Staff Product Manager — Reporting to the CTO Location: Brooklyn, NY, or Marina Del Rey, CA. Onsite Monday–Friday. About Flip Flip operates in 3 runaway B2B AI categories: coding, legal, and customer support. The company focuses on customer support, holding a one-of-one market position and serving hundreds of committed clients, including Under Armour, Tory Burch, and some of the largest healthcare institutions in the country. The market is split between generic tooling-and-FDE companies that build custom agents from scratch and industry-specific solutions that win client loyalty through speed of ROI. Flip is in the latter category. Retail and healthcare each represent $5B+ TAMs, and the company is still early in developing these markets. Flip’s growth model centers on building a reference list as long as its customer list. The team now includes 100+ people across offices in NYC, LA, and the UK. Employees describe Flip as both the best and hardest place they have worked. Responsibilities The role will address challenges such as automating complex customer calls involving subscriptions, billing, and healthcare workflows; designing AI agent behavior for ambiguous, multi-turn conversations; and building systems that combine voice, AI, APIs, integrations, and real-time decisioning. The work will also focus on client outcomes, including automation rate, resolution rate, revenue collected, retention, and ROI. Day to day, the manager will own one or more of Flip’s most complex product areas end to end, from identifying the client problem through achieving measurable outcomes. Responsibilities include working directly with enterprise clients, from executives to frontline agents; observing real workflows; identifying underlying problems; and challenging requested solutions when they are not appropriate. The manager will independently write SQL, call APIs directly, and use scripts, notebooks, and AI coding tools to prototype before asking engineering teams to productionize the work. The role requires running tight problem → prototype → client feedback → production cycles measured in days, not weeks. The manager will partner with engineers as a technical peer on architecture, integrations, evals, failure modes, latency, and reliability, and will debug production systems alongside them. Product work will ship as part of Flip’s WEEKLY product releases at https://flipcx.com/product-releases/. The manager will also turn one-off client solutions into scalable products used across hundreds of brands. The manager will build and lead a team by hiring, managing, and developing PMs and Product Owners, improving how decisions are made, and modeling a builder mentality. Qualifications Candidates should have 8+ years of experience in product, forward-deployed engineering, solutions engineering, or as a technical founder, including recent work that they personally built and shipped. They must have owned products where success depended on correct system behavior, such as AI agents, voice, LLM products, automation, integrations, or enterprise workflow software. Candidates must be equally credible with clients and engineers, without needing translation in either direction. They should be hands-on and technical, comfortable with SQL, APIs, data, and prototyping tools, and inclined to do the work rather than only coordinate it. They should focus on outcomes such as revenue, retention, and efficiency rather than merely shipping roadmaps. Relevant experience includes moving from a problem to a working prototype within hours or days and then taking it to production, as well as managing and growing product teams while remaining hands-on. Operating without dedicated analyst, researcher, or program-manager support is also expected. Even with seniority, the manager should remain engaged with the product, data, and client workflows. They should also be eager and willing to support teammates, as teammates will support them. Nice to Have Experience at an AI, agent, voice, or communications infrastructure company is preferred, as is healthcare or commerce/CX workflow experience. Other useful backgrounds include working as a Forward Deployed Engineer, Founding PM, or an engineer who transitioned into product, and experience with evals, model quality, or telephony. Company Details Flip is an international team spanning the US, UK, and Canada. The company has raised +$30M to date, including its recent $20M Series A, backed by Ridge, Next Coast, ScOp, Bullpen Capital, Data Point, and Forum Ventures, as well as founders and executives from Amazon Alexa, Ada, Attentive, and Simon Data. Benefits include 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. The role requires being in the office 5 days/week. Final compensation may vary based on location, experience, and qualifications. The role is also eligible for equity under company policy, subject to board approval. The compensation range is $150,000–$265,000 USD. Flip’s customers and offices span the globe. The company is committed to equal employment opportunities for employees, applicants, and covered individuals regardless of protected characteristics, and aims for the company to be as diverse and inclusive as its customers.

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