This Meeting Could've Been a Podcast

Josh wanted his ChiliPalooza moment. He also wanted a Toyota Corolla people could scream in. What he got was the Jess edit — and it involved ghosts. They already knew small private dinners worked. Drive by Exit Five had proved it. What if they just did it four times ? $45K for four cities. $880K in projected pipeline. Josh is still waiting for his ChiliPalooza, but this will do. Three words from J...

Jess opens a demand gen role. The brief: run ads, talk to customers, build in public. Sixty applicants land in her inbox in 48 hours. Six months later, still searching. Josh's read on the situation? "Do you just really suck at hiring?" Most candidates checked two boxes. Nobody checked all three… until Kelly showed up and had CTV ads running within two weeks. Hear how six months of searching ended...

Season three Jess is not season one Jess. Same goes for Josh. Raising $10 million will do that to a person.  Josh hits the road to raise Vector's Series A. Weeks later, he's back full of ideas. None of them related to Vector's actual business. While Josh is away, Jess and the leadership team stop waiting for permission. They figure out what to do without him. Turns out: they know what they're doin...

Gird your loins: Season 3 of This Meeting Could've Been a Podcast drops June 10. 

Josh wanted to redesign the website. Jess said no. A few months later, Jess came back with the same idea. She called it an Uno reverse. Josh may have finally admitted Jess is wiser than he is.  A repositioning gave them the green light — a new narrative, new pricing, two product pages that didn't exist before. What Josh thought would be a simple redesign turned into three mood boards, a glow up th...

Funnel Vision was supposed to be the thing . Six months of building. A slick product UI. A beautiful narrative about contact-level intent. Launch posts. Playbooks. Customer testimonials. Jess even made a scroll-stopping GIF with ghosts shooting lasers out of their eyes. Then reality hit. The product was buggy. Everyone ended up in the same two boxes. And instead of solving the "now what?" problem,...

Most companies guard their marketing plans like state secrets. We did a live podcast episode to show you everything. Josh tripled Jess's pipeline goal (classic CEO move), organic search is in chaos, and marketers everywhere are white-knuckling their way through what Josh calls "pipeline anxiety." So what's Vector doing about it? Ghost tours. Influencer programs. Adding a demand gen hire to the tea...

What does a CEO do when his head of marketing goes on vacation? Nothing much. Just go viral on LinkedIn asking for the worst marketing ideas imaginable, buy imsorryjess.com, hand-code a website that same night, and forget that Jess isn't in a third world country and does, in fact, have WiFi. Oh… and get cancelled. No biggie. Josh gave away Vector's swag to capture leads — shipped one by one from h...

Jess tells Josh that she's keen to start running ads. After all, you can't pivot to being an ad tech company without actually running ads yourself. All she needs is a designer, someone to launch the ads, and a budget of tens of thousands of dollars. Nothing huge. Okay, maybe a few heart palpitations from Josh. In this episode, Jess takes us through her advertising journey—from the creative side of...

Josh went to dinner with a CMO friend. A couple of drinks in, she showed him her entire 27-step influencer marketing strategy. Josh's takeaway? One step: tell Jess. She can just handle the other 26… So, she built Vector's first influencer pilot with seven creators, $12,000, and zero vanity metrics. The result? $1.1 million in pipeline, 82% ICP demos, and posts so good you couldn't tell they were s...

Jess had it all figured out. A five-star restaurant. 17 prospects and customers. Four months of planning. $15k on the line. The perfect setup to fill next quarter's pipeline…right? Just one tiny problem: there’d been a mix-up. The dinner wasn't tomorrow night. It was tonight. In three hours. Cue panic. Cue scrambling. Cue Jess and Josh praying people would actually show up. Hear how a last-minute...

Josh calls an emergency meeting and Jess packs a bag (...just an overnight one). The team lands in Boston to face a hard truth: Vector was spread too thin, chasing too many use cases, and diluting outcomes.  What followed was a full-company repositioning to focus on what our customers were actually winning with, and put a hard stop to everything they weren’t. No pressure. This is the story of the...

Season 2 is here—and we're kicking it off with the conversation every marketer loves: asking for budget. Jess has big goals, a solid strategy, and one tiny problem: she needs money. Real money. Not the "ask permission for every shiny sponsorship" kind—an actual, formal quarterly budget. So, she builds her first-ever marketing budget, wraps it in a killer deck, and presents it to Josh and Nick. The...

Season 2 of This Meeting Could've Been a Podcast drops November 5th. 8 new episodes. Same great taste. Peep the trailer to get a sneak peek of what's on Jess and Josh's agenda this time around.

Josh happily announces he’s redesigning the website. Jess smiles and nods while she internally screams in marketer. But Jess spots an opportunity. Maybe we don’t need a whole new website. But the messaging and a few key visuals? They might just need a little work.  Hear how Jess steered Josh away from climbing a mountain of redesign and dev work and toward small messaging and visual tweaks that do...

Jess didn’t tiptoe into her new role—she marched in, spotted the gaps, and asked for headcount by day 2. Josh? Still processing. In this episode, Jess and Josh unpack the thinking behind their first big hire at Vector, why product marketing came before growth, what made one candidate rise above 65 others, and how building the right team early on turned heads across the industry.   TL;DR: If you’ve...

Josh wants stardom. Jess wants structure. Co-founder Nick mostly wants to avoid another content calendar. When Jess joined Vector, she quickly sniffed out a classic case of wasted brilliance: the founders had great takes—they just weren’t sharing them consistently.  Vector’s LinkedIn presence was ghosting its own potential… until Jess built a system that turned sporadic founder inspiration into a...

Jess decides to update the entire site to push free trials instead of demos. Demos drop. Cue the sales teams' nerves. It definitely made for an interesting Monday. But, wait…the numbers start to rise AND the leads take a serious step up. So, how does ditching the “book a demo” button increase demos? Is this just reverse psychology or a cunning move disguised as chaos? Get to the good stuff: [00:00...

Josh admits to ordering 500 custom Cards Against Humanity decks without any plan for them, except a strong urge to fight against boring swag at events. Jess steps in to help turn his impulse purchase into a real strategy that works. Will custom swag really drive brand awareness? What kind of swag do marketers actually want? And will Josh finally get rid of all those boxes from his house? Get to th...

Jess pitches Josh on starting a podcast as part of Vector’s video-first content strategy. All Josh hears is “blah bah blah, flying to Florida to spend $20K on an in-person shoot, yada yada yada,” and wonders how she plans to measure ROI.  Can Jess convince him that some big, tough-to-measure bets are just as important as traditional lead-gen? Get to the good stuff: [01:00] Jess shares why she felt...

Josh returns from CMO Summit buzzing with ideas, like hiring 20 influencers immediately . Jess works with him to understand which ideas could move the needle right now, and which ones are more distraction than priority. Can she pull him out of his post-conference spiral and keep her sanity? Get to the good stuff: [01:02] Josh cops to the CEO tendency toward shiny object syndrome and offers some id...

Jess comes in hot, asking for an agency budget within her first two weeks at Vector. Josh is skeptical, cuz CEO. But there's a method to her madness—when you're building a category, you need reinforcements. Get to the good stuff: [00:00] Jess pitches the idea of hiring an agency and why it was on her mind from day one. [03:50] Jess explains how organic content agency, ércule , helps Vector earn to...

Head of Marketing Jess Cook, and CEO Joshua Perk let you eavesdrop on their one-on-ones to hear how they're building Vector into a standout brand and must-have tool for B2B marketers. Come for the big-picture strategy and day-to-day tactics. Stay for the jokes that make HR nervous. This Meeting Could've Been a Podcast drops May 21st on YouTube and all major podcast platforms.