Creating momentum by removing excuses.

^{From SDR to CRO. My sales career was a 13 year cannonball run.}

Most recently, I was a CRO from $500k to $50MM.

As a Seller I’ve always wanted to learn, grow, and push myself to do new things. I knew about midway through my CRO journey that I would want to start my own company next. There are few examples of non-technical sales founders building tech companies. This newsletter is going to be about that experience!

Hopefully this will help people who want to do this next!

So as a former CRO / Seller how does it feel to start a company?

Originally it felt slow. I joined LinkSquares at 10 employees and $500k in ARR. A year later we were over $3MM. That is the speed I am used to. That is not where we are right now. We are exiting the idea phase and entering the build. 

Originally it felt lonely. I’ve always been a big team guy. Being a solo-founder has been challenging! Not having a technical co-founder lined up is a reason why many non-technical founders never get started in the first place!

As a seller you learn that time kills all deals and that forward momentum is everything. Kinda slow, kinda lonely, no-technical co-founder. Sometimes you have to create momentum and eliminate the ability to have excuses.

I had to burn the boats.  

I called Kyle York and the team at York.ie to help me continue moving forward.

Kyle was the CRO at Dyn from $0-$100MM and he was one my mentors while doing $0-$50MM. I first met Kyle in early 2021 after sending him a cold LinkedIn DM after listening to him on a podcast... we’ve been in touch ever since!

Kyle’s company, York.ie, is a modern VC firm that also has a separate services business, comprised of the former Engineering, Product, Marketing, and Finance leaders from Dyn. (As a team they successfully sold the biz to Oracle for $600m).

Winrate is in the “York Labs” program which is basically an incubator-like program. The former Dyn execs serve as my fractional exec team. I have a proven CFO, CTO, CMO, VP of Engineering, etc. and they serve as a unified team, as an extension of my own. The rub is you give up a single digit percentage of equity and are on the hook for engineering spend.

In exchange for equity, the York Labs engineering pay rates are discounted making them more cost effective vs. other shops I spoke with (which you would expect considering they have equity). For me the real value is in having world-class functional leaders, on-shore, managing the development of the product… and they are under the same roof partnered with their functional exec peers (Finance, Marketing, etc.). Everyone is on the same page working within different areas of my biz.

It would have been more expensive across multiple contracting shops and much more challenging to stay aligned.

Are we going fast now? Yes.

Do I have a team now? Yes.

Not sweating the equity let me burn the boats and eliminate the #1 threat to my success: not getting started. Now we are cooking!

So what is my fundraising strategy? I’m bootstrapping Winrate.

If it makes sense to take outside capital later we will always have that option available to us.

Could I have done this 5 years ago?

Not a chance, I didn’t have the money… or the skills… both took time.

I spent 13 years or 156 months building pipe, chasing quota, leading teams and parlaying bet after bet toward this moment in my career. I ran as clean of a race as I could and I’m fortunate to be in this position.

Huge shoutout to my better half Julia for being comfortable and supportive of this! Julia is an SVP of Marketing, an incredible Mom, and my ride or die since the early AE days. She’s seen it all and without her I probably wouldn’t have broken into tech sales in the first place. She’s always supported the big moves and calculated bets along the way. With two little kids at home, risk aversion starts to climb, it’s easier to play it safe, but she’s all-in. This is rare and it’s not lost on me that without her support Winrate wouldn’t exist. For Fathers day, she even hooked up our family with the first batch of Winrate swag, t-shirts!

So… WTF are we building? What is Winrate!?

Tune in next week to learn more!

Tech I am using and loving

Apollo.io is outrageously value packed. CRM, contact database, call recording, you name it.

Hubspot CRM is so easy to use, and I have yet run into any of the limitations the salesforce zealots talk about. It’s a great CRM.

Copy.ai it’s awesome for meeting prep, I get a slack with a read out before every single call I have. The team has been great to work with!

Sendspark for easily recording personalized videos, it’s been super helpful for internal use cases like communicating with my product team.

Fyxer.ai this organizes my inbox and creates reply drafts that I frequently do not need to modify. Saves a ton of time. Similar vibe to when I had an EA as CRO.

🔊 Spotify Playlist of the Week