Senior Newsletter Writer

We're building one of the most-read business newsletters in the world. You'll work alongside a sharp team and big thinkers in business content; people who've built 800K+ weekly readers, created frameworks that get cited in boardrooms, and redefined what engagement looks like in premium business content. You understand what makes newsletters essential reading, and you're excited to be part of a team that's consistently on the map in business content.

We reach 800K+ newsletter readers every week, and we're on a fast track for growth. Our editorial team has built something rare: a system that consistently produces newsletters that get read, saved, forwarded, and referenced. Frameworks that people apply. Ideas that shift how entrepreneurs think about business. You'll be embedded as part of our large content team that tailors information for our growing audience, and collaborating with managers of each of our social platforms to master the balance between contrarian insight and mass appeal. You'll be in a creative environment where every newsletter is looked to as a touchpoint and example of what we stand for at the company, and that our other platforms look to for guidance on where to go next in content.

You'll write newsletters that hundreds of thousands of readers open, finish, and act on.

Craft hooks that convert. The first 100 words are everything. You'll write openings that make people stop scrolling and start reading. Subject lines that demand the click. Our editorial team will sharpen them with precision. Together, you'll iterate until the hook is perfect.

Engineer retention at scale. You understand pacing, curiosity loops, and payoff structure. You know why readers stay or bounce. You write with the scroll depth in your head. You’ll use that blueprint to create a structure that amplifies every beat.

Build narrative architecture. Long-form newsletters (1,500–3,000 words) require structure. You'll create the skeleton: tension points, frameworks, resolution, then execute it to live alongside the best business journalism out there.

You interviewed members of our community. You turned that interview into a newsletter that people identified with and wanted to act on. You distilled complex business ideas into simple, understandable terms that helped people learn and want to know even more.

A dense case study translated for mass appeal. You restructured a member case study as a story with rising tension and a tactical framework readers could actually apply to their own businesses.

You rewrote a newsletter five times. Each rewrite got sharper. Our founder kept pushing, 'Can we tighten the logic here? Can we add more specificity?' And by the final version, it was a great piece of business writing. This became the most-forwarded piece of the quarter.

A timely market shift happened. You spotted it, pitched the angle in Slack, and had a draft written in 48 hours. The team refined it. It went out while the topic was still hot and became required reading for thousands of business owners navigating the same decision.

You'll measure results in real time. You'll see what works and iterate, iterate, iterate.

Proven newsletter or long-form business writing credentials. Published work (1,500+ words) with real performance data preferred. Links required. We want to see where you've held attention at scale, driven engagement, and delivered actionable value.

Deep understanding of long-form business writing. You know how to craft a story, deliver payoff, and create tactical frameworks that people can act on.

Exceptional business knowledge. You understand topics like acquisitions, market trends, regulatory shifts, or deal flow and are able to find the narrative thread that matters to entrepreneurs.

Speed and openness to iteration. You move fast. You ship. You treat feedback as opportunities to get better & refine.

A distinct voice. You have a point of view. Your writing has personality and authority. You sound like a human with edge.

High comfort with AI-assisted workflows. You use AI tools for research, synthesis, and first drafts that become high-concept, human-written final pieces.

This is not a junior writing role. We're looking for someone who's done this before and wants to do it at the highest level.

• You've written for a 100K+ reader newsletter or major business publication
• You understand the newsletter industry & what drives opens, reads, and forwards
• You've studied engagement data and made editorial decisions based on metrics
• You've worked with large teams directly and are comfortable pitching in rooms with other writers, strategists & the founder
• You've built frameworks or concepts that became reference points in your audience
• You have a business mindset and understand entrepreneurs

• Open rates, read rates, and scroll depth
• Forward rates and inbox replies
• How many readers cite your frameworks
• How the editorial team talks about your work: 'This newsletter was a dream to edit.'
• Whether your piece becomes the one people save and return to

• Ad copy
• Short-form social media scripts
• YouTube long-form writing
• Editorial planning and content strategy

Contrarian Thinking helps people buy businesses, build cash flow, and think independently.

• 800K+ weekly newsletter readers across two newsletters
• 2.05M YouTube subscribers, 3M Instagram followers
• 12M+ followers across platforms
• Top-50 business podcast
• Courses, community, and an active investment fund
• Creative environment where excellence is the baseline
• Collaboration between writers, editors, and leadership that sets the standard for business newsletters
• Business acquisitions, investing, or SMB operations