✹ Is Your Proposal Data Tracking Process Is Leaving Money on the Table? Probably.

Across industries, the pattern is unmistakable: Proposal teams feel invisible. Leaders treat RFPs as a necessary evil, a cost center to be managed rather than a revenue engine to be optimized.

Yet the companies that consistently outperform their competitors have figured out something crucial. They treat proposals as a measurable channel for growth.

The difference isn't effort or good intentions, though that would be nice. The difference is in discipline around data, decisions, and what actually moves the win/revnue margins.

AI tools promise to help, and they can. But only after you've built the right foundation. Without that context layer, you're just generating content that reads smoothly but loses deals anyway.

If you lead sales, proposals, or revenue operations, ignoring this reality is a costly mistake. The choices you make about proposals shape everything, including your bookings, your margins, your speed to close, and your risk exposure.

Here are eight questions to help you stress-test your approach, and turn proposals into the growth lever they should be.

1. Where is your proposal work creating value, and where is it destroying it?

The clearest path to improvement starts with connecting proposals to actual revenue, in addition to the activity metrics you’re probably already following. Track which bookings came from RFPs and calculate the gross margin by segment. Then get specific about where value is leaking away.

Look for discounts that get applied without improving your odds of winning. Identify approvals that stall momentum. Find the security evidence that arrives too late to matter.

Start simple. Publish a single page each month showing bookings, margin, and the top three causes of leakage. Use it to decide what to fix first. This isn't about perfection; it's about visibility.

2. What decisions are you actually tracking from lead to loss?

Most teams will tell you they're rigorous about their process. But few are logging the decisions that actually determine outcomes.

Instrument the choices that matter: bid or no-bid, pricing posture, partner strategy, compliance trade-offs, etc. Capture the rationale in simple tags so you can analyze patterns later. After each award decision, win or loss, record what changed the outcome.

Over time, this becomes your decision spine. It also reduces endless debate.

3. Are you feeding AI real buyer context, or asking it to guess?

AI improves speed and consistency, but only when it's retrieving the right evidence before it starts drafting. Too many teams skip this step and wonder why their AI-generated content falls flat.

Build a retrieval layer that unifies your capture notes, prior wins, evaluator feedback, competitor intelligence, and public buyer signals. Constrain what the AI generates to approved sources. Then log the human edits that actually improved persuasion.

Most good proposal management tools already do this automatically, so make sure to choose one that does this already.

4. Which signals are you sitting on but not using?

Most proposal teams hold more decision-grade data than they realize.

The problem is that it's scattered, unstandardized, and impossible to query. Make it queryable and you'll unlock insights hiding in plain sight.

Consider standardizing these signals, like:

• Question drift by quarter, including emerging themes around AI use, privacy, and software bill of materials requirements.

• Security requirements versus the evidence you have on hand and how long it takes to compile proof.

• Pipeline conversion by geography and industry from received to won.

• Evaluator scores and feedback linked to actual outcomes.

• Competitor patterns and typical discount ranges.

• The relationship between discounts applied, win probability, and achieved margin.

• Cycle time by stage, owner, and buyer type.

• How complete your capture work was and its correlation to shortlist rates.

Literally no one else has this data other than the proposal team. It’s powerful, and you need to use it.

5. What does your CRO need that only proposals can provide?

Executives don't buy into process improvements, complaints of late-night work, or submission numbers. But they do buy into outcomes that show up on their exec-level scoreboard.

That means we need to do what we already do best: translate our proposal work into their language.

• Show them pipeline realization, the percentage of qualified RFP pipeline that actually books within a defined window.

• Report time to close, both median and 90th percentile, along with the top bottlenecks slowing deals down.

• Quantify risk-adjusted value at risk due to legal or compliance gaps, and attach a fix plan.

• Surface customer focus shifts visible in question and requirement trends.

• Calculate RFP customer acquisition cost and payback periods.

• Present discount curves by segment that balance win probability with margin protection.

• Track forecast accuracy for your RFP channel.

Bring these views to the table. Then ask for the one change that would move next month's bookings. When you speak the language of revenue impact, you get a seat at the table. When you speak the language of process and hours worked, you get ignored.

6. How fast do you learn after each award decision?

Most companies treat wins and losses as endpoints. High-performing teams treat them as data.

Governance only matters if it changes behavior. The companies that learn fastest win more often; the ones that don't repeat the same mistakes quarter after quarter.

7. Are you ready to disclose how you use AI?

This question matters more than most leaders realize. Buyers are starting to ask pointed questions: How are your models trained? What sources do you use? How do humans review AI-generated content?

Include a short, standardized section in every bid that addresses these concerns head-on. Name your data sources, validation checks, and oversight procedures. Treat it the same way you treat security evidence, which is as a requirement.

Clarity reduces risk and speeds approval. Opacity creates problems you don't need.

How to Put This to Work in 90 Days

You don't need a massive transformation. In fact, I wouldn’t suggest you do that at all. But you do need focused execution.

In weeks one and two, stand up retrieval before you worry about generation. Connect your capture notes, evaluator feedback, approved content, and competitor intelligence in a searchable repository.

In weeks three and four, instrument the loop. Add mandatory fields for bid/no-bid decisions, pricing posture, partner choices, compliance status, and the rationale behind each. Define what the 48-hour post-award update looks like.

In weeks five and six, create the CRO one-pager: bookings and margin with identified leakage causes, pipeline realization versus your commit, median and 90th percentile time to close, RFP customer acquisition cost and payback, expected value at risk with a fix plan, discount guidance by segment, and three recommended changes for next month.

In weeks seven and eight, deploy three foundational models, including win probability by segment, competitor, and capture completeness; price elasticity linking discount levels to win odds and margin; and message-to-score mapping that connects proposal sections and themes to evaluator outcomes.

In weeks nine through twelve, standardize your evidence packs. Pre-assemble security, privacy, AI disclosure, SBOM, and ESG exhibits. Measure the cycle-time reduction and score improvements. Use what you learn to refine your guardrails.

Improving proposal performance won't happen overnight. And you don't have complete control. I know budget constraints, legacy systems, and market dynamics all play a role. What matters is being deliberate about what you can influence.

You can keep treating proposals like paperwork. Or you can treat them like what they actually are: an asset class in your revenue portfolio. The companies that win consistently wire context before content, measure the decisions that matter, and publish the numbers that help leaders steer the business.

Small, disciplined moves create momentum. The result is fewer bad bets, tighter pricing, faster deal cycles, and proposals that actually win. You won't transform everything in a quarter, but you might just turn proposals into the competitive advantage they should be.

✹ Join the conversation in stargazy’s hub

Halloween Special 🦇

Matt Light asked what fancy dress (costume) was the best or worst we’ve ever worn! If you’ve ever been impressed by or ashamed of your Halloween attire, we want to know! Bonus points for pictures! Jump in and tell us your tale→

Factoring in competition?

Emeric Gabor shared a poll, asking everyone how much they research their competitors before writing their proposals. It turns out, you proposal people are… Have your say in stargazy→

Best AI tools for graphics in proposals?

Stephanie asked us if we could share our favorite software that is capable of adding a charge or graph with outcome data that supports formatting? Is there any AI for RFP’s that will export text + graphics without requiring post-export reformatting? Or perhaps a post-formatting AI tool
If you know of one, jump in!→

✹ Join the stargazy intelligence hub

Proposal leaders from AWS, Google, Deloitte, Mace, and Capita are already inside. Join us, too?

Happy Halloween to those who observe 🧙🏻‍♀️

See you under the stars,
✨ 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.

P.P.P.S. Do you want to contribute to a blog post or newsletter? Let me know!

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