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⚡️ Today’s level up ⚡️
Today’s edition reflects on a key moment in my career when I got hyper-intentional about learning how a (large) business operates inside and out. This dedicated effort (which ended up being a very joyful pursuit), was a big leap forward in quickly ascending out of the 6-figure earner category and into the 7-figure one. I’ll share my story and break down how you can make it a repeatable process.
Let’s go!
Read time: <9 minutes
Understanding businesses takes studying businesses
Way before Apple News and Substack, there was Flipboard and Mashable (yep, I have gray hair).
They would be my go-tos, well before social media (ugh Facebook…I shock myself that I spent time there?! 🫣).
But it hardened a habit, one that was a lot easier than what the greats before me had to do – which was to subscribe and read “the trades” and The WSJ, HBR, and other specialty papers or quarterlies that made sense.
Reading material that you’re genuinely interested in that also happens to overlap with the industry you sell in is certainly better for you than mindlessly scrolling your social feeds and swiping through what Doug’s wife cooked for the family last night.
It was my infotainment.
I learned a bit.
I escaped a bit.
I daydreamed a bit.
I got fascinated with keeping up with the latest tech trends. The emerging SaaS players. Where Silicon Valley VCs were investing their money.
I’d learn about valuations. I got good at understanding the right terminology. I studied how high-growth businesses did things – from customer UI, to customer UX, to design, to marketing.
It was a built-in education that I accumulated through 15, 20, and 30-minute drips here and there. All without leaving the comfort of my couch, half listening to the Netflix episode playing on the TV.
Taking things to the next level
A pivotal moment in my career came in 2014 when I was eager to leave an SMB SaaS AE role.
The office drama was out of control and the environment became highly toxic. It was very distracting and it started to affect my performance. I was definitely not happy.
Not to mention, I was commuting an hour and a half each way, often in busy rush-hour, stop-and-go traffic – adding an hour at least when I didn’t time my exit well.
(At least I negotiated down to only three days in the office)
An opportunity came up at a mid-market-focused IT consulting firm that was closer to where I lived.
It was definitely not in my wheelhouse when I interviewed, but I had two things going for me:
1. My tailored Ben Sherman suit was sharp AF, and
2. And the competition in the area was not exactly fierce
But I also had my sh*t together.
They knew where I lacked experience, I had the ability to make an impression on future clients while learning the ropes.
What ensued was one of the fastest-growing and most chaotic years of my career.
I was put in charge of growing the company’s multi-unit restaurant division. I had absolutely no idea what I was doing. I had no experience in the restaurant world (other than bussing tables at an Italian restaurant for a little bit in college).
My saving grace was that I:
– Knew what I liked as a customer eating out often, and
– I was already reading about tectonic shifts happening in restaurant tech
(I feel like I owe Flipboard an executive certificate fee or something)
Although that year at the consulting firm was my lowest-paying year in several years, it was worth it to have the chance to learn how to take over IT operations at a growing restaurant chain and then strategically add in tech-as-a-service that drove incremental revenue for the units, enabling them to boost their AUV (Average Unit Value) and thus be able to sell more franchises.
It was like getting paid to acquire an MBA. One that required immediate implementation of what I learned in the morning later that afternoon with a client.
Lesson 1: Making a move solely for money doesn’t always pay off in the long run. If you’re ever presented with an opportunity to add to your skill stack in a big way, it will pay for itself in a few years (like taking a $20K, $30K, or $50K pay cut for acquiring million-dollar-earning lessons).
If you weren’t in sales, how would you be spending your time professionally?
Although it was a great stepping stone, I knew my long-term future did not belong there.
I wanted to work at the type of exciting tech companies I had been reading about on Flipboard for the past few years.
And I did it.
BTW, my search and approach weren’t overly sophisticated. Here it was:
1. Kept a watchful eye on the top tech movers and shakers in the industry
2. Made key connections at industry events and built my network
3. Started writing a few articles on restaurant tech on LinkedIn and shared them
4. Began reaching out and interviewing, starting with ones I wasn’t all that excited about (to get comfortable interviewing again) before reaching out to the ones I really cared about
5. I always reached out directly to a contact at the org vs blindly sending in my resume
Eventually, I was able to parlay my restaurant operational experience at the consulting firm and landed an Enterprise AE position with a high-flying late-stage startup out of San Francisco that focused on the restaurant industry.
The last interview with the CEO was me walking her through how I structured large hardware + software + services together to create a high-margin, highly sticky deal with multi-unit restaurant brands.
I was able to use restaurant economics and terminology (front of house, back of house, COGS, FIFO inventory) to showcase I knew how operators thought.
They were impressed, and I was excited to get back to selling for a product company that was doing cool stuff.
In my own time, I became obsessed with dreaming up how to build a new restaurant concept or a coffee shop from the ground up, all using a tech-first approach. I started watching things like Restaurant Startup to further infotain myself.
Lesson 2: Ask yourself, “what would you do if you weren’t in sales?” Where does your daydreaming take you? Can you draw an overlap with the industry you serve or the current tech you sell? Exploring this curiosity can give you a different perspective – one business executives will come to appreciate.
Apply the 90/90/1 rule
I really enjoyed my time as an Enterprise seller at the startup.
I had a lot of freedom.
I was successful.
I had tons of fun.
But after nearly three years, I moved on after making a tough choice to do so.
By this time, I had graduated to become a Strategic Account Director at a top Conversational AI company.
It served a broader market beyond the restaurant and retail industries, but by this point, my business operator “hat” was permanently affixed to my head and could be easily applied to other industries.
On my list of 50 strategic accounts, I had anyone from big banks, to health insurance companies, to retailers, to major airlines, to big hotel chains, and some restaurant brands (although it wasn’t a big focus of the company…until I made it one).
After filtering my accounts down to the industries that interested me (retail, hospitality, and travel), I got really excited about using creative strategies to get noticed.
By working on fewer accounts, and ones where I could apply my business operations thinking, as well as ones that interested me because I was their customer, I effectively pointed my skill stack at the right things, which:
– Boosted my confidence
– Decreased sales cycles
– Increased my win rate
I went from earning $200K in 2018 to $1.5M in 2019 – a 7.5X jump because my TEA (time + energy + attention) was being applied in the most high-leverage way.
One of the secrets to up-leveling my income so quickly was carving out time for deep work and protecting it on my calendar.
A rule that I applied (that I didn’t know had a name until just recently), is something called the 90/90/1 rule, which comes from Robin Sharma, the author of The 5AM Club.
It’s really simple, but highly powerful:
– For 90 days,
– For the first 90 minutes,
– Focus on your one most important thing
For me, it became diving insanely deep into my Diamond Accounts.
I’d spend that quiet, peak energy time thinking big on how we could transform their business – ideating on creative use cases, coming up with a cohesive narrative to share, and understanding where they were trying to take their company.
This deep work paid off (literally).
Lesson 3: Carve out time on your calendar and commit to applying the 90/90/1 rule on your top account or leveling up your skill stack. BTW, if you want a great place to up-level your business thinking, I highly recommend subscribing to Category Pirates. I get so much out of their “mini-books” (FYI, it’s a paid subscription – but I have no affiliation or get incentivized to share…I just find it really valuable).
See you next week!
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