What does it actually take to build a 60–70% win rate and why do so many proposal teams fail to get there, even with AI?
In this episode of The Stargazy Brief, Christina Carter sits down with Gareth Meredith, a bid leader known for building consistently high win-rate systems inside complex, fast-moving sales organizations. Gareth has led capture and proposal teams at RingCentral and 8x8, worked inside proposal tech as a GTM leader, and now runs a central bid function at Softcat. He has seen every version of “modern proposals,” from rigid legacy processes to AI-first experimentation.
This conversation cuts through the hype to focus on the levers that truly move win rate.
You will hear why systems beat automation, how AI can support great teams without replacing strategy, and why answer planning remains the single most important skill most proposal teams underinvest in. Gareth explains where AI delivers real value today (compliance and cognitive load reduction), where it still falls short, and how teams accidentally devalue themselves by chasing tools instead of fundamentals.
The episode also goes deep on leadership. Gareth shares how to diagnose process leaks in a new team, which metrics actually matter at an executive level, and how proposal leaders can successfully advocate for change with CROs and sales leadership using revenue math and voice-of-customer evidence, not emotion.
If you are a proposal manager, bid leader, sales leader, or revenue executive trying to improve win rates, reduce burnout, and turn proposals into a strategic growth engine, this episode provides clear, practical guidance grounded in real operating experience.
Topics include:
- Why answer planning drives win rate more than drafting speed - Where AI helps proposal teams today and where it creates new risks - How to operationalize a lean, scalable proposal process - The metrics that matter (and why shortlist rate is mostly noise) - How proposal teams escape the “admin” label and earn strategic trust - What cultural debt looks like in bid teams and how to remove it
Listen in, then join the stargazy intelligence hub to continue the discussion and learn how other teams are building smarter, higher-performing proposal functions in 2026.
🌟 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/
Christina Carter (00:08) Hey, welcome to the Stargazy Brief where we navigate the future of proposals. Today’s guest is Gareth Meredith, and he is the bid leader behind some of the best win-rate systems in the industry. Think 60 to 70% close rates based on process and strong proposal team leadership.
He has run capture and proposal teams at RingCentral, 8x8, and now Softcat, and he has also been a go-to-market leader at Inventive AI, a proposal management platform.
We’re talking about what actually makes a difference in win rates. Answer planning that sells, AI that supports rather than replaces strategy, and how to advocate for your team with a CRO using data.
If you’ve ever led a bid team, tried to move proposals from being perceived as admin to strategic, or wondered which metrics really matter, this episode will be useful.
After the episode, jump into the Stargazy community to keep the conversation going with an AMA with Gareth. Share your own win-rate suggestions, learn how other teams are using AI without losing strategy, and finally stop being the RFP rescue squad.
Let’s get into it.
Christina Carter (01:12) Hey, Gareth, thank you so much for joining the Stargazy Brief.
Gareth (01:15) You’re welcome. It’s nice to reconnect. It’s been a minute since we last did a podcast together, so I’m looking forward to it.
Christina Carter (01:21) Last time we spoke, we were on Heather Melton’s podcast. That was a lot of fun. People know who you are from LinkedIn, but could you give a brief background on where you’re at now and your recent experience?
Gareth (01:24) I’ve been in bids for about 15 years. Over time, I’ve built a small profile around very high win-rate systems. I’ve spent much of my career implementing methodologies that help companies achieve 60 to 70% win rates while being actively embedded in the business, not just handing over a system.
I then moved briefly into AI RFP software and worked at Inventive AI as a GTM director. Now I’m running the central bid team at Softcat, a large UK-based IT reseller with around 2,500 people, building something market-leading.
I also try to share as much as I can with the community on LinkedIn.
Christina Carter (02:31) You’ve just moved from helping build AI software back into running a bid team. Given that experience, what parts of the traditional proposal process still work, and what’s changed with AI and buying behavior?
Gareth (03:02) My view has evolved. Having sold AI, it’s easy to drink the Kool-Aid. I still believe systems beat automation, but automation can empower great systems.
AI works best when it gives teams more time to focus on intelligence and strategy. There’s a big difference between dedicated AI platforms and tools like Copilot. In my experience, Copilot produces lower-quality output unless you bring your own models. ChatGPT, used properly, is much better for ideation.
Teams that expect AI to fix broken processes will be disappointed. AI doesn’t improve win rates on its own. Strong systems, methodologies, and human judgment still matter. AI should solve specific problems, not replace strategy.
Christina Carter (05:13) Are there specific areas where this really affects win rate?
Gareth (05:14) AI is excellent at compliance. If your content library is set up well and you choose the right platform, AI can handle factual, repetitive work like questionnaires. That reduces cognitive overload for bid managers and frees time for strategy.
The biggest lever in any process is answer planning. Understanding how to break down questions, how to structure responses, and how to score highly has the greatest impact on win rate. No AI platform does this well today, regardless of marketing claims.
If I had to implement one thing in any business, it would be answer planning. Other improvements add incremental gains, but answer planning fundamentally changes outcomes.
Christina Carter (07:40) Do you think there’s any role for AI in answer planning, or is that purely human?
Gareth (07:46) Yes and no. There isn’t a platform that truly understands RFPs well enough to break down questions strategically. Even if one did, competitors using the same platform would end up with similar structures.
AI prompting is a black box. Even advanced platforms lack the experience and contextual understanding that seasoned professionals bring. AI can assist, but it can’t replicate years of bid, marketing, and messaging experience.
Christina Carter (10:01) Some GovCon tools seem closer to this. What’s your view?
Gareth (10:47) They’re strong in highly specialized public-sector environments. But once you move beyond that into enterprise or commercial bids, their limitations show. Hyper-specialization works when it fits your market. General tools tend to collapse into compliance engines.
Christina Carter (12:25) If you were dropped into a large proposal team tomorrow and had one week to find the biggest leak, where would you look?
Gareth (12:38) Consistency of quality, which almost always comes down to weak answer planning. Many teams think they answer plan, but they’re really just summarizing questions.
The second issue is content. Teams rely too much on old RFPs instead of building deep, long-form, high-quality core content. Strong foundational content reduces effort, improves quality, and scales better.
If I had to pick one fix, it would be answer planning.
Christina Carter (14:52) Do you rely more on data or instinct to spot these issues?
Gareth (15:02) Both. Reading responses gives quick insight, but it’s subjective. Win rate is the most reliable metric, supported by quality scores where available. In software, average win rates tend to sit around 15 to 22%. Improving even a few points has a major revenue impact.
Tying improvements to revenue makes it much easier to secure investment in people and process.
Christina Carter (18:57) What’s most effective when pitching change to sales leadership?
Gareth (19:20) I focus on stabilizing the process before asking for headcount. I pitch it like a salesperson: revenue impact, voice of the customer, and a clear execution plan. When you do that, trust follows.
Christina Carter (21:43) What advice would you give proposal professionals who are nervous about advocating for change?
Gareth (21:57) You have to get out of your own way. No one is going to fix your career for you. Treat your proposal to leadership like a bid: evidence, structure, outcomes. Advocate for yourself using data, not emotion.
Christina Carter (27:35) What does a truly operationalized proposal team look like?
Gareth (27:57) Lean, front-loaded governance. Strong qualification. Consistent kickoff, answer planning, and minimal late-stage reviews. Governance belongs at the front, not in endless review cycles.
Rigid processes break. Scalable systems adapt.
Christina Carter (32:35) Which metrics actually matter?
Gareth (32:51) Win rate, quality scores, revenue, and gross profit. Shortlist rate is largely noise. If win rate climbs too high, qualification may be broken. If it’s too low, messaging or product gaps may exist.
Christina Carter (36:45) What cultural debt do you see most often in proposal teams?
Gareth (36:57) Underinvestment, burnout, and lack of visibility. Proposal teams are often treated as admin, which becomes self-fulfilling. Good leadership protects time, reduces crunch, and advocates for recognition.
Christina Carter (39:44) Is that the proposal leader’s responsibility?
Gareth (39:44) Yes. Someone has to own it. Leadership isn’t just managing workload; it’s creating an environment where people can grow and feel valued.
Christina Carter (43:14) Any recommendations for improving messaging skills?
Gareth (43:14) Talk to marketing. Learn from psychology, branding, copywriting, and business-building. Pull your interests into your work. That’s where differentiation comes from.
Christina Carter (46:03) What’s coming next for proposal leaders?
Gareth (46:03) Upskilling and strategic positioning. Be careful not to use AI in ways that devalue your team. AI should enhance efficiency, not replace thinking.
Christina Carter (48:32) Where can people find you?
Gareth (48:44) LinkedIn. I’m transparent about process and always happy to engage.
Christina Carter (49:30) If this episode helped you see proposals differently, share it with your team. The stronger the proposal community gets, the stronger the industry becomes.