54: My first 90 days at Mailshake
Top 3 takeaways...
Before we jump in, the HYPCCCYCL team interviewed 28 top GTM leaders to get their tech stack secrets.
If you're an SDR nerd like me, this stuff is super interesting. You can grab the PDF here (my fav part is the 4 major trends happening in SaaS sales).
Check it out and lemme know your thoughts!
It’s been 90 days since I joined Mailshake.
During that time…
I hired 1 AE & 2 SDRs
Built the AE & SDR playbooks
We booked 179 outbound meetings & won 11 of them so far
Set up the comp plans & the tech stack/CRM reporting (sales ops is f’n hard)
Identified our ICP & the messaging we should use to target them in a crowded market
Building an outbound team from scratch requires A LOT of foundational work in the beginning. Without that foundation, either you won’t scale or you’ll have literally no time as a sales leader… or both!
Test → refine → document → delegate → onto the next problem.
That’s the process I followed over the last 90 days.
Here are my 3 biggest takeaways.
Your network is everything
Selling a product that aligns w/ your brand is a cheat code
Small startups offer insane learning potential
1. Your network is everything
You need to learn a lot quickly when stepping up into a new role at a new company.
I leveraged my network in 2 ways to speed up this learning process:
#1 - I had calls with as many people as possible who (a) had also taken the jump from big to small startup. Or (b) had experience in my market and could provide insight.
Shoutout to Jesse Ouellette, Daniel Wax, Justin Michael, Max Sakiewicz, Luke Ruffing, Troy Barter, Chris Merrill, Morgan Ingram, Anthony Natoli, Joey Williams, Kevin Hopp, Matthew Roberts, Tito Bohrt so so so many more.
Some of my best ideas came from jumping on Zoom calls with people I only knew from LinkedIn. It exposed me to new ways of thinking that I could not have gotten anywhere else.
#2 - I identified my ICP, then found as many people in my network who fit that criteria to interview them. This helped me understand the market better and improve my messaging.
My network gave me a massive head start on my first 90 days.
If you’re still looking for a reason to create a personal brand, this is your sign!
2. Selling a product that aligns w/ your brand is a cheat code
Part of the reason I wanted to join Mailshake was because it’s a cold email software.
Which, if you’ve followed me for long enough, you know that’s like 90% of what I talk about.
But I didn’t realize how much of a cheat code it really was until I started prospecting.
The content I’ve always created was directly related to the product I now sold - making social selling easier than ever.
I’m all about the 80/20 rule.
So if I can figure out a way to book more meetings with less effort - while simultaneously building my brand - I’m going to double down on that so I focus on other things (like closing deals).
And I did exactly that - increased my cold email content and spent more time on social selling.
3. Small startups offer insane learning potential
When I left PandaDoc they had close to 800 employees. Mailshake has about 40.
Here are some things I’ve been exposed to that I would not get at a larger company:
Having my product requests heard and implemented
Helping to build, define, and maintain the culture early on
Getting a clear look at company finances and how a business operates
Beyond that, I feel very invested in the company’s success. Because my actions have a greater impact when there are fewer employees.
Booking an outbound meeting, or closing an outbound deal when it’s never been done before feels incredible.
Thanks for reading,
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