⚡️ Today’s level up ⚡️

In this edition, I’ll share the simple system I created to help me leave a cushy 6-figure earning Enterprise Account Executive role to take a big leap and start fresh at a new company (one that changed my life).

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Hey everyone 👋 ,

There is a lot of change happening in the job market right now – some being let go, others being heavily recruited, and others wondering if it’s time to move on?

Today’s system is all about helping you take the emotion out of an emotional decision – deciding where to go next.

BTW, I hope you like the new thumbnail art (I’m experimenting with DALL·E).

Let’s go!

Read time: <5 minutes

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How to know when it’s time to move on?

DALL·E prompt: Sketch of guy trying to decide next career move in colorful mid-century style

5 years ago, I was with a late stage SaaS startup out of San Francisco.

And I was happy, having fun, always in the top 5 of the leaderboard, and earning decent money as an Enterprise AE.

A recruiter came knocking on my door representing a company I didn’t know much about. At the time, I was receiving 5 or 6 recruiter InMails a week – most of them I ignored.

This one I followed through with because I had a mental list, and I promised myself I would pursue the request if it fit in one of these 2 categories:

1 / Marquee companies

2 / Transformative industries

This was 2017, so I believe the marquee companies that piqued my interest at the time were AWS, Salesforce, LinkedIn and a few others.

However, this company was not in that column, yet they did sit on the transformative industry list – Conversational AI.

I knew Artificial Intelligence was going to impact our lives as humans for decades to come, so I entertained the conversation.

The evaluation process

DALL·E prompt: Sketch of a bee leaving a company in colorful mid-century style

After a handful of conversations with the recruiter and a partner of the recruiting firm, I had my first conversation with Mike Ganci, who at the time was EVP Global Sales and Customer Success at LivePerson.

We hit it off and I was then introduced to more leaders at the organization (virtually and in-person).

I was really impressed with everyone I spoke with, and started getting excited about the prospect of joining this new organization on a brand new Strategic Accounts team focused on winning net new logos.

Long-story short, they were impressed, I was impressed…yet I wasn’t fully on board just yet.

There was not a whole lot of pain I had been experiencing in my other role, and I was due for a new comp plan that was guaranteed to nearly triple my current earnings for the following year.

The principles and process

DALL·E prompt: Sketch of cool guy’s back at computer creating plans in mid century modern yellow and navy blue style

I had a tough decision to make, and it was starting to stress me out.

On one hand, I was grateful to be in a position to be sought after, but on the other hand, I wanted to be sure I was making the right decision to progress my career in the best environment possible.

It reminded of the story of when LeBron James turned down a monumental endorsement contract with Reebok as a rookie leaving high school to enter the NBA (worth $117M) in favor of trusting his name with Nike (who only offered him $87M).

Don’t know too many 17-year olds who’d turn down an extra $30M, do you?

It made me think that long-term, strategic decisions are best suited using principles, rather than pure emotion.

I certainly wasn’t a rookie NBA player about to redefine the game of basketball, but I was an experienced sales pro that knew it wasn’t all about chasing the money.

So I stack-ranked my core evaluation criteria as follows:

• • People
• • Culture
• • Industry
• • Product
• • Comp

People

I chose people first, because who you work for (at the core) matters.

I want to know they are humans with high integrity, because decisions that can affect the trajectory of my career and life are in the hands of these people.

→ My favorite questions to ask:

• • Who is the longest tenured employee here and can I speak with them? (They’ll give you a true lay of the land)
• • Why are you trusting your career here? (Is this a meaningful place for people or is it just a stopover?)
• • Why should I not work here? (This forces the person to think objectively and not give you a fluffy answer – less fluff = authentic person)

Culture

Next, I look at culture, and a little hack I use is to divide the company’s annual revenue by total employees.

This number is telling – if this is a high number, it generally signals that the organization can do more with less (and more $ to go around during performance bonus time).

That’s generally good, especially if you see a lot of long-tenured people there.

→ My favorite questions to ask:

• • Is the team measured on activity or impact? (Check this out for the difference)
• • How does the company make big decisions here? (Are they an autocracy or democracy? Do they use guiding principles and systems or gut instinct?)
• • How does the company reward employees for doing good work? (Is it just about stuff, or is about substance?)

Industry

I always joke that I look for companies that make an unsexy space look sexy.

Unsexy spaces (think industries like supply chain, cyber security, logistics) are generally big ones because large enterprises rely on them to run their business every day.

The SaaS companies that bring a distinct vision for how this space should look and take a contrarian view – that’s sexy!

These are companies looking to shake things up, and that’s a rocket ship worth jumping on!

→ My favorite questions to ask:

• • What is (company’s) vision of the world? (This is better suited to be positioned as a statement into a question to show you’ve done your homework – “It seems (company’s) vision of the world is x. Is that right? What’s your perspective?)
• • How will the world be different in 10 years because of (company)? (Gives you insight into a couple of things 1.) If they have a big vision, and 2.) Glimpse into the strategy to get there)
• • Who’s posing the biggest threat to winning in this industry? Why? (A great way to unmask their perception on the competition)

Product

It’s hard to sell crap you don’t believe in.

I look for something I’d generally like to use myself.

Is it easy to use (so I can explain it and demo it on my own)?

Is the product winning awards?

Is the product reviewed well by customers?

Is it something that integrates easily with other core platforms used by major enterprises?

Pick the winner (not to be confused with the leader) or the one on the fastest rise.

→ Tips to evaluate the product:

• • Ask for a demo from their top Solutions Consultant (Great to build an early relationship)
• • Look for how many product people are being hired (I like this number being more than salespeople – shows they are committed to making the best product in the world and your chances for impact at the company will be higher)
• • Ask to peek at the product roadmap (Do you see true innovation or a boring wasteland?)

Comp

As I say often, to be a big money earner, you need to be in a big money environment.

Call it confidence, call it being brash, but I rank comp last because I know I am the biggest control factor in driving that.

Of course, I am looking to be in a position to make (considerably) more than where I was, but generally, I don’t get too eager too soon in this area.

→ Things I look for:

• • Simple to understand comp plan
• • Six figure base (for enterprise and strategic sellers)
• • A comp calculator I can play with (red flag if they’re not willing to provide)

Need some inside intel, check out RepVue.

What about things like territory, benefits, resources, tech stack, etc?

These are certainly important, but I wouldn’t rank them at the same weight as the core pillars listed above.

The system I designed to make the decision easier

→ Created a spreadsheet with two columns – current company and new company

→ Created core criteria and additional criteria and weighted them

→ Created a simple scoring system 1 (crap) – 5 (stellar)

→ Created 2 tabs – one at the start of process and one for the end of the process (after all the interviews were completed)

This allowed me to look more objectively at my situation and make a decision with less emotion.

If you’re in a spot where you need or want to make a change, I hope this helps you to take extra care with your due diligence.

See you next time!

🐝

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When you’re ready, here are 3 ways I can help you:

1 / Get the exact system I’ve used to go from earning $200K to over $1M a year in SaaS sales without burning out here. (2,500+ students)

2 / Join a community of Purpose-Curious™ sellers in the Make More Hustle Less Club where we develop a personal operating system together here. (400+ members)

3 / Book a 1:1 coaching session to up-level your performance here. (Limited spots available)