Building a Career in Sales: Hacks vs. Honing Skills for the Long Haul


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“Sales hack” refers to any trick, shortcut, skill, or novelty method that increases productivity and efficiency, in pursuit of a sale (or sales career) (Adapted from Wikipedia.

Thinking about and, more importantly, actively pursuing a career in sales, it’s sensible to ask: What’s the best route to success: the slow and steady or the quick/hot burn? The tortoise or the hare?

Earlier this week I listened to “Career Hacking for Millennial Salespeople” hosted by Quotable,’s digital magazine for salespeople. Max Altschuler, founder of Sales Hacker (recently acquired by sales engagement firm, was offering observations and opinions based on his experience. Max is 31 years old and has already started and sold his first company and invests in many (55+) start-ups.

A second occurrence this week, coincidentally with another 31-year-old, John, was a conversation in which I was asked, “How do I get someone to pay me thousands of dollars just to talk?” I’m a consultant to his employer and he was referring to a recent keynote I’d given in Brazil.

It was tempting to answer this question with how it’s necessary to have been around awhile (I’m older than Max and John combined), to have weathered a few storms, etc. But a better and more accurate answer would be, to have something to say. Something worth saying.

In Sales Hack, Max suggests your, “20’s are for learning, 30’s are for earning.” This suggests getting some experience, skill development and competence, before expecting to cash in. At the same time, it also suggests the learning stops, when the earning begins. I doubt this is the intended message but, to be clear, if the learning stops the earning will stop, too. Sales mastery, not necessarily the opposite of hacking but an extension of it, is lifelong learning and continuous growth.

This is the first point of this column: Beware people who hand you dualities.

The title, Hack v. Haul, is one such duality. Art v. Science is another popular one asked of sales. The caution is that it needn’t be one or the other, or even just two. It can be art and science, as well as, humor, tenure, and tenacity. Why stop with just a few? Either/Or choices, by definition, limit options and creativity.

A sales technique designed to do just this, is the assumptive close: Would you like that in red or black? Would you like to schedule delivery tomorrow morning or afternoon? Hey, let’s pump the brakes here, we haven’t even decided we want this yet! The natural reaction is to push back or bail out.

The same is true of career/learning choices. Why limit yourself in this abundant, unlimited universe?

More than choosing, you want to focus on balancing.

Another point made during the webinar that has everything to do with your developing a career as a sales professional, and the second point of this column: If you don’t like and are not excited about what you’re selling, go find something else. In this regard, Max and I are in 100% agreement. In fact, I’d add that liking what you represent is good but being passionate about what you represent is best.

The reason for liking or really loving what you sell is twofold. First, and this is critical, people/buyers want sellers who are genuine/authentic. Contrary to stereotypes of slick, glad-handing, bon vivants, top producers tend to be enthusiastic, expert, networked individuals. And when you love a thing, you’ll tend to want to spend time really getting close to it, whatever it is, and this will lead to greater knowledge and expertise.

Yes, going to work for a “good company” makes sense but only if you also truly believe in their purpose. Not just what the company does but why it does it. Beyond making a profit, what’s the company’s mission and is this something that resonates with you? Is this something that compels you?

If you have not already done so—nearly 5 million have—see Simon Sinek’s Start with WHY. He talks about the importance of not only what you do and how you do it, but why. And that really aligning with this connects you with your authentic self and purpose. Essentially, the company’s mission statement becomes, or at least reflects, your personal beliefs/purpose.

As you reach out to prospects and customers, whether virtually or in person, you will be perceived as more enthusiastic, genuine and authentic. Not incidentally, this will also make you more attractive; that is, those you are meeting with will be more receptive.

The fallacy of sellers being “coin-operated” (see SaaP: Perceptions, Misconceptions…) and just in it for the money, also misses this crucial and fundamental starting point. What is your purpose? “To make a lot of money.” Why do you work for XYZ Company? “To make a decent living.” Both of these are outcomes. What will making a lot of money enable you to do/be that you can’t now? What does making a “decent living” truly mean when you visualize it? (Note: most people don’t know.)

Even though there is always demand for successful and determined sales people, the employment picture right now (Summer ’18) is very positive, only increasing the marketability of clear-eyed sellers. Now is the perfect time to hack your way into the best role for you and hone your skills over the long haul.

Get started:

  • Whether you’re just starting out in sales or have been in your current role for 10 years or more, assess your own WHY. What is your purpose and how does it align with your company’s mission? If these are not aligned, get serious about finding a new job where they do match up.
  • Get a Coach. The #1 way to improve performance is to have a coach, dedicated to providing you guidance and feedback.
  • Set measurable, tangible targets for skills you want to hone, not just sales numbers you want to hit. Remember: quota attainment is a result. You don’t do results; you do things and your results reflect the things you do and how well you do them.
  • Lather, rinse, repeat. Your purpose/values won’t change dramatically over time but don’t take for granted that they never will. Whether starting out or winding down, be true to your beliefs.
Barry Trailer
Barry has been involved in complex B2B sales for over 30 years and is intrigued with how it's changed/changing and what this means to Sales as a Profession (SaaP). Salesware, the analytics company he co-founded, was acquired by Goldmine Software in 2000 and his next company, CSO Insights with Jim Dickie, was acquired by Miller Heiman Group in 2015. He has twice been published by, and been a keynote for, Harvard Business Review, and is author of Sales Mastery, a novel.


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