The Stargazy Brief: Proposals & RFP Win Strategy

Get the RFP Analysis Report from this episode: https://stargazy.io/reports/rfp-analysis-report ✹ Simon and Arthurian Labs are providing stargazy podcast listeners with a 30-day free trial and a discount for purchases. Bid teams put the most effort into the parts of RFP analysis that predict wins the least. That is the headline finding of the RFP Analysis Report, stargazy’s survey of 448 organizati...

Revenue leaders don't care how many RFPs your team completed, but they do care what those RFPs did for pipeline. Betsy Matthies is VP, Global Revenue Operations & Enablement at GitHub. Before that she ran the proposal center of excellence at AWS, so she knows what proposal teams see and what revenue leaders need from them. She and Christina Carter talk through how proposal leaders speak the la...

Iris Young thought she knew the size of her market. Then one correction to her opportunity search took her from twenty-four qualified matches to 157, and none of her capabilities had changed. Iris handles proposals, business development and marketing at Emerging Technology Integrators, a network infrastructure and cybersecurity firm in Columbus, Ohio, selling to state, local and education buyers a...

You can't blame a solution consultant for losing an RFP they never had the power to win. Tom Josephson, Director of Solution Consulting at Braze, joins Christina Carter to explain how he runs enterprise RFP responses without a dedicated bid team, and why the way most leaders measure this work falls apart under scrutiny. Tom has managed solution consulting teams that own RFPs end to end and teams t...

Christina Carter talks with Philip De-Bodene, a federal and SLED proposal consultant behind more than $8 billion in pursuits and a 65% win rate on priority bids. They get specific about how evaluators actually score a submission, and what that means for the way you build every response. Philip walks through his shred, the outline that maps requirements to scoring, run-in headings that earn Strengt...

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, ma...

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 igno...

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 wi...

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...

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...

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 fu...

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 work...

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...

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...

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 ch...

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,...

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 reve...

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 fee...

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 w...

✨ 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 wh...

✨ 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, sm...

✨ 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, fac...

🌟 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...

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 partn...

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 befo...