Case Study: Thoughtful
Directing content for an AI startup at scale
Background Information
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As Director of Content at Thoughtful, I built an editorial department from zero — hiring a team of 20, editing 500+ pieces, growing a newsletter to 20,000 subscribers, and pioneering a social strategy that transformed the brand's digital presence.
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500+ Articles & guides edited
20K Newsletter subscribers
75% Social follower growth
125% Engagement boost
01: The Challenge
Starting from Scratch
Thoughtful was a stealth-mode app and AI tool designed to help users improve their relationships through meaningful connection. When I joined as Director of Content, the content operation didn't exist. I was hired to build it — from the first hire to the last published piece.
The challenge was twofold: create a high-volume editorial operation covering sensitive topics like mental health, illness, family, and friendship — while doing so with the care, accuracy, and empathy those topics demand.
02: The Work
Built & managed the content department
Edited 500+ pieces across the platform
Launched and grew a newsletter to 20,000 subscribers
Pioneered a social media strategy
Built brand partnerships & advisory board
Established KPIs & performance frameworks
Hired and oversaw a team of 20 freelance and full-time writers and editors — setting editorial standards, assigning work, and managing the full pipeline from brief to publish.
Line editing, copy editing, and fact-checking for guides, how-to articles, and narrative pieces on the Thoughtful app and web pages — covering mental health, illness, family, and friendship with accuracy and empathy.
Conceived, authored, and operated a newsletter on Substack and Customer.io that grew to more than 20,000 subscribers through consistent editorial quality and audience-first thinking.
Developed and executed an organic social strategy that resulted in 75% follower growth and a 125% boost in engagement — turning social from an afterthought into a genuine audience-building channel.
Developed partnerships and an advisory board of 25+ doctors, researchers, and media professionals — lending clinical credibility to the brand's content.
Created content effectiveness metrics and monitoring systems, adapting strategy based on real performance data.
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NONFICTION: A Reminder of Laughter
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WHAT TO SAY GUIDE: Wedding Anniversaries
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SOCIAL CUSTOMS: Dining Out
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HOLIDAYS: Independence Day
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EDUCATION: How to be a Good Neighbor
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CONNECTION STYLE: Truth Teller
03: The Results
04: Why it Mattered
Content as product, not afterthought
Depth + Volume
Department Architecture
Audience Ownership
Editing 500+ pieces on mental health and relationships requires both editorial skill and emotional intelligence. Every piece had to be accurate, empathetic, and readable, at scale.
Building from zero meant designing the entire editorial operation: hiring criteria, style standards, editorial calendars, review processes, and KPI frameworks. The department I built outlasted my contract.
A 20,000-subscriber newsletter is an owned audience — not an algorithm-dependent one. Growing that list gave Thoughtful a direct relationship with readers that no social platform can take away.