PIE Presents: Tales from the Pitch

Updates on PIE, Japan and Bad Portals

Ben Klein is back from Japan and rejoining Rachelle Ray in this jam-packed episode of Tales from the Pitch! The two swap stories, dive into updates from PIE's ever-evolving platform migration, and recap two standout webinars: Brianna Carter’s UX panel and Jeremy Brim’s Growth Ignition session.
Inside the episode:
The wild ride of switching platforms mid-webinar 🎥
Updates on PIE’s move to Disco (spoiler: mobile app included!)
Call for Camp PIE (RFWin 2024) speaker applications
How global procurement practices vary—Ben’s Japan trip sparked a big idea 💡
Which is it—NAICS or “Nakes”? The community weighs in!
🎙️ And to close: a Tale from the Pitch featuring the ultimate portal nightmare—an RFP drops, but the portal says no access... for five days. Cue stress.
 
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Rachelle Solo, PIE Updates and Magenta Printers

In this special solo episode of Tales from the Pitch, Rachelle Ray flies solo (and maybe streams on the wrong platform?) to deliver a full rundown of what’s happening inside Proposal Industry Experts.
From Pi Day celebrations and AI-powered proposal panels to PIE’s new community platform and upcoming webinars, Rachelle covers:
Sneak peeks at two new webinars: UX in Proposals (March 14) and Career Growth in Bids (March 19)
Details on the new Growth Ignition training partnership
Why PIE is moving to a sleek new home on Disco
A shout-out to RFP 101 and the launch of premium content
Industry trends in GovCon vs. SLED and how AI is shifting expectations
And of course, it wouldn’t be Tales from the Pitch without a story. Rachelle closes with a toner disaster of magenta proportions in this unforgettable printer fail meets proposal deadline moment.
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Choosing the Right AI with Chris Basilla and Ceri Mescall

In this episode of Tales from the Pitch, Rachelle Ray is joined by proposal tech nerds and consultants Ceri Mescall and Chris Basilla to tackle a real challenge in the industry: choosing the right AI tool in a market that’s flooded with options.
They break down:
Why tech adoption fails (and how to avoid it)
How to spot vendor bias and shiny object syndrome
The danger of building AI tools on broken processes
How to think strategically about team buy-in and empathy
What 400+ hours of market research taught them about tool viability
Plus, they unveil My Proposal Pathway—a 3-step service to help teams cut through the noise and find tools that actually fit their workflows, budgets, and proposal environments.
And you don’t want to miss Kerry’s Tale from the Pitch: a sticky situation involving wet paint, orals coaching, and the world’s most reluctant presenter.
📍 Learn more at: https://www.myproposalpathway.com💼 Connect with Chris & Carrie on LinkedIn
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RFP 101 is live on PIE

In this episode of Tales from the Pitch, Ben Klein and Rachelle Ray reunite in their first shared 2025 Temperature Check—and it’s a whirlwind.
Fresh off a live D&D show, SMPS’s Southern Regional Conference, and a whirlwind trip to London, Rachelle shares key insights on creative burnout and why proposal professionals need messy creative space to thrive. Together, she and Ben explore the tension between productivity and innovation, with helpful tips from their own personal creative practices.
Plus, big PIE news:🚀 RFP 101 is live! A crash course for newbies and solo-preneurs navigating the proposal world.📱 A sneak peek at PIE’s new learning and community platform, hosted on Disco.🧠 And thoughtful reflection on AI’s impact—what’s hype, what’s real, and why proposal writers are still essential.
Stick around for laughs, community shoutouts, and a reminder that PIE is here to support you, whatever stage you’re in.
🌐 Join PIE / Official Website: https://www.proposalindustryexperts.com
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Loopio Annual Trends Report

In this Tales from the Pitch episode, Ben Klein and Rachelle Ray dig into the freshly released Loopio 2024 Trends Report, unpacking the most telling data points shaping the proposal industry this year.
They call out:
The ongoing disconnect between leadership and frontline proposal staff
Why AI isn’t replacing you yet—but execs think it might
The real cost of proposals (spoiler: it's not $900)
The importance of go/no-go discipline and the myth of “we can do the work”
And of course… yes, we’re still dealing with burnout 😬
From hilarious chart errors to smart insights on selectivity and strategy, Ben and Rachelle don’t just break down the data—they give it context, with real-world commentary you won’t get from a download link.
🌐 Join PIE / Official Website: https://www.proposalindustryexperts.com
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UX in Proposals: Reimagining How We Communicate with Clients

This episode of Tales from the Pitch dives into the future of proposals—with a human touch. Ben Klein and Rachelle Ray welcome Brianna Carter, marketing strategist at Page and a member of PIE’s advisory board, to preview her upcoming expert panel on user experience (UX) in proposals.
Together, they explore what it means to make proposals more readable, engaging, and accessible—from microsites to multimedia storytelling, from AI integrations to the audacity of actual innovation in procurement. They also dig into the reality of juggling proposals, parenting, and professionalism (spoiler: twins and snow days are involved).
Plus, don’t miss Brianna’s Tale from the Pitch, which might be the most relatable work-from-home story in proposal land.
🎉 Her panel drops on Pi Day (March 14)—mark your calendar and register!
🌐 Join PIE / Official Website: https://www.proposalindustryexperts.com
📺 Subscribe on YouTube: https://www.youtube.com/@ProposalIndustryExperts
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Growth Ignition Launch

In this episode of Tales from the Pitch, Ben Klein welcomes UK-based bidding powerhouse Jeremy Brim to officially launch Growth Ignition—a new educational partnership with Proposal Industry Experts (PIE). Jeremy brings 25 years of experience in bids, capture, and business development, and he’s worked with everyone from scrappy startups to billion-dollar firms.
They dig deep into the strategy behind winning more (and better) work: why capture is the make-or-break phase, how strong sponsorship changes outcomes, and what the future of proposal education should look like. This episode pulls no punches—complete with insights, laughs, and the occasional British swear.
Plus, Jeremy shares a Tale from the Pitch that haunts him every time he passes London’s King’s Cross Station. Yes, it involves Google. Yes, it involves senior executives with big egos. And yes, you’ll want to hear it.
🔥 PIE members: keep an eye out for exclusive Growth Ignition discounts and access soon!
🌐 Join PIE / Official Website: https://www.proposalindustryexperts.com
📺 Subscribe on YouTube: https://www.youtube.com/@ProposalIndustryExperts
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Christina Carter - Taking a Seat at the Table

Welcome back to Tales from the Pitch, the podcast where we mix humor, expertise, and a dash of procurement chaos! In this episode, Ben Klein kicks off the first Temperature Check of 2025 solo—well, not really. While Rachelle Ray braves the wilds of Houston for the SMPS conference (and, let’s be honest, probably disrupting the local weather in the process), Ben is joined by none other than the fantastic Christina Carter!
Christina, a powerhouse in the proposal world, shares insights from her time with major companies like Zendesk and Amazon Web Services, her experience running her own consultancy, and her role as part of the PIE Baker’s Dozen. The conversation covers proposal processes, bid libraries, and the realities of managing proposals across industries. Plus, Ben and Christina swap stories from their recent meet-up in London—complete with restaurant side-eye from a particularly unimpressed waiter.
Stick around for all the laughs, lessons, and of course, a classic Tale from the Pitch. Don’t miss it!
🔗 Like what you hear? Join us for free at Proposal Industry Experts!
Want more Chris Carter - Find her in the PIE Community or on Linkedin https://www.linkedin.com/in/christinagcarter/

Posted Late - Proposal Graphics, GPT Agents, and Holiday Deadline Chaos

It’s the most wonderful (and stressful) time of the year—at least for proposal professionals! In this episode of Tales from the Pitch, Ben Klein and Rachelle Ray dive into the classic end-of-year crunch, swapping stories about last-minute procurements, unrealistic deadlines, and the hidden toll of "holiday bids."
But it's not all doom and deadlines. The duo also explores how proposal professionals can level up their game with AI. From using Midjourney to enhance proposal graphics to creating a custom ChatGPT assistant, this episode is packed with practical tips and laughs. Ben and Rachelle walk through building a "recruiting proposal consultant" GPT, share holiday travel vibes, and tease OpenAI's latest contender in the image game.
Plus, PIE is hosting its first-ever Town Hall in January, and you're invited! Tune in to find out how you can help shape the next RFWin and make your voice heard in the proposal community.
Like what you hear? Join the PIE community: https://www.proposalindustryexperts.comFollow us on LinkedIn: https://www.linkedin.com/company/proposal-industry-expertsWatch more episodes: https://www.youtube.com/@ProposalIndustryExperts

Beating Burnout: Boundaries and Balance

 📌 Summary:In this episode of Thursday Temperature Check, hosts Ben Klein and Rachelle Ray get real about burnout and how it intensifies during the holiday season. They share personal stories, practical strategies, and tips for setting boundaries, managing guilt, and finding moments of rest amidst the chaos.
🚩 Highlights:
Recognizing the signs of burnout before it’s too late.
Why incremental self-care beats all-or-nothing approaches.
Setting boundaries at work and learning to say “no.”
How to reframe rest as productivity.
🎯 Takeaway:Burnout isn’t inevitable—small changes and supportive networks can make a big difference.
💬 Join the Conversation:How do you tackle burnout? Share your tips in the comments or our community forum at https://proposalindustryexperts.com