How to Get Hired in Sales

Surprisingly, I was never offered a job because of my stunning good looks.

I’ve been hired as a rep 8 times, a manager 5 times and received at least twice that many offers that I’ve turned down.

Contrary to conventional wisdom, only once did I have an inside “connection” who helped me get an interview.

I never brought a “rolodex of C-level contacts”.  Sometimes, I was even entering an entirely new industry, region, or market selling something I had never sold before. Usually I did not meet all of the job prerequisites.

Today I am going to tell you how I did it, and more importantly, how you can too.

(Hint…it wasn’t my stunning good looks.)


Let’s walk through a brief interview history and lessons learned:

Pittsburgh Computer Store- My entry into sales

Do More than Expected.  As the warehouse guy for a computer store, during downtime I taught myself how to use computers and created a database to track our inventory in real-time. I also spent my lunch breaks learning to repair computers. When our services team was backed up, I’d even do installations.

After I’d been there for a year, a sales position opened up. I wasn’t planning to go into sales, but I made $15K/year and I knew some of the reps were making $60K+. I begged the manager to give me a shot. He told me he’d give me a shot because of my work ethic.

Lesson learned: Work hard. Do more than what’s asked. Always look for ways to help even if there’s no clear payoff. 


Tell Them Specifically How You Will Help.  I interviewed for a position as the Director of Information Systems for a marketing firm.

Although I had zero marketing experience, I doubted any other candidates would have my combination of technical and the sales skills. During my interviews I proposed concrete solutions to upgrade their network, email, and printing capabilities. I offered to train the staff and create a “technical handbook”.  Then, I jumped into the sales side and presented my plan for growing their Internet marketing business.

Lesson learned:  Tell the interviewers specifically what you will do to help them – especially if you do not have experience in this industry.


Stargate – My first and favorite startup job experience

If You Love the Company, Cold Pitch Them for a Job.  My favorite local ISP had just received $10M in VC funding. I wrote a letter to the CEO that said,

“I love Stargate! You have the fastest service and the best customer support but you have a problem – almost nobody knows who you are. I’ve used your service for over a year and have recommended you to dozens of my clients. You need me to help you sell to more businesses.”

It turns out they had just hired a VP of Sales who was planning to hire a few Account Execs so my timing was perfect.

Lesson learned:  If you love a company, don’t be afraid to “cold pitch” a CEO for a job.  If they recently received funding, that’s even better.  Make a compelling pitch and they may even create a job for you if one doesn’t exist. (Note: Over the years,  I received 4 other job offers using this tactic.)


Headhunters/Recruiters Open Up a Hidden Job Market. I wanted to relocate to Florida but got no responses to hundreds of resumes.  A friend connected me with a headhunter who knew of a position. The headhunter got me an interview, coached me through the interview process and helped me negotiate a relocation package.

Lesson learned: A good headhunter can change your life. He will have access to jobs that are not advertised. He can bypass the resume screening and give you inside information about the job.  I always respond to headhunters and try to help them out, even if I’m not personally interested in making a job change. (Note: At many companies, senior level positions like Manager, Director and VP are never advertised and only filled via 3rd party recruiters.)


Ask for Help and Be Willing to Take It.  I had just been laid off in a company RIF.  I emailed  everyone I knew saying I’d been laid off and would consider any sales rep or manager position.

At least 6 people contacted me with job leads. I had 4 different interviews within a week and was hired as VP of Sales (and sole sales rep) for a startup 2 weeks later.

Lesson learned: Don’t be afraid to ask your network for help in finding a job. It also helps to be willing to take a step backward for the right job. Even in down markets, good sales people are in demand. 


Research Your Way Into a New Industry.  My only job prospect was with a company in the Title Insurance industry – which I knew nothing about.

Before I interviewed, I spent a week intensively studying the industry, the company, and its competitors. I drafted a plan for my first year that detailed how I would tackle my own training, prospecting, and closing. I included a list of questions about customers, differentiation, concerns, market tactics and sales processes.

When I presented my plan, it changed the entire course of the interview. We became allies working on the same side of the table to solve a common problem. I  knew then, I’d get the job.

Lesson learned: Do extensive research and prepare a comprehensive sales plan before the interview. You will likely be the only candidate who does more than a cursory website scan. Even if your plan is off track it demonstrates your ability to take action & make something happen. 


If the Offer is Not Good Enough, Say What You Need.  The Director and I clicked right away. He whiteboarded his plan for growing sales in his division from $2M to $50M in 2 years. It was identical to what I had done in my last two positions, just scaled up with marketing, sales staff and support. I liked everything he said and vice versa.

Unfortunately, he had budgeted for a junior level rep and the salary was just too low.

I told him I had 2 other offers in hand (true), needed to make a decision quickly because I was just laid off (also true), and that I couldn’t live on the salary he had proposed (unfortunately true too).

He asked me to give him 2 days to see what he could do.  The next day, he made a better offer that I was able to accept.

Lesson learned: If everything seems right about the job, but it’s not enough money (PTO, Benefits, Wrong Hours, Commute, etc.) be upfront with the hiring manager. If he really wants you, he’ll do whatever he can to offer more.  


In addition to being a candidate, I have also interviewed and hired hundreds of sales reps, managers and directors.

Make yourself standout as a candidate. You might want to skip the wrestling outfit though.

Here are some of my recommendations to candidates coming from the hiring side of the table:

  1. Know the business – Show you’ve done your research by bringing a strong understanding of the company, the products/services, the market and the competition. Basic knowledge is expected but if you go the extra mile by talking to the company’s customers, competitors, employees, and others in the same space, it will set you apart.
  2. Bring your plan  – Always have a plan for what you will do to ramp up and become productive. The plan won’t ever be perfect but it shows you have a methodical approach and won’t just be sitting around waiting for instruction.
  3. Show and Tell – During the interview, share slides, sample reports, sales collateral you developed, email scripts,  written processes, awards, etc.
  4. I want to hear about numbers and facts – Back-up your experience with numbers, data and facts. What was your quota? Your ASP? The sales cycle? Your best customer? Your worst customer?  How did you prospect? Close? Upsell? Deal with a failure?
  5. Use the ISD Ben Franklin Close Tell the interviewer, “I made a list of concerns I’d have about hiring me if I was in your position.” Then go down the list of concerns and make sure address every one of them.  Most candidates are hoping I don’t ask about some glaring area of concern. Set yourself apart by meeting this head on. It demonstrates to me how you can anticipate and address customers’ concerns & objections.
  6. Follow up with everyone and tailor the message individually– Always send thank you notes to every person who interviews you. Try to highlight something specific that we discussed. For example, reinforce how you would approach a situation, make up for a lack of experience or overcome a weakness. I guarantee that almost no other candidate will do this.  At best, most candidates send a generic “thanks for the interview” email.
  7. Tell me you want the job and ask what it will take to get hired. Just like that. Many candidates leave the interview with me wondering, “Do you even want the job?”

In closing, here’s some advice from the first headhunter I worked with. I was scheduled for a series of interviews and was having second thoughts.

It is not your job to decide whether you want this position when you are on the interview.  Your job is to get them to make you an offerSell them on you.  

Only then, after they make you an offer, should make your decision.

This was great advice that has never failed me.  


If you want my help building your sales team or improving sales, contact me here. I’d love to hear from you. 


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