The Proposal is Dead. Long Live the Proposal.

🔭 The Proposal is Dead. Long Live the Proposal.

Let’s get one thing straight, proposal folks. Proposals aren’t paperwork. They’re prophecy.

According to Ben Hills, CEO of Iris, who argues that RFPs aren’t admin. Nope! They’re the first real sales conversation.

And with AI finally taking the more admin pieces of work off proposal teams’ plates, an often-ignored function is now sitting on a goldmine of strategic leverage.

Here’s why the smartest revenue teams are putting proposal managers in the pilot’s seat and why the rest are going to lose altitude fast.

According to recent surveys, 96% of enterprises now deploy AI in some part of their core business processes. For proposal teams, this shift is especially consequential. Your competitors are already using AI to qualify opportunities, generate first drafts, and personalize responses. If that’s all you’re doing, then you’re not actually at an advantage.

And teams that persist with purely manual processes will struggle with slower response times and diminished competitiveness.

Yet AI is not a simple plug-and-play solution. Successful adoption requires addressing the challenges of data quality, system integration, security, and organizational culture.

RFPs Are Now the Entire Sales Cycle? You heard me.

Thanks to expired contracts, overwhelmed buyers, and GenAI-fueled RFP automation, prospects are skipping the usual sales cycle courtship. They’re using proposals to shop, not just to confirm.

That means:

• If you wait for a sales call, it might be too late.

• If you treat an RFP like a formality, you’re a formality (I was proud of this line.).

• If you build proposal strategy like you build outbound motion, you’ll win deals your competitors never saw coming.

Remember: not all RFPs are rigged anymore. As we are about to roll into 2026, RFPs are the only real game in town.

AI’s Real Proposal Superpowers (Spoiler: It’s Not Drafting)

Most sales teams think AI is for writing boilerplate faster. Sure? But use it better than your competitors, like:

• Auto-qualify opportunities in minutes, not hours.

• Create instant post-win checklists for your account or professional services team handoffs.

• Spot shifting buyer concerns by analyzing question trends across industries.

• Nudge everyone to hit deadlines without Slack-splosions because AI agents don’t mind reminding that one SME who keeps ignoring you but really needs to respond.

Think of AI more as a project manager and strategic analyst rolled into one emotionally-unavailable robot that needs your oversight always.

Context Engineering = Proposal Personalization That Actually Scales

Most teams aren’t doing this, but if your AI knows who the buyer is (and what freaks them out about moving to a new service or product), it can write a response that doesn’t sound boring or generic.

You can do this if you feed your tools the right ingredients:

• Industry benchmarks

• Content from your customer stakeholders (podcasts, blogs, LinkedIn posts)

• CRM notes

• Call transcripts

• Public content (financials, investor reports)

• Competitor positioning

You’ll get responses that feel like you wrote every line after deep analysis.

The Post-Win Handoff Is Where Most Deals Die Quietly

Winning the deal is only halftime. What happens next, handoff to customer success, is where buyer trust either compounds or collapses.

I usually see most teams treat handoff like a game of telephone. AEs promise a gazillion things to the customer, but once it’s sold, the CS person inherits a black box.

Ben Hill suggests you use AI to help with the handoff. AI can pull commitments directly from the proposal (yes, even the fine print), and generate:

• Implementation checklists

• Milestone timelines

• Customer-facing onboarding briefs

It’s like sending your CS team into the new relationship with a cheat sheet and a love letter.

More importantly, it protects trust. Because if you promised one thing in the proposal, but CS delivers something else, that’s not a hiccup; it’s a churn risk.

Action: Build a “handoff kit” that’s automatically generated from every submitted proposal. Make it part of your close/won process, not an afterthought.

Proposal Questions Are Buyer Intent Signals in Disguise

Every question a buyer asks in an RFP is a clue. Track them, and you’ve got a telescope into shifting market expectations.

Tracking these trends is a lot more possible with AI, and doing this gives you a real-time pulse on what buyers actually care about, before your competitors even notice.

For example:

• A spike in cybersecurity questions? Buyers are nervous.

• Everyone asking about integrations with a certain tool? That tool’s eating market share.

• Requests for outcome-based pricing? Your old sales model may be aging out.

This is market intelligence your exec team should be drooling over, and you can start surfacing it to them like the strategic professional you are.

🌌 Pro move: Use AI to auto-tag and cluster questions across proposals. Then send a monthly "buyer signals" briefing to sales, product, and marketing.

✨ Final Thought

We’re in a weird, wonderful moment. Proposal managers have a shot at becoming more recognized as revenue power players, if you start thinking and giving your data to leadership like forecasters.

RFPs are no longer the afterparty. They’re the main event.

↣ ↠ Get the full runthrough: Rethinking Proposal Management in the Age of AI

Join the conversation in Stargazy

Magno vs. Parvo: Two Brains in One Proposal
Ashleigh Applegate, Global Content Manager at ATS Global, wrote a killer post in Proposal Best Practices that blends neuroscience with proposal design. She explains how our brains process content through two pathways: Magnocellular (Magno): fast, big-picture, contrast-driven and Parvocellular (Parvo): slow, detail-oriented, color-driven.
Add your perspective → 

Debate: Compliance vs. Story. Which matters more?
Arthur Runno at Proposal Pilot raised the point: “Compliance is the price of admission. Story only wins once you’re at the table.” Do proposal teams spend enough time on compliance before polishing the narrative?
Jump into the debate →

Poll + badges
This week’s badge drop is all about Steerlab, the AI-native platform rethinking content management. Four exclusive Stargazy x Steerlab badges are on the line, but you only get a badge if you vote. Which one fits you be
Choose your content library archetype →

Interview with Ben Hills

What Buyer Behavior is Changing & What That Means for Proposal Professionals

Ben Hills (CEO of Iris) broke down how buyer behavior is shifting and what it means for proposal teams.

The conversation covered:

• How AI can streamline capture, handoffs, and project management

• Why single sources of truth often fail, and what to do instead

• The art of “context engineering” for personalization that wins

• The evolving role of proposal professionals (and how to future-proof careers)

Ben also shared common mistakes teams make and the balance between speed and quality.

The Stargazy Buyer’s Field Guide for Content Librarians

Everyone says they love their content library. (Okay… maybe “love” is a stretch. But we know how critical they are.)

And we all know that all content libraries are far from equal. Some keep you buried in tagging and non-stop upkeep. Others just content with every other team’s content and let you write your library content without having to tag.

If content is your battlefield (as it has been mine for 500 years), here are four tools reshaping the way proposal teams manage, trust, and scale their libraries:Let’s dive in:

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See you there,
✨ Chris

P.S. Follow us on LinkedIn for launches, playbooks, and upcoming AMAs.

P.P.S. You can review your proposal software tool on stargazy. That gives us proposal people a better idea of what tools our peers love…and which ones aren’t for us.