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So Many Tech Sales Jobs it’s Time to be Selective

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Sales Job Envy?

Now’s Not the Time to Sit on the Sidelines. Instead, Find the Right Tech Sales Job for You Before the Best Job Market in the Last 20 Years is Over.


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 to choose from, how do you decide what’s the best tech sales job for you?

With one of the best job markets in the last twenty years, the job market is on your side. So what will you do with it? Now more than ever, it’s time to set yourself up for success and put yourself on the fast track to success. 

The Best Tech Sales Jobs: Know Yourself to Find the Best One for You

The first rule of job searching is to know yourself. 

There is only one of you. And you’ll need to take some time to investigate what you want and what you need in a company, position, leader, product, and compensation plan. Figure out what works for you. 

Get to know yourself and your strengths. 

Some people refer to this as self-awareness. It can be challenging to grasp but essential. The sooner you know how you are, the better.

Finding the right sales role will be challenging if you don’t understand your strengths and non-negotiables. 

Know Your Strengths

And you may waste one of the best job markets you’ll see in the next ten years. For example, suppose you are four or five years into AE experience, and your friend leaves your org to go to a series A startup. He calls you up and tells you to come over because he’s killing it!

He’s closed three deals already in his first 60 days and is already getting noticed by senior executives. 

You think you might want in on all the fun. You, too, want to smash the cash! So you leave your tedious sales job and go to the new startup.

After you get there, you realize your relationship with your 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. So you find yourself concerned about hitting quota. But, on the other hand, your friend is seeing more success with each passing day, getting more leads and closing more deals than ever. 

Only One of You Yet Many Sales Jobs

The lesson in the story is that your situation will be unique to you. 

What works for you is not necessarily what works for the former colleague. Even if you view yourself as more skilled than they are, you may both go to the new company and face entirely different situations and experiences.

Similar circumstances, skills, and even backgrounds will not guarantee similar results. 

So you must think carefully about what you need, where you are in life, what you want, and where you’re heading. You’ll also have to consider how hard you are willing to work when things get difficult. Which they inevitably will.

Consistent sales success never comes easy. 

I don’t care who you are.

Sure, you may have a few good years here and there, but if you want a long-term career in sales, you’ll need to look for more than a good tech sales job. Given your goals, personal situation, and strengths, you’ll need to consider what a good tech sales job looks like. 

And then overlay that on the situation you’ll be walking into, knowing that it can and will change quickly.

Ten Major Factors to Consider when Exploring a New Tech Sales Job

There are several factors worth evaluating when exploring new tech sales jobs:

#1: Prospecting – Cold Call Threshold

Prospecting is a significant consideration.

It makes or breaks sales careers and roles depending on how much prospecting is expected. So how much prospecting are you willing to do? Some reps will make ten calls on average a day, and others have a self-imposed minimum of 35 calls.

Some see prospecting as a pure numbers game, while others believe success comes down to the quality of the calls. Some reps tell me they are unwilling to do any prospecting calls.

Some AEs won’t work at a company that doesn’t have BDRs/SDRs. Other AEs have SDRs/BDRs, then realize that this SDR team isn’t any good at driving demos.

So you’ll need to evaluate your willingness to prospect for new business and fill the top of your sales funnel.

#2: Brand Recognition –Meaningful or Meaningless?

How much of a brand do you need to crush your numbers?

Are you a confident and strong enough seller to work with a good product with minimal brand recognition? Is the product you sell so new that brand recognition doesn’t matter? Can you overcome the lack of brand recognition with your passion? Do you rely on marketing for sales material and email marketing?

It’s no secret that marketing support can make a difference.

But how much marketing support will you need to make your mark and hit your goals? Unfortunately, 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 could care less about what they sell. They get enthusiastic by the mere idea of getting paid well when they close new business. Others need to feel emotionally connected to their solutions’ impact on customers.

Are you someone who needs to feel passionate about your solutions? 

Or are you more interested in building relationships with clients? Do you feel that an average product will work with exceptional support, or do you need to sell the most recognized solution?

What about the product do you need to believe in to do your very best work and meet your goals?

Is the product something people feel they need, or is it a solution to a low-priority problem?

#4: Executive & Sales Leadership

Sales leadership is a moving part of the overall 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, ensure you have more than one person at the company you can get behind. Maybe the CEO is inspirational, and you feel you can learn from the CRO.

If you are interested in staying with a tech company long-term, you’ll need to be able to adapt to many different managers. 

Naturally, some will be better than others.

But, the average VP of Sales has a tenure of 18 months, so if you can remain flexible and adaptable, you won’t let leadership movement affect your company tenure.

#5: Company Stage-New or Established?

Companies are like people in more ways than you might imagine. Companies have growth stages; some are more fun and challenging than others.


Startups are figuring things out. 

They are in their infancy. If you hate risk and ambiguity, avoid them. They are moving forward but don’t usually have much experience driving the car. But not all startups are in the same phase. Pre-series A is the highest risk stage, with Series C and D being much less risky. (And also less lucrative with less market opportunity for a salesperson.)


Private companies are focused on working towards profitable and sustainable growth. 

As a result, they tend to spend the money they make, not the money they take. For the average private, money spends differently than it does in a startup.

Growth at a private company usually is more slow, steady, methodical, and measured. Private companies may not be the flashiest but tend to be fiscally responsible and make deliberate decisions. If you value stability, working for a private tech company might be a great option for your sales career.

Now Let’s look at pre-IPO companies.

Pre and Post IPOs

Pre-IPO companies are in the stage of adolescence. 

They are intelligent, proven, and somewhat experienced. They’ve come a long way from the initial ground zero startup days. They’ve surpassed numerous challenges and obstacles and have carved out a space in the market.

But they are not as bright and experienced as they think. 

This level of teenage arrogance kills some companies and stunts growth in others. Some companies IPO and then fizzle out. But a good number also move forward and continue to grow.

As for Post IPO companies, having already gone public, they are structured, well organized, and tend to have better brand recognition.

However, they already have many customers, so there may be less market share for new sales reps to capture. It might also feel like you are part of a large selling machine rather than an individual making a difference. Some salespeople, however, find stability, internal job opportunities, and career contentment in working for a post-IPO tech company.

Others quickly feel like they are doing low-impact work and becoming corporate zombies.

#6: Culture and Values-Meaningless Dribble or Something to Notice?

What is often discussed, publicized, and never accurately described, especially by people who are part of it?


It’s in vogue for companies to post their values on their websites. Unfortunately, it’s also something most employees read with skepticism.

Culture takes a while to identify and is difficult to define to an outsider. And it’s one of the most underrated organizational characteristics with a high impact on employee job satisfaction.

I have yet to recruit for a company that can publicly describe its sales culture for what it is. Some organizations are getting better at defining and rewarding behavior that demonstrates the company’s culture and values, but they are still rare.

For the most part, some of the most outwardly facing “professional” companies look entirely different once you’re on the inside. 

For example, let’s say you work for a tech company that has a habit of only promoting a certain kind of person and say you aren’t that particular type of person. Will it take you three years to finally realize no matter how much you crush it, you are never getting that promotion? Or will you have to perform 2X better for the same opportunity as the typical promotable person?

So go ahead and review Glassdoor and read the values page of the website, but at the end of the day, it won’t help all that much. 

Instead, focus on taking a deep look at who is in charge. Look at who’s getting promoted. Notice what behavior is rewarded, compensated, and celebrated.

Look at the C suite. Don’t be distracted by watching middle management. Most of the time, middle management carries out what the execs want. Executive leadership also selects middle management, explaining what success looks like at this company.

So who’s at the top? Who’s calling the shots? Is the CFO in charge? What about the COO? Is the CEO the one holding all the cards? What sorts of historical decisions have these leaders made? What beliefs do they have about salespeople? How do they encourage, pay, and reward the people who bring in new business? What changes have they implemented to grow the company, and what are their beliefs around customers and employees?

Chances are, you aren’t going to change a company’s culture unless you’re running it. So what is the context you’ll be operating in? 

Can you make it work for you?

#7: People Power or Just another Resource

It may be impossible to find out how a company perceives its employees by asking. You’ll need to do some detective work.

Start with, who works at this company?

Look at what kind of career progression they have made. What can you do together that will make an impact? What are these people doing to get ahead and advance their careers?

Times of Personal Challenge

How do they treat employees during times of personal crisis—maybe a spouse is going through cancer treatments, and an employee needs to be available to shuttle the spouse to and from treatment. Does the employer make accommodations to help? Is the boss understanding, or is it inconvenient and burdensome for the employer?

The people you meet and the relationships you develop or don’t develop can impact your ability to move seamlessly in and out of other companies.

Pick a company that cares for its employees.

Find a place where you have a mentor and a team of people who support you.

#8: Risk

How much risk exists here?

On the cusp of acquisition? How about a purchase from a PE firm? Maybe this company is trying like crazy to get a B-round?

What sort of risk exposure are you able to endure?

Making a wrong move is easy to recover from in a good job market. In a terrible job market, finding another sales job is a challenge. What was once risky but easy to fix could now be risky and more difficult to repair.

Know where you are so you can assess the situation correctly for your level of 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 and get their take on the situation? Keep in mind sales targets, like people, are constantly moving around. 

Territories change, and so do comp plans and bosses.

#10: Flexibility

When evaluating these variables, it’s worth looking at your ability to be flexible.

The one thing about business that keeps things interesting is nothing ever stays static except that you can count on changes ahead. Change as a constant was never more evident than during COVID. We think we know the future, but we have no idea.

Being in sales is a tough job. You’re paid based on results, not effort, tenure, degrees, or the hours you clock. It combines skills, work ethic, luck, context, product, opportunity, timing, and circumstances.

And like any job, you will never be without challenges. 

But the real question is can you remain flexible and continue to adapt to company changes? What areas are you not able to bend? 

Understanding your snapping point and working on your flexibility can help you turn adverse conditions into prosperous ones with a bit of time, optimism, and determination to see something through.

Advocate for Your Career

Since you’re here, you probably know I’m a headhunter. 

So, 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 am willing to give in an email or message chat without having a quick phone call. These people almost always talk about how they don’t have time to speak with headhunters. 

However, they find time to write long emails to headhunters. So here is one piece of critical advice to keep in mind.

Learn about the Best Tech Sales Jobs and Take the Headhunter’s Calls

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. The more people inside and outside your company know you, the better. But only you–will be on the lookout for your next career move. 

If you don’t take 10 minutes here and there for a conversation, you will potentially miss out on potential opportunities.

The Obvious Answer

As a headhunter, I’d encourage everyone to keep this rule as a guiding principle. 

If you are interested enough to ask a headhunter for more information about an opportunity, it’s a sign you should spend five minutes on yourself to learn more about a role. And yes, this may even require a phone call. And like most things, successful career management is not something you do once in a while. 

Career management is something you should be thinking about daily. And, of course, you’ll uncover roles that aren’t right for you. Sometimes people say they don’t want to “waste their time or mine.”

To that idea, I feel spending time exploring an opportunity for yourself is never a waste of time for you or me. 

In my book, making a connection with another person is never a waste of time. It would simply be impossible. And 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 the conversation having added value on the call even if the role I’m working on today isn’t the right match.

Finding 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 and explore potential opportunities. Find out as much as possible so you can get a clear picture of what you’re stepping into. Recognize that all companies have inherent risks. 

And you’ll be better prepared for a positive, lucrative, and rewarding sales career.

Together We Can Find Your Next Software Sales Job

Are You Ready for a New Challenge?

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