AIContent Generation

AI with no playbook

Teaching a model by hand to write fundraising emails that win, before AI was everywhere.

The Quiller editor showing a fundraising email draft with a Rate this draft and Try again buttons, and a proofreading disclaimer

Role

Product Designer at Able, an agency building software for startups, in partnership with our client Authentic

Timeline

2022–2023

Scope

Collaborative product design on a 0->1 agency team: co-designer, tech lead, AI specialist, product manager, and client C-suite.

Status

Shipped 2023. Acquired in August 2025.

We had to design the model before we could design the product.

Grassroots candidates and small nonprofits need professional fundraising content and can’t afford the agencies that write it. We built an AI tool that could — years before AI was everywhere, when only two models on the market would even allow political content. We hand-tagged the training data ourselves, hit the wall every underfed model hits, and traded volume for quality until the outputs earned trust. Then we designed an interface that made an imperfect model safe to use. Quiller raised $1.2M in pre-seed funding, drew 200+ waitlist signups, won four industry awards, and was acquired in August 2025.

The bet

Authentic's homepage: 'AUTHENTIC is a digital marketing and fundraising agency that creates lasting and inclusive change.'
Mike's agency, Authentic — the source of the training data.

A founder bet his agency's best work could be taught to a machine.

Mike ran Authentic, an agency whose fundraising emails had won awards and raised millions for Democratic campaigns. He saw the gap clearly: the candidates who need that writing most — school board, city council, small nonprofits — are exactly the ones who can't afford an agency. His idea was to train a model on his agency's library of high-performing emails, so anyone could generate that quality on their own. That meant solving the same bottleneck from two sides: campaign teams that could not afford professional help, and agency strategists buried in repetitive drafting. Authentic hired Able, the product agency where I worked, to turn the idea into a usable MVP in less than six months.

The preview

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Quiller on MSNBC.

The prototype made national TV before the product ever shipped.

I created the early prototype featured in an MSNBC segment about AI's growing role in political advertising. It made the idea tangible before we had solved the much harder problem of turning it into a product campaigns could actually trust. The prototype sold the possibility. The work that followed was figuring out how much context, guidance, and control the real product needed.

Roadblock one

There was no playbook — and most models wouldn’t take our content.

This was before AI went mainstream. There were no established trust patterns, no prompt-engineering guides, no “AI-generated content” disclaimer conventions to borrow. And there was a problem specific to us: most available models prohibited political content outright. We tried fine-tuning at least three different large language models (Cohere, Meta, and NLP Cloud) in an effort to produce higher-quality content, given our limited options.

The curriculum

Tone taxonomy FigJam board, categorizing tone by news type, formality, urgency, emotion, and directness
We had to create our own tone taxonomy.

No taxonomy for great fundraising writing existed, so we invented one — one tagged email at a time.

We had a bank of high-quality fundraising content, but we had to tag it ourselves, iterating on the parameters of tone and urgency as we worked. Since we were new to the fundraising space, we made sure to consult with Authentic's experts on both what tones were most important and what the different levels of urgency meant. The dataset was a design surface. We treated it like one.

FigJam board with Authentic strategists' line-by-line comments on draft emails, including suggested deletes and replacements
Line-by-line feedback from Authentic's strategists on every draft the model produced.

The model could imitate the form. Strategists could hear what it got wrong.

My design colleague set up regular output review with Authentic's digital strategists, which we synthesized into themes together. They caught problems we never could have identified from the dataset alone: language a real fundraiser would never use, appeals that felt too formal or generic, and subtle differences between urgency that motivated someone and urgency that sounded desperate.

Roadblock two

We realized our dataset was too small when our model kept hallucinating.

At one point it generated content invoking Donald Trump — in a product built for progressive campaigns. One wrong draft, copy-pasted by a trusting volunteer, could end a candidate’s campaign and the product with it. We needed a lot more data, so we spent hours scraping open-source fundraising emails from the web. This introduced a new conundrum: if we fed the model too many lower-quality fundraising emails, the quality would suffer in a different way. We partnered closely with Authentic to quality-check all new content.

The threshold

Local candidate persona board with pain points, tasks, email-specific tasks, feelings, and tools grouped by theme
We synthesized the interview data together, focusing on what pain points we could address first.

Once we addressed the accuracy issues, we learned we needed to create more customized content.

I led interviews with two very different groups: agency strategists writing fundraising emails at volume, and grassroots candidates often writing alone. Both needed a first draft that wasn't overly generic before they would adopt Quiller into their existing workflow: candidates were already hesitant to fundraise if it didn't feel authentic, while strategists could write a decent first draft themselves.

A great first draft

Quiller drafting a new version, asking users to rate the last draft they saw with a five-star scale
We built in frictionless opportunities for continuous user feedback.

We gave the model more context, and users more control and error recovery options.

Campaign profiles carried each candidate's voice, positions, and talking points into every generation. Inside the writing experience, users could adjust tone and urgency, add more specific context, rate the result, explain what felt wrong, and keep refining the draft without starting over.

Because most users were new to generative AI, the interface also taught them what the model needed to produce something useful.

Quiller disclaimer modal reminding users to proofread and fact-check all AI-generated content

Launching fast

The Quiller team at their Netroots Nation launch booth, with the product running on a monitor

We launched Quiller's beta in 6 months at Netroots Nation, with 200+ waitlist signups.

Before handoff to the Quiller team, we helped shape the roadmap proposal for what came next. We accomplished all of this in 6 months by prioritizing research, quick iteration, using existing design and UI kits, and working nimbly as a team.

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You'll see some differences in UI here versus other screens - this was the state at launch.

The impact

Adweek AI Awards artwork

Adweek AI Awards

AI Efficiency of the Year

Netroots Nation logo

Netroots Nation

'Best New Feature' nomination at Netroots Nation

Campaigns & Elections logo

Campaigns & Elections

Best Use of AI for Content Production

Adweek Media All-Stars 2024 award artwork

Adweek Media All-Stars

Awarded to Authentic for their work on Quiller

$1.2M

Raised in pre-seed funding

160+

Waitlist signups at launch

3

Industry awards shown above

2 years

From launch to acquisition by Grassroots Analytics

We turned a hand-tagged spreadsheet into an award-winning product.

This is my kind of zero-to-one work: helping define the system, the quality threshold, and the product together when none of them exists yet.