Get paid to talk to strangers (dream job alert)

The most valuable skill in 2026 is being able to communicate clearly, build connections AI can't build, and talk to a stranger without a script. We think it's disappearing, so we're running a social experiment to find out if we can change this – and what it takes. We're paying someone $2,000 a month to help us do just that.

Even in big metropolitan cities - London, New York, Paris - loneliness is on the rise. People now spend over 6 hours a day on their phones, and meeting someone IRL has started to sound like an old-fashioned idea – especially for digital-native Gen Z and Gen Alpha.

And yet, people want authenticity and real connection more than ever. RiseGuide's own research found that only 34% of people (1 in 3) would actually strike up a conversation with a stranger. Approaching strangers and engaging in conversations is one of the most common confidence blockers.

At RiseGuide, a self-improvement mobile app, we believe starting a conversation with a stranger is a trainable skill that almost nobody treats as one. That's why we're hiring someone to be paid to hang out and initiate small talk – scout public places, talk to strangers, and document their findings. The hypothesis: meeting people IRL and fighting loneliness takes three C's: confidence, charisma, and courage - and we believe all 3 could be mastered with practice.

Sounds like a perfect gig? Only for those ready to get out of their comfort zone.

New role: Chief Small Talk Officer

For 30 days, the CSTO will visit a different spot in their city: cafés, bookstores, sports clubs, cocktail bars, parks, community spaces – you name it. There, they start a conversation with a stranger (or several). Learn something real about them, give a genuine compliment, talk about the latest movie they've seen – and see what happens next. Was it easy, or did you talk yourself out of it at first? How did they react to you? Were they open to a conversation? What subject was easy to pick up, and which didn't land so well?

They will document their findings for RiseGuide in the form of notes, observations, short videos and stories.

Their outings at the end of the month become a published ranking of the best (and worst) places to strike up a conversation in their city, tips for those who want to master small talk, and an actual lesson inside the RiseGuide app where they'll teach our 400k+ users the skills they picked up along the way.

Who we're hiring

• Outgoing and naturally social — the one who talks to the person next in line;
• Comfortable being on camera;
• Strong communication skills and emotional intelligence; can read a room and know when to walk away;
• Genuinely curious about strangers;
• No specific degree or professional background required;
• Based in the U.S. and legally eligible to work here.

What we offer

• $2,000 per month
• A generous "hanging out" budget for the entire month (for coffees, drinks, museum tickets and other adventures)
• Proprietary lesson inside the RiseGuide app, reaching our 400k+ global user base.
• Promotion on RiseGuide's social channels.

How to apply

Record a short self-presentation pitch video and tell us why you'd make a great Chief Small Talk Officer. Send us the link through our application form below. CVs are optional.

Apply now

Applications are accepted through October 31st. Conditions apply - please read before applying.