Top 10 Lessons I’ve Learned as a Sales Leader & Entrepreneur

Jamie Shanks
Jamie Shanks

Sales Leader & Entrepreneur

I started my true sales career on November 1, 2004 – 10 months after finishing my MBA. I’d had a role at BMO Nesbitt Burns from 2000-2002, but I wouldn’t consider that true sales. On November 1, 2004, I walked into a corporate real estate firm, housing 30+ sales reps all in crisp white shirts, dark suits and polished shoes, ready to do battle. The only problem was, I had no formal sales training – so I was scared. I didn’t know what I was capable of accomplishing in the sales world. I also had a massive $50,000 MBA debt that I dragged around like a boat anchor.

Over the last 8 years, I’ve been a sales rep, sales manager, sales director, and now sales leader. I’ve also been an entrepreneur for 3 years, giving me a first-class ticket to 100’s of sales departments across North America. I thought I’d share the top 10 lessons I’ve learned so far (in no particular order).

1. Selling is a Learned Behaviour

My father-in-law might be the only person alive that came out of the womb with a bullet-proof handshake and a story to tell about his last 9 months. Most of us need to learn to become great sales leaders. Some elements of sales comes natural to me (meeting new people), and asking for the business (I went door-to-door and cut lawns as a kid). Most of sales is about developing a pragmatic process that shortens sales cycles and gets results. None of this I would have learned without guidance from mentors, literature, webinars, etc.

2. Opportunities are Earned

The way I got my job in corporate real estate was actually 2 separate interviews failed. I was rejected in February 2004 and September 2004, at different stages of the recruiting process. Being -$50,000 and no means of making next month’s rent, how a person handles the next step separates sales leaders from sales followers. I didn’t fold up my tent and move in with my parents – I put a suit on, walked past reception into the CEO’s office and demanded a job. He was so impressed; he took a chance on me. I earned that opportunity, not my recruiter who wouldn’t go to bat for me.

3. Do Whatever it Takes to Win the Deal

In early 2005, I had won a manufacturing client that was supposed to pay me $50,000-$75,000 in commissions after-tax (in 90 days). I was inches from being debt free, when the deal went sideways. It went so sideways that our company was fired from the project on the spot (Saturday morning in an industrial park). I came home, flopped on the couch and sulked. Then, an idea hit me… I went to the liquor store, bought a $100 bottle of Scotch and drove 45 minutes to the CEO’s house in a gated community. I hopped the fence, walked up the driveway where he was sitting, smoking in his bathrobe. I apologized, we had scotch, and the deal was back on. (The deal fell through again months later, but I was given a 2nd chance).

4. The Grass is Definitely Not Always Greener

In late 2005, a client of mine offered me money I couldn’t refuse – 6 figures and a Director title. I was to build a sales team of 12 across Canada. I was 27 years old and thought I was “king of the hill”. I bought a Jaguar, watches, clothes – oh, and helped build a pretty successful system at Captive Channel. Yet, the business wasn’t for me. I wasn’t passionate about the business and 6-figures in a role that I didn’t enjoy, was not worth it. I began to detest being there and longing for my own enterprise. I also realized I had enjoyed the sales environment more at CRESA Partners.

5. Believe in Your Process

In 2008, I was recruited to a new start-up Firmex. There were 12 employees, most of which were software developers. They had 2 sales reps, and needed a third to build & lead a growing team. After a few days of training, it was time for business development. Up until that point, Firmex has been running email campaigns, but was not accustom to hard-core cold calling. I was used to 100+ dials a day. On my first day, I came up with Goose-Eggs (0) meetings booked. In our small office, everyone could hear rejection-after-rejection. The CEO came to me and said “I’m not sure cold calling will work for this product”. I went home very nervous – all that I’ve known seemed ineffective. The next day I came in, pretending yesterday didn’t happen. Then came meeting 1, then 2, 3, 4, 5… within 1 month, we began building out a cold-calling factory. I stuck to my guns and it worked.

6. Experiment

By early 2009, the world of Sales 2.0 was starting to really emerge. We at Firmex experimented with early marketing automation, power-dialers, live chat, sales intelligence alerts, anything that could help. We were not afraid to try these products out because we all wanted to build the best mousetrap in the business. Our product was strong, but not as strong as our ability to sell it.

7. Don’t Starve the Mother to Feed the Baby, or Vice Versa

Trust me when you’ve heard cashflow is king… its 100% correct. When you start a business you end up wrestling with the truth that someone needs to sacrifice. In early 2010 when we started our consulting firm, it was the mother (me) that starved, and I barely made it out alive (thank you wife). In 2011, we took too much from the baby (business) to live a little larger than needed. This left the company in a position that couldn’t even afford a client going +30 days on receivables. Not good.

8. When Starting a Business, Take Your Ramp-up Forecast and Double it

I’ve probably read every edition of Inc., PROFIT, Fast Company and Entrepreneur since 2007, and while there are 100 articles on this – you say “but not me”. Well, yes it will happen to you too. Every start-up business is in extreme survival mode. Our business plan looked fabulous on paper, but the real world has dozens of variables you didn’t account for. Simple one’s like – what happens to your cash-strapped business if a client takes 30 extra days to pay you… or simply doesn’t pay. These variables, mixed with a “cat-with-a-string syndrome” that happens as you see new opportunities, makes your business pivot on priorities. Each pivot is like sailing, you know you need to get from A to B, but you end up zigzagging up wind for a while.

9. Be a Sponge, Even When You Think You’re Full

One of the only reasons I’m still an entrepreneur and sales leader is I’ve kept myself relevant. Without continuous learning, I would be no different than the average sales rep. When we started in 2010, I learned as much as humanly possible about Sales 2.0. I read every book, went to every conference and brought home thought-leadership and insight. Then in 2011, the market started presenting an opportunity around Social Selling. With Sales 2.0, my thought-leadership is more following that innovating. By investing every waking minute into Social Selling this last 12 months, I now lead the innovation curve. If I had have cruised on Sales 2.0 information, I would have been late to Social Selling.

10. This is a Marathon, Not a Race

This is probably the most difficult beast to overcome being a 34 year old with 20+ years of sales leadership ahead. I panic when I don’t hit short-term goals, or a deal falls off the table. I’m learning that I have 100’s more deals to come in my lifetime, and I need to enjoy the ride. I can’t believe the sales information I’ve learned in 8 years, I can’t imagine what I’ll know in 20 more.

Sales Professional

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