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

HeyMilo Labs is looking for experienced customer success professionals to participate in paid, recorded conversations with peers. You’ll discuss how to manage customer relationships, debate account strategies, and work through the tradeoffs behind difficult customer decisions.

These conversations will help train and evaluate AI systems.

What you’ll do

• Discuss onboarding, implementation, product adoption, account health, renewals, and expansion.

• Debate how to approach situations such as low adoption, an unhappy executive sponsor, a missed implementation milestone, or a renewal at risk.

• Explain and defend an account strategy, including the assumptions behind it.

• Challenge another participant’s recommendations, ask clarifying questions, and consider alternative approaches.

• Discuss customer expectations and product limitations using fictional or anonymized examples.

What we’re looking for

• Professional experience in customer success, implementation, strategic account management, or professional services.

• Hands-on experience managing business customers through onboarding, adoption, or renewals.

• Fluent spoken communication in the language of the session.

• The ability to explain customer and business tradeoffs clearly.

• Confidence engaging in substantive, unscripted discussions and responding thoughtfully to disagreement.

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 customer success professional who has a similar background. You’ll discuss a topic within your shared expertise, defend a proposed approach, and constructively challenge each other’s thinking.

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 customer success background, customer segments and product areas, availability, time zone, and spoken languages.