Staff Product Manager

There are 3 runaway categories in B2B AI — coding, legal, and customer support. We're at the center of the third, with a one-of-one market position and hundreds of diehard fan clients, from Under Armour to Tory Burch to some of the largest healthcare institutions in the country.

The market is dividing into two camps: generic tooling-and-FDE players building custom agents from scratch, and industry-specific solutions winning on client love due to speed of ROI. We're firmly the latter. Retail and healthcare alone represent $5B+ TAMs each, and we're still early.

We built the company on a simple idea: the best way to grow is to have a reference list as long as your customer list. We're a team of 100+ now, with offices in NYC, LA, and the UK. Many people here will tell you it's the best place they've worked and the hardest they've worked. Both are true.

You’ll work on problems like:

• →Automating complex customer calls (subscriptions, billing, healthcare workflows)
• →Designing AI agent behavior in ambiguous, multi-turn conversations
• →Building systems that combine voice, AI, APIs, integrations, and real time decisioning
• →Moving client outcomes: automation rate, resolution rate, revenue collected, retention, and ROI

• Own one or more of Flip’s most complex product areas end to end, from the client problem through measurable outcome
• Work directly with enterprise clients, from executives to frontline agents; watch real workflows, find the underlying problem, and push back when the requested solution isn’t the right one
• Get your own answers: write SQL, call APIs directly, and use scripts, notebooks, and AI coding tools to prototype before asking engineering to productize
• Run tight loops of problem → prototype → client feedback → production, measured in days, not weeks
• Partner with engineers as a technical peer on architecture, integrations, evals, failure modes, latency, and reliability; debug in production alongside them
• Ship as part of our WEEKLY product releases (https://flipcx.com/product-releases/)
• Turn one-off client solutions into scalable product used across hundreds of brands
• Build and lead a team: hire, manage, and develop PMs and Product Owners, sharpen how we make decisions, and model the builder mentality

• 8+ years of experience in product, forward deployed engineering, solutions engineering, or as a technical founder, with recent work where you personally built and shipped
• You’ve owned products where success depended on getting system behavior right: AI agents, voice, LLM products, automation, integrations, or enterprise workflow software
• Equally credible with clients and engineers; no one needs to translate for you in either direction
• Hands on and technical: comfortable with SQL, APIs, data, and prototyping tools, and you default to doing over coordinating
• You think in outcomes (revenue, retention, efficiency), not roadmaps shipped
• You have stories where you went from problem to working prototype in hours or days, and from there to production
• You’ve managed and grown product teams while staying hands on, and you’ve operated without a big support structure: no dedicated analyst, researcher, or program manager
• You still love getting into the product, the data, and the client workflow yourself, even with years of seniority
• Eager and willing to support your teammates, just like they will with you!

• Experience at an AI/agent, voice, or communications infrastructure company
• Healthcare or commerce/CX workflow experience
• Background as a Forward Deployed Engineer, Founding PM, or engineer who moved into product
• Experience with evals, model quality, or telephony

• We're international, spanning the US, UK, and Canada
• We’ve raised +$30M to date including our recent $20M Series A - backed by Ridge, Next Coast, ScOp, Bullpen Capital, Data Point and Forum Ventures, as well as founders & executives from Amazon Alexa, Ada, Attentive, and Simon Data
• Comprehensive healthcare and unlimited vacation, including a mandatory half week for everyone over July 4, and a full week off at the end of the year
• In office 5 days/week