Fiveleaf
Sales Development Representative (Self-Employed, Commission + Meeting Fee)
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Our first sales hire.
Commission only, no base, and the first two months are lean. If that's a no, stop here.
If it isn't: this is a real seat at an AI company small enough that you'd shape it, with uncapped upside and nobody above you in the funnel. It needs someone who wants that and will hold themselves to it. We're not looking for someone to fill a role, we're looking for someone who actually cares how it goes.
Who we are
Fiveleaf builds conversational AI for mid-market and enterprise businesses. One system that handles a company's conversations across whatever channel their customers use: phone, web chat, WhatsApp, social. It answers from the business's own information, qualifies, books, takes action in their systems, and hands over to a human properly when it should. It runs both directions. Inbound, it absorbs the enquiry volume burying a support team. Outbound, it works leads, chases cold enquiries and renewals, and books appointments at volumes a human team can't cover. We also build internal AI automation.
These are deployed systems connected to a client's actual stack, running in production on real customer volume. We're a Meta-approved Technology Provider, a barrier most agencies here haven't cleared. You'll be briefed in detail on anonymised deployments you can talk about with confidence.
The role
You open. The founder closes.
Your job is getting the right person at the right company to agree to 30 minutes. You're not running discovery, not pitching in depth, not negotiating, not quoting. Book the meeting, hand it over, move on.
That's where it starts, not where it stays. As you learn the market, the intention is to hand you more. Sitting in on calls, then running parts of them, then closing your own. Beyond that, real input into how we sell: which sectors we push, what the messaging should be, what's working and what we should stop doing.
That means we want someone who thinks about sales rather than just executes it. If you spot that a message isn't landing, or that we're calling the wrong job title, or that there's an angle we've missed, say so. You'll be closer to the market than anyone else here and we'd be wasting you if you only ever reported numbers.
The phone is the primary channel. LinkedIn and email support it, they don't replace it. If you want a role where you build sequences and wait for replies, this isn't it.
What we expect
Plainly, so there are no surprises:
- ~100 dials a day. That's the number the maths needs, not a stretch target
- LinkedIn connection requests and follow-ups, from your profile and the founder's
- Email outreach and follow-ups, from a dedicated warmed sending domain we provide
- Target lists built together. We fund the data, you have a big say in who's worth calling
- 10 to 20 qualified meetings a month, ideally, once you're up to speed
- Everything logged in the CRM the same day. It's how you get paid
- Prospects responded to fast. A director who replies at 4pm shouldn't wait until tomorrow
- Pipeline sessions with the founder a few times a week, and you turn up with your numbers
Reasons to use Rodeo
Start with a chat, not a search bar
Grad scheme, placement, apprenticeship? Not sure what you want yet — that's fine. Your agent talks it through with you and turns "I have no idea" into a shortlist.
It searches the market for you
Every day your agent scans the market matching roles against what actually matters to you, not just keywords on a CV.
Only hits
No noise. No "maybe this fits." Just roles with a clear explanation of why they're right — and where to focus when applying.
How you arrange your week around that is your call. But if the volume sounds like a lot, this is the wrong role and better we both find out now.
On call recording. Calls through our dialer are recorded, and we review the calls behind every booked meeting. It's how we tighten the messaging and how you get better fast. A coaching loop, not surveillance.
You need to actually understand AI
Non-negotiable, and the thing most sales applicants will fall down on.
You'll be telling operations directors we build conversational AI specifically for their market. What comes back is often a real question, and half the time it's sceptical, because they've been pitched AI by six agencies this year and burned by at least one. You can't handle that from a script.
You use AI tools yourself, properly, most days. ChatGPT, Claude, whatever it is. Not "I've had a play with it"
You can explain in plain English what an AI agent is, and how it differs from the chatbot a prospect already has
You have a view on what these systems are good at and where they still fall over, and you'll say so honestly on a call rather than overselling
You're curious about the space and you follow it
You don't need to be technical and you'll never write code. But if AI is just a buzzword to you, a prospect will work that out in forty seconds and so will we at interview.
How you get paid
Self-employed and results-paid. There is no base salary. You invoice us monthly, set your own hours, work from wherever you want.
- Per qualified meeting you book that is actually held. £50 per qualified meeting for your first 20 meetings, £100 after that.
- Commission on every client you originate, paid on invoices we collect. Average commission on a closed client is around £2,500 across the first 12 months, paid as we collect the money rather than on signature.
Steady state OTE is around £45,000, uncapped. That is not a base plus commission. There is no base. It's what the maths produces at 10 to 20 qualified meetings a month with a normal cold conversion rate, and we'll walk you through the arithmetic line by line at interview.
The ramp, honestly
Meeting fees are settled monthly based on meetings actually attended, so that side pays out almost straight away. Commission is slower. Our sales cycle runs around three months from first meeting to signature, so meetings booked in month one turn into commission around month three or four.
The fees are yours to earn and you control them entirely. Commission is the bigger half of the money, but it can't land until a deal closes and the client has actually paid.
So the first two months are lean, month three is solid on fees alone, and month four onwards is where it gets interesting. You'll need to cover your own costs through that stretch. It's the part of a commission-only role that catches people out.
Get help with your application
Your very own career expert that helps elevate your application to the next level.
We pay meeting fees against your invoice at the start of each month.
What counts as a qualified meeting
You're paid on qualified meetings held, so this is unambiguous. All of the following must be true:
- Fits our ICP: 50+ employees, UK-based, in or adjacent to ISPs, telecoms, utilities or high customer contact volume
- The attendee holds a decision-making or budget-influencing role
- They showed up and stayed at least 15 minutes
- They weren't already in our CRM as an active opportunity
- It was booked through your own outreach
- No-shows don't count.
Where this goes
For the right person this doesn't stay an SDR role. The path we see is opening into closing your own deals, then into a Sales Director seat building the team underneath you. Someone who does well here may end up employed by us eventually. It depends on results and where the business gets to.
Be honest with yourself about the trade. For a lot of good people this is a step back before it's a step forward. If you're on a comfortable base somewhere with a brand and a marketing pipeline, the first few months here will pay less and be harder work. That's the deal.
What we provide
- Dialer and CRM
- Dedicated, warmed cold email sending domain and sequencing tool
- Budget for lead lists and data. We'll expect you to work with us on this
- Full sales pack: ICP, anonymised case studies, pricing, objection handling
- Direct access to the founder several times a week. Small company, no layers
- Ideally you have LinkedIn Sales Navigator already. If not, tell us. You'll need your own laptop and phone.
Who this suits
- Cold calling experience selling into mid-market and enterprise. Not SMB, not inbound, not a queue of leads handed to you by marketing
- Experience selling into ISPs, telecoms, utilities or high-contact-volume businesses is a real advantage
- You've personally sourced your own meetings and can put numbers on it
- You've sold something without a strong brand behind you
- You can hold a call with a busy director who doesn't want to speak to you and not fold at the first brush-off
- You can follow up with relevant stakeholders and gain more information
- You're self-sufficient and don't need micro-managing
- You have opinions about how to sell and you'll voice them
- You want to build something rather than clock in, and to be part of a startup with real growth potential
Who this doesn't suit
- Anyone who needs guaranteed income from month one
- Anyone whose meeting numbers have always come from marketing or an inbound queue
- Anyone who hasn't picked up a phone to a stranger in the last year
- Anyone who wants a job title more than the upside
Process
Stage 1. 30-minute call with the founder. Your
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