How to buy proposal software you won't hate

THE STARGAZY GAZETTE

BUYING SOFTWARE DESIGNED FOR A PROBLEM YOU DON’T HAVE

Look, most of us have used some sort of proposal or bid software in the past - and in that not-so-distant past, that proposal software was a great proposal content library, where you could store and reuse that 5,000 Q&A pairs that you hoarded like a dragon.

But, that’s not really the way it has to be anymore.

And sure, you have literally 300+ proposal software to choose from now, which is actually a bit chaotic and scary and overwhelming!

How do you not drown in demo hell and how do you shortlist to the proposal software that GENUINELY makes sense for your team?

Well…this is why we’re friends.

At stargazy, we took 5 months to do some deep analysis, a lot of thinking, and far too many demos to write up the 2026 Proposal & Bid Software Report. It exists for one reason → to fix your proposal team diagnosis before the prescription.

Before you sit through another demo, our humble suggestions:

1. Diagnose the constraint. What breaks first: speed, coordination, governance, or compliance? Who touches a proposal before it ships?

2. Match it to a lane. The Report maps the five architectures to the constraints they remove. Pick the one that removes yours, and ignore the other four.

3. Pilot before you commit. Run a twelve-week pilot with real reviewers and a real deadline. Track SME latency and review throughput; demo fluency is not a metric.

Just go read the report before you even think about buying anything.

Read the 2026 Report →

PODCAST SPOTLIGHT

Kristina Nolan, Proposal Strategy Manager at HubSpot, doesn't read an RFP as a checklist. She reads it to see whether the buyer has already decided, and whether the document is a real evaluation or procurement theater.

What she argues in this episode:

• Win rate is the wrong metric for revenue leaders to grade proposal teams on

• The 80/30 gap: AI gets you 80% compliant, but only 30% compelling

• Why most RFPs aren't fair fights, and how to spot the pre-decided ones

• How proposal leaders earn trust and resourcing from a CRO who only watches win rate

• When to bring executive sponsorship into a deal, and how to title-match the buyer

Listen on YouTube · Spotify 

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ANALYST DESK

Forrester's January 2026 State of Business Buying report found the typical B2B purchase now involves 13 internal stakeholders and 9 external influencers, with procurement as the decision-maker in 53% of cycles. More than 60% of buyers run a trial before committing. Among procurement specifically, 28% reported losing confidence in a decision because of inaccurate AI output, and 22% reported wasting time on poor AI information.

At stargazy, we read this and took away four concrete moves for proposal leaders:

1. Map the buying group on every active deal. Identify the procurement lead, the security reviewer, the C-suite sponsor, the technical owner, and the line-of-business champion by name before you submit. If you don't know one, the deal is not qualified.

2. Make every material claim source-traceable. Procurement is fact-checking responses with their own AI. Pin every capability statement to a customer reference with a dated outcome, an independent certification, a published case study, or a third-party benchmark.

3. Build a structured trial into your response. Sixty percent of buyers expect one. Your proposal should propose who runs it, what success looks like, the timeline, and the off-ramp.

4. Lead with proof of outcomes before capabilities. The first page should reference comparable customers and the outcomes they realized. Forrester is explicit that 2026 buyers reward evidence over reputation.

In 2026, whether they’re using AI or not, procurement is calling more of the shots.

Read the Forrester release →

STAKEHOLER MANAGEMENT: A Webinar

Save the date for May 19! We’re partnering with BidScript to chat about stakeholder management and keeping them aligned throughout the RFP process.

Christina joins Henry Brogan of BidScript for a working session on what most proposal teams struggle with (because it’s difficult!) stakeholder coordination across the bid lifecycle. The session is built around the 10-stage process that most proposal teams roughly use, mapped against six stakeholder types (legal, pricing, executives, prime partners, sub-prime partners, and SMEs).

What you'll learn:

• The 10-stage stakeholder map: who needs to be in the room from pre-RFP to award

• A framework for building executive trust before the RFP drops

• The Avoid Seagulls rule for stopping last-minute rewrites that kill carefully-built bids and have also made Christina cry in the past (true story)

• Why treating legal and pricing as downstream gates costs ten times more than catching issues early

Register for the webinar →

More on BidScript in the stargazy analyst write-up. 

TRIBBLE WEBINAR

WIN INTELLIGENCE ASSESSMENT: A Recorded Webinar

Sunil Rao, CEO of Tribble (ex-Salesforce Managing Director), makes a strong case for why AI in proposals and sales should be about winning instead of being super quick.

What you'll learn:

• Why speed doesn’t necessarily win bids in 2026

• The "AI talking to AI" problem that's hurting pharma and healthcare RFPs

• Why the revenue case for AI beats the efficiency case when your CISO is the gatekeeper

• What the “deal brain” does that a static content library cannot

• How proposal teams become the AI champions inside their own companies

Watch and learn here → Anti-AI Slop Webinar for Regulated Industries

More on Tribble in the stargazy analyst write-up.