Practitioner Contributor, Insurance & Wealth Sales AI

About Hupo

Hupo builds AI-powered sales coaching specialized for Insurance and Wealth, and we already partner with numerous blue chip Insurers and Banks internationally. Our cutting edge roleplay AI simulation experience enables advisors and agents to practice realistic client conversations, customised with real carrier and policy content, to rapidly gain competency across various types of client conversations. This is powered by data-led, structured feedback, provided in real time in a personalized manner.

To elevate the experience, the AI-roleplay is continually modelled after best-in-class craft; i.e. how top advisors actually sell. We work with experienced practitioners to use the product, stress-test it, and contribute the ground truth that powers it.

The Role

You are an active practitioner whose agency field experience helps us fine tune the service. You are not authoring training material and you are not delivering training. You are using Hupo, telling us where it gets the conversation right and where it does not, and providing the raw inputs (re-enactments, critiques, sample interactions) that we use to improve scenarios and scoring.

Your work feeds into a structured process: Hupo's product team turns your input into scenarios, personas, and evaluation logic, with strategic sign-off from our Senior Advisor Council of former insurance C-suite executives. You provide the field reality; we handle the productisation.

Approximately anywhere between 1-3 hours per week, hourly basis. Remote-first with occasional in-person working sessions. Cash-based compensation, disclosed in the first conversation.

Important: We are looking for former industry operators (e.g. ex-MDRT insurance agents) and are not considering candidates currently employed by banks or insurance companies.

What You Will Do

• Use Hupo's product in depth — run through scenarios, complete roleplay sessions, and form a view on what feels real and what does not.

• Provide structured critique on scenarios, objections, persona behaviour, and AI feedback quality: where it works, where it misses, what a top producer would do differently.

• Participate in re-enactment sessions where you play the agent side of a sales conversation (Hupo plays the client), so we can capture realistic transcripts and cadence.

• Review AI evaluation outputs (LLM-as-judge scoring) and flag where the AI's assessment of an agent response is misaligned with how the field would actually judge it.

• Surface objections, scenarios, and edge cases that you have personally encountered but do not see represented in our content.

Who We Are Looking For

• Ideally, MDRT qualifier within the past 3 years, or 10+ years of frontline insurance advisory experience.

• Active or recently active in the field, with current familiarity across life, health, ILP, and savings products.

• Strong opinions on what good selling looks like, and willing to articulate them under questioning.

• Comfortable using software tools and providing written feedback.

• Conversational English required; Cantonese or Mandarin a plus for HK re-enactments.