AI can write your bid, but can’t guarantee a win

22 April 2026

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Speakers

Christina Godfrey Carter

Founder, Stargazy

Debbie Oxberry

Operations Director

Connor Holbert

Demand Generation Manager

Overview

90% of bid teams are using AI in their day-to-day. Most are working with generic tools like ChatGPT, Claude or Copilot.

The problem is that AI can get you 80% of the way to a compliant bid, but the last 20% is where bids are actually won.

That last 20% is also where the horror stories live: fabricated team members, invented citations, and a Big Four firm fined half a million dollars after winning a government contract with AI-generated content it never reviewed.

In this 45-minute session, Debbie Oxberry (Operations Director, Ocean City Bids) and Christina Godfrey Carter (Founder, Stargazy), hosted by Connor Holbert (Growth Manager, Stotles), break down how the best bid teams are using AI to accelerate without cutting corners, and where human judgement is still non-negotiable.

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What you will learn:

How AI misuse has cost teams contracts, fines, and client relationships, with specific anonymised examples from public and private sector bids.

Why evaluators are now using AI to score bids, and how that shifts the weight from polished writing to hard evidence, proof, and buyer-specific insight.

What a living content library actually looks like, and why connecting to upstream sources like legal, product marketing, and security beats a static library updated every quarter.

How to run a pre-submission review that catches AI hallucinations before an evaluator does, including the prompts and techniques the speakers use on their own bids.

How to build an AI learning habit across your team, including which newsletters, frameworks, and re-testing rhythms are actually worth the time.

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About the speakers:

Debbie Oxberry is Operations Director at Ocean City Bids, a bid consultancy based in the South West of the UK. She has led bidding work across public, private, and charitable sectors, and serves as her organisation's AI lead.

Christina Godfrey Carter is the founder of Stargazy, focused on win intelligence for proposal teams globally. Her background includes leading capture, pursuit, and proposal teams at AWS, Zendesk, and Instructure.

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Key takeaways

The stakes are public and severe. A Big Four firm was removed from a government contract and fined roughly $500K after submitting AI-drafted content it never reviewed, and roughly half the webinar audience had already caught AI-introduced errors in their own bids before submission.

Inputs now matter more than output quality. AI has made compliant first drafts easy, so the bids that win are the ones drawing on a living content library that connects directly to legal, product marketing, security, and CRM sources rather than a static document refreshed every quarter.

Evaluators are using AI too, which strips emotion from scoring and weights concrete evidence like customer quotes, metrics, and case studies far more heavily than polished narrative. Compliance is now the floor, not the ceiling.

Human review is non-negotiable, and the best reviewers use AI against itself: prompting it to flag unsupported statements, suggest evidence gaps, and even read the bid aloud to test whether the prose actually means anything beyond sounding good.

Staying current is a deliberate habit, not a one-off. Appoint an internal AI lead, pick a small number of newsletters and channels to follow consistently, schedule time to actually try things on real bids, and re-test what failed three months ago because the models have almost certainly caught up.

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Resources

Slides

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