Salary Progression in Tech Sales: How I Got A $110k Salary In 2 Years

$100,000/yr seems to be a magical marker for a lot of people. Most of my friends are ecstatic when they break that point and I was exactly the same. Unfortunately, for people who aren’t in tech, it can seem like an impossible goal to reach. For others, they waste years trying out different jobs before settling on one that actually has decent upward mobility. This post will outline how a star sales performer would get a $100k/yr job in tech sales in 2 years.

I’ll be using my past and data to back up this post. My tech sales salary + bonus compensation equaled $110,000 after 2 years of experience. Here’s a typical progression for a great salesman:

6-12 months, Entry level salesperson (aka sales development representative).

According to Glassdoor, there are over 40,000 positions open alone. This is the entry level sales job where you’ll be contacting potential buyers of your company’s software to meet with the closers of the company. Average comp is $72k [1].

If you’re good, there’s usually two ways to progress from here:

– You get moved internally moved into a closing role.

– You interview for and land a full cycle sales position (explained in more detail in the next section). This is what I did. I moved to a full cycle closing position in a different company after 9 months.

1-2 years, Full cycle closer or SMB (Small to medium business) account executive.

A full cycle closer is somebody who finds new customers and does the legwork needed to close them. Closing is typically much more difficult than simply finding the customer and getting him to agree to a meeting. You have to be prepared to educate the customer, help him fight internally to get buy-in / budget, learn to negotiate, and more.

You’ll have an advantage competing for the full cycle role after a successful stint as an SDR because a lot of people competing for the full cycle role don’t have strong entry level sales skills. Similarly, you’ll have a disadvantage because you have no closing experience. It’s up to you to sell the company on your hunger and desire to learn.

An SMB account executive typically just focuses on closing deals for small to medium businesses. The reason SDRs normally only get allowed to close small to medium deals is because companies normally don’t want newbies working with multi million dollar deals  with no experience.

The SMB account executive path is usually only open if you get promoted internally. Most external companies won’t give you a chance to jump right into closing without experience.  If you want to get promoted internally, it’s important to join a company that is growing quickly. These companies can’t hire fast enough and will promote their best people quickly. Companies doing okay or worse rarely have the budget or open roles to promote their best talent. This may force you into relying on a manager leaving in order to get promoted, which definitely isn’t ideal.

Comp wise, you’ll likely start in the $80k [2] range and get in the $100k – $120k range at the end of your 2nd year. My personal experience was that I had an $80k role at the end of year 1, and a $110k role at the end of year 2.

Beyond – Enterprise Account Executive.

Oh boy, here’s where the big money is. Here, you’ll be closing six, seven, and even eight figure contracts. Many of the companies you’re dealing with will have over a billion dollars in revenue, and you’re going to be talking to C level executives and helping them solve huge pain points. And you’re going to get compensated like a champion. Enterprise account execs typically make $200k+. [3] Of course, the best enterprise account executives can make $1,000,000+ per year. I’m currently an enterprise account executive.

To be completely honest, becoming an enterprise account executive takes a lot of work and some luck. It’s not for everyone.There is absolutely no shame in becoming a great SDR manager or SMB account executive making $120k-$150k/yr. The best part is that this is totally achievable in 2-3 years.

Beyond knowing your role’s progression, I would make sure that the companies I joined were selling expensive and valuable software. Who do you think can pay their salespeople better: a company that sells software for $1,000,000 a year or a company that sells software for $5,000 a year?

If you’re interested in learning more about tech sales, check out another post I wrote on the 3 myths of entry level sales jobs. In it, I go into detail on:

  • How you don’t need to be extroverted to succeed in sales
  • How you don’t need sales or technical experience
  • How you don’t need to trick people to succeed.

Notes: .

[1] According to the Bridge Group’s Research. It’ll likely be $60k-$70k range if you’re just starting out. Also, Glassdoor may have lower numbers because they don’t calculate salary + bonus together. Obviously, performance based bonuses are a large part of a salesperson’s salary.

[2] Zenefits lists $80k for their SMB Account Execs on Glassdoor, Glassdoor lists a similar total comp. Salesforce lists $113k,  LinkedIn lists $188k. I would guess that LinkedIn’s SMB account execs generate much more revenue and have much more stringent requirements than other SMB execs.

[3] Salesforce lists Enterprise AE compensation at an average of $233k, VMWare has an average of $230k, Glassdoor has an average of $207k, Marketo has an average of $198k, etc etc.

3 Myths About Tech Sales Jobs

Myth #1: You need tech or sales experience to get a job in tech sales.

This is just blatantly untrue. Here are three entry level sales listings [1] on Glassdoor. You’ll notice none of these positions requires sales or technical experience. They’re linked below, with their requirements written out.

Upwork’s SDR Position:

What it takes to catch our eye:

  • A Bachelors degree
  • Excellent writing and communication skills
  • A thick skin and competitive nature

How to really knock our socks off: *note from Darius – aka NOT a requirement

  • At least 1 year of HR, staffing, sales, customer service, or marketing experience
  • A quick dialing finger
  • SFDC proficiency
  • A basic understanding of two-sided marketplaces and Enterprise SaaS products
  • The drive and organizational skills to maintain a high volume of daily outbound calls and emails to multiple audiences for multiple product lines and multiple campaigns
  • A desire to become an Account Executive as the eventual next step in your career

Entelo’s SDR Position asks for:

Your background:

  • Strong written and verbal skills
  • Ability to work in a fast-paced, startup team environment
  • Willingness to try new concepts and open to coaching
  • Desire to continuously learn
  • You are highly motivated, tenacious, and a self-starter
  • Ability to thrive without structure and under minimal supervision
  • Passion for technology
  • Experience using Salesforce, SalesLoft, Hubspot, Google Apps is a plus
  • Four year university/college degree preferred

Pagerduty’s SDR Position asks for:

  • Prior sales development experience preferred
  • Fearless attitude – proven track record at achieving measurable goals
  • Ability to work in a time-sensitive and high volume environment
  • Experience using preferred
  • Team player–working with your Account Executive to develop a territory plan
  • BA/BS

Some sales development representative postings will ask for sales experience, but you should apply for these jobs anyway. If you’re new to the job market, and especially if you’re a woman — here’s a bombshell for you:

You do not have to meet all of the requirements on a job post to get the job.

A recent study showed that men will apply for positions when they only meet 60% of qualifications but women generally apply only if they meet 100% of requirements. Many requirements aren’t important and experience is definitely not a very important one for an entry level sales job.

Here’s why: hiring managers create their requirements with dream candidates in mind. But this is real life, and not fantasy land. Hiring mangers can’t afford to wait 6 months for the perfect candidate because their chances of hitting sales goals will be hurt. They’ll be very happy with pretty damn good hire today instead of perfect hire later.

Experience is pretty low on a list of desired skills companies are hiring for. Being good at communicating, having a good work ethic, and an ability to persist through hard times are all more desirable than experience. Experience itself doesn’t always translate to skill, although it sometimes can. The skills themselves are more valuable than experience could be.

Myth #2: Extroverts are the best salespeople.

When people think of a successful salesman, they think of someone like Dwayne “The Rock” Johnson – someone charming, charismatic, and outgoing. A guy who can post a Facebook video and generate laughs and thousands of likes. This is the type of guy that can strike up a conversation anywhere with anyone. And this is certainly is one type of successful salesperson.

But being an extrovert isn’t the only way to succeed. The Corporate Executive Board surveyed over 6,000 salespeople and found out that the extroverted relationship builder is not the most common type of successful salesperson. The type of salesperson they found the most successful was the “Challenger”, described here:

Challengers use their deep understanding of their customers’ business to challenge their thinking and maintain control of the Sales conversation. Challengers aren’t afraid of expressing controversial views and are assertive with everyone they communicate with. Among top performing Salespeople, Challengers are most common.

Being extroverted or smooth talking is not found in the Challenger profile. Instead, it’s more important for Challengers to be honest, even when it’s controversial, and to be assertive. These are skills that you can learn over time. I’d even say that my introverted side has actually helped me become a challenger.

I started out not being afraid to challenge because I just wasn’t aware I was being awkward. In one my first sales roles, I remember asking a potential customer – “X Customer is a Leader in the Market, they’ve evaluated us, and they’re making Y million dollars with us. Do you think you’re going to do a better job evaluating tools than them?”

The execution clearly sucked here – there’s a million better ways to say what I said. And I put the customer in a really weird spot. But even though I was weird about it, the customer didn’t take it personally and thought about my suggestion seriously. They came to the conclusion that I was right, and decided to sign a deal worth six figures with us. The principle of being able to stand for what you believe and challenge the potential customer is what’s important. And it’s a skill you can improve over time.

Myth #3: You need to trick your customer to succeed

Before getting into sales, I ran into salesmen that tricked or tried to trick me. This experience made me believe for awhile that many, if not most, salespeople were shady. We’ve all been there – we were sold something that just didn’t live up to the salesperson’s expectations.

My sales experience has made me realize you can be honest and succeed. In fact, you can be such a good salesperson that your clients will rave about your sales skills. Check out what one of my mentor’s clients said about him:

The expression “surround yourself with good people” rings true when I think about working with Andrew. He was an integral part of a successful RolePoint launch with me at a previous employer, so when I came to ThinkingPhones he was one of the first people I contacted to help take our talent acquisition function to the next level. He is extremely knowledgeable and passionate about the impact that employee referrals can have on a company and he is able to explain how and why RolePoint can make employee referrals the #1 source of hire for a company without being sales-y or aggressive. He is highly intelligent, articulate and responsive. He also has a great sense of humor, which, when dealing with the recruiting, is imperative. I have absolutely ZERO hesitation in recommending Andrew and look forward to a long, prosperous and employee referral-filled relationship!

Here’s what I didn’t realize about selling. A great salesperson cares about making their buyer succeed and will put in hours of work to do so. As a result, buyers have a much better experience with them and even adore them as you can see above. In any given deal, here are some things I’ll do to help my buyers succeed.

  • Spend 30 minutes asking questions about their business and their problems. This way, I can show them the parts of the product that are going to be most likely to help them succeed with their personal goals. They also don’t get their time wasted by getting shown 70% of the product that doesn’t affect them personally.
  • Spend 3 hours building custom presentations for buyers to use internally. Buyer’s reputations are on the line when they push internally for a product. They have to present a strong case to their bosses and boss’s bosses about the business value of the product they want to adopt. And since I’ve helped make the case for a lot of buyers, I can provide unique insight into what upper management typically cares about.
  • Spend 2 hours building a customized demo of our product. It can be hard to see from a cookie cutter demo or video how a product would solve a customer’s unique demands. So I try to put together custom demos with their business data and understanding of their problems.

A bad or average salesperson doesn’t care. He will unintentionally be less effective by selling without understanding a buyer’s needs. Here are some things a bad salesperson will do:

• Always recommend the highest priced item. The salesperson is thinking selfishly about his own commission and doesn’t really care about what the buyer’s needs are. We’ve all had this happen to us before, whether it’s at a restaurant or a car dealership. It sucks.
• Pitch the entire product. Most products are fairly complicated and can take hours to go over fully. Hours a buyer would rather spend getting cavities filled in a dentist’s office. The buyer doesn’t care about the entire product, he only cares about the parts that make his life easier. A good salesman cares about his buyer’s time and won’t waste it.
• Let the buyer do the internal pitching alone. A lot of times, buyers don’t understand what upper management cares about or what are the best tactics to get tools adopted. A good salesperson will empower the buyer by sharing his experiences and building tools to make the buyers successful.

It’s quite easy to be an average salesperson because there’s so little effort involved. All you do is whatever serves your best interest and is easy. Being a great salesperson is much harder. You’re spending a lot of time and energy understanding them and helping them look good. It’s a lot more work and it ends up being much more rewarding. It’s more fulfilling because you know you’re helping another person succeed in their career and look good. Financially, you’ll also close a lot more deals because you’ll end up offering a tailored answer to the company’s problem instead of a generic, scripted one.

You have the power to choose what type of salesperson you become.


[1] Found by searching “Sales Development Representative” on Glassdoor. Sales Development Representative is the name for an entry level sales role. There’s 40,000 SDR roles in the US alone.