Winning bids are decided before the RFP arrives, and again by whether the buyer trusts you enough to call you back.

Chris Carter sits down with Simon Cuthbert, founder of Arthurian Labs (Bid Manager Pro), a sales leader turned cybersecurity advisor who speaks at InfoSec and advises across Parliament on cyber. They work through the full pursuit: shaping the opportunity before the document drops, mapping buyers by role, priorities and relationship, qualifying (and re-qualifying) with discipline, and building the bid story before anyone writes a word. Then Simon turns to the risk most teams ignore: what happens to your IP when you paste a live bid into a public AI model.

• ✹ Why the pre-RFP window is a strategy phase, not a preparation phase
• ✹ The two qualification traps that quietly kill win rates: revenue optimism and sunk-cost thinking
• ✹ Where AI belongs in a proposal, and where only a human can win the work
• ✹ The security questions to ask any AI vendor before you upload your data

If you run bids, write proposals, or own a revenue number, you will leave with a sharper way to decide what to chase and what to walk away from.

• ✹ Simon Cuthbert on LinkedIn: https://www.linkedin.com/in/simoncuthbert/
• ✹ Arthurian Labs (Bid Manager Pro): https://stargazy.short.gy/DC8HtH
• ✹ The Stargazy Brief and Stargazy community: https://www.stargazy.io
• ✹ Bid qualification survey referenced in the episode: https://docs.google.com/forms/d/e/1FAIpQLSckMSbM-sOc8ACa9cSU8jb5DDmZVbHS09A2zGz2O-fvMCgIog/viewform?usp=sharing&ouid=107704204777263607772

The bid you win was decided long before you opened the document.

John Witt, Co-Founder and CEO of Stotles, audited government procurement for six years before building a platform that reads the public sector market for revenue teams. In this episode he splits bid teams into two groups: the ones who use data to get leverage, and the ones who use it to do research.

We cover the data most teams ignore, why frameworks are a licence to drive with no car attached, and the question that should kill half your bids before you start writing.

✹ Why 92% of suppliers now use AI to draft bids, and why that stat hides what actually wins

✹ Document intent data: the meeting minutes, FOI requests, and strategy docs that signal demand 18 months early

✹ How to read an incumbent and know when a contract is already lost

✹ Why qualification should be scored like a sales funnel, not a gut call

For revenue leaders, heads of bid, and anyone selling into government who is tired of losing bids they should have walked away from. We'll see you at http://www.stargazy.io

We cover where the human in the loop is disappearing, when buying software beats running on Claude and a spreadsheet, how to answer a CISO who has banned AI, and what happens to win rates in 2027 when every team automates at once.

This is Jasper's second time on The stargazy Brief. He spent more than a decade running enterprise sales and RFP processes before building AutoRFP.ai, and has worked with over 200 companies moving off legacy systems.

✹ Test the import of your messiest documents and the branded export before you trust the middle

✹ Go/no-go, first drafts, and fact-checking are already automated; SMEs are often a safety blanket teams do not need

✹ Volume and FTE-hours are the two signals that tell you when to buy

✹ Zero data retention, zero training, and data residency are the questions that unblock AI in a compliance-heavy sale

For heads of proposals, CROs, and solution engineering leaders deciding what to buy and why the last tool did not fix what it was supposed to.

✨ Explore 1up on Stargazy: https://stargazy.io/proposal-tech/1up...What if proposal and questionnaire software were designed for a world where AI reads your RFP before a human ever does?In this episode of The Stargazy Brief, Chris sits down with George, Founder & CEO of 1up, to unpack how RFPs, DDQs, security questionnaires, and technical responses are actually being evaluated today, and why many proposal “best practices” are breaking/broken.George previously founded and sold a cybersecurity company that lived inside RFPs, security questionnaires, and enterprise due diligence. That firsthand pain led to 1up, and to a strong point of view on automation, qualification, knowledge management, and the risks hiding inside modern proposal tech.This conversation goes beyond tools. It’s about how proposal work is changing when AI is reading, scoring, and filtering responses at scale.⭐ WHAT YOU’LL LEARN✵ How proposals are already being reviewed and scored by AI before humans see them✵ Why “confidence scoring” in proposal tools is misleading and actively harmful✵ The popular proposal tech feature that often makes answers worse, not better✵ Why completeness matters more than “quality” in AI-evaluated RFPs✵ How feature gaps are coming back in machine-based evaluation✵ Why bad AI answers usually come from bad content, not bad models✵ Why pulling Slack into proposal AI systems creates dangerous misinformation✵ How proposal teams can increase influence by thinking more like AEs✵ Why the traditional go / no-go process breaks down once automation exists✵ The emerging “knowledge engineer” role,and why proposal professionals are well positioned to fill it🌟 FIND ON STARGAZY 🌟✸ Community: https://stargazy.circle.so/join?invitation_token=0856b517503bca21eecbae1d058313543675481b-28d54c10-c886-4708-8b3b-ffd62cd3c935✸ Newsletter: https://the-stargazy-brief.beehiiv.com/subscribe✸ Website: https://stargazy.io/✸ LinkedIn: https://www.linkedin.com/company/stargazyproposals/🌙 GUEST LINKS 🌙✸ 1up Website: https://www.1up.ai/✸ 1up on LinkedIn: https://www.linkedin.com/in/george-avetisov/✸ George on LinkedIn: https://www.linkedin.com/in/george-avetisov/✸ 1up’s Stargazy Page: https://stargazy.io/proposal-tech/1up

🌟 Trampoline on Stargazy: https://stargazy.io/proposal-tech/trampoline-aiWhat if proposal software actually understood your documents, your experts, your case studies and your procurement evaluator?In this episode, Edouard Reinach, CEO and co-founder of Trampoline AI, reveals how AI-native proposal tech is really changing AEC, professional services, and enterprise bidding.Edouard has worked on both sides of RFPs, procurement and proposals, so this conversation is pure insider intel. You’ll hear how teams are rewriting their entire workflow using visual language models, agentic flows, and automated knowledge management that actually works in real bids.⭐ WHAT YOU'LL LEARN:✵ Why AEC and professional services proposals are NOT “too bespoke” for AI✵ How Trampoline reads PDFs, tables, images, and even video, with spatial understanding✵ How to use AI to extract CVs, project sheets, and case studies without ruining quality✵ The “journalist method” for case study collection (SMEs respond instantly)✵ What procurement reviewers really scan for in the first 2–3 minutes✵ How evaluators use AI right now and why structure is your biggest advantage✵ Why you should start every proposal with a “Save the Cat” moment✵ How to build a modern proposal team using judgment + AI (not prompts)✵ How proposal teams can prove strategic value to CROs and sales leadership✵ The ROI argument that gets tools like Trampoline approved✵ Why the Go/No-Go engine changes team behavior in 3 minutes🌟 FIND ON STARGAZY 🌟 ✸ Community: https://stargazy.circle.so/join?invitation_token=0856b517503bca21eecbae1d058313543675481b-28d54c10-c886-4708-8b3b-ffd62cd3c935✸ Newsletter: https://the-stargazy-brief.beehiiv.com/subscribe✸ Website: https://stargazy.io/✸ LinkedIn: https://www.linkedin.com/company/stargazyproposals/🌙 GUEST LINKS 🌙 Trampoline AI Website: https://www.trampoline.ai/Go/No-Go Engine (Free): https://gonogo.trampoline.ai/enEdouard Reinach on LinkedIn: https://www.linkedin.com/in/ereinach/Trampoline LinkedIn: https://www.linkedin.com/company/trampolineai/✸ Trampoline AI's Stargazy Page: https://stargazy.io/managed-services/tendium-managed-services⭐ TIMECODES00:00 Intro — Why Trampoline is different01:03 What AEC firms misunderstand about “non-standard” proposals01:49 How Trampoline reads any format (PDF, Excel, images, video)03:12 Why writing isn’t the hard part, but project management is04:39 Fixing case studies + CV chaos in AEC06:02 The “journalist” method for SME interviews07:21 How SMEs actually respond (and why disagreement is gold)08:11 What procurement really looks for in CVs + case studies09:49 Why structure beats long responses in evaluation10:00 Do procurement teams use AI to score RFPs?12:18 Can AI improve win rates? What’s realistic vs hype13:52 How teams safely increase RFP volume without burnout14:06 Go/No-Go engines and objective qualification15:46 The real quality-of-life impact of AI in proposal teams16:14 How proposal teams should talk to leadership about budget17:44 Turning proposal work into revenue math19:11 Why some proposal teams get treated like strategists21:59 Building a defensible business case for AI-native tools23:11 What to automate first (and what AI still can’t do well)24:38 Document shredding preferences and customization26:30 The future of storytelling in proposals28:21 Why exec summaries fail—and how to write the first 3 pages29:44 How to build a modern proposal team from scratch31:44 The missing piece: win-loss synthesis as strategy32:58 Writers, judgment, and the human side of narrative35:03 Why proposal teams should take demos without waiting for permission35:57 Where to find Trampoline

What are GovCon hiring managers really looking for in proposal and capture talent right now, and how is AI changing who gets hired, promoted, or passed over?

In this episode of The Stargazy Brief, Christina Carter talks with Al Vega, a US federal GovCon recruiter, about what’s happening in the proposal/capture job market in 2026. This is a tactical conversation for proposal professionals who feel underpaid or underleveled, want to move into better-paying roles (including DoD), or want to avoid common LinkedIn and resume mistakes that quietly disqualify strong candidates.

You’ll hear what skills are standing out, how strict GovCon requirements shape hiring decisions, why clearances and certifications can move salary, and how to use AI as an advantage without letting it “interview for you.”

In this episode, we cover:

• The top skills hiring managers want in capture + proposal roles

• How AI is affecting GovCon hiring and interview trust

• The #1 LinkedIn mistake that turns recruiters off

• When it’s still worth applying if you don’t meet every requirement

• How to move from civilian agencies into DoD roles (and what tradeoffs to expect)

• Clearances, certifications, and other salary levers

• Smart questions candidates should ask to avoid bad-fit roles

• How proposal writers can future-proof their careers as AI adoption grows

  
  

  🌟 FIND STARGAZY 🌟✸ Website (shortlist tools + vendor profiles): https://stargazy.io/✸ Community to join the conversation: ✸ Newsletter: https://the-stargazy-brief.beehiiv.com/✸ LinkedIn: / stargazyproposals 🌙 GUEST LINKS 🌙✸ Al Vega on LinkedIn: / vegarecruits

✨ Explore Turingon on Stargazy: https://stargazy.io/proposal-tech/proposal-pilotWhat if proposal software were built not by generalist engineers, but by people who have lived through GovCon deadlines, FAR audits, and price-to-win pressure?In this episode, Arthur Runno, CEO of Turingon and a veteran of twenty years in federal proposals, explains how the rapid changes in US federal procurement, small-business policy, cyber standards, and AI-assisted evaluation are reshaping how contractors compete.Arthur breaks down how Turingon is designing AI-native tools directly from GovCon experience: tools that understand compliance, substantiation, price realism, teaming strategies, and the structural demands of federal proposals. You’ll hear why the next era of GovCon bidding will reward teams with higher throughput, stronger qualification discipline, and AI systems built specifically for federal work.⭐ WHAT YOU’LL LEARN✵ How FAR 19 reforms and small-business rule changes will alter capture strategy and competitive landscapes✵ Why fixed-price dominance increases pricing discipline and makes compliance-driven writing more decisive✵ How AI-assisted evaluation is changing what evaluators score and how teams should structure their proposals✵ Why GovCon proposal teams should expect higher volumes in the coming years, not fewer✵ The new role of cyber: FedRAMP inheritance, secure environments, and why proposal tools must meet federal expectations✵ Why general-purpose AI tools struggle in GovCon and what “AI built by proposal managers” looks like in practice✵ Practical steps for integrating AI into your capture and proposal workflow without compromising quality or control🌟 FIND ON STARGAZY 🌟✸ Community: https://stargazy.circle.so/join?invitation_token=0856b517503bca21eecbae1d058313543675481b-28d54c10-c886-4708-8b3b-ffd62cd3c935✸ Newsletter: https://the-stargazy-brief.beehiiv.com/subscribe✸ Website: https://stargazy.io/✸ LinkedIn: https://www.linkedin.com/company/stargazyproposals/🌙 GUEST LINKS 🌙✸ Turingon Website: https://www.turingon.com/✸ Turingon on LinkedIn: https://www.linkedin.com/in/arunno/✸ Arthur Runno on LinkedIn: https://www.linkedin.com/in/arunno/✸ Turingon’s Stargazy Page: https://stargazy.io/proposal-tech/proposal-pilot⭐ TIMECODES00:00 Introduction to GovCon and Proposal Management03:01 Impact of FAR Reforms on Business Development04:38 What Small Businesses Can Do Right Now06:06 Strategies for Small Businesses in a Changing Landscape07:05 NEWCHAPTER07:21 Pricing Strategies in a Firm Fixed Price Environment09:41 AI's Role in Pricing and Proposal Evaluation10:39 How Proposals Are Getting Evaluated Now13:43 Compliance Shifts and Cyber Standards in Proposals19:07 Navigating AI Tools in Government Contracting19:20 Questions to Ask Proposal Tech Companies before You Buy24:25 Adapting to Cultural Shifts in GovCon26:48 How Can Proposal Professionals Adapt to the Constant Changes28:56 Preparing for Government Shutdowns32:13 Investing in Future Skills for Proposal Managers36:59 Podcast Intro.mp4🔥 Subscribe to future-proof your GovCon proposal, capture, and BD team.#GovCon #ProposalTech #Turingon #RFP #FAR19 #AIinProposals #ProposalManagement #CaptureManagement #BDStrategy #FederalContracting #GovConAI #ProposalAutomation #ComplianceWriting #PriceToWin #FedRAMP #CMMC #GovTech #RFPSoftware #AcquisitionReform #ProposalThroughput💬 Your TurnWith FAR changes, pricing pressure, and AI-assisted evaluation accelerating, what part of your federal proposal workflow needs to adapt first?

If you’re a GovCon contractor still waiting for RFPs to hit SAM.gov, you’re already behind. In this episode of The Stargazy Brief, Chris and Derek unpack how modern capture teams use AI-driven intent signals, early partnership strategies, and FedRAMP-secure proposal tech to win before opportunities ever reach SAM.gov.Hoyt shares the insider mechanics of how government deals are shaped months before posting and how small and mid-size contractors can still compete by focusing on meaning over data, qualifying smarter, and adapting to the new intent-driven capture paradigm.🎯 GovSignals helps GovCon professionals modernize proposal management with AI, intent data, and secure tech, so they can win more bids with less waste.