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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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Your First day

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!

Continue reading AI or Bots Won’t Make You $200,000+ in Your Next Sales Job

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Have you ever wondered how sales job opportunities “open up”?  Is it because someone left the company? Did someone not hit their number and get fired? Does it come from the budget surplus of a sudden growth initiative? Maybe there was extra budget left over in Q4, and management is saying “it’s got to go somewhere!” or the hiring manager has the “use it or lose it” mentality.

Continue reading Your Dream Sales Job Is Probably Not Open

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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

Continue reading Killing the Headphone Jack for Sales Hiring

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If you are a salesperson starting to sense that a big career move is on the horizon, you might be asking yourself, “When is the best time to change sales jobs?” This is a common question we hear from our community of data driven, high performing salespeople at Upsider.

NFL Quarterback Ryan Fitzpatrick was coming off a career year on the veteran’s minimum salary, and recently signed his 2016 contract with the New York Jets on the first day of training camp after a long, drawn out negotiation. If Fitzpatrick held out any longer, he would have missed his ramp up period to get ready for the regular season. Because he understood the value of starting at the right time, he decided to compromise on the up front contract value to get the start he needs. This will help his performance, and if he hits the right incentives and bonuses, he’ll make up the difference and then some.

Ryan Fitzpatrick signs with the New York Jets on the first day of training camp.

Ryan Fitzpatrick signs with the New York Jets on the first day of training camp.

Like with Fitzpatrick, timing matters for salespeople having a “career year.” Top salespeople with a consistent track record of over-performance face a big risk and have more to lose than most others when deciding to change jobs. When the consistent commission dollars are at stake, lowering your risk profile so you can feel confident enough to go for the big time career growth and an upside payday at a new company is essential. Continue reading Why September Is the Best Time to Start a New Sales Job

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Sales Data upsider

Using data in your day to day sales role is the new normal, but have you thought about how to store, access and use it to help make sense of your sales career? Do you routinely use it to measure and analyze your personal sales success on a weekly, quarterly and annual basis? Do you compare notes with teammates? Salespeople at other companies? Is that enough data for you to feel good about it as a reference point? Do you happen to have a safe, organized place to store your data as you shift from company to company? Is it in a spreadsheet? A little black book? How about that old Windows machine sitting in your closet? You may be data driven when it comes to plugging in to your sales organization’s sales stack, but with a demanding job, accurately collecting and analyzing data to measure your career growth and upside can prove challenging. Continue reading Is Your Sales Job More Data Driven Than Your Sales Career?

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If you are the #1 or #2 ranked salesperson at your company, do often wonder, “could I be making more money somewhere else?” and “who are the companies that could offer me the right upside career opportunity?” What would it take to offset the risk of leaving your company where you are the top dog? Do you know when it’s time to leave, or when to jump at a great opportunity? How do you approach finding the absolute best opportunity? Continue reading 5 Tips for High Performing Salespeople Who Hate Searching for Jobs

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Solid Sales Reads is featured on President’s Club – our Medium Publication. 


John Paul Narowski talks about the value of asking for referrals and explains that timing is everything in The Best Time to Ask For Referrals.

Inside the Deal

Tal Vinnik informs us that B2B Sales Cycles are getting longer and reassures that this is a good thing for salespeople in B2B Sales Cycles are Getting Longer — And That’s Okay.

Russ Heddleston gives us 4 top notch pointers to make sure we learn from Nike’s big time deal blunder in What Every Seller Should Learn from Nike’s $14bn Steph Curry Mistake. -via Sales Hacker

Mind Over Matter

Daniel Meek is kind enough to share the most common trends he sees in great sales hires over time in Lessons Learned Interviewing 1,000 Sales Candidates.

Jermaine Edwards explains why making some time to think can provide a great personal ROI for your sales in 5 ways better thinking will transform your sales.

Chris Spurvey shares the what it takes habitually, to be a high performing salesperson in Seven Habits of Highly Effective Salespeople.

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Solid Sales Reads is featured via President’s Club – our Medium Publication. 


Jon Westenberg writes about the illusion of fast money and reminds us that putting in the hard work and persistence pays off in You are never going to get rich quick. Ever. — Life Learning

Lolly Daskal gets right to the point with this powerful and inspiring post — 18 Harsh Business Lessons You Don’t Want to Learn the Hard Way


Morgon Duke tells us how communication works, where it breaks down, and how if done effectively, it will drastically improve your rapport building with prospects and clients. Active Communication — Building Rapport with Prospects and Clients

Darius Foroux talks about not talking so much, and why great listening is tied to great success in Why Too Much Talking Is Detrimental To Your Success — Life Learning

Andreas Mahringer uses a simple example to show there is more to just practicing what you say and how you say it, it’s choosing your words carefully that make all the difference in How a Single Word Increased a Bar’s Salesby +50% — The Startup

EBQ writes about chatbots and their potential impact on sales. Before you grumble and look away — they provide context and make the argument that they will enable real, natural conversations with humans in How Chatbots Will Change Sales Forever.

Thank you for reading!

Have you written or read something you want us to share? We’d love to check it out — send us a note at

Want to learn more about how Upsider uses data-driven personalization to help optimize sales careers?  Check us out at or sign up for our Newsletter!

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