I Spent 24hrs Working at This $205M Startup

This is Shane. He's the co-founder and

CEO of Air, a creative operations

platform founded in 2017.

>> Seven years ago, my co-founder Tyler, I

noticed that every company around the

globe was becoming a media company,

creating and scaling a bunch of content.

And so, we built this company Air to

help businesses scale the amount of

images and videos that they work with

every day.

>> Think of it as a Dropbox meets frame.io

meets chatbt. Right now, the company is

at a turning point. After raising their

series V of $35 million earlier this

year, Air has entered go to market fit

or what Shane calls the second phase of

building.

>> We're living through this like 18 to

24month hellhole where you roll up your

sleeves and you refine.

>> They have customers. They know the

product works, but now it's figuring out

what actually drives growth and where to

invest in their salesunnel. But we'll

get back to that later. Okay. So, we're

Air and we manage I

>> You're all good. You're all good. And

that's me. I'm Payton, a producer on a

mission to see what it really takes to

run high growth startups and what

founders do dayto-day to keep scaling.

So I spent 12 hours inside air getting a

front row seat into team meetings,

product reviews, and how Shane leads the

company through this critical stage. But

when I arrived, Shane upped the stakes.

By the end of the day, I was given one

job. Pitch the product back to the CEO.

>> What do you want to do? everything.

>> Shane ran me through his schedule. My

day was now packed with back-to-back

meetings, design reviews, one-on- ones

with the sales team, all leading up to

the goal of delivering a full sales

pitch back to him.

>> Basically, by the end of today,

>> okay,

>> you're going to be able to walk me

through this deck and give me a sales

demo of a workspace. And then you're

coming to the event. So, you're going to

be smoozing at the event and trying to

sell some software.

>> All right. So, I had less than five

hours to learn the product, pitch the

product, and try to sell it by the end

of the night at their social mixer on

the future of creative work. I feel like

there's no time.

>> We'll figure it out. Can you

do deck demo with Payton at 11:00?

>> Yeah.

>> Great. Lovely. Here you go. There's your

coach.

>> Okay.

>> All right. Why don't we give Why don't

we give Payton the like quick overview

of the new brand just so she can see it?

>> Oh, like the brand brand. the brand

brand.

>> People didn't love our logo. I think

>> that's Lou. She walked me through Air's

rebrand, which was going live in just 2

weeks.

>> Here's kind of a summary of what our new

visual identity will look like. It's all

very centered on the idea of space to

breathe, which is kind of trademark

message.

>> But the real purpose of this meeting was

to align with Hector, their brand

designer, on exactly what needed to be

done and when to make sure every asset

was ready for launch.

>> The thing that's going to take the most

time is the sales side.

>> I agree. So that's going to be a work of

art.

>> Can you move the rebrand renewal deck

and expansion deck into planning?

>> Are you [ __ ] We got to go. Give me

another meeting.

>> Hi guys. Thanks for a great meeting.

>> Lovely.

>> Can't wait to see the final product.

>> We've been building this product for 7

years and we've added so much new

functionality in the last three. And

over the last 3 years, we're like

constantly bolting things on. And so UI2

gives us the opportunity to like sit

down, think holistically about the

experience, and reinvision it from the

ground up. To explain it simply, Air

provides search, storage, collaboration,

feedback, and distribution for its

users.

>> This is like a reskinning of the entire

platform. What do you want? A dare shirt

or do you want a sweater back?

>> Yeah.

>> Okay. Wait, you want me to put it on

right now?

>> Correct. Yeah. Yeah. You're becoming a

salesperson.

>> Um, okay. I got you an intern for the

day.

>> Wow.

>> All right. All you.

>> Okay. Well, where are you going?

>> I got stuff to do.

We offer you some tin fish, a bone

broth, hot sauce.

>> What's a tin fish?

>> You don't like tin fish?

>> Eric spent the next 45 minutes walking

me through their sales strategy. And it

was a lot, especially for someone like

me whose only experience was selling

chocolate bars in the third grade. But

one thing that stood out to me was how

soft their sales approach actually is.

And what I mean by that is unlike most

SAS companies which rely heavily on paid

ads and cold outbound, Air generates

most of its leads through inbound. Now

let's run through an example of how this

plays out in real time. Air hosts about

two networking events a month for

creatives which gives the sales team a

chance to ask questions and learn about

the real challenges potential customers

are facing. And instead of pushing for a

sale on the spot, they follow up later

with messages like, "Hey, it was great

meeting you. I'd love to grab 20 minutes

to dig a bit deeper into some of the

challenges that we talked about." From

there, the account executives meet with

the prospects, give their deck and demo,

and figure out if air can actually be

the solution to their problems. And the

strategy is clearly working. According

to Shane, after a customer talks to one

of these sellers, they close about 40 to

60% of deals, which is way above average

for most SAS companies.

>> Any questions, concerns, thoughts?

>> Um,

I mean,

I think I'm I think I'm processing.

>> I mean, you got a demo in 4 hours.

opportunities back to Shane,

>> right?

>> I have a lot of information in my brain

right now that I don't want to lose.

Hello,

>> this is nice to meet you at HubSpot.

Great to meet you.

>> She's been following us.

>> Love it.

>> She's like an AE for a day.

>> Amazing.

>> Alex Lieberman is the founder and

co-founder of Morning Brew and Story Arb

along with a bunch of other companies.

Shane tries to meet with like 12

founders a month so he can try and learn

how others approach their business

strategies and reflect and refine his

own playbook for scaling air. So, I

decided to tag along or in this case

behind.

>> All right, Peyton, what's your question

for Alex the guru himself is here.

>> What's What's

>> my favorite restaurant in Hoboken?

>> Yeah. No, actually, I'm curious.

>> Um, I love Martha's and I love

margaritas.

>> How have you built a mindset to be a

founder of so many different companies?

>> Um,

>> wow.

>> One is I think I'm entirely

unemployable. I've always been deeply

creative and like love the feeling of

invention of going from like I have an

idea to willing it into existence and it