The Stargazy Brief: Proposals & RFP Win Strategy

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 saleFor 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.

What are enterprise buyers actually scoring during a proposal, beyond the document itself?Greg Ellis, Senior Solution Consultant for enterprise deals at Zendesk, ran proposal operations at Fujitsu, Freshworks, and OneTrust before moving into technical sales. In this episode he sits with stargazy founder Christina Carter to map the gap between proposal teams and solution consultants, and why that gap costs deals long after the RFP is submitted.✹ The dilution effect: why working on fewer bids almost always wins more✹ Why a 40% price drop without a commercial breach reads as broken trust, not benevolence✹ The 18-month rule for turning a lost bid into next year's pipeline✹ What "just send the previous proposal" actually costs your weekendFor proposal managers, solution consultants, and revenue leaders who suspect the centrifuge model of the bid is what is breaking their win rate.

What an RFP reveals about a buyer often hides in plain sight. Kristina Nolan, Proposal Strategy Manager at HubSpot, knows what to look for.In this episode of the stargazy brief, Kristina draws on a career spanning operations, finance, and revenue execution to unpack what makes proposal teams a strategic asset, not an internal print shop. She and Christina Carter cover signal-reading inside an RFP, qualification discipline, the limits of AI in proposal writing, and why executive sponsorship changes deal economics.Highlights:✹ Why no-go rate matters more to a CRO than win rate✹ How to read competitor language and procurement signals in an incoming RFP✹ The 80/30 gap: AI gets you compliant, not compelling✹ How HubSpot uses executive sponsorship and title-matching on RFP deals✹ Why proactive, prescriptive proposals are the offensive capability most teams ignoreBeyond the metric debate, Kristina explains how AI is moving the proposal function from defensive responder to offensive prospector, and how proposal leaders can earn the trust and resourcing they need from revenue leadership.For revenue leaders, proposal directors, and practitioners who want to think about RFPs as commercial discipline.

Bid and proposal teams generate up to half of all organizational revenue. So why are most of them still treated like admin?Matt Light is Director of International Proposals at Acela Health and Deputy CEO of APMP UK. He has built proposal teams that consistently hit 80%+ win rates across healthcare and public sector. In this conversation, Christina and Matt dig into what separates strategic bid functions from compliance-driven ones, and what it takes to get bid professionals into the rooms where decisions happen.✹ The revenue data that should make every CFO pay attention to their proposal team✹ Annual birthday reviews: a rebid strategy that prevents incumbency complacency✹ Why 82% of high performers promoted to leadership fail within two years, and what bid leaders can do differently✹ How to use the language of risk to get ethical no-bid decisions past the C-suiteIf you lead a bid or proposal team, manage proposal professionals, or sit in a revenue leadership seat, this episode shows you exactly where the leverage is.

The biggest fear pre-sales leaders have about AI isn't job loss. It's being blamed when the AI is confidently wrong and nobody catches it.Manisha Raisinghani, Co-founder and CEO of SiftHub, interviewed over 200 sales and pre-sales leaders before building her platform. In this episode, she and Christina Carter dig into why trust, not speed, is the real design principle for AI in deal-critical workflows, and what that means for how you evaluate, implement, and measure proposal technology.✹ Why percentage confidence scores (78%, 85%) give reviewers nothing actionable, and how a red/yellow/green system tells SEs exactly where to spend their time on a 500-question RFP✹ How one SiftHub customer saw deal stage advancement jump from 65% to over 90% by improving response quality, not speed✹ The concept of a persistent deal graph: why your AI layer should span the entire deal cycle, not end at the questionnaire✹ Why the proposal leader of the future is an agent manager, training and tuning AI agents the same way you'd manage a team of fast junior analystsWhether you run a proposal team, lead pre-sales, or sit in a CRO seat wondering why your AI investment hasn't moved win rate yet, this conversation will reframe how you think about what good looks like.

Most GovCon leaders treat bid protests like a panic button. David Timm, partner at Bernd Foreman and chair of the Federal Bar Association's Bid Protest Committee, explains why that instinct costs money.In this conversation with Christina Carter, David breaks down the three forums for filing protests (agency, GAO, and the Court of Federal Claims), explains why GAO's tightened pleading standard in 2025 has already cut sustained protests to three in early 2026, and addresses the question every contractor should now ask in debriefings: was GenAI used to evaluate our bid?✹ Pre-bid protests have higher success rates because there's no intervenor with a vested interest in the outcome✹ The Court of Federal Claims provides less deference to agency decisions than GAO, often reversing outcomes GAO denied✹ GAO has sustained only three protests in the first two months of 2026 after tightening its pleading standard✹ AI hallucinations in bid protest filings have resulted in losses in every documented case so farIf you lead a GovCon proposal team, run capture, or make bid/no-bid decisions, this episode changes how you think about protest as a strategic option rather than a last resort.✨ David Timm's Links & Resources✹ David Timm's LinkedIn: https://www.linkedin.com/in/timmdavid/✹ The 2025 GenAI Misuse Report: https://www.burr.com/government-contracting/gen-ai-misuse-in-procurement-litigation✹ Burr & Forman Government Contracts Blog: https://www.burr.com/newsroom/blogs✹ Implications for the procurement system for NCMA: https://content.ncmahq.org/contractmanagement/library/item/march_april_2026/4325685/✹ GAO/COFC Splits: https://mcsmag.com/gao-cofc-bid-protest-splits/✹ Dean Jessica Tillipman (GW Law) on AI in procurement: https://jessicatillipman.com/✹ GAO Bid Protest Decisions: http://gao.gov✨ Stargazy Links & ResourcesIf you’re evaluating proposal technology or AI tools for a regulated environment, use Stargazy to compare options, see peer insights, and build a shortlist designed around governance and defensibility.✹ Explore vendor profiles and shortlist tools: https://stargazy.io/✹ Join the proposal leadership community: https://stargazy.circle.so/✹ Subscribe to The Stargazy Brief: https://the-stargazy-brief.beehiiv.com/

If you lead an RFP team in a highly regulated market, proposal strategy starts with defensibility: where data goes, what’s provable over time, and how approved messaging stays differentiated. Perry Robinson (CEO, RocketDocs) breaks down the risks teams miss when they focus only on hallucinations instead of data flow visibility, contractual control, auditability, retention, and governance.What you’ll learnHow to evaluate proposal tech in regulated environments using a defensibility lensThe 3 vendor questions that surface real risk: data flow, ownership/control, audit trailHow “system of record” thinking changes approvals, retention, and traceabilityHow to prevent AI-assisted responses from drifting into generic, look-alike languageHow to involve compliance, privacy, legal, and security earlier in the buying processHow to reduce SME burden while strengthening governanceChapters00:00 The real compliance risks for regulated RFPs02:40 Governance, control, and AI risk in regulated proposals02:59 The gatekeepers: compliance/security in the buying process03:57 What teams fear vs. what actually matters11:35 Automation that reduces SME burden16:26 Evaluation checklist for regulated teams16:51 3 vendor questions: ownership, data flow, audit trail19:04 Proposal leaders as enterprise knowledge stewards21:36 System of record: retention, approvals, and content libraries28:45 Staying manual: version control, auditability, compliance exposure32:30 Recap: defensibility + differentiationLinksRocketDocs: https://bit.ly/4u8lSeHStargazy (compare proposal tech + build a governed shortlist): https://stargazy.io/Stargazy community: https://stargazy.circle.so/The Stargazy Brief: https://the-stargazy-brief.beehiiv.com/CreditsStargazy x RocketDocs (with Christina Carter)

Proposal teams sit on a goldmine of revenue intelligence. But most organizations don’t realize it.In this episode of the Stargazer Brief, we explore why bid and proposal teams are still treated as cost centers, and how AI is creating an opportunity to reposition them as strategic revenue partners.This conversation breaks down how proposal leaders can shift perception, earn influence, and stop chasing deals they already know they won’t win.✹ Why revenue leaders often misunderstand the bid function✹ The difference between proposal automation and proposal intelligence✹ How AI should be used for structuring and enriching, not replacing, strategic thinking✹ Why recurring internal insight updates change executive perception✹ What metrics revenue leaders actually care about beyond win rate✹ How agentic AI workflows streamline complex proposal processes✹ What to look for when evaluating proposal software in 2026✹ The one industry habit proposal teams must stop immediatelyFollow Stargazy on Spotify for executive-level insights into proposal strategy, AI workflows, and the future of revenue intelligence.🌟 Check out Altura at https://bit.ly/4l9l5Xa🌟 Connect with Matthijs on LinkedIn: https://www.linkedin.com/in/ai-driven-bid-management/🌟 Altura's Stargazy profile: https://stargazy.io/proposal-tech/altura

In professional services firms, CVs and experience sections are often treated as administrative documents. In reality, they directly influence RFP evaluation scores, perceived delivery risk, and ultimately win rates.In this episode of The Stargazy Brief, Christina Carter speaks with Erling Linde, CEO and Co-Founder of Flowcase, about how proposal teams can improve bid performance by structuring, maintaining, and tailoring CVs strategically.As AI accelerates drafting across the industry, solution narratives are becoming more uniform. What remains defensible is documented proof of expertise. Erling explains how high-performing firms treat CV data as a strategic asset rather than static HR content, and why executives increasingly expect proposal teams to align with board-level priorities such as cost efficiency, AI ROI, and measurable revenue impact.Topics covered include:How CVs affect RFP scoring criteriaThe difference between claims and documented proofBest practices for tailoring resumes to specific bidsUsing CV data in go/no-go decisionsWhere AI adds value in proposal workflowsWhy reputation and past performance remain decisiveThis episode is relevant for proposal leaders, bid managers, CROs, and professional services executives navigating AI-driven change in RFP environments.Learn more about Stargazy at stargazy.io.

In this episode of The Stargazy Brief, Christina Carter speaks with Ray Meiring, CEO of QorusDocs, about how AI is changing the role of proposal teams across AEC, legal, GovCon, and professional services.Ray shares insights from conversations with CEOs, CROs, managing partners, and sales leaders on how proposal functions are shifting from compliance-driven document production to strategic revenue contribution.The discussion covers:Why proposal teams are still viewed as cost centersHow AI is reducing transactional and compliance-heavy workThe importance of early capture involvementData-driven bid/no-bid qualificationWhat differentiates winning proposals in an AI-saturated marketHow proposal leaders can increase strategic influence inside revenue teamsThis episode is designed for proposal leaders, sales leaders, solution teams, and firm partners who want to increase win probability and reposition the proposal function as a strategic driver of growth.Learn more at: https://stargazy.ioConnect with Ray Meiring and QorusDocs at: https://www.qorusdocs.com/request-a-demo?utm_source=stargazy_podcast&utm_medium=podcast&utm_campaign=stargazy

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 rolesHow AI is affecting GovCon hiring and interview trustThe #1 LinkedIn mistake that turns recruiters offWhen it’s still worth applying if you don’t meet every requirementHow to move from civilian agencies into DoD roles (and what tradeoffs to expect)Clearances, certifications, and other salary leversSmart questions candidates should ask to avoid bad-fit rolesHow 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  

In this episode of The Stargazy Brief, Christina Carter sits down with Gareth Meredith (Softcat; formerly RingCentral, 8x8, Inventive AI), a bid leader known for building 60–70% win-rate systems through disciplined process, leadership, and one underrated lever... answer planning that sells.They break down what actually moves win rate in 2026:Why systems beat automation (and why AI only works when it supports a strong process)Where AI helps today: compliance, questionnaires, and reducing bid-manager overloadWhere AI still fails: breaking down questions, building persuasive structure, and “reading between the lines”How to operationalize a proposal function: front-loaded governance, repeatable kickoff, lean reviews, fewer late-night fire drillsHow to pitch change to a CRO: revenue math + voice-of-customer evidence, not emotionWhat to track (and what to ignore): win rate, quality scores, revenue/gross profit (and why shortlist rate is mostly noise)Cultural debt in bid teams: underinvestment, burnout norms, and the “admin label” that kills strategic impactFollow Gareth Meredith on LinkedIn for practical, transparent breakdowns of bid systems, quality, and process that scales.🌟 FIND STARGAZY 🌟✸ Website (shortlist tools + vendor profiles): https://stargazy.io/✸ Community (join the conversation + Gareth AMA): https://stargazy.circle.so/join?invitation_token=0856b517503bca21eecbae1d058313543675481b-28d54c10-c886-4708-8b3b-ffd62cd3c935✸ Newsletter: https://the-stargazy-brief.beehiiv.com/✸ LinkedIn: https://www.linkedin.com/company/stargazyproposals/🌙 GUEST LINKS 🌙✸ Gareth Meredith on LinkedIn: https://www.linkedin.com/in/gareth-meredith/

✨ 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

✨ 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?

✨ See mytender.io on stargazy: https://stargazy.io/proposal-tech/mytender-ioWhat if bid-writing software actually understood your past tenders, subject-matter experts, case studies, and evaluation criteria...and drafted winning proposals for you?In this episode, Jamie, Co-Founder and Chief Product Officer of mytender.io, walks us through how AI-native bid writing is transforming procurement, facilities management, construction, and enterprise tenders. Jamie explains how mytender.io automates repetitive writing tasks so proposal managers can refocus on strategy, storytelling, and winning. You’ll hear about how AI is already streamlining bid writing workflow and what to watch out for when bringing AI into your proposal process.⭐ WHAT YOU’LL LEARN:✵ Why sectors like construction, facilities management, and general contracting are ripe for AI-driven bid writing✵ How mytender.io learns from previous submissions to generate relevant first drafts and minimise manual rework mytender.io✵ Why bid writers remain essential: AI drafts, humans refine, preserving tone, compliance, and organisational voice✵ How to use AI for bid/no-bid decisions, capture-phase research, and faster response turnaround✵ What high-performing bid teams do differently, like balanced win themes, clear storyboarding, and strategic review, not just automated writing✵ Practical tips for embedding AI tools into existing workflows without disrupting team dynamics or quality🌟 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 🌙✸ mytender.io Website: https://mytender.io/✸ mytender.io on LinkedIn: linkedin.com/company/mytender-io/posts/✸ Jamie Horsnell on LinkedIn:https://www.linkedin.com/in/jamie-horsnell/✸ mytender.io's Stargazy Page: https://stargazy.io/proposal-tech/mytender-io⭐ TIMECODES00:00 Why mytender.io was founded02:15 The pain point: why bid writing frustrates SMEs & agencies06:42 How AI learns from past bids and drafts first versions12:34 Where human bid writers add strategic value18:20 Challenges: tone, compliance, formatting, org readiness24:57 Practical advice for integrating AI today31:44 What mature bid teams do differently (win themes, storyboarding, review)35:03 When AI + humans move you from admin to strategy

🌟 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

In this episode of The Stargazy Brief, Christina speaks with Elliot and Oliver from Tendium to unpack how modern bid teams navigate proposal tech, RFP software, AI in proposals, and today’s rapidly changing world of proposal management. They share how real bid/no-bid decisions are made, why sales and proposal teams often misunderstand buyer expectations, and what a healthy consultant–client partnership should look like in high-volume, high-pressure bid environments.You’ll hear how EU and global public-sector buyers are beginning to use AI in evaluation, and what proposal teams must do to pass AI-driven shortlisting models. Elliot and Oliver also break down how they balance automation with hands-on strategic work, how to maintain strong client relationships even when delivering tough news, and the compensation models that prevent bid-team burnout while increasing win rates.This episode is essential listening for proposal managers, bid writers, sales leaders, and anyone who wants to lead a modern, efficient, and insight-driven RFP function.Highlights:How to coach clients through unrealistic RFP expectationsWhy true bid partnerships require shared incentivesThe rising impact of AI in tender evaluationBalancing automation with strategic, contextual bid workHow Tendium’s team avoids burnout while scaling globallyThe RFP habits that should disappear—and what to replace them withMentioned in this episode:✸ stargazy Community: https://stargazy.circle.so/join?invit...✸ stargazy Newsletter: https://the-stargazy-brief.beehiiv.co...✸ stargazy Website: https://stargazy.io/✸ stargazy LinkedIn: https://www.linkedin.com/company/star...✸ Tendium LinkedIn: https://www.linkedin.com/company/tend...✸ Oliver LinkedIn: https://www.linkedin.com/in/oliver-st...✸ Elliot LinkedIn: https://www.linkedin.com/in/elliot-ea...✸ Tendium Website: https://tendium.ai/uk/✸ TendiumManaged Services: https://tendium.ai/uk/managed-services/✸ Stargazy Page: https://stargazy.io/managed-services/...🌠 TIMECODES00:00 Introduction to Bid Management and Technology01:32 The Role of Bid Teams in Tendium's Product Development01:32 Understanding Buyer Behavior in RFPs01:48 Navigating Tough Conversations with Clients07:03 Building Healthy Client-Vendor Relationships07:57 The Importance of Communication and Transparency10:57 Leveraging Technology in Bid Management12:54 Balancing Automation and Personal Touch15:56 The Shift in Bid Evaluation Criteria19:46 How to Run a Busy Bid Team without Burning them Out19:58 Managing Bid Teams Effectively22:43 Aligning Bid Team Compensation Plans with Sales24:32 Celebrating Wins and Building Team Morale27:14 Rethinking RFP Habits and Workflows29:55 Leveraging Data Insights in Bidding33:11 Understanding AI's Role in Bids

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.

In this episode of The Stargazy Brief, Christina talks with David Bremner, Manager at 3Search, about the state of the proposal, pursuits, and bid hiring market. From AI in proposals to salary trends, career strategy, and the evolving proposal management landscape, David shares insider data from across the UK and beyond. This is a must-watch for anyone navigating proposal tech, RFP software, or AI-driven proposal management, especially if you want to understand where the best opportunities and highest-impact roles are emerging.🌠

What’s real and what’s noise in AI for proposals? In this episode of The Stargazy Brief, Dean Shu, CEO and co-founder of Arphie, breaks down how proposal and RFP teams can use AI agents to actually win—not just look modern.Learn how to:Write for evaluators, not algorithmsTell hype from genuine AI breakthroughs in RFP techDecide if your content library should stay static or go live-connectedHandle sales leaders who think AI is a “magic bullet”Track the KPIs that make AI adoption credibleIf you manage proposals, RFPs, or presales, and you’re trying to future-proof your process, this conversation is your 2025 playbook.

Henry Brogan, CEO and co-founder of BidScript, joins Christina Carter to reveal how AI, proposal tech, and data-driven bidding are transforming the RFP industry. From his early days observing chaotic tender kickoffs to leading a next-gen proposal platform, Henry breaks down why RFPs remain one of the most undervalued revenue channels in enterprise sales. He shares how AI can supercharge pre-bid research, reshape post-mortem analysis, and empower proposal teams to think—and win—smarter.🌟 Stargazy LinksCommunity: https://bit.ly/4hgoVeXNewsletter: https://the-stargazy-brief.beehiiv.com/subscribeWebsite: https://stargazy.io/proposal-techLinkedIn: https://www.linkedin.com/in/christinagcarter/👤 Guest LinksHenry 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=allBidScript on stargazy: https://stargazy.io/proposal-tech/bidscript

How proposal managers and sales leaders can win more RFPs with AI-powered proposal software, with Ben Hills, CEO at Iris. 🌟 Key Takeaways - 50%+ of private-sector revenue flows through RFPs — buying behavior is shifting fast - “Context engineering” is the new AI personalization superpower for proposals - Cut RFP qualification time from 5 hours to 30 minutes with AI-powered workflows - Knowledge bases fail after 6 months without AI-powered content management - Personalization trumps speed, and AI helps compress timelines without losing quality🐝 Who this is for: Proposal managers, pre-sales professionals, and sales leaders facing increased RFP volumes and rising pressure to respond faster without sacrificing quality.⏰ Timecodes00:00 – Intro and guest background02:21 – Why Ben built Iris after 1,500+ RFPs08:58 – AI tools for proposal teams beyond drafting16:54 – How buying behavior is reshaping RFP strategy25:35 – AI-powered knowledge bases and content library strategy28:45 – Personalization techniques that actually win33:07 – The future role of proposal managers with AI34:44 – Practical next steps to boost win rates36:19 – Where to find Ben and Iris36:44 – Wrap up and next steps🌟 Stargazy Links✹ Community: https://stargazy.circle.so/join?invit...✹ Newsletter: https://the-stargazy-brief.beehiiv.co...✹ Website: http://stargazy.io✹ LinkedIn: https://www.linkedin.com/company/star...👤 Guest Links✹ LinkedIn: https://www.linkedin.com/in/benhills✹ See Iris on stargazy: https://stargazy.io/proposal-tech/iris✹ See Iris on stargazy's community: https://stargazy.circle.so/c/iris/✹ Iris website: https://irispro.ai?utm_source=stargaz...🔥 Subscribe to future-proof your proposal team.💬 Your TurnHow is your team balancing speed vs. personalization in proposals?Connect with me:👨‍💻 Linkedin: https://www.linkedin.com/in/christina...🌍 My newsletter: https://the-stargazy-brief.beehiiv.co...FAQ:• What’s the fastest way to qualify an RFP with AI? Use AI to parse requirements and match them against your capabilities, reducing qualification from hours to minutes.• How can proposal teams use AI beyond drafting? By improving go/no-go decisions, client handoffs, knowledge management, and win-rate insights from aggregated RFP data.Credits: Christina Carter, Stargazy founder.Topics covered: RFP automation, proposal software, AI knowledge bases, content library strategy, retrieval-augmented generation (RAG), vendor selection, win-rate uplift, build vs buy.ProposalTech #RFP #ProposalManagement #AI #ProposalAutomation #SalesAI #ProposalSoftware

Guest: Thad Eby, CEO at Ombud.In this episode, we unpack why bolt-on AI isn’t enough, how a Fortune 50 SaaS team cut proposal cycles from 3 weeks to 1, and what it means to move from reactive RFP responses to proactive, consultative proposals.What you’ll learn today:Why 90% content reuse is possible with the right workflowsThe “2-Week RFP Reality Check” to assess your processHow proactive proposals change the game for proposal managersThis episode is for proposal managers, bid teams, and sales leaders facing growing RFP volume and pressure to win more with fewer resources.

Stop speeding up losing. Learn how proposal AI actually wins. Sean Williams, CEO of AutogenAI, shares the 10/10 answer formula, how to end hallucinations with RAG and source control, a 6-vendor bake-off for picking tools, and the revenue math CROs care about.You’ll learn:- High-density answers that score- Traceable sources and human review- Build vs buy lessons from the field- More submissions x higher win rateChapters:00:00 Cold open00:49 Sean’s background04:14 Misconceptions in 202507:14 10/10 vs 5/10 answers10:51 Exec zoom out vs security deep dive16:27 The 6-vendor bake-off18:09 Build vs buy20:15 Accuracy and RAG28:24 The real business caseJoin the Stargazy community: https://stargazy.circle.so/join?invitation_token=0856b517503bca21eecbae1d058313543675481b-28d54c10-c886-4708-8b3b-ffd62cd3c935AutogenAI: https://autogenai.comFind your next favorite proposal tech: https://stargazy.io/

Kill RFP library bloat and ship answers that shortlist. AutoRFP.ai’s Jasper Cooper shares how “light libraries,” strong context, and deterministic workflows beat agent hype.You’ll learn:• When to keep a library—and when to skip it• How to cut hallucinations with source priority + folder lineage• Agents vs workflows: where each actually works in RFPsChapters:00:00 Intro + Jasper’s background02:02 What broke with legacy tools03:50 The library myth06:20 Hallucinations vs missing context08:30 Buyer checklist for RFP AI tools12:58 Connect less, win more17:10 The “single source of truth” myth21:50 Agents vs deterministic workflows26:36 Data trends: longer answers, higher shortlist rates33:00 The Knowledge Team era + skills to buildLinks:• Join the Stargazy community → https://stargazy.circle.so/join?invitation_token=0856b517503bca21eecbae1d058313543675481b-28d54c10-c886-4708-8b3b-ffd62cd3c935• AutoRFP.ai → https://autorfp.aiTopics covered: RFP automation, proposal software, AI knowledge base, content library strategy, deterministic workflow, agentic AI, retrieval, compliance