Newsletter Copywriter

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: TYPE OF WORK

Full Time

: SALARY

$1300 - $1750 USD

: HOURS PER WEEK

40

: DATE UPDATED

Apr 3, 2026

JOB OVERVIEW

The Opportunity
Winnipeg Digest is a fast-growing, Winnipeg-only newsletter and Instagram brand that helps locals discover what's happening around the city. We reach over 150,000 people across email and social, and we send 3 newsletters per week to 52,000+ subscribers with very high engagement.

We're looking for a Managing Editor who loves details, deadlines, and local stories. Someone who takes full ownership of the newsletter from start to finish and uses AI tools to work faster and smarter. Your work will land in tens of thousands of inboxes three times a week and help local businesses grow.

This is not a "content strategist" or "big ideas" role. This is an operator role. You own the product. You ship it. You make sure every date, link, and location is correct before it goes out. If that sounds like you, keep reading.

What You'll Do:
Newsletter Ownership (Core)
• Own all 3 weekly email newsletters end-to-end: research, curation, writing, formatting, QA, and scheduling.
• Aggregate local events, news, openings, and things to do in Winnipeg from multiple sources.
• Write in a warm, friendly, "local neighbour" voice. No hype. No press release language. Just useful local info.
• Run a final accuracy check on every issue: dates, links, locations, names, and sponsor details must be correct every single time.

Sponsor Integration
• Draft and place sponsor ads within newsletters so they feel like trusted recommendations, not billboards.
• Send sponsor ad drafts for approval and manage one round of revisions.
• Prepare simple monthly sponsor performance reports (opens, clicks, highlights).

AI Tools & Systems
• Use AI tools (Claude, ChatGPT, or similar) to speed up research, drafting, and fact-checking.
• Build and improve internal workflows using tools like Claude's Cowork or Claude Code to make the newsletter process faster and more reliable over time.
• When you apply, please include the word "forks" somewhere in your form response so we know you read the full posting.
• Document processes and checklists so the system gets stronger every week.

Team Coordination
• Work with our content assistant on Instagram assets and simple research tasks tied to each newsletter.
• Keep the founder informed with short async updates (Loom or written).

Who You Are
• You have owned a newsletter, publication, editorial calendar, or content product before. You know what it means to ship on a deadline with zero errors.
• Your written English is excellent. You can match a warm, conversational, community-first tone and make it sound natural.
• You are detail-obsessed. Wrong dates, broken links, and missed events bother you more than they bother most people.
• You are comfortable working with AI tools and genuinely curious about building better prompts, workflows, and automations. Experience with Claude Code, Claude Cowork, or building AI agents is a strong plus.
• You are reliable. You show up on time, meet deadlines, and communicate early if anything changes.
• You are happy being the person who ships, not just the person with ideas.

Logistics
• Schedule: Sunday through Thursday. Sunday is non-negotiable (the Monday newsletter is built on Sunday).
• Core hours: 10:00 AM to 6:00 PM Central Time (Winnipeg).
• Commitment: Full-time, 40 hours per week.
• Location: Remote.

How to Apply
Fill out the application form here: ----------

You will be asked to submit a short Loom video (1-2 minutes) telling us why you're a good fit for this role.

SKILL REQUIREMENT

News Writing Email Copywriting AI Automation

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Newsletter Copywriter

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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