Most proposal teams think their biggest problem is speed. Henry Brogan thinks it’s understanding why they’re responding in the first place. In this episode, Henry (CEO of BidScript) its down with Christina Carter to unpack what’s really broken in the world of bids and RFPs, and why layering AI on top of bad process doesn’t fix it.
He argues that RFPs aren’t “paperwork”! They’re one of the most predictable, defensible revenue channels any company has. But most organizations sabotage themselves with fragmented capture data, late engagement between sales and proposal teams, and legacy tools that create more admin than insight.
Henry explains how AI can finally make good capture scalable: surfacing buried context from CRMs, past conversations, and public data to help teams think smarter, not just write faster. He shares why retrieval-augmented generation (RAG) is the real breakthrough (not the hype around chatbots), and how top proposal teams use AI for pre-bid intelligence and post-mortem learning loops that improve every submission.
They also tackle tough questions:
What should you ask vendors before buying any AI proposal tool?
Why are buyers changing how they write RFPs?
How do you separate “AI-washed” tools from true AI-native systems?
And why does transparent pricing matter in a market full of bloat?
If you lead a proposal, bid, or revenue team and you’re trying to decide what AI is actually worth your time, this episode is a masterclass in positioning AI as a thinking partner—not a typing assistant.
Christina Carter (00:08) Hey Henry, how are you?
Henry Brogan (00:09) Hey Christina. Very good, thanks. Thanks for having me on the podcast.
Christina Carter (00:13) Yeah, thanks for being on. I'm going to dive right into it. You all already know Henry as CEO of BidScript, and I'm going to jump right in with my first question. And that was really about the moment where you realized that something within the bid industry, within the proposal industry, needed to change and that BidScript was really the answer to that.
Henry Brogan (00:37) Yeah, so it was a funny story, actually. So my co-founder, Tyler, and I were building software on freelance for different organizations. We were just asking people their problems and building solutions to them. And there was one period of time where we went into a lot of mechanical engineering, civil engineering, industrial contracts and businesses. And they all said the same problem. They all were talking about bids at that time. There was PQQs and SQs as well. And we actually watched one of them do a tender kickoff, which was painful to watch. And then we also watched one of the office administrators try to pull together information to fill in one of those questionnaires. And we were just like, there's got to be a better way to do it. So yeah, it all started from there, really.
Christina Carter (01:29) I think it’s really interesting that you saw immediately how painful it was just to even start the kickoff call and then pull that information together. But there’s kind of a change I’ve seen — a lot of execs nowadays, like sales leaders, see proposals and bids as paperwork. They don’t see them as a driver of revenue, which we all know RFPs are. So I’m curious what you say to CROs who aren’t looking at RFPs the right way.
Henry Brogan (02:07) Yeah, it’s a talked-about pain point. A lot of execs dish it out — that sales-proposal handoff — and CROs often favor sales over proposals. But look at the stats. Enterprise value tied up in RFP and tender processes is insane. U.S. federal government spends close to $700 billion a year on contracts. Globally that’s $1.5–$2 trillion in public sector spend. Private sector adds another $3–$4 trillion through supplier contracts. Most of those go through RFPs. If a CRO is reluctant to engage or resource proposal teams, I’d tell the CEO they need a new CRO.
Henry Brogan (03:23) When you build pipeline value and forecast revenue, some RFPs become five-year contracts with steady cash flow. It’s a probability game. With good people and a strong process you get a repeatable hit rate and a sustainable revenue pipeline purely from RFP wins.
Christina Carter (04:21) I see this often with SMBs now forced to respond to RFPs for the first time — they just don’t know what they don’t know.
Henry Brogan (04:36) Exactly. Once they see how much thought and skill winning takes, they realize this is not admin paperwork — it’s a sustainable revenue channel if done properly.
Henry Brogan (05:18) Biggest failure is sales and bid teams working in silos. Capture info is lost because CRMs aren’t used right. Sales hold diamonds of context that never reach proposal teams. Another issue is underestimating effort — delayed engagement and short timelines cripple quality.
Christina Carter (06:36) So basically they’re not getting to know the customer before the RFP and they misunderstand the effort required. What’s your advice to fix that?
Henry Brogan (06:56) Culture. If you’re lucky to have an accountable culture, propose new methods. If not, sometimes you have to find a better company. But start with critical conversations and explain what you need to convert leads into wins.
Christina Carter (08:45) That’s a hard conversation with sales leaders. Let’s talk AI — everyone is throwing it at everything. Where does AI actually add value?
Henry Brogan (09:50) I feel for bid pros who get pitched AI daily. Some use freemium tools like Claude or ChatGPT. I encourage experimentation. Every team has different workflows. AI’s real value is making people think and work smarter. Yes, automation helps, but contextual intelligence is the prize. Upload an RFP for the U.S. DOJ — AI should surface past deals, contacts, pain points, and summaries from public data like board minutes. That intelligence drives better responses.
Christina Carter (12:47) So that data fusion sounds like the main use case you see for RFPs?
Henry Brogan (13:03) es — pre-bidding is the highest ROI area: research, capture, answer planning. Writing copy is secondary. Post-bid analysis is next — capturing lessons to improve next time.
Christina Carter (14:09) When writing the first draft, how does AI actually use that pre-sales info?
Henry Brogan (14:36) Through RAG — Retrieval Augmented Generation — and contextual embeddings. A good system links client context, win themes, and keynotes to generate relevant snippets. But humans still elevate the copy; LLMs alone can’t meet rubrics for scored proposals.
Christina Carter (16:27) What should buyers ask to ensure they’re choosing the right proposal tech?
Henry Brogan (17:17) Start with your use case, not “Which LLM do you use?” Ask about database logic — vector or relational? Scalability? Infrastructure? Legacy vendors on old code can’t evolve fast. Check if their library stores collaboration data, scores, client info, and win/loss links for querying.
Christina Carter (19:50) You also talk to buyers — are they changing how they write RFPs because of AI?
Henry Brogan (20:09) Depends on sector, but we’re in an era of self-declaration: “Have you used AI in this proposal?” No penalty for using it responsibly. Future RFPs may be more prescriptive to counter generic AI answers — requiring comparisons and context AI can’t easily fake. Eventually we may see video responses or microsites as procurement tech evolves.
Christina Carter (22:52) What patterns are CROs missing because they don’t analyze past proposals?
Henry Brogan (23:33) The best teams do deep post-mortems; the rest don’t. That’s where huge insight lives. Track why you won or lost, task timings, edits, review cycles, and scores. AI can map those to show cause and effect and drive continuous improvement.
Christina Carter (26:33) How should teams leverage AI in post-mortems?
Henry Brogan (26:52) Let AI track it for you in the background. When you log feedback and scores, it auto-creates reports on what worked and why. It links incremental tasks to outcomes for a clear story of performance.
Christina Carter (27:36) Cheeky question — most vendors hide pricing. You don’t. Why?
Henry Brogan (27:53) Bloated prices have plagued bid tech. Pros can’t experiment because tools start at £10k and require months of sales calls. AI is evolving too fast for that. We keep BidScript accessible and open — value shouldn’t be locked behind absurd pricing.
Christina Carter (29:04) What beliefs should proposal people let go of?
Henry Brogan (29:11) First: that AI can’t help. It’s not a fad like blockchain — it’s here to stay. Ignore it and you’ll be left behind. Second: thinking AI is just the LLM. Capability depends on infrastructure and system design. Knowing that helps teams choose tools that fit their workflow and cut through vendor hype.
Christina Carter (31:05) AI used to be bad, but it’s improved so fast it’s hard to keep up. You don’t need to be an expert — just follow one trusted voice to stay current.
Henry Brogan (31:34) Exactly. Compare GPT-3.5 to today’s models — they’re incomparable. Experiment yourself. That builds fluency and personal value. BidScript is built for bid pros, but we keep it accessible so anyone can try and learn.
Christina Carter (32:36) Where can people find you if they want to learn more about BidScript?
Henry Brogan (32:42) Follow me, the team, or BidScript on LinkedIn. From our page you can find everyone posting daily insights. We’re also on Instagram, Facebook, and YouTube for longer content and demos.
Christina Carter (33:09) We’ll link everything below so people can find you easily. It was lovely talking to
Why RFPs represent trillions in untapped global contract value and why CROs must take them seriously.
How AI delivers the biggest impact in pre-bid intelligence—not just automated writing.
What questions to ask when evaluating proposal tech and AI tools.
How to close the gap between sales and proposal teams for better capture management.
Why transparent pricing and system design matter more than hype in proposal tech.
Community: https://bit.ly/4hgoVeX
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Website: https://stargazy.io/proposal-tech
LinkedIn: https://www.linkedin.com/in/christinagcarter/
Henry on LinkedIn: https://www.linkedin.com/in/henry-brogan/
BidScript: https://www.bidscript.co.uk/
BidScript on LinkedIn: https://www.linkedin.com/company/bidscript/posts/?feedView=all
BidScript on stargazy: https://stargazy.io/proposal-tech/bidscript