The Stargazy Brief: Proposals, Bids, Capture, and RFP Win Strategy

Christina Godfrey Carter
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We speak to proposal and revenue leaders about how to win competitive Requests for Proposals. stargazy is the win intelligence company, an independent analyst firm covering the capture, bid and proposal industry. We measure why teams win and lose competitive RFPs across 1,000+ organizations, evaluate the software vendor landscape annually, and certify proposal professionals against evidence of what actually wins.

  1. Oct 14

    How Do Proposal Teams Earn a Seat with Revenue Leaders? ✹ Betsy Matthies, VP Global RevOps @ GitHub

    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 language of RevOps, which proposal data belongs in front of a CRO, and how to get a seat at the business reviews where strategy gets set. ✹ Report outcomes, not activities. "We unblocked $3M of pipeline this week" lands with a sales leader. "We completed 15 RFPs" does not.✹ Track go/no-go accuracy, content utilization against win rate, and the SME bottleneck tax. Revenue leaders want this data and rarely get it.✹ Your team reads more RFPs than anyone in the company. Bring what you see to QBRs as win/loss and market friction reports, and you will be invited back.✹ Betsy promoted leaders who brought her solutions to scale the business, not requests for more headcount to handle more paperwork.For proposal and bid leaders who want revenue leadership to treat their team as a revenue driver, and for RevOps and sales leaders who want to know what their proposal team is sitting on. Full episode page and transcript: https://stargazy.io/podcasts/how-proposal-teams-earn-a-seat-with-revenue-leaders

  2. Sep 29

    Finding Revenue Your Competitors Never See, with Iris Young (ETI)

    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 across the country. Four pipelines, one person. This conversation is about how she finds revenue other bidders in her market never see, and how she keeps it compounding. The engine is what happens at the end of a project rather than the start of one. A capability enters her opportunity search the day a first implementation closes successfully, never the day it was sold, so the revenue it opens up comes with proof already attached. ✹ How a market that looked thin turned out to be six times larger✹ Why every delivered project is a revenue stream nobody has claimed yet✹ How a single new phrase reaches buyers 600 miles away with no competition✹ Why a wider funnel needs a pursuit lane set by quarter, or it becomes work you cannot staffShe also puts a number on what automation gave her. Ten to twelve responses a month became the same in a week. For anyone running bids into state, local or education buyers with a team smaller than the workload. Watch and learn more at: https://stargazy.io/podcasts

  3. Aug 4

    The RFP Is Your Scorecard ✹ Tom Josephson, Director, Solution Consulting (Braze)

    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 that work alongside proposal specialists. He breaks down how to decide which RFPs deserve effort, how to get SCs to own the work, and how AI changed the job from writing answers to editing them. ✹ Why the SC who fills out the RFP should own the deal it becomes ✹ How relationship depth and influence over the document decide priority ✹ Why win rate is the only fair KPI, and losses can't be pinned on the responder ✹ How evaluators score with a checklist, and how to respond and demo to it If you lead SCs, sales engineers, or a proposal team that leans on SMEs, this one gives you a sharper way to run and measure RFP work ✨ Links & Resources ✹ Tom Josephson on LinkedIn: https://www.linkedin.com/in/tom-josephson/ ✹ Braze: https://www.braze.com ✹ 2026 Proposal and Bid Software Report: https://stargazy.io/offers/2026-proposal-and-bid-software-report ✹ Join the Stargazy community: https://stargazy.circle.so/join ✹ Subscribe to The Stargazy Brief for weekly conversations on how teams win RFPs

  4. Jul 22

    Winning Federal GovCon Bids ✹ Philip De-Bodene, Proposal Development Specialist

    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 Strengths, and where teams quietly bleed points on self-scoring vehicles. ✹ Read Sections L, M, and C before writing a word. Often only 30 of 150 requirements matter.✹ Clear the gates in order: compliant, then responsive, then compelling.✹ Shred the solicitation into an outline that ties each requirement to how it will be scored.✹ Use run-in headings that echo the evaluation language so an evaluator can score you fast. If you write proposals or run bid teams in government contracting, this episode hands you a method you can apply to your next solicitation. ✹ Philip De-Bodene on LinkedIn: https://www.linkedin.com/in/pdebodene/✹ The PDS: https://www.thepds.com✹ Stargazy proposal software market report, updated monthly and unbiased: https://stargazy.io/offers/2026-proposal-and-bid-software-report

  5. Jul 8

    Winning RFPs before the RFP ✹ Simon Cuthbert, Sales, Cybersecurity Expert, Co-founder Arthurian Labs

    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 dataIf 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. ✨ Links & Resources✹ 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

  6. Jun 24

    How Winning Bid Teams Use Procurement Data as Leverage ✹ John Witt @Stotles

    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

  7. Jun 16

    Proposal Automation Software isn't One-Size-Fits-All ✹ Jasper Cooper, CEO of AutoRFP.ai

    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.

  8. May 19

    Why Buyers Score Trust, Not Just RFPs, with Greg Ellis (Zendesk)

    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 weekend For proposal managers, solution consultants, and revenue leaders who suspect the centrifuge model of the bid is what is breaking their win rate.

    Why Buyers Score Trust, Not Just RFPs, with Greg Ellis (Zendesk)
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We speak to proposal and revenue leaders about how to win competitive Requests for Proposals. stargazy is the win intelligence company, an independent analyst firm covering the capture, bid and proposal industry. We measure why teams win and lose competitive RFPs across 1,000+ organizations, evaluate the software vendor landscape annually, and certify proposal professionals against evidence of what actually wins.

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