So You Want to Sell Software? How to Interview for & Nail That Prime AE Role

In my blog last month I promised to write something interesting about stage duration analysis for my next post. I started something deep and metric focused and was then distracted by a few interviews.

I’ll be straight, I like interviewing. I get excited about bringing top talent into our team, and selling software is a lucrative, fun world to be a part of. All that said, I have a pretty busy schedule, and if you really want to get the gig, you need to come in prepared.

So rather than talk sales performance KPIs (don’t worry – we’ll get to that next month), I thought I would write something that might help readers secure those sales roles they’ve been eyeing.

Bring a Resume

Yep, you read that right. I have had more than a handful of candidates show up without a resume. Sure, I looked you up on LinkedIn and read my recruiter’s notes about you, but I want the piece of paper. Call me old-fashioned, but this small gesture shows preparation and sincere intent on your part.

Beyond a resume, do you have a notepad? Yes, another small detail but it lets me know that you have arrived with an organized list of questions or intend to take notes. Remember, if you become a top rep, you will be out in the field calling on clients. Would you show up with a rumpled pricing sheet or an unfinished presentation?

Research the Company

Business Woman Working Planning Ideas Concept

This potential place of employment will be where you spend the majority of your waking hours for the coming years. Don’t you think it makes sense to learn as much as you can before showing up and trying out? First, you want to make darn sure that you like this company, the product that they offer and the team that you will be working with. Second, you are applying to be a salesperson….a salesperson who sells software to businesses. Don’t you think you will need to do research on the future businesses you will be trying to sell to?

Spend at least 30 minutes on the company website poking through product videos and testimonials. Scope out articles online and work to understand who might be the top competition. If you really want to get your hands dirty, go ahead and sign up for a free trial (if available). Not only will you see the technology live, but you may also get to see how the team sells. Perhaps you get an automated email after you sign up, or maybe a rep will actually call you. Feel free to tell the rep you are an applicant who wants to learn more. Heck, ask the rep what they like about working there!

I can’t emphasize enough how important this step is. Research, research, research. Bonus points to applicants who subtly weave their learnings into the interview: “Kathleen, I loved the Fortune article about Base. Can you tell me if that is what got you excited about joining the company?”

Research Your Interviewer/Hiring Manager

This is really an extension of the research you started on the company. When the recruiter sets the on-site, he or she will let you know who you will be meeting with. If she doesn’t, make sure you ask! Now is the time to do your homework. Spend time on LinkedIn looking up his background. Where did he go to school? How long has he been with the company? Can you figure out who he reports to?

Beyond researching your interviewer, spend some time looking at the other Account Executives already in the role. Many good sales reps will share quota attainment in their LinkedIn profile. If you see someone that appears to be an absolute rockstar, feel free to ask the hiring manager what she feels that individual is doing to set himself above the pack.

Hint: Many good hiring managers will ask you questions like, “How did you prepare for this interview today?” When I get a blank look and a long pause, it is the beginning of the end. Selling enterprise software is a long, methodical process that requires a tremendous amount of thoughtful preparation before each stakeholder meeting. If you can’t suitably prepare for an interview, you likely won’t be preparing for client interactions at the level of excellence that’s needed.

Be Thoughtful

Hanging glowing light bulb on blue background

What do you want to do when you grow up? Where do you see yourself in 5 years? What type of work environment do you perform best in? What type of manager do you like to work for? You should be considering all of these questions BEFORE you show up for the in-person. I will very frequently ask candidates what they are looking for in their next opportunity.

Because we are in Silicon Valley, there are a lot of young professionals who tell me they want to work for a startup, that they are excited by building something new and different and want to be a part of explosive growth. Hey, I love the sentiment, but when I later ask what other companies you are talking to and you tell me Oracle, Hewlett-Packard or Insert-Another-Legacy-Company-Here, I realize you aren’t REALLY passionate about startup life, you were just feeding me a line.

Prepare to be Challenged

Perhaps you are hoping to make the jump from a development or supporting role to a closing role. If this is the case, consider your lack of experience as an Account Executive before you come in for the interview, because you can be sure someone will ask. If they do, how will you respond? What have you been doing to improve your sales skills outside of work? How do you plan to make the jump from a sales development role to running a full deal cycle?

Hint: I love when candidates use a soft close on me like, “Do you have any hesitations continuing with me?” Or, “Based on our conversation, do you feel I will be a valuable addition to your team?” Again, you are trying to become an Account Executive…close me!

One other thing to note is that I will ALWAYS pose a challenge toward the end of an interview I feel is going well. I’m a careful buyer, after all, and the wrong hire is an expensive mistake that I won’t make. Do expect hiring managers from strong sales organizations to drop a hesitation on your candidacy. This is where you separate the wheat from the chaff. Please, don’t go soft and give up here. You will have prospects telling you no all the time in a closing role; are you comfortable being uncomfortable? Here is your time to lean in to the interviewer and show off your incredible objection-handling skills.

Now Go Get ‘Em!

Best of luck to those of you searching for new opportunities. If you have any additional insights (or funny interview stories) please feel free to comment below. Also, if you are or know an incredible AE, I would love to talk to you about Base.

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