Passionate Pineapple
Outreach & Conversation Support (Part-Time | Remote | Flexible)
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Passionate Pineapple is a small UK-based digital support consultancy helping time-poor business owners improve their websites, marketing and digital setup - without jargon, overwhelm or unnecessary overhauls.
The work is there.
The challenge is simply starting more of the right conversations with the right people consistently.
We’re now looking for 1-2 self-employed Outreach & Conversation Associates to support with that.
This is a flexible, remote role for someone who enjoys genuine conversations, understands people well and prefers a more human, relationship-first approach over hard sales tactics.
What the role involves:
- Identifying and connecting with UK business owners on LinkedIn
- Starting natural, human-first conversations (no spammy scripts)
- Understanding, at a high level, what someone may be struggling with
- Spotting when someone is genuinely open to improving things
- Introducing the founder when a conversation naturally makes sense
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This is not a pushy sales role.
You won’t be cold-calling people all day, pitching services or handling proposals.
The role is more about building rapport, creating momentum and opening the right doors.
The founder handles:
- Discovery calls
- Recommendations
- Proposals
- Delivery
Most clients currently come through word of mouth and natural conversations already — this role is about helping create more of that consistently.
Compensation Structure:
- Small monthly base (£100-£200 depending on experience/availability)
- 15% commission on one-off projects secured from clients you introduce
- 10% commission on monthly retainers (first 3 months)
Commission is paid once cleared client payment has been received.
A single introduction could realistically lead to anywhere from £300-£1,500+ worth of work depending on the project.
Who this may suit:
- Someone naturally good with people
- Someone who enjoys starting conversations
- Someone who dislikes overly scripted or aggressive sales
- Someone organised and comfortable working independently
- Someone with the time and consistency to genuinely build momentum
- Someone looking for flexible work alongside freelancing, consulting or other commitments
Get help with your application
Your very own career expert that helps elevate your application to the next level.
Experience in outreach, partnerships, customer success or relationship management is helpful but mindset and communication style matter more.
A quick note on approach:
This role is very much quality over quantity.
The goal isn’t to message hundreds of people for the sake of it.
The goal is to start good conversations with business owners who:
- know something isn’t quite working
- are open to improving it
- and are willing to take action when the right support is there
Interested?
Apply and we can have a relaxed chat to see if things feel like a good fit both ways 🍍
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