PIE Presents: Tales from the Pitch
by Proposal Industry Experts
”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 a
Episodes
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The Post RFWIN Episode - Behind the Scenes at Camp PIE 2025
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...
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RFWin Teaser - The AI + Tiered Support Crossover
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...
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RFWIN2025 Teaser - Olivia Hazelwood and Amanda Haven - Consulting Tips
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...
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AI, Arrows & Aliens — Still Chasing the Perfect Proposal Graphic
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,...
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Consulting, AI, and RFP Chaos — Featuring Kevin Thompson
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: Federal vs. commercial client work Small business AI adoption (or lack thereof)…
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RFWIN Teaser - Donald Silwick and Jeremiah Williams
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…
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From Conference Chaos to AI Creep — What’s Next in Proposals?
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...
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RFWIN Teaser 2 - Ana Berkovich, Anne Walker - Storytelling & Change Management
🎙️ 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...
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Data Dreams and AI Schemes — Can We Predict Procurement?
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...
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RFWIN Teaser - Exploring the Future of Bid Writing with Leonie Thomas ✍️
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…
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Temp Check - Ben talks about LGBTQIA+
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...
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Tales from the Pitch – RFWIN 2025, Disco Migration & PIE Swag Chat
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...
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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....
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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...
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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…
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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...
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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...
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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…
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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...
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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...
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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…
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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…
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The build a chatgpt 'GPT' episode
This is better watched on youtube. In this special 'Tales from the Pitch' episode, Rachelle Ray steps into the role of Tech Expert, guiding co-host Ben Klein through the process of creating a GPT agent. Dive into an educational and fun-filled session where complex AI concepts are broken down into...
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Ben Johns on Competitive Insights of Metadata in Proposals
In this episode of Tales from the Pitch, Rachelle Ray, Ben Klein, and special guest Ben Johns (SME) discuss harnessing the power of metadata to gain competitive insights from proposal documents. The conversation delves into strategies for turning data into actionable intelligence, offering...
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Community Updates
Welcome to 'Tales from the Pitch,' brought to you by Proposal Industry Experts. In this episode, hosts Ben Klein and Rachelle Ray share an unexpected twist—coming to you from the same location but separated by a few technical challenges. As they settle into a snowy New Mexico backdrop, they offer...
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Navigating from a response tool.
In this episode of 'Tales from the Pitch,' Ben Klein and Rachelle Ray tackle a topic that resonates with many in the proposal world: transitioning away from a response tool. With humor and practical advice, they share their experiences, discuss the challenges of migration, and outline steps to...
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Writing - Community Challenges to AI Editing: Tales from the Pitch
Join Ben Klein and Rachelle Ray on this episode of 'Proposal Industry Experts' as they explore the power of community and creativity in proposal writing. They dive into their latest community writing challenge, highlighting why strong writing skills are crucial in the proposal industry. The hosts...
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AI Fumbles, Vacation Juggles, and a Printed Bid Nightmare
In this episode of Tales from the Pitch, Ben and Rachelle from Proposal Industry Experts dive into the lighter and more challenging sides of proposal management. First, they discuss the amusing and often frustrating limitations of AI in understanding proposal meeting notes, offering some laughs…
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Navigating People Pleasing in Proposal Management with Steven Alvarez
In this episode of Tales from the Pitch, Ben Klein of Proposal Industry Experts (PIE) is joined by Steven Alvarez, a member of the customer advisory board (Bakers Dozen), to delve into the challenge of people pleasing in the proposal response industry. Steven offers his unique insights on how...
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The Proposal-Product Connection: Lessons from the Field with Lauren Styczynski
Join hosts Ben Klein and Rachelle Ray, founders of Proposal Industry Experts (PIE), as they sit down with Lauren Styczynski from their customer advisory board to explore the powerful connection between product management and proposal management. In this episode, Lauren shares practical insights…
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Creativity in Government Contracting: Proposal Graphics with Lauren Leulu
In this episode, Lauren Leulu, a seasoned expert in U.S. government contracting and proposal graphics, shares her unique approach to creating impactful visuals for proposals and breaking down complex concepts in government bids. Lauren’s insights offer a fresh perspective on how to balance...
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Temperature Check 12 09 24 Creative Problem Solving & Career Growth with Ama Cobbina
We strongly recommend watching this on our youtube channel as Ama literally draws out how she makes sense of what is going on in her thinking. https://youtu.be/kr246rjYVwo?si=0YTqdXJIyeMAgVy_ In this episode, Ama Cobbina shares her unique approach to career development and problem-solving without...
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Sales, BD, and Proposals with Kevin Thompson | Tales from the Pitch
In this episode of Thursday Temperature Check, Rachelle Ray and Ben Klein sit down with Kevin Thompson to explore where sales and business development (BD) intersect with proposals. The conversation is broken into three engaging parts: Part 1: Introduction to Kevin Thompson Get to know Kevin...
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Post-Conference Reflections & AI Proposal Updates
In this episode of Thursday Temperature Check, Rachelle Ray and Ben Klein share their post-conference reflections, offering a mix of casual banter and valuable insights for the proposal industry. They discuss Javier Escartin’s thought-provoking newsletter, which questions the relevance of…
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Leadership Changes at PIE and our 2024-2025 Year
In this episode, Rachelle Ray from RMR Consulting and Ben Klein from Geek Proposals discuss significant changes within Proposal Industry Experts Inc., including Ryn Bennett's departure. As the team prepares for 2024-2025, Rachelle and Ben share their thoughts on how this leadership change will...
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Future-Proofing Proposals: Embracing AI and Effective Mentorship
In this episode of "Tales from the Pitch," hosts Ben Kline and Rachelle Ray dive into the transformative impacts of AI on the proposal industry and discuss the power of effective mentorship. They explore how AI is reshaping proposal processes, addressing both the challenges and opportunities that...
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Navigating Proposal Crunch Time
In this lively episode of "Tales from the Pitch," hosts Ben Klein and Rachelle Ray tackle the high-energy world of proposal management. Rachelle shares her strategy for handling emergency bids and discusses the nuances of charging for rush services. They also highlight the upcoming RFWin event,...
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Survey Results: Finding Joy and Inclusion
Join us for a warm and engaging episode of "Tales from the Pitch," where the hosts share laughs and insights about finding balance in our hectic lives. They chat about the small victories in doing just enough to stay sane and productive, and how taking it easy can sometimes be the secret to...
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The Power of Clear Writing in Proposal Success with Chris Gillespie
Tired of writing proposals that vanish into a black hole? Join our chat with Chris Gillespie, CEO of a content studio focused on making writing clear. In this episode, you'll learn: The secret sauce to clear writing that makes proposals stand out (hint: it's not jargon!) How to write for the busy...
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AI, Onboarding & Networking: Must-Knows for Proposal Professionals
Is it a recipe for disaster or a delicious opportunity? Join us as we explore the upcoming Proposal Industry Experts (PI) conference, RFWIN, focusing on AI in proposals and the future of the field. We'll also dish on hot topics like: The onboarding struggle: Balancing comprehensiveness with time...
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Proposal Power Up: Industry Survey, RFWIN Conference & More!
Is AI the future of proposal writing? We chat about Pi AI Day and explore the potential of AI tools in the proposal writing process. While some are embracing this new technology, others are taking a more cautious approach. Find out where your clients stand on AI-powered proposals. Calling all...
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Balancing Acts: Navigating Workloads and Wellbeing in Proposal Management
In this episode, Ben and Rachelle discuss the ongoing challenges of balancing work demands with personal life, particularly in the context of proposal management. They share personal stories about upgrading technology and the impact on their work efficiency, transitioning to cloud computing, and...
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AI and Bidding with Chris Bassila: Simple Frameworks for Smart Strategies
In this insightful episode of our podcast, we explore the transformative role of artificial intelligence (AI) in bid management and proposal development. Our special guest, Chris, a consultant with extensive experience in the aerospace and defense sectors, shares his journey into integrating AI...
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Smarter Not Harder: AI Integration Essentials for Your Tech Stack
Dive into the transformative world of artificial intelligence in this episode of "Tech Tides" with special guests, Ryn Bennett and Ben Klein from the startup PIE. They explore practical ways to integrate AI into your existing tech workflow, enhancing efficiency and innovation. Ryn provides a...
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Finding Balance: How to Transform Proposals and Sales to Value Well-being
Join us as we welcome Amy Herodacek, a renowned figure in the sales landscape with a rich background in enterprise software sales, sales enablement, and as a successful C-level executive. Amy shares her expert insights into the troubling statistics highlighted in recent reports by Pavilion and…
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Beyond Boundaries: Embracing Diversity & Innovation in AEC
Dive into this week’s episode of "Thursday Temperature Check," where our hosts return from Portland with fresh t-shirts and fresher insights. From discussing the latest fashion choices to unpacking the rich learnings of the Pacific Regional Conference for SMPS, the team explores vital industry...
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Enhancing Document Appeal for RFP Submissions
In a compelling episode of the Proposal Industry Experts (PIE) podcast, the co-founders shared their insights on making RFP (Request for Proposal) submissions more appealing. They emphasized the importance of understanding the reader's needs and preferences, advocating for a tailored approach…
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Exploring the Dynamics of Federal Proposals with Liz Kepner
In this episode of the Proposal Industry Experts podcast, host Ben welcomes Liz Kepner, a seasoned proposal professional with extensive experience in government contracting. They delve into the intricate world of federal proposals, discussing topics ranging from team formation and relationship...
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Crafting Success: Writing Samples & Strategic Hiring in Proposal Management
Firstly, we explore the importance of writing samples in the proposal industry. Our expert hosts discuss how writing samples serve as a window into a candidate's communication skills, attention to detail, and ability to tailor content to specific audiences. We provide insights into what makes an...
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Remote Work Strategies for Proposal Management Success
In this episode, our proposal management expert discusses crucial strategies for remote work in the proposal management field. Explore upcoming webinars focused on software buying guides, avoiding burnout, and remote work challenges. Gain insights and actionable tips from an industry veteran to...
About this show
”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 a
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Proposal Industry Experts
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