PIE Presents: Tales from the Pitch
”Step into the wild world of proposals with ’Tales from the Pitch’ – the podcast that’s here to make your proposal management journey both enlightening and ridiculously fun! Hosted by the savvy co-founders of Proposal Industry Experts, this weekly show is your ticket to the proposal universe. Get ready to dive into the nitty-gritty of the industry while sipping your morning coffee (or energy drink, we don’t judge). Join us as we spill the beans on the latest proposal buzz, dish out practical tips juicier than your favorite gossip, and unravel the mysteries of successful proposal wrangling. Whether you’re a rookie just starting or a seasoned pro looking for fresh tricks, we’ve got your back. Expect lively chats, occasional hilarity, and stories that’ll make your jaw drop – and maybe inspire a victory dance or two. So, if you’re into industry insights served with a side of irreverence, welcome home. Tune in to ’Tales from the Pitch’ and let’s make proposal management the most thrilling adventure of your career!”
Episodes
Still riding the high from RFWIN 2025? So are we! In this special post-event edition of Thursday Temperature Check (aka Tales from the Pitch), Rachelle Ray is joined by a dynamic trio of camp counselors—Beth Fiset, Lauren Leulu, and Kevin Thompson—who helped make this year’s event one for the PIE history books.
From favorite sessions to unexpected insights, this episode is a heartfelt, funny, and inspiring debrief of what went into...
Welcome to Tales from the Pitch, your Thursday temperature check from Proposal Industry Experts. In this RFWIN countdown episode, Ben Klein sits down with two powerhouse speakers from the upcoming conference: Harpreet Singh, co-founder of Thalamus AI, and Patty White, global proposal leader at Plante Moran.
Harpreet unpacks the world of Agentic AI—where digital assistants don't just help, they learn, coordinate, and scale like a co...
In this RFWIN teaser episode of Tales from the Pitch, Ben Klein welcomes two powerhouse consultants in the AEC proposal world: Amanda Haven and Olivia Haselwood.
Amanda and Olivia—both speakers at the upcoming RFWIN conference—share their deeply personal and practical journeys from full-time employment to full-blown solopreneurship. From juggling proposal deadlines with field trips and farm chores to navigating tax surprises and se...
We’ve done it again—another AI image tool test, and the results are better than ever (but still kind of weird). In this episode, Ben Klein and Rachelle Ray revisit their quest to generate a usable business graphic using the latest AI platforms.
Using a single prompt, they run tests across Canva, Google Gemini, Adobe Firefly, and ChatGPT to see who delivers the cleanest, clearest image for a proposal deck. Spoiler: we’re getting clo...
In this episode of Tales from the Pitch, Ben Klein is joined by Kevin Thompson of Thompson Consulting for a consultant-to-consultant chat about what’s really happening in the proposal space right now.
They explore:
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Federal vs. commercial client work
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Small business AI adoption (or lack thereof)
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The myth of perfect proposal software
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Managing the ebb and flow of client demand
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And the hunt for scalable, ethical swag (yes,...
In this RFWIN teaser episode of Tales from the Pitch, Ben Klein and Rachelle Ray welcome two standout voices from the upcoming RFWIN conference: Donald Silwick and Jeremiah Williams.
Donald, a Sales Operations Manager at Jacobs, shares insights from his world of global defense proposals and federal pursuits, while Jeremiah, a proposal strategist at Schmidt Associates, discusses the power of structured strategy—making the case that ...
Rachelle’s back from the road! After a whirlwind month of travel, conferences, and tech summits, she joins Ben Klein to unpack what’s trending in the proposal world. Spoiler: we’re still struggling with SMEs, AI is speeding ahead, and yes—Monday deadlines are still a villain.
In this episode, the hosts swap lessons from both sides of the procurement table, talk about how AI is reshaping proposal workflows, and reflect on the future...
🎙️ Audio Note: Heads up—there are some audio hiccups during Ana Berkovich’s segment. Hang tight! Her insights on storytelling are worth the extra effort.
This episode of the Thursday Temperature Check offers a sneak peek into two exciting RFWIN Camp PIE sessions. Host Ben Klein is joined by Ana Berkovich and Anne Walker—two professionals bringing fresh, honest perspectives on the challenges of modern proposal work.
💬 Meet Ana Be...
In this solo episode of Tales from the Pitch, Ben Klein explores the intersection of procurement data, political trends, and new AI tools that just might help us make sense of it all.
With access to 50 years of tender data from Canada, the U.S., and the U.K., Ben lays out a plan to analyze procurement patterns around key economic events—housing crashes, pandemics, and political shifts. He's got the data and a new AI tool to crunch ...
In this episode of Thursday Temperature Check, Ben Klein is joined by UK-based bid writing consultant Leonie Thomas, a featured speaker at this year's RFWin and Camp PIE (August 7–8). With Rachelle Ray on the road, Ben dives into a fascinating conversation with Leonie about the evolving role of the bid writer—especially in an era increasingly influenced by AI.
🚧 Leonie shares her journey in the construction and infrastructure engi...
In this solo episode of Tales from the Pitch, Ben Klein steps in without a guest to take a moment for reflection. With recent legal decisions in the news, Ben pauses to consider how larger societal shifts impact the vulnerable and us all.
He shares updates on the PIE community and revisits PIE’s core values of inclusivity, awareness, and support. From a Canadian perspective, Ben unpacks the ripple effects of U.S. policy decisions a...
This week on "Tales from the Pitch," Ben holds down the fort while Rachelle travels for SMPS, delivering a solo update session packed with insights and community news.
From announcing the new “Camp” theme for RFWIN 2025 to breaking down the transition to the Disco platform, Ben keeps the PIE community in the loop. He talks accessibility for new speakers, community conversations about branded swag, and offers humorous reflections on...
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:
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The wild ride of switching platforms mid-webinar 🎥
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Updates on PIE’s move to Disco (spoiler: mobile app included...
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:
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Sneak peeks at two new webinars: UX in Proposals (March 14) and Career Growth in Bids (March 19)
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D...
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:
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Why tech adoption fails (and how to avoid it)
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How to spot vendor bias and shiny object syndrome
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The danger of building AI tools on broken processes
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How to think...
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 innovati...
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:
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The ongoing disconnect between leadership and frontline proposal staff
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Why AI isn’t replacing you yet—but execs think it might
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The real cost of proposals (spoiler: it's not $900)
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The importance of go/no-go ...
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 int...
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: w...
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, ...
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