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

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 staff

She 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

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

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

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.

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.

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 ignore

Beyond 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-suite

If 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 analysts

Whether 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.