HeyMilo Labs | Remote | Independent Contractor | $40–$100 per hour

HeyMilo Labs is looking for experienced product managers to participate in paid, recorded conversations with other product professionals. You’ll discuss product decisions, debate priorities, and explain how you weigh customer needs, business goals, and technical constraints.

These conversations will help train and evaluate AI systems.

What you’ll do

• Discuss product discovery, strategy, prioritization, roadmaps, launch decisions, and success metrics.

• Debate realistic product questions, such as whether to build a requested feature, delay a launch, or invest in a new customer segment.

• Defend a recommendation and explain the assumptions, evidence, and tradeoffs behind it.

• Challenge another participant’s perspective, ask follow-up questions, and explore alternative approaches.

• Revise your recommendation when new information warrants it, using fictional or anonymized examples.

What we’re looking for

• Professional product management experience, including responsibility for discovery, prioritization, or delivery.

• Experience working with engineers, designers, customers, and business stakeholders.

• Fluent spoken communication in the language of the session.

• The ability to explain complex decisions clearly and support an argument with reasoning and examples.

• Comfort with ambiguity, constructive disagreement, and unscripted conversation.

Professional acting experience is optional. Domain expertise and conversational ability are essential.

The next step

Following an initial screening, selected applicants will be invited to a paid, recorded conversation with another product professional who has a similar background. You’ll discuss a topic within your shared expertise, debate possible decisions, and challenge each other’s reasoning.

Compensation and recording

Pay is $40–$100 per hour. The rate, expected time commitment, and recording-use and licensing terms will be shared before you accept an assignment. Recordings may be licensed to AI developers for training and evaluation under the agreed terms.

You’ll need a quiet environment, reliable internet, a clear microphone, and a webcam. Be comfortable appearing on video with your face visible and filters and background blur turned off.

How to apply

Share your product management background, product areas, availability, time zone, and spoken languages.