In this episode, Francis sits down with Hayden Anderson, a top AE at MadKudu, to unpack a few “off-the-record” tactics—some that worked, some that almost got him yelled at.
It’s a fun, honest look at what reps actually try when no one’s watching, and what they learn along the way. You’ll also hear how Hayden uses AI in surprising ways to improve deal flow, and how a niche tool saves him days of work on security reviews.
If you’re in the weeds of selling and want real talk—not theory—this one’s for you. Here is what you'll hear about:
Getting IT admins to take a meeting at Lucidchart was nearly impossible. Hayden’s solution?
Skip the ask and drop a meeting straight on their calendar. Out of 20 calendar drops, he booked 6–7 conversations and even landed a major opportunity—but also got chewed out by one very angry prospect.
The play worked—but it felt a little shady. So he’s since evolved it: now, when he has a relationship, he simply proposes a time with an opt-out note. Many just show up.
It’s a scrappy, real-world tactic for dealing with ghosting and overloaded inboxes—and one that reminds us how small nudges (like putting a meeting on someone’s calendar) can remove friction for everyone involved.
Instead of doing a traditional QBR, Hayden ran his Q1 retro with ChatGPT using voice mode.
He loaded up deal data, crafted prompts, and let GPT play manager—asking questions, helping reframe answers, and even digging into pipeline drop-off points.
This wasn’t just for fun. It helped him identify better discovery questions (like swapping “What are you doing today?” for “How long does that take?”), refine his pitch, and even reconsider when to demo.
The takeaway? AI can create a safer, less rushed space for deep reflection—and help reps sharpen their process without the pressure of a live call.
Hayden realized that even well-crafted Loom demos weren’t getting watched.
So with ChatGPT’s nudge, he made a switch: do the demo live, right in the first call—just a focused 2-minute segment based on what the prospect shared. This lets him guarantee they see the value, while still personalizing the experience.
It’s a simple adjustment with big upside: less ghosting, faster next steps, and more control over the narrative.
Security reviews are a silent deal killer—slowing down sales cycles and forcing reps to ping half the company for answers. At startups, it’s even worse: reps are often left chasing compliance info without support.
Hayden’s solution? A tool that reads through company policies and legal docs to auto-fill security questionnaires.
It’s saved him days of back-and-forth and let him keep control of the deal instead of waiting on InfoSec. For reps handling complex software sales, this kind of shortcut can turn a slow “maybe” into a signed contract.
Hayden Anderson is a top-performing Account Executive at MadKudu, who started his sales journey in tech with high-volume PLG deals at Lucid, before moving upmarket and mastering larger contracts.
Before tech, Hayden took on what he still calls his hardest sales challenge: selling religion door-to-door in Korea. Outside of work, he's a proud dad to “two and a half” kids, caretaker to a small rabbit crew, and a believer that boldness, empathy, and a little AI can take you far in sales.
