How to Land Your First Technical Sales Job

I’ve been in the cybersecurity industry for over a decade and a lot has changed when it comes to being a technical sales role. The tactics once used to land a job have been completely turned on their head. Fear not though because with change, comes opportunity. Social media, personal brands, side projects…all have given rise to ways for individuals to differentiate themselves.

If I were to reflect on lessons learned and changes to the industry, here are three key pieces of advice I would give to my (younger) self as a new Sales Engineer trying to land my first role:

1. Before applying to a single job, understand the skills you need first
2. Choose your initial path into the industry (values + organization type)
3. Apply to a specific set of roles with targeted outreach

The name of the game is value. Whether you are applying for a job or meeting with a customer, the best way to establish trust and build a relationship is to continuously deliver value.

Assessing the Skills You Need

Everyone has skills, most of the time we just don’t stop and take inventory of what those skills are. Before you try and hunt for a technical sales job, it’s important to make sure you have a baseline level of your current skills, address any gaps in your knowledge, and set yourself up for the best chances for success. I’ll cover the three main groups of skills you’ll need for a technical sales role.

Learning the Business

The first skill set you should master is all about how businesses work. Regardless of what business you work for, sell too, etc. there is a core set of functions that are common to all of them. The high level process looks something like this:

• Build a product (physical or digital)
• Market to the world that your product is for sale
• Review the price and decide to purchase the product
• Agree to any legals or terms and conditions (if applicable)

Sounds simple enough, right? For a small product it might be. Think about buying an iPhone. Apple builds a new version of the phone, markets it to the world at a global event, and hours later it is available for sale on their website. Consumers review the price, complain it’s too expensive, and then buy one anyway. During the checkout process you agree to Apple’s terms and conditions as well as acknowledge you need a separate phone agreement for cell service.

Now instead of marketing this new iPhone to consumers, Apple wants to sell it to 30,000 employees who work for a defense contractor that frequently have access to classified data. Suddenly this deal takes on several layers of complexity. How will the phones be provisioned for each user? How can we keep the data on them safe? I don’t want to pay for 30,000 iPhones in one fell swoop, but I want a deal so what terms work for both parties? Once turned on, what data does Apple have access to on these phones? See where this is going?

Let’s take our high level process and abstract it one final layer higher. Now it looks something like this:

• Product
• Marketing
• Sales + Procurement
• Legal + Compliance

Each of these areas have certain nuances to them as you sell to various organizations of different sizes, but each component still remains critical to the whole. The more you understand how businesses work, the teams involved at each phase, and the pain points they experience…the better you’ll be able to connect to those individuals and help provide them with value (hopefully in relation to the solution you are selling).

Soft Skills

Some people see the words “soft skills” and suddenly anxiety sets in, particularly if you tend to be more technical in nature. But you aren’t looking for a developer job, you want to be in technical sales, and that means half the job is about, ya know, selling. Don’t worry, in this second skill set we’ll talk through some of the key soft skills you need.

Communication - this one seems like a no brainer, but you’d be surprised how complicated communication can be. Communication also happens in many forms. Are you a good presenter? Perhaps you excel at verbal communication. But are you also a good listener? What about written communication? No one is good at everything, but when taking inventory, be honest with yourself.

Critical Thinking - everyday you make decisions, perhaps without even thinking about them. What to have for breakfast. What music to listen to while working. Critical thinking goes beyond these mundane choices and pushes you to really analyze situations and make informed decisions. This often requires you to be creative, adaptable, and to a degree, curious.

Teamwork - there is no flying solo in sales so working together as a team is a huge aspect of the job. Not only that, but this category includes working with others outside of your organization. This means collaboration, empathy, and accepting feedback are all big parts of the job. The greatest way to build a relationship is to see a situation from someone else’s viewpoint.

Leadership - you probably aren’t taking on a leadership role for your first technical sales job, but knowing how to display leadership qualities will certainly help you advance quickly. Keep in mind that having leadership skills doesn’t mean that you need to head straight for a manager role. Some people enjoy being individual contributors, but still benefit from the ability to lead a team on a project or big sales deal.

In order to see where you shine, and where you could use some work, we pulled together a list of skills for each of these categories. While it is not an exhaustive list, it is enough to point you in the right direction. You can grab it here.

Niche Down

The final skill set is actually more about how you present yourself (and your current skills). Ask yourself the following question; what do you want to be known for? The world of cybersecurity is HUGE (seriously there are so many areas you can specialize in). While many people just starting out in technical sales are often generalists, you will often have some skills already. Maybe you aren’t ready to niche down just yet, but it’s something that will help you stand out.

If you aren’t ready to pick a niche just yet, think about some of the areas that interest you most. Think of them as goals and figure out what you really want to be known for.

Tip: Just because you have skills in a particular area does not mean you are tied to that area forever. As your skills grow you might develop expertise in a different area or even a broader one.

The last step is to figure out which channel makes the most sense for you to showcase your expertise. Maybe it’s a blog. Perhaps LinkedIn or even YouTube. There are endless amounts of channels to choose from, the most important part is that you choose ONE and show up consistently. Yes this is hard, but you are in it for the long game and this is how to make an impact.

Real World Example - You are applying for your first technical sales role, but want to find a way to stand out. Let’s say you have five years of work experience and your current expertise is in project management. You start a YouTube channel where you post 3 - 5 minute videos twice a week talking about an aspect of project management. Imagine you post a video on how you collaborated with multiple teams (teamwork skill), another video on how you dealt with conflict resolution on a difficult project (leadership skill), or you do a video on the process you use to keep project participants updated with the pertinent information (communication skill). When you apply for your technical sales job you can highlight your YouTube channel in your LinkedIn profile, resume, and cover letter. This will not only help you stand out, but it provides real examples of how you can both execute an idea and how you were successful in your current role.

If you have a side hustle, personal brand, or even a half decent social media following…think about how you can shape this to showcase your current skills and how they would apply towards the technical sales role.

Defining Your Initial path

The last piece to the puzzle before you start applying for jobs is to outline what your initial path into the technical sales career path will look like. The type of organization you work for, their culture, and your own core values all need to jive in order for you to be successful.

Startup World vs Established Company

Are you looking for a role that is super fast paced, lacks official processes, and brimming with endless opportunities? You are probably looking for a technical sales role within a startup. Perhaps that is not you though and you prefer an organization with clear policies, structure, and rather focus on just your role vs. the whole company changing. You are probably looking for a technical sales role within an established company.

Each path has its pros and cons, but will also have a big impact on the skills you develop in the role as well. Let’s look at how you can align your own values with a given path.

Understanding Your Core Values

Everyone has core values, but oftentimes we don’t think about them when we are trying to break into a new role. As the market has shifted to give job seekers more choices, it’s time to make sure you stand firm in your core values, not just because they are important to you, but also because they will help ensure you have a greater chance of success in your future role.

If you don’t have one already, make a list of your core values. For example:

• Remote work - I need a job that offers fully remote or a hybrid option
• Family first - I have kids with unpredictable schedules and limited childcare, does that fit with the company’s culture?
• Caring about health - Do I have the cash to cover healthcare if not offered by the company (e.g. startup)
• Giving back - How does giving back and volunteerism fit into the company culture?

This is obviously just a small sample, but you get the idea. Know what’s a make-or-break for you when it comes time to apply for jobs and evaluate offers.

The last component worth mentioning in this section is cash vs equity. Most technical sales roles come with a combination of both, but that combination looks really different depending on the type of company you work for. While it’s not a core value per se, make sure you know if having more cash right now or more equity (potential longer term payout) is more critical for you right now.

Putting it All Together

Alright, you have your skills, core values, and company types all mapped out. Now let’s put it all together to execute a plan to get you hired! First, we need to start building out a list of companies that you want to target.

Building Your Ideal Companies List

There are two places you should look to source jobs from when starting to build out your list; private communities and LinkedIn. Private communities might be a mailing list, a slack channel, or some other medium where you have access to a community of other like minded individuals. Most of these communities have a job posting section which is a great place to start. They definitely aren’t as easy to search or filter, but data is data.

Tip: Did you know that we also have a job board? You can check out our cybersecurity technical sales job board here.

I recommend pulling all of this information into a Google Sheet, or Excel if you like that kind of thing, to keep it simple. Fields to track include:

• Company Name
• Funding
• Role Name
• Location
• Contacts
• Link to Job Posting

Once you’ve combed through your private communities, pivot over to LinkedIn and start running some searches for the types of companies that you want to work with (remember the criteria you defined earlier).

Tip: If this is your first technical sales job it’s ok if you don’t meet all of the requirements listed in the job description. Most cybersecurity job descriptions are completely unrealistic, and almost none of them are geared towards entry level applicants. If you meet 50% of the skills they are looking for, add it to your list.

Applying + Outreach

All finished with your list? Excellent, now it’s time to pull together some outreach templates. This should resemble something like a cover letter, but adjusted for social media. You don’t want to email a straight list of your accomplishments, but rather find a way to connect with (ideally) the hiring manager and secondly any other contact that you have within the company.

At this point you should have enough to begin applying to some of the jobs on your list and also conducting outreach at the same time. There is really no right order to the sequence. Some people like to see if their outreach gets a response before they apply to a position while others apply first and then begin outreach. You do you.

The most important part of this process is making sure that you stand out. Your outreach has to help differentiate you vs all the applicants also messaging the hiring manager. Make sure that your message tries to connect on a personal level while also highlighting a few reasons why you would be a good fit.

The Art of the Follow Up

Let’s face it, not everyone is going to respond to your messages. Persistence is certainly key in any sales role, but make sure that you don’t over do it. If you don’t hear back from someone, you should follow up at least once. The timing could have been off, maybe they were out of office, or maybe they just aren’t interested. Following up is important, but so is the language you use. Make sure to frame your message in a way that doesn’t come across as nagging or pushy!

Preparing for the Interview

You did it! A few folks have responded to your outreach, HR has called over, and you have a handful of intro calls booked. No time to rest because now is where the fun begins! Review the messages you used for each contact and ensure that you have a clear set of talking points. Technical sales interviews are often lengthy and well, technical. The worst thing you can do is blow this chance by being unprepared (but you’d never do that…right?).

Tip: Never been through the technical sales interview process before and feeling a little nervous? We can help you with that.

Remember, job hunting in any market is rough. In a fiercely competitive industry like cybersecurity it can rise to a whole new level. Patience, persistence, and creativity are the key to help you land your first technical sales position.

Happy hunting!