I Will Hire You If… (Interview Advice From a VP of Sales)

If you’re looking to join a start up, and you’re not an engineer—this post is for you.

When I first joined Looksharp, I was tasked with building a kickass sales team. I inherited a team of zero, and my first order of business was hiring a sales development representative. It was an entry-level position in San Francisco and I received a ton of applicants. Along the way, I was surprised at some of what I saw, and I decided to document the process.

First things first, this article is one man’s view and is not the end-all-be-all of sales interview advice. However, having worked in the field for over 15 years and conferred with countless other execs at different companies, I know that my views are mainstream and uncontroversial.

Dream a Little Dream

So let’s start at the beginning. You’ve identified a startup that you like. Maybe you’re a great fit for the job, but probably not. Understand this. Startups are founded and staffed by dreamers. We’re all here trying to build something great. If you dig that and your dream is to be a part of it, let’s hear it.

For your application, don’t be afraid to keep the cover letter short. Typically, I will scan the first part of the cover letter for key skills (like Salesforce experience) or anything quirky that stands out, and then move on to the resume. If I like the resume I will go back to the cover letter and look for typos. If you have typos in your cover letter you will not get an interview. I cannot overstate this enough. The main purpose of the cover letter is to showcase your mastery of written English.

Fortune Favors the Bold

Okay, so you’ve applied. What happens next? You call. You email. You don’t stop until you get a response. You’re probably worried about striking a balance between being polite and being assertive. This is a mistake. Successful startups are tenacious. If you bother me enough, you will almost certainly get an interview.

The Importance of Studying Up

So you got the interview. What happens next?

First up, make sure you study up on a company for two hours before your first interview. If you can’t dedicate this much time, you’re probably interviewing at too many companies. Come in with 3-5 awesome ideas. If your interviewer doesn’t give you an opportunity to share, make your own opportunity. Candidates that do this get job offers. Happens all the time.

Second, print your resume. Looksharp  &  LinkedIn are zooming towards a paperless process. Assume your new employer will be the last one to get the memo.

Thirdly, look sharp, if for no other reason than to prove you can.

Acing the Interview

Ok, let’s talk about the interview itself. Because you have no/limited work experience, I always ask for examples of leadership, as well as successes, failures, and how would you handle X, Y, or Z. You will struggle to give answers. You’ve probably only ever worked at the Chili’s by your parent’s house. You might be thinking, what work examples could you possibly draw from? This is a mistake. You have lived 20 years on planet earth. Don’t be afraid to dig deep to give examples of leadership, hardship, and thinking outside the box. If you challenge yourself, I guarantee you can come up with 10 great work-relevant life lessons that you can draw from. Did you fall on your face in the middle of cheerleading tryouts? Adversity. Ran for StuCo and lost? Lesson learned. I was interviewing a candidate recently and he referenced that when he was in a band in college he handled all of the bands bookings. Great example of B2B sales. Tell me how you made the most of your very modest skills.

I know your parents are probably really embarrassing (my dad still wears his iPhone on a clip on his belt), but if you can mention your parents in a way that shows respect, you will stand out. Most executives are looking for someone who has the ability to learn without being told. If you worked with your dad in high school to help him rebuild that old VW, it shows you can take direction, are not a vegetable, and most importantly, have the patience and willingness to work alongside people who are different than you.

Express your hunger. If you want to be VP Sales by age 28, say it. No good executive is ever, EVER, going to be threatened by an entry-level hire. When you say, “I want your job” you might mean that you want to learn from me and then eat my heart, but all I hear is “I want to be like you.” If you’re interviewing with someone two or three levels above the position you’re interviewing for, tell them your 10-year plan is to have their job. Yes, it’s brown nosing, but executives love that shit (in moderation).

Even if your interviewer is very easy going, make sure you never head  further off script than they do. I see a lot of candidates talking about partying during the interview because I slip in a couple references about how nice it is to have a keg in the office. Don’t be that guy.

The Questions to Ask

This one is critical. Come in with good questions about the company. This goes back to the 2 hours of homework you did before interview #1. Ideally, you will have one question specifically for your interviewer (what made you decide to work here?), one about the company (what do people like most about working here?) and one about the role (what will some of the keys to success be in this position?). Frequently, your time for Q&A will come at the end of the interview. If you get a chance to ask questions earlier, always do so, the answers to these questions will frequently help you craft better answers to interview questions along the way.

The Art of Follow-Up

So your interview is over. You’ve just got back home. Now what?

Follow-up letters matter. A LOT. Don’t wait until days after your interview. Startups move fast. The time between when I post the position and when I fill it is a matter of days. Get in the game.

If you don’t hear something back, push again. Until you hear a definitive “no,” find ways to keep your name in the conversation. “No” is the second best answer you can get behind “yes” and ahead of “nothing.” More often than not, execs are looking for hunger and drive over polish and politeness. Especially since they know they will reap the benefits of your type-A personality once you get the job.