Maybe your work bestie just left for a $20K base pay raise. You know you outsold him every quarter, and yet you’re still at the same base salary and low commission rates you had a year and a half ago. You’re wondering if it’s time to leave.
With so many tech sales jobs posted at any given moment, how do you decide which one is right for you? Whatever the market is doing, hot or cautious, the math of a bad move stays the same: a year or two of your best selling years spent in the wrong seat.
So it pays to be selective, and being selective starts with knowing what to evaluate.
The first rule of job searching is to know yourself: your strengths, your non-negotiables, and the environments where you do your best work.
I’ve written a whole piece on getting the sales job you want by understanding what you’re good at, so start there if you haven’t done that thinking. Because your situation is unique to you, and what works for a former colleague is not necessarily what works for you.
Suppose you’re four or five years into AE experience, and your friend leaves your org for a Series A startup. He calls you up and tells you to come over because he’s killing it: three deals closed in his first 60 days, senior executives taking notice.
You want in on the fun. So you leave your tedious sales job and join the startup, and then discover your relationship with your new manager is not so hot, and your territory is a smattering of states, a mixed bag of tier-three areas that go together as well as stripes and polka dots.
Meanwhile your friend keeps closing.
Similar circumstances, skills, and even backgrounds will not guarantee similar results. So think carefully about what you need, where you are in life, and how hard you’re willing to work when things get difficult, which they inevitably will.
Consistent sales success never comes easy. I don’t care who you are.
With that settled, here are 10 factors worth evaluating when exploring a new tech sales job.
#1. Prospecting: Your Cold Call Threshold
Prospecting makes or breaks sales careers and roles, depending on how much of it is expected. So how much prospecting are you willing to do?
Some reps make 10 calls a day on average, others hold a self-imposed minimum of 35. Some see prospecting as a pure numbers game, others believe success comes down to call quality, and some reps tell me flatly they’re unwilling to prospect at all.
Some AEs won’t work at a company that doesn’t have SDRs. Other AEs have SDRs, then realize the SDR team isn’t any good at driving demos. Evaluate your willingness to fill the top of your own funnel before you sign, not after.
#2. Brand Recognition: Meaningful or Meaningless?
How much of a brand do you need to crush your numbers? Are you a confident enough seller to work with a good product and minimal brand recognition? Can you overcome the lack of a name with your passion? Do you rely on marketing for sales material and email campaigns?
It’s no secret that marketing support makes a difference. But marketing is something you may not notice much until you sell without it.
#3. Product Quality and Market Fit
How much does the product mean to you? I’ve met reps who couldn’t care less what they sell; the mere idea of getting paid well when they close is enough. Others need to feel emotionally connected to their solution’s impact on customers.
What about the product do you need to believe in to do your best work? And beyond your own feelings, is the product something buyers feel they need, or is it a solution to a low-priority problem? That second question matters more than most reps realize, because the best roles sit where buyers have real urgency and budget.
#4. Executive and Sales Leadership
Sales leadership is a moving part of the job happiness equation.
The reality is the sales manager who hires you may be gone in six months, so if you need a connection with leadership, make sure there’s more than one person at the company you can get behind. Maybe the CEO is inspirational and you can learn from the CRO.
The average VP of Sales has a tenure of around 18 months. Staying with a company long-term means adapting to many different managers, and naturally, some will be better than others. Remain flexible and leadership movement won’t have to end your tenure.
#5. Company Stage: New or Established?
Companies are like people in more ways than you might imagine. They have growth stages, and some are more fun and challenging than others.
Startups are figuring things out. They’re in their infancy, moving forward without much experience driving the car. Hate risk and ambiguity? Avoid them.
And not all startups share the same risk: pre-Series A is the highest-risk stage, while Series C and D are much less risky (and also less lucrative, with less market opportunity for a salesperson). Weighing one? Here’s how to tell if a new logo role is worth taking.
Private companies focus on profitable, sustainable growth. They tend to spend the money they make, not the money they take, so money spends differently than it does at a startup. Growth is slower, steadier, more methodical.
Privates may not be the flashiest, but they tend to be fiscally responsible and deliberate, and for anyone who values stability, one might be a great option for a sales career.
Pre-IPO companies are in adolescence: intelligent, proven, somewhat experienced, a long way from the ground-zero startup days.
But they’re not as bright and experienced as they think, and that teenage arrogance kills some companies and stunts growth in others. Some IPO and fizzle; a good number keep growing.
Post-IPO companies are structured, organized, and carry real brand recognition.
But they already have many customers, so there may be less market share for a new rep to capture, and it can feel like you’re part of a large selling machine rather than an individual making a difference. Some salespeople find stability, internal mobility, and career contentment there.
Others quickly feel like corporate zombies doing low-impact work.
#6. Culture and Values: Meaningless Drivel or Something to Notice?
What is often discussed, publicized, and never accurately described, especially by the people who are part of it? Culture.
It’s in vogue for companies to post their values on their websites, and it’s also something most employees read with skepticism. Culture takes a while to identify, is difficult to define to an outsider, and is one of the most underrated organizational characteristics for its impact on job satisfaction. I have yet to recruit for a company that can publicly describe its sales culture for what it is.
For the most part, some of the most outwardly “professional” companies look entirely different from the inside. Say you work for a tech company that habitually promotes only a certain kind of person, and you aren’t that kind of person.
Will it take you three years to realize that no matter how much you crush it, you’re never getting that promotion? Or that you’ll have to perform twice as well for the same opportunity?
So go ahead and review Glassdoor and read the values page, but at the end of the day, they won’t help all that much. Instead, look at who’s in charge.
Look at who’s getting promoted. Notice what behavior is rewarded, compensated, and celebrated, and watch for the culture red flags that show up early.
Look at the C-suite, not middle management, because middle management mostly carries out what the executives want, and executive leadership selected them in the first place. Who’s calling the shots? What historical decisions have these leaders made?
What beliefs do they hold about salespeople, and how do they encourage, pay, and reward the people who bring in new business?
Chances are you aren’t going to change a company’s culture unless you’re running it. So the real question is: what is the context you’ll be operating in, and can you make it work for you?
#7. People Power, or Just Another Resource?
It may be impossible to learn how a company perceives its employees by asking, so you’ll need to do some detective work. Start with: who works at this company?
What kind of career progression have they made? What are these people doing to get ahead?
And how does the company treat employees during times of personal crisis? Maybe a spouse is going through cancer treatments and an employee needs to shuttle them to and from appointments.
Does the employer make accommodations, or is it treated as an inconvenience?
The people you meet and the relationships you develop can impact your ability to move seamlessly in and out of companies for the rest of your career. Pick a company that cares for its employees, and find a place where you have a mentor and a team of people who support you.
#8. Risk
How much risk exists here? Is the company on the cusp of acquisition? A purchase by a PE firm? Trying like crazy to land a B round?
What sort of risk exposure can you endure? A wrong move is easy to recover from in a good job market. In a difficult one, finding another sales job takes longer, so what was once risky-but-fixable becomes risky-and-slow-to-repair.
Know where the market is so you can assess the situation against your own risk tolerance and security needs.
#9. Target Attainment
Can you hit the sales targets? Will you have a good chance of being successful? Can you speak with another rep on the team and get their take?
Keep in mind that sales targets, like people, are constantly moving. Territories change, and so do comp plans and bosses.
#10. Flexibility
When evaluating all these variables, it’s worth looking at your own ability to be flexible. The one thing about business that keeps it interesting is that nothing stays static, except that you can count on changes ahead. We think we know the future, but we have no idea.
Being in sales is a tough job. You’re paid on results, not effort, tenure, degrees, or hours clocked, and the results combine skill, work ethic, luck, context, product, timing, and circumstances. You will never be without challenges.
The real question is whether you can remain flexible and keep adapting to company changes. What areas can you not bend?
Understanding your snapping point and working on your flexibility can help you turn adverse conditions into prosperous ones with time, optimism, and determination.
Advocate for Your Career
Since you’re here, you probably know I’m a headhunter. Every day, I persuade talented salespeople to meet with me about their career goals and challenges. Occasionally I encounter salespeople who want more information than I’m willing to give in an email, but who talk about how they don’t have time to speak with headhunters.
However, they find time to write long emails to headhunters.
So here’s one piece of critical advice: no one will advocate for you regarding your next career move. Not your spouse, not your mother, and certainly not your boss. Only you can take the time to investigate, explore, and build your network.
And when you don’t take 10 minutes here and there for a conversation, you will miss out on opportunities.
Interested enough to ask a headhunter for more information about a role? That’s a sign you should spend 5 minutes on yourself to learn more, and yes, that may even require a phone call. Career management isn’t something you do once in a while; it’s something to think about regularly.
Of course you’ll uncover roles that aren’t right for you. Some people say they don’t want to “waste their time or mine.” To that I say: exploring an opportunity for yourself is never a waste of time, for you or for me.
Making a connection with another person is never a waste of time. I don’t get paid by the phone call, and I don’t make money on every candidate or client I speak with, just like you don’t close deals with everyone in your funnel.
That’s not how it works. But I do try to leave every conversation having added value, even when the role I’m working on today isn’t the right match.
The Perfect Tech Company Is an Illusion
There may be no such thing as the perfect tech company, only the ability or inability to tolerate a set of changing conditions that are out of your control. The more you learn about a company, the better.
Take the time to advocate for your career, explore potential opportunities, and find out as much as possible so you get a clear picture of what you’re stepping into.
Recognize that all companies carry inherent risk, and you’ll be better prepared for a positive, lucrative, and rewarding sales career.
These 10 factors are the deep dive in the complete guide to evaluating sales jobs and offers.
