Chili Piper

Hey, I’m Jenn Castillo 👋🏼, Principal of Channel Partnerships here at Chili Piper, tuning in from London, Ontario! If you know me, you know I’m a big believer that the future is partnerships. There’s just something magic about bringing two teams together, finding that spark, and building something that helps everyone win. That’s what I love most about what I do, spotting synergies, creating stories that connect, and turning a “we should collaborate” chat into real results. Outside of work, life’s been a whole new kind of adventure. I became a mom this past year (hi Sophia), and let’s just say the #Jennergy has officially leveled up with some serious #momergy. I’m also super passionate about championing women in tech and leadership, because we need more of us at the table. So if you want to chat partnerships, co-marketing ideas, or how to build connections that last, my DMs are open!

Why spend millions on ads to get more leads… when fixing the 2% → 5% conversion gap would give you 2.5x the pipeline overnight? Imagine you’re generating 1,000 MQLs every month. The team’s hustling, campaigns are working, the top of funnel is healthy. Only 2% of those leads become sales-qualified. That’s 20 SQLs. Now picture this: you tweak your process. Leads get routed instantly to the right rep. Hand-raisers are treated like VIPs, not stuck in a queue. No-shows get nudged with an easy rebook. Suddenly, your conversion rate jumps to 5%. That’s 50 SQLs from the same 1,000 MQLs. It doesn’t sound dramatic at first… until you realize you’ve more than doubled the number of qualified opportunities your sales team can work without spending a dollar more. That’s the magic of fixing demand conversion. Sometimes the biggest growth lever isn’t at the top or the bottom of the funnel. It’s right in the messy middle. This riff came from Principle #3 in our Demand Conversion guide. It’s from Mark Kosoglow, CRO at Docebo, one of 30+ revenue leaders who dropped gems in this playbook. 👉🏼 https://lnkd.in/dNyfx-DB

Here’s exactly how Reachdesk turned inbound bottlenecks into a 35% win rate. Most teams try to book more. They focused on booking better. Here’s how 👇 1️⃣ Tightening qualification rules. They stopped sending every inbound to sales. Leads were segmented by fit and readiness, so only real buyers made it through. 2️⃣ Automating routing. Using Chili Piper Handoff + Concierge, leads were instantly routed to the right AE. No round-robins, no manual follow-ups. 3️⃣ Nurturing instead of disqualifying. If an account wasn’t ready, it went straight into a nurture flow, not the bin. 4️⃣ Measuring what matters. Instead of lead volume, Ben’s team tracked win rate and disqualification rate. This led Ben Smith 💜 and his team to: → A +35% win rate → A –23% disqualification → 2000+ meetings in H1 2025 So, if you make it harder to create pipeline, you’ll actually close more of it. 🔗 https://lnkd.in/ddGWZFVd

🔥 You weren’t really gonna skip this Dreamforce party, were you? ChiliPalooza is back, and it’s the hottest ticket in SaaS. This event is a Red Carpet Affair, so please dress as fancy as you'd like. Last call before we hit capacity → https://lnkd.in/eA4M4Vke

Your leads move fast. Your forms… not so much. Let’s fix that. 💜🧡 We’re going live with Lusha! October 21 at 11 AM ET Join Tal Barnoy and Guilherme Valle Marques as they show how to enrich, route, and book meetings in one click, before your hot leads turn cold. Save your seat 👉 https://lnkd.in/d-R6XGvj 

AI won’t replace your GTM team... but it will replace your “let’s figure this out next quarter” strategy. We’re teaming up with Polaris for their AI Roadshow to talk about how real teams are using it to drive pipeline. You’ll get: Stories from GTM leaders Roundtables with CROs, CMOs, and RevOps folks & a happy hour 🍸 Two stops: 📍 Austin – October 23 https://luma.com/hfvexfxn 📍 Chicago – November 5 https://luma.com/twq7c3k9 If you’re in town, come hang, learn some AI tricks, and maybe fix your follow-up workflow while you’re at it.

Every SDR has lived this day once. Chat AI makes sure it never happens again. Built by a team who’s cried in Salesforce too. 👉🏼 https://lnkd.in/d6uqXg_2

While your team sleeps, Chat AI converts. Qualifies leads. Answers buyers. Books meetings. All while syncing with your CRM in real time. Your reps rest. Chat AI doesn’t. 🌶️ https://lnkd.in/d6uqXg_2

Recap of the last day in Tenerife. A perfect mix of goodbyes, new friendships, and a few deep chats that went way beyond work. We talked about moving cities, learning to sing, trying new things and all the stuff that makes us human outside of our job titles. Juan Jose Diaz caught the final day on camera, and it’s a good one. Can't wait to see you all next year again 🧡

Day 3 in Tenerife started the only way it could: beach time. Then came the legendary Piper Games. Think chaos, creativity, and some very questionable athleticism. Even a few engineer–SDR alliances no one saw coming. To top it all off, we ended with a surprise comedy show starring our own teammates. Juan Jose Diaz José Díaz caught it all on camera! And thanks Wyld Ones - a team building company for the support!