LetterFestFractional CTOSince March 2026, first conversations in October 2025

Two years of backlog in four months: LetterFest's AI transformation

How fractional CTO advice helped LetterFest adopt AI safely across the whole business, and change how it builds software.

~£500K
saved this year on development and running costs, with fractional CTO guidance and AI across the business1
4 months
to clear two years of backlog1
~10x
more ads shipped, from ~100 to ~1,000 a month1
~$20K
a year saved by moving from AWS to Supabase1

The challenge

LetterFest wanted to ship faster than a traditional development process allowed, and its backlog kept growing. The CEO saw agentic AI coding as the way forward. What the business needed was a safe, structured way to adopt it, with the right guardrails and a clear roadmap everyone could follow.

What we did

Lev worked with LetterFest as an adviser: one-to-one sessions and workshops with the management team, the board and the lead developer. Together they agreed a roadmap and tech stack for adopting AI across the business, and LetterFest’s own team made the change, with people kept in charge of product thinking and requirements.

  • A roadmap first

    An agreed plan and tech stack for adopting AI, department by department, before anything changed.

  • Guardrails before speed

    AI tools work in a sandbox, with no access to production keys or database credentials.

  • Riskiest part first

    The plan put the backend first, and it was migrated without breaking production.

  • AI code review

    Greptile now reviews every change.

  • More people building

    Four non-technical team members now build software day to day, with AI and with guardrails.

  • Leaner infrastructure

    A move from AWS to Supabase, saving around $20K a year.

“Totally transformational. We've done two years of backlog in four months.”
LetterFestJames Reader, CEO, LetterFest

Before and after

Before

  • A backlog that kept growing
  • A traditional development process
  • Around 100 ads shipped a month
  • Infrastructure on AWS

After

  • Two years of backlog cleared in four months
  • Idea to live product in about a week
  • Around 1,000 ads shipped a month
  • Infrastructure on Supabase, around $20K a year cheaper

What changed across the business

  • The CEO builds his own tools

    LetterFest's own marketing ad tool was built by the CEO with Lovable and Claude. It is still in daily use.

  • Around £500K saved

    An estimated £500K saved this year on development and running costs, including an automation built in-house.

  • Savings into growth

    Better margins are going back into marketing.

“It multiplies bad decision-making really quickly.”
LetterFestJames Reader, CEO, LetterFest

How it unfolded

  1. October 2025

    First conversations

    The CEO gets in touch with Lev, on a founder friend's recommendation.

  2. March 2026

    Advisory sessions start

    Workshops and one-to-ones with management, the board and the lead developer.

  3. Four months in

    Two years of backlog done

    With non-technical team members now shipping software too.

  4. Now

    Periodic consultancy

    Lev stays on hand to keep LetterFest at the edge of what is possible.

Sources

  1. Case study interview with the CEO of LetterFest.
  2. CTO advisory session notes, 19 March 2026.

Last checked against these sources on 15 October 2026.

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