← Careers · Role 01 of 5
Creative Director / Head of Content
Own the strategy behind a personal brand 111,000 people already watch.
- Location
- Kelowna, BC (in person, relocation window negotiable).
- Employment
- Full-time
- Base pay
- $85,000 to $120,000 CAD plus content performance bonus.
Every role: base pay plus uncapped performance incentive. Hit the number, the pay follows.
[ 00 ] · The role
What you would own
You own the Cooper Simson brand and the Actionable AI content engine: the positioning, the series, the topics, the hooks, the scripts, and the calendar across Instagram, the newsletter, and the YouTube channel we are launching. You write first and direct second. Cooper films, sells, and speaks; you decide what the world sees and why they keep watching. Your scorecard is follower growth and views across every channel.
[ 01 ] · About Actionable AI
Actionable AI teaches business owners to build their own AI operating system. Founded by Cooper Simson (111K on Instagram, 32K newsletter readers, 10M+ views in 2026). Two-person team today, Cooper and Josh, hiring the first four people to take a single $15K, 3-month AI Operator program to 20-30 clients by December and $20M in 2027. Based in Kelowna, BC.
[ 02 ] · The work
Responsibilities
- Own the personal brand strategy: what Cooper Simson stands for, the series he runs, the angles nobody else is taking.
- Pick the topics and write the hooks and scripts, then storyboard them shot by shot before Cooper films.
- Run the weekly calendar across Instagram, newsletter, and YouTube; brief the videographer and the pipeline.
- Read the numbers every week (views, retention, follower growth) and change next week because of them.
- Build the YouTube channel from zero: formats, titles, thumbnails, cadence.
- Learn the AI content pipeline we run on Claude and make it your second pair of hands.
What we need
- You have grown a creator or founder brand and can show the follower and view numbers you drove.
- You are short-form native: you think in hooks, retention curves, and the first two seconds.
- You have built or run a YouTube channel, long-form included.
- You deeply understand the psychology of why people stop, watch, and share, and you can explain it in plain words.
- You write. Hooks, scripts, overlays, captions, without a committee.
Nice to have
- You can cut a reel yourself when the edit is the bottleneck
- You have run a newsletter or an email list
- On-camera comfort for the occasional co-host moment
What you get
- A founder who films whatever you plan, most days
- 111K on Instagram and 32K readers to test ideas on the day you have them
- A YouTube channel that is yours from episode one
- Kelowna lakeside office, in person with Cooper
- Direct line to the founder, no layers, scorecard you own
[ 03 ] · How hiring works
Fast, direct, no surprises.
Seven steps. Most people finish in under three weeks. You always know where you stand.
01Apply with a 60-second intro video
The form takes 5 minutes: your links, a short Loom, three questions. No cover letter.
0215-minute intro call
A quick call with Josh. We set expectations and check there is energy on both sides.
03Strengths assessment
Not a test. A map of how you think, learn, and execute, so we put you where you are strongest.
04Hiring manager interview
A deeper conversation on values and how you work. We hire for alignment first, skill second.
05Paid test project
Real work from the actual role, paid at a real rate, on a real deadline. You see the job, we see the work.
06Final call with Cooper
The last step. If we are both fired up, we move fast.
07Offer
If we are both excited there is no reason to wait. Start date set on the call.
You hear from Josh within 5 business days either way. Most people go from application to offer in under three weeks.