Technical Support Lead

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

About PointFive

PointFive finds the cost buried inside enterprise infrastructure, from the cloud to coding agents. We pioneered DeepWaste across cloud and data platforms, and we are now doing the same for AI token spend with TokenShift.
Fanatics, H&M, Hertz, Nubank, Citizens Bank and other Fortune 500 companies use PointFive to see and cut what their infrastructure and AI actually cost.

We have raised $96 million, most recently a $60 million Series B led by Accel. Engineering sits in Tel Aviv and our go-to-market team is focused on North America. PointFive Labs, our research arm, publishes original work on how infrastructure and AI actually get paid for.

CRN named us one of the 10 hottest cloud computing startups of 2026, Forbes Israel put us on its Next Billion Dollar Startups list, and Redpoint selected us for its InfraRed 100, its ranking of the private companies shaping the future of cloud infrastructure.

About the Role

As PointFive's first Technical Support Lead, you'll own technical support for our enterprise customers. You'll design and build an agentic solution to triage, diagnose, and resolve customer issues end to end. You'll also measure how well it's working, and own the escalation path to Engineering for anything that needs a fix.

This is an individual contributor role with ownership of an entire function, based in our NYC office (hybrid).

What You'll Do

• 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.

What We're Looking For

Must-have

• 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.

Nice to have

• Cloud or FinOps knowledge (AWS, Azure or GCP billing)

• Hands-on experience with AI support tooling (Pylon, Intercom Fin, Zendesk AI or similar)

Compensation & Benefits

• Base Salary Range: $130,000 - $175,000. Actual salary will be based on job-related skills, experience, and location.

• Health, dental, vision (yes, all three!), equity in something early-stage and exciting, generous PTO, 401K, meal & commuter benefits, a team that will actually challenge you and much more

Why PointFive

• Founders with a track record: Built and sold IntSights to Rapid7. Backed by top-tier investors with deep conviction in this category.

• Category-defining product: DeepWaste detection and agentic remediation with clear, measurable ROI for both engineering and finance teams.

• Early-stage leverage: Your work directly shapes the product, the culture, and the go-to-market playbook.

• Own a function, not a queue: You'll build Technical Support from scratch as an AI system, on real enterprise data, with exec backing from day one.