How to Break Into Tech Sales (and Stand Out From Other Applicants)
When Jacob Gebrewold applied for an open account executive position at Klue, he knew the company wouldn’t be looking to hire someone like him — an outsider to the tech industry. While he had five years of sales experience, a lack of tech background is often all it takes for a resume to sink to the bottom of the stack.
But Klue was his dream job. So, Gebrewold started picking the minds of various tech sales leaders on LinkedIn to learn more about the industry and sales methodologies. He then built relationships with HR and the top AE at Klue, sent video messages to the hiring manager and persuaded sales leaders from Klue’s prospect list to recommend him for the role.
He knew he’d have to outsell his competition for the role, and that’s what he did.
“The central thesis of how I broke into Klue was that I have to show them that I’m significantly more creative than anyone else they can hire,” Gebrewold said.
Gebrewold’s persistence paid off, but his experience also underscores how difficult it can be for someone outside of the industry to break in.
Before launching the sales bootcamp Prehired, Josh Jacobs heard from thousands of sales reps who applied for tech sales positions and never hear back. Some of that has to do with the differences between software sales and other industries like advertising or insurance, Jacobs said. There are typically more stakeholders involved in a SaaS sale, more complex relationships and more tools to master compared to other fields.
“The central thesis of how I broke into Klue was that I have to show them that I’m significantly more creative than anyone else they can hire.”
But the gulf between tech and other industries isn’t as wide as it may seem.
If a rep knows how to communicate value and tailor their approach to different buyer personas, they have the skills to succeed in tech sales, Gebrewold said. Breaking into the industry then requires understanding how those skills fit into a tech environment, learning the latest sales methodologies and employing a little creativity.
Five Tips For Breaking Into Tech Sales
- Network with other tech sellers to become familiar with the industry. Read up on the books and sales methodologies they recommend.
- Find mentors who are willing to help you throughout the interview process.
- Treat the hiring company and manager like a prospect.Research their team, product and mission and use that information to ask questions and showcase your communication skills.
- Get multi-threaded within the company. This helps insulate you from being rejected based on a lack of experience.
- Find unique ways to tell your story and showcase your skills. Send a video message or audio recording to the hiring manager to stand out.
What’s Different About Tech Sales?
When Jordan started his sales career in the late 2000s, he was often told that sales was an art form — you either have it or you don’t. And as a capital “E” extrovert, Jordan had it.
At least that’s what he thought.
He thrived in his first sales role working for a serial entrepreneur in Japan, but he started to struggle in his tech sales job in the U.S. He quickly learned that success in one sales job doesn’t necessarily translate to another. It’s not an innate skill. It requires mastering tools, skills and sales workflows to solve problems for customers.
“I remember in my early days in sales thinking how ridiculous people were when they would talk about sales [saying], ‘You’re a superstar.’ But really you’re not,” Jordan said. “It’s something that’s learned, it’s taught. It’s not something that you’re born with.”
During the hiring process, software firms are typically looking to see if a candidate has a grasp on modern sales methodologies and can fit within the tech sales culture.
After speaking with other tech companies to launch Prehired, Jordan learned that this is where many candidates outside of tech fall short. Part of that stems from the differences in industries.
“What they really want is proof that you can do the job better than most of the other applicants.”
Reps in fields like retail or insurance primarily sell to buyers at the tail end of the sales funnel. The buyer has already made their decision, and the main difference maker is whether the rep is likable or not, Jordan said. That success doesn’t always translate to tech sales, where buyers have more choices and the deals are more complex.
Tech sales culture may also be different. Some candidates come from places that still promote a “coffee is for closers” culture. As a result, they may think their ability to sell sawdust to a lumber mill is an attribute, but it’s an immediate turn-off for hiring managers at tech companies.
“That’s the worst thing you can say to a tech sales hiring manager in your first interview, because it says: ‘I have no character. I’m willing to trick someone into buying something that they don’t need,’” Jordan said.
Combined, those differences make it more difficult for sales reps from other industries to break into higher-level tech sales roles like AE.
But companies also share some blame for making it more difficult on outside candidates. A lot of tech companies will post jobs that require some software sales experience, even for entry-level roles. This creates a barrier that prevents talented reps from other industries from even applying, Jordan said.
Until that changes, it’s important to be aware that companies don’t treat that as an automatic disqualification.
“What they really want is proof that you can do the job better than most of the other applicants,” Jordan said.
Instead, the hiring process often comes down to whether the person can manage tools like Salesforce and Outreach, understands how to listen and communicate well and shows aptitude for methodologies like relationship selling, Jordan added.
Connect With Other Tech Sellers
After joining LinkedIn in June of 2020, it didn’t take Gebrewold long to note that tech sales had its own jargon and values.
If he wanted to work in tech, he realized he’d have to be seen as part of the tech sellers community. Fortunately, he found it to be one that welcomed outsiders eager to learn and join the fold.
To immerse himself in the industry, he joined sales communities like Rev Genius and engaged people in the comment sections of sales posts that caught his attention. When a rep shared something he wanted to learn more about, he’d reach out asking if they’d be open to meeting with him on Zoom to discuss. More times than not, they obliged.
He used those opportunities to ask which frameworks and methodologies they found useful. Then, he bought the accompanying books and read them. Over time, he picked up important tech sales jargon — like average recurring revenue, mutual plans and embedding/iFraming — and became well-versed on a variety of sales methodologies. By the time he applied to Klue, he knew how to talk and think like a tech sales rep.
“If you want to get on the inside of someone’s psychology — the company or hiring manager — find the people they want to impress, get them to recognize you have that ‘thing.’”
In addition to education, mentoring relationships can also have a huge impact on a candidate’s odds of breaking into tech sales, Gebrewold said. Expanding mentorship opportunities is now a critical part of the sales community for Black sellers he went on to co-found, called Sales for the Culture.
Gebrewold frequently sought feedback from his mentors on what to prepare for in each interview. In one instance, a mentor alerted him that the sales motion he was used to running at his current job in talent recruitment would be different than what Klue ran, so he’d need to go off-script to satisfy the manager’s requirements during the interview.
He also reached out to many of his connections to see if they’d vouch for him to Klue. Their notes to the hiring manager played an integral role in helping him get the position.
“If you want to get on the inside of someone’s psychology — the company or hiring manager — find the people they want to impress, get them to recognize you have that ‘thing,’” he said. “That person saying the same exact thing you can say in an interview is a million percent more [effective].”
Show You Can Listen and Communicate
While there are differences between tech sales and other industries, the two most important skills tech managers look for in a candidate are universal: communication and listening.
Tech sales is all about understanding a customer’s problem and perspective, clarifying it for them and then explaining how you can help solve that issue and the value behind your product. Even if a rep isn’t familiar with gap selling, if they can showcase the ability to communicate and listen, they have a shot at the job, Jordan said.
The best way to show those skills during an interview is to research the company like a prospect. Brush up on the company’s mission, its product and the team, Jordan said. Find out the hiring manager’s name ahead of time, study the role and read the company’s most recent news.
“That takes effort. It shows me they’re willing to learn and that they’re hungry.”
During the interview, take the time to explain how you fit into the company’s mission and how you can help solve a challenge relevant to the role you’re applying for, Jordan said. Sprinkle the conversation with pertinent questions, like how a funding round or the launch of a new product will impact the team’s growth.
When a candidate can do that, it shows the manager that they have the foundational skills necessary to succeed in sales.
“That takes effort. It shows me they’re willing to learn and that they’re hungry,” Jordan said. “They took the time to care enough to do the research and show that they care about our company mission and me and my team. That does set them apart.”
No matter how well a candidate communicates their skills, they still have to overcome the experience barrier.
This stood as one of Gebrewold’s biggest challenges when he applied to Klue. The company was only looking for five-year tech sales veterans to fill its open AE roles. He knew if he wanted one of those roles, he’d need to plant a hunch — a tiny voice in the back of the manager’s mind that doubted that requirement because of his skills.
“So much of making it past the applicant tracking system and all of this stuff that is like: ‘We’ve got a process, you are not our process, do we take you or not?’ is about planting a hunch,” Gebrewold said. “You gotta do things that don’t happen in their typical process.”
The key is to get creative.
Gebrewold started with expanding his relationships within Klue. He first connected with a former HR manager on LinkedIn, who then introduced him to the top AE on the staff. He then sent her a voice note asking if she’d be willing to connect. She helped shed light on what it was like working at Klue and introduced him to the sales director and HR director.
From there, he sent the sales director a report he thought would be relevant to him and a video message that hinted at Gebrewold’s background. He also added that he’d follow up after his first interview. This turned out to be crucial.
“You are in a sales process like any other, and you need to sell yourself against your competition option.”
As he later learned, the HR director didn’t recommend him for the position after the first interview. While he was a culture fit, she suggested that they look for someone more experienced. But the manager loved Gebrewold’s enthusiasm in the first video, and his second video message solidified his intrigue.
“I did little things like tell a bit of my story, weaved in the values, tied back to the original story, and then at the end, I did something funny to stand out. I snapped a crayon in half, [the name of] one of our competitors, and said ‘I’m excited to help ya’ll totally out compete your competitor,’” Gebrewold said. “I don’t know what sales director isn’t like, ‘I want to meet that guy.’”
Each of those steps helped Gebrewold stand out in the mind of the sales director and insulated him from being eliminated from the process because of a lack of experience.
Ultimately, it can be challenging to break into tech sales from other industries. But if a candidate can get creative with their outreach and plant a hunch, they have a shot of standing out from the crowd, Gebrewold said.
“You are in a sales process like any other, and you need to sell yourself against your competition,” Gebrewold said. “So get good at concise storytelling that [provides] evidence of who you are and what your special sauce is, and leverage social proof. For the love of god, leverage social proof.”