Most sales jobs look great on paper.
The offer letter, the OTE, and the hiring manager’s pitch are all designed to make the role feel like the right move. Taking the job is still a leap of faith, because sales never stands still and you are never stepping into a static environment.
After 22 years recruiting for software sales roles and meeting with hundreds of CEOs, CROs, and sales professionals, I have found three factors that must line up before you make your next move.
Fit Factor #1: Product Fit
If the product solves a real problem but you cannot get passionate about it, can you get passionate about the clients it helps? Can you get excited about the headaches it takes away?
The product matters, but what matters most is how you feel about it. Your customers will read that feeling. If you do not believe in the solution, find a different opportunity.
I once placed an Enterprise rep who finished number one year after year at a large public company. He understood the product well enough, but he did not sell it with a three-hour technical presentation.
He sold a complex, analytical solution on belief.
He knew it changed lives because he had seen it firsthand. Customers welled up during a demo because the software meant no more missed dance recitals, no more 3 a.m. quarter-end scrambles. That belief, in the product and in what it did for the people who used it, made him the best rep in his company.
Fit Factor #2: Executive Leadership Fit
If you have been in sales a while, you have probably started a new role only to watch your boss get fired or quit two weeks after you onboarded. It happens more often than you would think.
Your boss matters, but the leadership system around your boss matters more.
Because bosses come and go, look at the executive leadership team. They set the pace. They decide the company’s near-term and long-term priorities. And they will choose your next boss.
So aim to align with the team, not just the person you report to today. How do you read a leadership team before you have taken the job? Start with turnover. How long do leaders and reps stay?
Then treat the interviews as data. Notice what they ask, the themes that surface again and again, and what they treat as a priority. How do they describe their own leadership, and what does the team say about it when you ask?
Take notes as you go. Write down what they emphasize and what they say it takes to succeed in this seat. Then trust your gut on the one question that matters: do you want to work with these people?
Fit Factor #3: Compensation Is Really Sales Motion
You are in sales to solve problems and make good money doing it. Your pay rides on commission, so seniority only takes you so far. A rep two years in can out-earn one with two decades of experience. That is the power of this profession.
Tenure alone will not increase your income. You are better off picking the right seat to begin with.
The plan itself should be fair: stable, uncapped, with a reachable quota. You cannot make what you do not bring in, but you also should not have a ceiling on it. Go all in, and you should be able to hit your on-target earnings (OTE).
It will not come easy. Strong selling never is. But you should get out what you put in.
That is table stakes, though.
The number on an offer is the output of a sales motion: the deal size, the cycle, the support around you, the type of buyer, and the way deals actually get won.
Two reps can sit in the same seat at the same OTE and take home very different paychecks, because one is running a motion they were built for and the other is fighting it.
So before you judge the comp plan, judge the motion behind it.
When you look at the comp, think about the sales cycle. Think about the customer. Think about the support model. Think about where your strengths let you win.
Knowing the three factors is one thing. Weighing them against a real offer is another, because they never show up one at a time. Here are three opportunities, each evaluated on all three factors.
Case Study: $300K OTE, Payroll/HCM SaaS
A role pays $300K OTE at a payroll and human capital management (HCM) company. Plenty of reps hit that number, and plenty do not. But you are not a believer in payroll. You know it matters, but you cannot see why one vendor beats another. That makes it hard to create the displacement you need to pull customers off a competitor and onto you.
Verdict: Hard pass.
It might be $300K for someone, but the motion does not fit how you tend to win.
Case Study: $240K OTE, Established Supply Chain SaaS
The product tracks the supply chain end-to-end. You see the value and the market need. Leadership is tenured and solid. Now the comp, which means the sales motion. Does this cycle play to your strengths? Look at the specifics. The company has name recognition. The territory spans multiple states. A pre-sales team handles demos. Their website and LinkedIn page stay current. There are no sales development reps (SDRs), but deals run $100K+ in annual recurring revenue (ARR), so you would need to close five or six a year to hit quota. You love hunting big deals.
Verdict: Go for it.
The number is lower than the payroll position, but the motion is built for how you sell.
Case Study: $400K OTE, New AI Company
The product is AI, with endless use cases across a broad set of buyers. The company is known in the space. They want the sales team in the office, and nobody is winning yet because the solution is new. The whole team is new. There is zero support: no pre-sales, no leads, nothing. You believe in the product and see the market need. You do not mind the daily commute. For $400K, you will do it. Now the sales motion. You are not comfortable driving new business without SDRs, inbound leads from marketing, or demos already on your calendar.
Verdict: Hard pass.
The highest number on the page, but the motion is everything you struggle with.
Most sales opportunities that meet these three criteria are what you make of them. But the rest is up to you.
The key to a great sales career is simple: sell something you believe in, work with people you respect, and get into a seat where the company’s sales motion matches the way you naturally win. If you are specifically evaluating a new logo hunting role, I wrote more about what makes that kind of opportunity worth taking here.
