In May of 2021 when I messaged Zain Jaffer, I didn’t know him as the young CEO who sold his company for nearly a billion dollars.
I just knew he was a proptech VC and and I wanted money for my startup, Maxable. Little did I know that five years and 7 months later he’d hire me as his CMO.
It all started with a LinkedIn connection.
After this brief exchange we never met, but I followed him on LinkedIn. He was good at publishing content and he’d talk about what he was investing in and the buildings he was buying.
(Content marketing is real people!)
In the spring of 2026 I saw he was starting something new. He was building in public, but still in stealth. I was curious so I sent him a message, asking what he was up to.
He didn’t respond.
LinkedIn inboxes are a black hole where messages go to die, so I didn’t think anything of it.
Over the next few months I started to become obsessed with LinkedIn as a way for companies to build top of the funnel organic growth. I started listening to podcasts, studying LinkedIn content, and took a course by Matt Lakajev.
I was sold.
I began consulting and with no website, no existing customers, and no email list I grew my consulting business to 40 companies 100% through LinkedIn content and outreach in 70 days.
I started to make a lot of money.
I noticed Zain viewing my profile. In fact, he viewed my profile ~10 times in a two week span. So I sent him another message,
(I had to google what f2f meant)
We met for two hours that day and a handful of times more the following two weeks.
Initially, I wasn’t that interested in the role, I was screaming along with my own consulting, but my husband encouraged me to explore it deeper.
There’s never harm in having conversations. (he’s 100% right)
He said something that really stuck with me,
“In this role, can you pull forward the pieces that you love most about your current work and delegate the pieces you don’t like?”
Two things shifted for me:
The more time I spent with Zain the more impressed I was and felt he was someone I could work well with.
I started to imagine what might be possible with VC funding and a team.
Then, I realized – what the hell am I dithering on about?!
This is nuts. This role was made for me and handed to me on a silver platter. Wake the F up Caitlin and grab it with two hands.
I met with Mark Fernandez at Sierra Ventures and Blazel’s board head, and he asked me politely,
“How do you turn this into a billion dollar company?”
I rambled something that I’m sure he saw straight through.
Later that night Zain called me as I was leaving the gym and offered me the role.
I accepted it and took this photo in the car.
TLDR;
Play the relationship long game. I proactively reached out to Zain four times over nearly six years.
LinkedIn inboxes are black holes. Keep following up.
Get out of your own head and wake up to the opportunities in front of you.