Why September Is the Best Time to Start a New Sales Job

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.

There are many variables to work through when looking at upside opportunities, including but not limited to: comparing new products to what you are currently selling, how much it costs, the company culture, the compensation plan, sales leadership, influence sales has on the direction of the company and the relationship sales has with internal teams like product and engineering. Even with thorough research and interview time, there are a lot of assumptions to navigate, which is why it is important to ground your decision with certain things you can control and when to make the move should certainly be one of them.

5 Reasons Why September Is the Best Time to Start a New Sales Job

September is here and happens to be a great time to dig your heels in, start interviewing and land a new sales job. Here are 5 reasons why if you are itching to crank up your comp and take on a new challenge, now may be the best time to jump in head first:

1.) Q4?… Q4!

Like Hubspot points out here, Q4 is typically always the biggest quarter of the year as “many buyers are trained to buy at the end of the quarter or year… and if business leaders don’t spend their budget, they may lose it altogether.” This raises your odds of blowing out your ramp and gaining the momentum, new clients and testimonials to help you sell to new prospects in upcoming Q1 and beyond. A great Q4 + Ramp could be your ticket you to get the snowball rolling and grow your numbers, commission dollars and your career.

2.) Your buyers will be in the office for most of your ramp up period

It also helps to have your buyer actually be at work to sign a contract! According to fast growing HR software company Namely, the top two months for vacation are August and December, so avoiding those months is a must. You can’t sell to buyers who are in Disney World with the kids or exploring Machu Picchu with their best friend.

3.) Make your first year a fully ramped up 12 months

Rolling into a new year fully ramped is an ideal situation, especially if award designations are important to you. Starting the new year already ramped up will give you the best chance to ensure you are eligible for all those annual awards, perks and accelerators, presidents clubs, etc. Many companies also have sales compensation plans that require their salespeople to be on fully ramped quotas to have access to the accelerators.

4.) It’s budget season!

Whether or not your target customers have budget to burn is one thing, but finding that information out as it happens and how the process works to get ahead of the competition is crucial. October and November is budgeting season for many companies, being able to gain valuable real time insight on what’s left for the current year and how much is available for next year is critical, and a great reason to start the conversation with that first cold email / call.

5.) You get a few scheduled opportunities to take a breather

Starting a new sales job is stressful and requires a ton of hard work. Knowing that you have a consistent pattern with a few days off here and there with Thanksgiving and the Holiday season will allow you go full tilt and get the mental breaks you need to get off to a great start. As Dan Enthoven of Enkata points out in this Inc. piece about productivity, top sales people smartly avoid frustrating times to sell, take their time to relax and know how to recharge to maximize their efforts.

The time to find your upside may be… right now!

Now that you have thought about making the move, it does require much time to research the right companies, network, fire your resume around via sales recruiters or the same old sales jobs websites. That takes a lot of time and still doesn’t guarantee you the very best opportunity. Then, factor in interview time, etc… and you better get going!

With September already here to cut down on the time it takes to find the perfect opportunity you should check out Upsider, it’s a data-driven talent marketplace for salespeople.  You provide your compensation and performance metrics (AOV, Sales Cycle and % to Goal), and we score you against job opportunities — only matching you to a curated list of hiring companies guaranteed to pay you more for the right reasons. Our algorithm also considers industry, selling environment and more. For example, if you are in in marketing or ad tech software sales in New York City, you’ll get matched to only software sales jobs that pay more with bigger deals to sell that fit your industry profile.

Whichever way you choose to go about it, if you can smartly and quickly get your September groove on, you’ll roll into 2017 at a new company, ramped up and ready to have your best year ever.  

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