Ben shares common mistakes teams make, the balance between speed and quality, and actionable first steps for anyone looking to level up their RFP process.
Whether you’re in sales, proposal management, or executive leadership, this episode offers clear insights on how to compete, and win, in today’s rapidly changing RFP landscape.
Christina Carter (00:09): Welcome to The Stargazy Brief. Today we’re learning from CEO Ben Hills of Iris. I walked away with three big insights:
Buyer behavior is shifting dramatically, changing how we respond to RFPs.
Content management is evolving in ways I’d never considered.
There are new, practical steps we can all take to personalize responses and win more RFPs.
Chris @ Stargazy (01:03): Hey Ben, welcome to the show.
Ben Hills (01:07): Thanks for having me—excited to be here.
Chris (01:08): You’ve got such deep experience in proposal writing. What made you decide to build software for RFPs?
Ben (01:28): It started when I was managing every proposal at my last company. I’d done around 1,500 RFPs, and I saw firsthand how broken the process was. With the rise of LLM-driven software, I realized we could finally build a Jetsons-era solution to a Flintstones-era problem. That’s why I founded Iris—to create the tool I always wished I’d had.
Chris (04:33): Marketing often dismisses RFPs, but more than half of private-sector revenue flows through them. What should proposal teams know about leadership’s perspective?
Ben (05:35): First, your work matters more than you think. Proposal quality gets discussed at the board level. Executives see RFPs as a critical business process, not busywork. And as more renewals require RFPs, leadership is waking up to just how central this function is.
Chris (08:35): Many people think of AI only as a drafting shortcut. What other uses should proposal professionals explore?
Ben (08:58): AI can:
Speed up the go/no-go decision process.
Extract commitments from RFPs for smoother customer handoffs.
Surface buyer trend insights directly from proposal questions.
Automate project management reminders, saving 10+ hours a week.
It’s not just about faster drafts—it’s about connecting the whole process.
Chris (13:23): What mistakes do you see proposal teams making most often?
Ben (13:55): Two big ones:
Missing tactical requirements—like notarizations or physical deliveries—that derail submissions at the last minute.
Assuming every RFP is unwinnable unless it’s “baked” for them. Buyer behavior is shifting, and many RFPs are now genuinely competitive.
Chris (28:15): With AI making it easy to churn out responses, how can teams stand out?
Ben (28:45): Through “context engineering.” Instead of asking AI to “make this persuasive,” feed it the right context: buyer goals, industry specifics, competitor landscape. That transforms responses from generic to compelling.
Chris (32:27): If you had a crystal ball, how will proposal managers’ roles change in the next year?
Ben (33:07): Proposal leaders will expand pipeline coverage—delivering quality input across 100% of opportunities, not just the top few. They’ll also play a bigger role in helping executives understand shifting buyer expectations.
Chris (34:32): What are two things proposal teams can start doing right now?
Ben (34:44):
Map out the true ingredients of a winning proposal and where that information lives across your company.
Use AI not just to save time, but to scale high-quality work that used to be impossible at volume.
Chris (36:02): So much to take away here. Where can people find you and Iris?
Ben (36:19): Visit irispro.ai or connect with me on LinkedIn. I respond to every message.
Chris (36:44): Thanks, Ben. This was fantastic.
Ben (36:48): Thank you for having me.
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