and resolve customer issues end to end, with ownership of the escalation process to Engineering.

The position is based in NYC and operates in a hybrid model. You will shape success metrics, build self-serve docs, and collaborate with Engineering and Product on recurring issues while feeding insights back to the product

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 & debugging

Customer-facing technical exp

End-to-end ticket ownership

Agent evals & QA

Clear writing for customers/engineers

Startup environment agility

AI support tooling (optional)

Tools

Pylon

Intercom Fin

Zendesk AI

Job description

PointFive is seeking a Technical Support Lead to own enterprise support for our AI-driven platform. This role centers on designing an agentic solution to triage, diagnose, and resolve customer issues end to end, with ownership of the escalation process to Engineering.

The position is based in NYC and operates in a hybrid model. You will shape success metrics, build self-serve docs, and collaborate with Engineering and Product on recurring issues while feeding insights back to the product