Careers at The Wager
If selected — come prepared.
We keep this simple: if you’re exceptional, submit your resume and answer one process question. We open roles rarely; we meet talent always.
Join the Talent Bench (Remote Only)
Apply once, be considered continuously. Choose your department, upload a PDF resume, and complete one short, human-written prompt.
1) Choose Your Department
Strategy & Ops • Marketing & Communications • Partnerships & Business Development • Legal & Compliance • IT & Security • Finance & Accounting • People • General Application
2) Upload Your Resume
PDF only. Max 10 MB. No cover letter needed.
3) Process Question
Prompt: How do you pack for a 2-day, carry-on-only work trip? Walk us through your packing system.
Answer Requirements
120–250 words, 6–10 sentences.
Privacy & Data Use
Your resume is used solely to assess fit for future roles at The Wager. We don’t sell or share applicant data.
Who Thrives Here
Systems before style
You document, test, and improve.
Craft over chatter
Your work is calm, clean, and accountable.
Ownership
You ship end-to-end, then measure the impact.
Discipline
You optimize for process rather than impulse.
How Selection Works
Step 1 — Intake
We review resumes weekly.
Step 2 — Signal
If there’s a fit, we’ll contact you with a short, practical task.
Step 3 — Deep dive
Conversation with the team. Expect specificity and candor. If you’re selected, come prepared.
FAQs
Are there any open roles at The Wager right now?
We hire selectively. Jobs open infrequently, but we review submissions weekly. Upload your PDF resume and complete the human-only question to be considered for future openings.
Is The Wager fully remote? What time zones work best?
Yes — remote-only. We collaborate across time zones, with a preference for North America overlap. If you work cleanly async and document well, you’ll fit our cadence.
Do I need a cover letter to apply?
No. We only require your PDF resume (≤10 MB) and a human-written answer to our prompt. We auto-reject AI-generated answers; originality and clear thinking matter here.
Which departments accept resumes?
Choose a department in the form: Strategy & Ops, Marketing & Communications, Partnerships & Business Development, Legal & Compliance, IT & Security, Finance & Accounting, People, or General Application.
What happens after I submit my resume?
We review weekly. If there’s signal, we’ll reach out with a short, practical task, then a focused conversation. If you don’t hear back, we’re holding your details for future opportunities.
Careers.
If selected – come prepared.
We keep this simple: if you’re exceptional, submit your resume and answer one process question.
We open roles rarely; but we meet talent always.
Join the Talent Bench.
Remote Work Only
1. Choose Your Department
2. Upload Your Resume
PDF only. Max 10 MB.
No cover letter needed.
3. The Process Question
••
How do you pack for a 2-day, carry-on-only work trip?
••
Walk us through your packing system. Think of it as a mini-case study in how you organize, prioritize, and adapt.
Human-written answers are preferred because we want you. But if you use AI, make it count – surprise us, impress us, or show us you can bend the tool to your style. Lazy prompts won’t cut it.
Hint: We hire process-driven thinkers. Whether it’s your brain or your brain + machine, show us how you work.
Your resume is used solely to assess fit for future roles at The Wager. We don’t sell or share applicant data.
Who Thrives Here.
Systems before style.
You document, test, and improve.Craft > chatter.
Your work is calm, clean, and accountable.Ownership.
You ship end-to-end, then measure the impact.Discipline.
You optimize for process rather than impulse.
How Selection Works.
Here’s how The Wager works from start to finish:
Intake.
We review resumes weekly.
Signal.
If there’s a fit, we’ll contact you with a short, practical task.
Deep Dive.
Conversation with the team. Expect specificity and candor.
If you’re selected, come prepared.