sales careers

Here is a story of how one superstar candidate who sold pharmaceuticals made the transition into a different role, overcame all objections before we could make them, and ended up getting hired by a sales manager who would never consider someone with her background.

Before working as a Talent Parter at Upsider, I recruited for a Consumer Packaged Goods (CPG) company where we hired Territory Sales Managers. For context, they sold product into brick and mortar locations. We had an opening in Eugene, OR, and I remember my hiring manager explicitly telling me on our intake call, “I don’t usually interview pharmaceutical sales reps”. Selling into pristine doctor’s offices with air conditioning and nurses walking around in scrubs was not the same environment as run down retail stores with bullet proof glass. The environment and products were on complete opposite spectrums.

So, when I came across a resume for a “National Award Winning Medical Sales Professional” who spent her entire career in pharmaceutical sales, I was hesitant. But, her accomplishments and numbers spoke for themselves, so I thought it would be worth a phone call.

Boy did she WOW me.

On our first phone interview, she demonstrated all the desirable soft skills such as visible displays of excitement and clearly communicating specific examples of her accomplishments and work history. She used the word “fun” way too many times, enough to get the point across.

But what really differentiated her from any other salesperson I’ve interviewed before and what sealed the deal for me was when she told me that before our phone interview, for 2 hours, she had driven around town visiting several local retail shops to see to see where we had distribution, spoke with the business owners about what determined price points and display space, and even bought a few of our products to see what the packaging was like. (Did I mention she didn’t even use our product?)

Needless to say, she carried that momentum into the rest of the interview. Throughout each step of the process, she wrote personalized notes to each interviewer explaining her key takeaways, reaffirming how she could contribute to our success, and thanking us all for our time. She even CC’ed the hiring team, including the hiring manager’s superior on an e-mail that pointed out qualities about the hiring manager that made him a desirable person to work under and learn from. People love genuine compliments.

The research she put into our company and products differentiated her, making her far more desirable than candidates even with relevant experience. The icing on the cake — after she was hired, she sent me a handwritten card.

Talk about building relationships. Every step of the way, she went above and beyond to stand out as the best salesperson I’ve ever interviewed.

Are you looking for a new job or know someone who is? Share these 5 tips with them on how to have the perfect interview.


1) Smile and Dial

Trust me. A recruiter can tell the difference between someone who is beaming with excitement versus someone who is sighing on the other end of the phone like it’s the end of a long day. Even if it is a bad day, suck it up. You have to sell yourself in an interview like you’re selling a product to a prospect.

2) Quantify your accomplishments and contributions

Anyone who watches Shark Tank understands that an investment rarely happens unless the financials make sense. My star candidate was a top performer so she wasn’t afraid to mention her numbers. 167% in 2015, 140% in 2014, 155% in 2013…. need she say more?

3) Use Stories

Maybe you’re not an exceptional performer or you sell Galaxy Note 7’s so you haven’t hit any of your goals. You need to use stories to explain why things did or didn’t go your way. She told an awesome story about how she managed to wiggle in the back door of a client and had a doctor throw a shoe at her, yet she still somehow managed to close the sale 10 minutes later. Make people like you, believe in you, and relate to you, especially if you don’t have the results to prove it.

4) Prove you can do the job before you get the job (especially if you’re changing industries)

Hiring managers, as my founder Drew Koloski sometimes says, can have incestuous hiring tendencies, only speaking with candidates who have relevant experience. It’s easy to prove you can do the job you are interviewing for if you have done it before. For someone looking to change industries, you need to research and hustle.

Do a pre-interview project. For my star candidate, that meant buying our product, pitching the idea to the retailers, and selling the concept. If you’re a salesperson in HRTech trying to break into MarTech, go onto the companies website, create a presentation of their product, and reach out to potential clients. I guarantee if you walk into your interview with 3 potential companies interested in buying their product, you’re chances of landing the job will skyrocket from “lost in the abyss of resumes” to “negotiating a 30% raise”.

5) Be likable

People want to work with people they can sit with 10 hours a day. After her last interview, our star candidate praised the hiring manager and CC’ed his boss. A little flattery goes a long way. After I got my own handwritten note, all of a sudden I wanted to move to Eugene, OR.


Daniel Ahn is currently a Talent Partner here at Upsider and helps salespeople use data to better understand and advance their career.  To learn more and get connected with Dan – visit our home page.

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Picture yourself as a hotshot Account Executive with three years of selling experience in your first sales job.

You are selling data-driven marketing software as a service (SaaS) to businesses.  You earn a $70,000 base salary and made about $160,000 all in this past year. Not too shabby for 3 years of sales experience (mom was so proud over the holidays). Your Average Order Value (AOV) is $18,000. Sales Cycle, only 38 days.  You hit over 125% of your goal the last two years since you graduated from the Sales Development Rep (SDR) program.  You doubled down early on and took a “blue-collar” approach by applying a tireless work ethic to prospecting.  You still use the skills you learned early on and continue to grind.  You cold prospect systematically, network, you are a leader, are creative – whatever it takes.  Your sales career is off to a fast start!

Now – Fast Forward to 2020. 

Trump is campaigning (and still tweeting…) for a second term, wow did that go fast! Life is good because you leveraged your sales metrics via Upsider to finally landed your first true Enterprise Sales Director role at a big time company. You start right away, congrats! You are excited. Big time deal sizes, challenging sales cycles, C-level decision makers, a legit expense account. Onward and upward, baby!

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After a 17 minute Hyperloop from 217 miles away, you walk in the door to your new office on your first day feeling confident, if not a little cocky.  Your awesome new company has a powerful brand, hot product and has invested heavily in the latest and greatest in sales development and inbound marketing.  First up? Sales team orientation. You put on your standard issue Virtual Reality (VR) headset for the new hire presentation and pass out some virtual fist bumps to your new teammates in other locations.  You are all sitting in a virtual tent at a virtual base camp on virtual Mount Everest. Nice touch, inspiring!

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typewriter_upsiderQ4 is coming soon, are you ready? It’s a critical time of year if you are in sales and it’s important to roll into October full steam ahead. Sure you can make more calls, send more emails – just do more, right? Alternatively – you can try to work smarter, and do something to differentiate yourself. What are you doing to start adding your knowledge or relevant personal experience to your prospecting to help convert outreach and move the sales cycle faster? Continue reading Q4 is Coming. Salespeople Write Something Immediately.

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After a lot of speculation, leaks and poorly kept secrets Apple announced the newiPhone 7 today. The big reveal: it doesn’t include the familiar analog headphone jack. There’s already much controversy and opinion on this potentially bold, if not risky, move for Apple. Not that they haven’t done it before.

Innovation always comes with risk. But sometimes it takes much longer than you may think for mainstream adoption.  It took about 3 years for the New York Times to mention the Wright brothers after their first flight — and that was for the accomplishment of enabling humans to fly.

The ways in which salespeople discover jobs and employers find salespeople is in need of the some serious innovation, particularly in regards to “the headphone jack of sales recruiting”: the resume.

James Martin/CNET

James Martin/CNET

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How often do you think about what your B2B sales career is worth at any point in time?  Take a minute to think about NFL Quarterbacks Aaron Rogers, Peyton Manning, Tom Brady and Joe Flacco. In the context of this group, where would you rank Flacco? I’m guessing not anywhere close to the top (unless of course you’re from Baltimore). Yet in 2013, Flacco signed a contract that was significantly larger than anyone else in the group. He did this while finishing 2012 season with the 12th best passer rating in the league. The year before, his passer rating was 18th best in the league.

Flacco, with a history of average success in the regular season and one good run in the playoffs, was able use timing and leverage to his advantage. What drove his massive contract? He happened to win the Super Bowl during the last year of his then current contract. As the hot Super Bowl MVP winning quarterback, his value was at an all-time high. Continue reading The Last Year of Your Salesperson Contract

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