Strategist and Senior Copywriter

Ideas, events & copy · 4–5 years’ experience · Fully remote, Cape Town-based · Full-time

About us

OSS Group is the commercial engine behind luxury travel. We use data, AI and a whole lot of creativity to help our clients build real human relationships. Events are in our DNA — online, offline, collabs, dinners, things nobody has done before. Our clients are one-of-a-kind luxury properties, DMCs and operators, so our events have to match that. We’re new, we’re growing fast, and we look nothing like a traditional agency.

The role

You’re the ideas person. Our job is to get the world’s best travel advisors into a room with our clients — and make them want to come back. You work out how. The event, the format, the hook, the invitation nobody deletes. Then you write it, shape how it looks and feels, and see it through to the night itself. Original thinking is not a bonus here. It is the job.

What you’ll do

• Have the ideas: Event concepts, formats, hooks, moments. Original — not last year’s version of what the sector already does. You’ll be asked for ideas constantly, and judged on how good they are.

• Understand the client’s client: You need to know the make-up of each client’s audience. Who they are, what motivates them, what bores them — then design around that.

• Write the words: Invites, emails, briefings, campaign copy. In the client’s voice. Personal enough to get a reply. Never a template.

• Use the tech: Data and AI tell us who matters and why. You work out what to do about it. Use the tools hard; they can’t have the idea for you.

• Sell the idea: Present your thinking to the team and hold your ground. The best idea in the room is worth nothing if you can’t get a yes.

What you’ll need

• 4–5 years: In a similar role.

• A body of work: Show us what you’ve made — ideas, copy, events, campaigns.

• Proper writing: Copy that stops people and gets a reply. Non-negotiable.

• Judgement: You know what works for one brand and not another, and you can explain why.

• AI already in your workflow: Not on your to-learn list.

• Follow-through: Ideas that stay in your head don’t count.

Where it goes

Creative Catalyst → Senior Creative → Creative Lead → Creative Director. We’re new and small, so this isn’t a queue you wait in — the creative function here is mostly unbuilt, and whoever is good enough gets to build it.

Not for you if

You wait to be briefed · your ideas need someone else to build them · you’ve only ever worked to a template.

The deal

Fully remote, Cape Town strongly preferred · Full-time, ~40 hrs with overlap into US, UK and Europe hours · Salary 40k negotiable on experience · Reports to the C)O · Start ASAP

Apply

• Send your CV and a link to your work