Produce clear, objective prediction contests at volume. Write concise, unambiguous questions with resolution criteria, follow evolving templates, revise from feedback, and stay current in a chosen specialty area.
We’re building a new kind of social wagering entertainment experience — one that’s
intuitive, design-led, and built for modern audiences. Backed by top investors and fresh out of
A16Z’s Speedrun 4 program, we’re on a mission to create something that blends play,
community, and competition in a way that’s never been done before.
As a team, we move fast, think boldly, and care deeply about the details. We believe great
design is a business advantage as we build joyful experiences for mass-market wagering communities. If you're someone who thrives on collaboration, loves shaping
products from the ground up, Cheddr might be the place for you.
Why this role is interesting
You’ll be directly responsible for the content people interact with every day.
That means:
- deciding what users predict on
- shaping how contests are structured
- helping ensure everything is clear, fair, and engaging
This is a hands-on role where your work goes live quickly and has an immediate impact on the product and user experience.
You’ll also learn how to:
- turn real-world events into structured, product-ready content
- think about clarity, edge cases, and user experience at a granular level
- operate within a fast-moving, live content environment
Associate content creator, contests
You are a reliable, detail-oriented content creator responsible for producing clear, structured, and unambiguous prediction contests at a consistent pace.
You will work within evolving templates and guidelines. You are expected to apply strong judgment to ensure all content is clear, objective, and easily resolvable, even when instructions are incomplete.
Please read the application instructions carefully.
What you’ll do
- Create prediction contests and questions within your assigned domain
- Work within evolving templates and formatting guidelines, applying judgment when needed
- Write clear, concise, and unambiguous questions with objective outcomes
- Ensure each contest includes complete resolution criteria, including:
- source of truth
- resolution timing
- handling of edge cases such as ties, cancellations, or delays
- Deliver content on a consistent schedule and meet agreed-upon volume targets
- Revise and improve content based on feedback from the contest manager
- Stay current on relevant events within your specialty to ensure timely and engaging contests
- Apply judgment when guidelines are incomplete and prioritize clarity, consistency, and resolvability
Operating in ambiguity
- Apply judgment when templates or instructions are incomplete
- Default to clarity and resolvability over creativity
- Ask questions when something is unclear, but do not block on perfect direction
- Adapt quickly as guidelines and standards evolve
Must-have qualifications
- Proven ability to produce structured written content with close attention to detail
- Strong written communication skills with a focus on clarity and precision
- Ability to follow guidelines and formatting rules consistently
- Comfortable producing high-volume output on a recurring schedule
- Able to write questions with clear, objective, and verifiable outcomes
- Reliable and responsive when given feedback or revision requests
- Comfortable working in environments where processes and templates are still being defined
- Proficient in using AI tools (e.g., ChatGPT) to generate, refine, and scale structured content efficiently
Specialty areas (Must explicitly choose one)
Reality TV
Keeps up with competition and elimination-style shows (Love Island, Survivor, American Idol, etc.) and can create timely, outcome-based questions tied to episodes and contestant progress.
Entertainment and pop culture
Follows movies, awards, celebrities, and trends, and can create questions based on measurable outcomes such as winners, rankings, or performance.
News and world events
Tracks current events and breaking news and can frame developments into verifiable, time-bound prediction questions using credible sources.
Nice to have
- Experience writing trivia, quizzes, or structured content formats
- Background in journalism, blogging, or editorial content creation
- Familiarity with prediction markets, fantasy sports, or wagering-style formats
- Ability to identify engaging or trending topics within your specialty
- Experience working with content guidelines or editorial standards
How you will be evaluated
- Clarity and correctness of submitted questions
- Adherence to guidelines and formatting rules
- Volume and consistency of output
- Number of revisions required per submission
- Timeliness of delivery
- Ability to apply judgment in ambiguous situations
How to Apply
IMPORTANT: Read These Instructions Carefully
The successful applicant will submit a three-page PDF document with the document name set to their first initial, their last name, and an ISO-8601 date stamp for the date of their submission. All of this will be separated by underscores (_).
The first page of the document must be a cover letter that contains two paragraphs. These two paragraphs must answer the following two questions:
- What makes for an engaging predictive marketplace question?
- Why are you the best candidate for (Specialty above)?
The second page must be a single-page version of your resume.
The third page must contain a sample contest. Create 2-3 prediction questions for your specialty area. For each question, include:
- Question
- Answer options
- Resolution criteria
- Source of truth
- Resolution timing
All of the above steps must be taken for the candidate to be considered for this role; no one-click submissions that fall outside the submission requirements will be accepted.
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