Senior AI/ML Engineer

Careers at Pypestream | Build Enterprise AI AgentsAI Agents for Enterprise Customer Service | Pypestream

We value your privacy

We use cookies to improve your experience, analyze site traffic, and personalize content. By clicking "Accept All" you consent to our use of cookies. You can manage your preferences at any time. Privacy Policy

Manage PreferencesReject AllAccept All

Careers at Pypestream

Build AI that actually does something.

Pypestream is a small team with a large footprint. We deploy AI agents that handle millions of real customer interactions every month for some of the most demanding enterprises in the world. If you want your work to matter from day one, this is where you do it.

View open roles on Wellfound

~80

Team members

11 years

Serving enterprise clients

Series B

Stage

"We are not building demos. We are running production AI."

Pypestream Engineering

50M+

AI interactions / month

Our mission

Deploy AI agents that resolve real customer problems at enterprise scale.

AIVoiceChatHITL

Why Pypestream

We are not building demos. We are running production AI.

Most AI companies are still in the proof-of-concept phase. Pypestream has been running AI agents in production for over a decade. Our technology handles real customer conversations for insurance carriers, telecom providers, and healthcare organizations where the stakes are high and the tolerance for failure is zero.

That means the problems you solve here are real. When you improve containment rates by 5 points, that is hundreds of thousands of calls deflected. When you reduce average handle time by 30 seconds, that is millions of dollars saved for a customer who depends on us.

We are a small team that punches well above our weight. We do that by hiring people who want ownership, move fast, and care deeply about the quality of their work.

Outcomes over activity

We measure success by what our customers achieve, not by how busy we are.

Every decision starts with the question

does this move the needle for the people we serve?

Ownership without ego

Everyone here owns something real. We move fast because we trust each other to make good decisions, and we hold each other accountable without politics getting in the way.

Serious problems, serious craft

We work in industries where the stakes are high -- healthcare, insurance, financial services. We take that seriously. We build things that are reliable, compliant, and built to last.

Compound growth

We hire people who want to grow faster than they would anywhere else. We invest in that growth through mentorship, access to leadership, and the kind of challenges that build careers.

Benefits

We take care of the people who take care of our customers.

Comprehensive health, dental, and vision

Remote-first with flexible hours

Equity in a high-growth company

Unlimited PTO with a real culture of taking it

Learning and development budget

Parental leave for all parents

Open Roles

Current openings

View all on Wellfound

Enterprise Account Executive

Senior

Own a territory of Fortune 500 accounts in insurance, telecom, and financial services. You will run complex, multi-stakeholder deals from first meeting through signature and expansion.

SalesNew York, NY / Chicago, ILFull-time

Apply

Solutions Engineer

Mid-Senior

Be the technical voice in enterprise sales cycles. You will build custom demos, run proof-of-concept deployments, and translate customer requirements into Pypestream architecture.

Pre-SalesRemote (US)Full-time

Apply

Agent Designer

Mid-Senior

Design and build AI agent workflows for Fortune 500 enterprise clients. You will translate complex customer service processes into production-ready agentic experiences using Pypestream's platform.

Product & ImplementationNew York, NYFull-time

Apply

Data Analyst, AI & Automation

Mid

Analyze AI agent performance data to surface insights that drive containment rate improvements and cost savings. You will build dashboards, run ad-hoc analyses, and partner with client teams on ROI reporting.

AnalyticsNew York, NYFull-time

Apply

Don't see the right role? We hire for talent ahead of headcount.

See all open roles on Wellfound

Join the team

Ready to do the best work of your career?

We are building something that matters in industries that cannot afford to fail. If that sounds like the kind of work you want to do, we want to hear from you.

View open roles Send us your resume