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

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If you caught Silicon Valley on HBO Sunday night (spoiler alert), as soon as Gilfoyle (a software developer) half-heartedly quit, he updated his LinkedIn Status and was instantaneously bombarded with phone calls and showered with gifts from recruiters. I laughed out loud, because while that is mostly an exaggeration, recruiters will pounce on developers the second they sense one little thing is throwing them off at their current job.

Have you ever wondered why top developers are so much more discoverable to recruiters than top salespeople? Naturally with the skills gap debate front and center these days, you may attribute it to supply and demand, right? Well that is certainly part of it, but I think it has more to do with data and information… let me explain. Continue reading Salespeople, You All Look the Same

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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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Ever since Drew Koloski and I updated our LinkedIn profiles to say “Co-founder at A Startup” we constantly get asked what we’re working on. We wanted to share a quick update.

We’re starting a company called Upsider (, and our goal is to create more visibility, efficiency, and long-term success for salespeople looking to upgrade their careers and for the companies that want to hire them. We want to solve a lot of the problems we’ve had over the course of our careers as both salespeople and hiring managers.

Sales teams have 33-50% annual attrition.
40% of salespeople miss their quota.

The current state of sales team performance has a lot of room for improvement, and the numbers make it hard to argue otherwise: Sales teams average 33-50% annual attrition, and 40% of salespeople miss their quota.

Obviously training, coaching, support, and proper goal setting all impact performance numbers.  However, in our experience, the biggest impact to high (or low) sales team performance is finding and hiring the right people. The problem is salespeople do not have an efficient way to identify or access the pool of companies who will provide the perfect next step in their career. In addition, hiring managers struggle for ways to find and connect with the ideal salespeople who would be the perfect fit for their team and sales process. Continue reading Sales Hiring is Broken and We’re Going to Fix it.

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