TITLE: Staff Product Manager
REPORTING TO: CTO
LOCATION: Brooklyn, NY OR Marina Del Rey, CA (Onsite Monday - Friday)
Who Is Flip?
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.
What You’ll DoYou’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
Day-to-Day
- 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!
Nice to Have
- 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
More About Us
- 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
#FlippinLegend
Final compensation may vary based on location, experience, and qualifications. This role is also eligible for equity, in accordance with company policy, and subject to board approval.
Our customers span the globe, and so do our offices. Flip is committed to providing equal employment opportunities for all employees, applicants, and covered individuals regardless of protected characteristics. We want our company to be as diverse and inclusive as our customers.
Skills Required
- 8+ years of experience in product, forward deployed engineering, solutions engineering, or as a technical founder
- Recent experience personally building and shipping products
- Experience owning products involving AI agents, voice, LLM products, automation, integrations, or enterprise workflow software
- Ability to work credibly with both enterprise clients and engineers
- Technical proficiency with SQL, APIs, data, and prototyping tools
- Outcome-oriented approach focused on revenue, retention, and efficiency
- Experience taking ideas from prototype to production
- Experience managing and developing product teams while remaining hands-on
- Experience at an AI, agent, voice, or communications infrastructure company
- Healthcare or commerce/customer experience workflow experience
- Background as a Forward Deployed Engineer, Founding Product Manager, or engineer transitioned into product
- Experience with evaluations, model quality, or telephony
Flip (flipcx.com) Compensation & Benefits Highlights
The following summarizes recurring compensation and benefits themes identified from responses generated by popular LLMs to common candidate questions about Flip (flipcx.com) and has not been reviewed or approved by Flip (flipcx.com).
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Equity Value & Accessibility — Equity is part of the package for employees, with early‑stage upside highlighted for a small, venture‑backed startup. This aligns with expectations for companies of similar size.
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Leave & Time Off Breadth — Paid holidays are supplemented by company‑wide winter and summer shutdowns alongside generous PTO. These elements create extended, predictable breaks beyond standard leave.
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Healthcare Strength — Health, dental, and vision coverage are explicitly included as core benefits. This establishes a conventional baseline of medical support for a startup.
Flip (flipcx.com) Insights
What We Do
In a world of products that are AI everything for everyone - all channels, use cases, industries, languages, etc - Flip stands out by doing the single most important thing 10x better for brands in a few very specific verticals. Flip automates millions of phone calls per week for hundreds of retail eCommerce, healthcare, and transportation brands. Our reference list is as long as our customer list. Our team is the best thing we’ve built. To learn more: www.flipcx.com Be a #FlippinLegend
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