On Choosing Your Next Job


On Choosing Your Next Job

Note: The below is not scientific. But it is better than the alternative.

(Credit: Shirt.woot.com)

A candidate for a sales role recently talked to me about a few roles she was looking at. She’s accomplished, and the talent market is in her favor because of her track record.

“I like this one company,” she said, “but the others are offering higher base salaries.”

“What do you like about it?” I asked.

“The management. The market. Their product. The opportunity. They’re all great.”

“But the base is the issue?”

“Yes,” she said.

“How far apart are they?” I asked.

“There’s up to a 60k difference in the base.”

“Hmm. What about the upside, though? Who offers the most?”

“Well, clearly the company I really like. Lots of low-hanging fruit, proven product, and market.”

“Is it close?” I asked.”

“Not really.”

“But we’re still talking about the base?”


This is when the advocates for the worker would yell, “Well, if they really want her, they should just pay her more.”

And they’d be missing the point. So if you’re in that camp and have an open mind, read on. If you’re not, you’ll only be angered by what I have to say. Feel free to exit stage left.


The company has to decide what to shell out, true.

But our rockstar rep also has to make a decision about where to place her bet. And that’s the point here: it’s for her to think through, and make the best decision.

Because you can’t always get everything you want. Didn’t Jagger tell us that?

(Credit: Loudwire.com)

Let’s see if we can’t offer her a way to think about this decision. And maybe you, too.

While the below is focused on someone in a sales or sales management role, you in other roles are free to use this information however you like.


Here’s the too-long-don’t-read-the-rest-of-this note:

If you’re looking for the next right gig, the biggest mistake you can likely make is focusing on comp alone.

What?! There’s more to a role than the offered base, bonus, benes, and commission!?


Let us count the ways people, especially in sales, incorrectly value a role.

(Credit: Sesame Street, of course)


Ok. There’s the base. Real, mostly guaranteed money. What else, other than bonus and commissions should you consider?

  • The customer
  • The industry
  • Product-market fit
  • The competition
  • The company’s funding model
  • The company’s culture
  • The commute (does that still exist?)
  • The quality of management, especially your manager
  • What you’ll learn
  • Financial upside

Quick note: you should quantify all of these.

“But I can’t do that!” you might say. Actually, you can. It won’t be perfect, but it’s a start.


Some customers are better to work with/sell to than others, at least based on your experience and skill set.

Personally, I want to sell to owners and CEOs of SMB and mid-market companies. It’s a much faster process and a much more open and clear process. I’m not great at dealing with mid-level managers, and certain departments I don’t want to sell into (like HR). That’s me, not necessarily you.

Some roles, you don’t want to deal with.

Again, HR and I didn’t jive. Some people kill it in that market. Others will find it incredibly challenging to sell into.

When you look at those dangling commissions, ask yourself, “Can I sell that to that customer?”

The industry is similar to the customer and is often the same thing.

Banking, for instance, may be harder for some to sell into than small, funded tech companies. The compliance issues and culture of banks create friction that not everyone is ready for. And not every industry is as ready as the founders (ever optimistic, by necessity) of the company believe they are or should be.

And then there’s product-market fit, which, when combined with the above, makes a nice meal. If the ingredients are right.

In talking to a coaching client recently, he shared with me the product, the industry, and the customer.

I’d been in the space and sold to that customer, and I understood enough about the product.

“Wait? What? You’re trying to sell what? To whom?”

He told me again.

“Get out of that space. It won’t go and you’ll waste time trying to help the company and prove out something that doesn’t work.”

It’s nice to be in a company where someone has sold and validated that the market wants what you are trying to move. Meaning, the founders and/or executive team have customer validation for your product, at your price point, against their alternatives. consistently. Not in a one-off way.

Too many companies have a great new idea. And I, as a consumer, am grateful because that’s progress. That doesn’t mean you or I should be the ones to take it to market. Because the odds of failure are often much higher than any hiring manager will admit.

Remember those bonuses and commissions you were looking at and counting as a given when considering the role?

Add an expected value to them. Discount them by the likelihood you can sell that product to that customer in that industry.

Here’s how I might super-scientifically look at and value the role:

(Credit: Me and Google Sheets)

And that’s the beginning.


Ah. We didn’t address competition.

Do you know what conference you’re playing in? Is this the Sun Belt, where you can win 10 games a year running a great program? Or the SEC West where you’ll get smashed every year by ‘Bama and either LSU, A&M, or Ole Miss under Kiffin?

At some point (or not), you’ll be in a space where there’s an 800-lb gorilla. And your ability to win depends on the company’s ability to compete.

Yes, I’m sure you’re a stud or lady stud, but there are real factors. You need to know whom you’re competing with. In some spaces, your competition can and will buy your customers. Look at employee benefits.

Look at M&A in light of the last year. Big firms are coming down the market to gobble up what was once considered a small market left alone by bigger investment banks.

You have to be ready to compete. And have a way to win. Other than brute force. Go ahead and calculate that into your comp.


How does the funding model play into your assessment of the role?

Like knowing there’s a lot of pressure from the PE firm that just bought or funded your company? Going from monthly pipe reviews to weekly?

Or having to now report on numbers unrelated to productivity?

Perhaps knowing there will be a new process forced on your company may or may not make sense?

This isn’t to say that external money necessarily makes silly decisions, though it sometimes does. It’s that it necessarily involves change. And a different set of expectations.

Ever worked in a bootstrapped environment? One that grows slowly and deliberately, plowing money back into the firm as experiments prove out?

Can you live with that, especially if you come from the world of crazy PE/VC money, where you build out full teams in 4 weeks?

You may find yourself asking, “Are they really committed to growing the right way?”

The funding model matters. To how fast you can go, and how fast you’re expected to go.

(Credit: Amazon!)

And this relates to culture.

Like getting emails at night and on weekends? And being expected to answer them?

What about a more laid-back approach for your A-type personality?

Like working from home? Or working in an office?

Travel? Or doing all meetings via Zoom?

Does the CEO rage for no reason?

Or act slowly, despite the need to do differently?

All of these play into the culture. Know what you’re signing up for. Because that nice base and bonus package may not make sense if you’re hating life, trying to be a turtle in a bird’s nest.

Here’s a way to think about it: stress has costs. I’m not sure how to quantify it, but if you think you need to take 1-2 more vacations per year because of the culture, factor that into your calculations.

Do the same with the commute.

A 30-minute commute, total, is drastically different than one requiring an hour each way. (Are people still commuting?) I didn’t have a perfect way of quantifying it, but the easiest is to put a dollar value on your time and plug that in as a cost.

And do the same with the likelihood that you won’t be there in 2 years because of:

  • Your jerk manager
  • The insane culture
  • The fact that there’s no product-market fit

It might look like this if you plugged it all in:

Subtract that from the adjusted value of the role.

Is it an exact science? Nope. But it’s closer.


Let’s talk long-term.

Nothing may be more important than your relationship with your manager.

This can’t be overstated. Not all managers are created equally. Great managers are worth their weight in gold. Will they develop you? Challenge you? Help you advance your career? Advocate for you? Tell you when you’re whining and acting like an entitled brat? Push you in the right ways?

This goes from a BDR looking at their manager to a C-level candidate looking at the CEO: what will come from your time working for that manager? How will you grow? What impact will this have on your success there, and in the future?

A great one can literally have an enormous impact on your lifetime earnings.

A bad one will either not really help you along, or cause you to leave within two years, with little to tell the next hiring manager.

Start thinking about it deeply. What is this person’s track record for developing talent? How will they invest in you? Yes, salespeople (and sales leaders) love to impress and don’t want to admit what they need to learn. But let’s be honest – this is likely not going to be your last ride. Find more value than in the pay.

You may look at my numbers and think, “No way that’s the sort of impact a manager can have.” But if you’re with the right leader, they could potentially double your earnings over the next decade. Were I employable and on the market, I’d run some sort of calculation like the one below after interviewing the manager I’d work for.

Could that happen in scenario 1? Possibly. I made up the numbers. Looks like in companies A and C, you’d end up owning a small business, or going back in time to invest in Bitcoin. Option C looks like you became a rockstar enterprise seller, or found some great residual income.

The point is that we are calculating the impact of a great manager.

The multiple below – 2, .25, or 1 – is on earnings over the next decade.

Another way to think about those increased earnings is in what you’ll learn.

Looking at roles: Is it in an industry you want to be in?

If so, will you learn the players, build the relationships, and understand the customer the way you want to over the next 5-10 years?

Will you pick up new skills working in a different type of role or stage company?

Will you grow up working in a different type of team? With a certain type of person?

When I was assessing options coming out of business school, there was a well-funded company in Austin, Texas I was interviewing with, and a small, boutique consultancy. I knew I’d make more money faster at the startup, but that I’d learn more and have greater earning potential if I went with the consulting firm, despite a few hard years.

I think my choice has worked out. But that may be confirmation bias.


Financial upside

All of the above go into this item. Your manager. The culture (and funding model) and thus your emotional and mental health. The product-market fit. The customer. The competition.

Yes, company C is offering X + bonus + uncapped commissions…. But company A will be less stressed, provide a much better manager, and have a greater likelihood of hitting my commission and bonus targets.

Ask: Where am I more likely to have success? And enjoy life? And learn and grow?

Oh, and that equity.

Do we ever really figure out what it’s worth? Consider the following:

  • Given your shares, what does the company need to sell for to make them meaningful?
  • Is the team in place to hit that target?
  • How realistic is the target?
  • How long will it take to get there?
  • Will you be fully vested by then?
  • What will the multiple be?

For giggles, I threw out some of the larger multiples on revenue we’re seeing now. Plug in your own numbers, and use your own formula. But the logic holds.

Will you make all the money you think you’re looking at?

But there are many variables. And if you don’t start thinking about the role they play in your income, you’re looking at the wrong numbers.


Now, in brief defense of Mr. Burns….

(Credit: The Simpsons!)

A company owner recently talked to me about the senior manager he was looking to hire for a key role.

The owner told me, “He wants to make 400k a year.” (It’s in a business with recurring revenue, so income accrues over time.)

“I want someone who wants to make two commas. But he’s asking for 60k over what we’re willing to pay in base. That’s all wrong. I’m prepared to have this person make a lot of money, but in terms of fixed costs, we need other key hires that will help him achieve his goals.”

Here’s the question: will conceding on that 60k -so the company can make the next key hire – help this person reach his goals? And is he more likely to make that money in this role, or somewhere else offering him the additional 60k?

Look at the GOAT of NFL QBs – Tommy Brady. During his time with the Pats, he routinely gave up (especially early) additional earnings SO THE TEAM COULD SPEND MORE ON THE TALENT AROUND HIM. It’s worked for him, to the tune of 7 Super Bowl wins. And plenty of money.

Think. Long. Term. Big. Picture. Whole. Package.



Adam Boyd