CoverAI · Product & feature bets
From a focused product bet to acquisition and enterprise growth.
CoverAI began with one task job seekers consistently disliked: writing tailored cover letters.
I led the bet from discovery through product, pricing, go-to-market and acquisition—then led its transition into WriteSea’s flagship enterprise product.
At a glance
- My role
- Founder. I owned all product, commercial and growth decisions, working with engineering on delivery. After the acquisition, I led product at WriteSea.
- Initial timeline · 2023
- May: public MVP
July: expanded product
September: acquired by WriteSea
Within 90 days, with no paid marketing. Acquired by WriteSea in September 2023.
99.5% enterprise partner renewal, with contract size growing 8× over the same period.
Choosing the right starting point
In early 2023, several friends lost their jobs. Conversations about their next steps revealed the work behind each application: preparing CVs, writing cover letters, practising for interviews and reconnecting with contacts.
Generative AI offered a way to help, but I had limited time. Most people already had a CV; writing a tailored cover letter was the task they consistently disliked. Desk research reinforced what I was hearing.
Releasing early enough to learn
The MVP was built in a few days and released publicly in May 2023. Users signed in with Google, provided their CV and a job description, and generated a cover letter.
I shared it with friends, then on LinkedIn. More than 200 people registered in the first two weeks. Their feedback gave me a basis for deciding what deserved further investment.
From a CV to a tailored cover letter
Expanding around demonstrated needs
The MVP treated the CV as an input for a cover letter. About 78% of the first 200 users requested CV tailoring for individual jobs. Users also wanted to add context their existing documents didn’t capture. That feedback changed the scope of the next release.
I spent the following month gathering feedback and directing the broader release. Requests for help beyond applications shaped contact management, networking assistance and offer-negotiation support. July’s release also introduced interview practice, helping job seekers prepare for the conversation after their application.
From application to interview
Growing through LinkedIn and personal networks
Distribution began through LinkedIn and personal networks. I introduced role suggestions and earning estimates as additional ways to discover the product, with sharing in mind.
CoverAI reached 13,000+ registered accounts within 90 days without paid marketing.
Finding the right acquisition opportunity
WriteSea approached me because CoverAI’s AI capabilities could help scale its existing CV and cover-letter services. I believed it was better positioned to take the product into its next stage.
I led the acquisition process, and WriteSea acquired CoverAI in September 2023. TechCabal and Techpoint Africa subsequently covered the transaction.
Building for a different buyer
After the acquisition, I joined WriteSea and led the move from individual job seekers to higher-education and workforce-development organisations.
I translated that change in buyer into product priorities:
- Manage access and responsibility
- SSO, super-admin and staff roles, and permissions supported organisational access and administration.
- Understand activity
- Reporting gave staff visibility into how the product was being used.
- Fit existing services
- APIs, integrations, white-labelling and a job board supported delivery through partner organisations. Accessibility improvements broadened who could use it.
The product became WriteSea’s flagship offering and helped enable a seed funding round. Over two years at WriteSea, ARR crossed $1.1M, with a 99.5% enterprise partner renewal rate and 8× growth in contract size over the same period.
“Chris led our pivot to enterprise and shaped the product around what those customers needed. His product work helped us retain 99.5% of our enterprise partners and cross $1.1M ARR.”
Carrying the bet through its next stages
At CoverAI, I owned all product, commercial and growth decisions: which problem to solve, what to release, how to price it, how to reach users and when to pursue an acquisition. After the sale, I led the product towards a new buyer and business model.
When you hire me for a product or feature bet, you get that same end-to-end ownership. I handle discovery, design, build and testing for the agreed scope, while your team stays focused on its roadmap. You provide one point of contact for context, access and decisions. After four weeks, you receive:
- A focused, working pilot for one agreed use case, with the scope and assumptions to test defined upfront.
- Evidence for the next investment decision: user research, feedback from testing and a recommendation to continue, change or stop.
- A practical handover: source code, design files, findings and documentation, so your team can take the work forward.