Founding Head of Sales

Orchard · Remote · UK

Base: £65K–£95K
OTE: Not disclosed
Posted: 1mo ago

Still open · checked 2h agoon Orchard's careers page

Apply on Orchard →

The job

What you'd do: Build and run sales for Orchard, which sells guaranteed organic creator views with product placement at a fixed CPM to brands, agencies and labels. Founding role covering pipeline, pricing, contracts and first hires.
Who you'd sell to: Still reading the posting. Check back within the hour.
Where deals come from: Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay: Base is listed but not OTE. Ask what the variable is and how many people hit it.
Transparency: Says nothing about quota, attainment, deal size, territory or sales cycle.
Time on market: Open 32 days. Normal, but not fresh.
Company hiring: This is their only open sales role.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
2.
What's the OTE, and what did the median rep earn last year?
Base is what you're guaranteed. OTE and the median show the upside.
3.
What's the annual quota, and how was it set?
A quota built from real data is a target. Otherwise it's a hope.
4.
What share of last year's closed deals did reps source themselves?
Shows how much pipeline you'll have to build on your own.
5.
How long is ramp, and what's the quota during it?
Full quota on day one means you start behind.
6.
Why is this role open? Did someone leave, or is it new?
New headcount is growth. A replacement means someone left. Ask why.

› When the offer comes

Save these for later. They land better once they've said yes to you.

1.
Can I see the full comp plan in writing, including clawbacks and accelerators?
What's in writing is what gets paid. Read it before you sign.
2.
Can I see the actual comp distribution for the team last year, not just the OTE?
The spread shows what most reps really take home. OTE is just the target.
3.
I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?
Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

Got an offer from Orchard? Not sure about it?Ask me. I read every message myself. · JoshAsk Josh

Full posting

About Orchard 'Orchard' began as the in-house creator programme behind 'In Print We Trust'. That programme took the brand to over a billion views a month and the 13th most-mentioned fashion brand on TikTok UK, and put thousands of creators on contract. We have now launched it as a business in its own right, selling guaranteed organic views with product placement to brands. This is how brands grow now. Celsius, Bloom, Cal AI and Polymarket became big because thousands of creators had the product in their videos at the same time. The business is at multi six-figures in its first month operating from inbound. You'll build the sales side from scratch: pipeline, pricing, contracts, the first hires. About the role What brands buy is simple: a number of views, at one CPM, guaranteed. You'll take the machine and find every way it can be sold. Some we can see: white-label it to agencies; sell it to labels as sound seeding; sell it to retailers and CPG brands as launch momentum; sell managed supply to creator platforms in the markets they can't cover. Some we can't see, and that's where you step in. Perhaps you've got a way in at an AI lab that buys creator footage by the thousand hours, or another channel we aren't even aware of yet. This is a high-ownership opportunity to build/run sales/growth. So you need to have built revenue from a standing start before, at an agency, a platform or your own company, and have hired and run people who sell. Requirements - You MUST be DTC/ecommerce/Meta native. - You are comfortable being first: no marketing team, no SDR, a product whose packaging you will change. - You have extreme agency and can be scrappy/inventive. - You've personally closed $100K+ sized deals with agencies, brands or platforms, and you've hired or managed people who sell. - Experience selling to SaaS, ecommerce, DTC, retail and founder-led companies. - You know the UK and US agency and creator world well enough to get 20 meetings from your own contacts in month one. Benefits - £65,000 - £95,000 base + commission - Unlimited PTO - 6% pension contribution - Travel budget for meetings, US trips included - Remote first, with a London desk when you want one

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