Jumping Ship: 8 Things to Consider When Changing Jobs

Questions to ask before transitioning to a new company

If you’ve been in sales for a while, you develop a sixth sense. It’s sort of environmental detection equipment set, where you can pick up on small cues based on conversation, body language and your surroundings. Unfortunately, this tied with the desire to succeed, and constant ADD, can lead us to the desire to jump ship at what may look like a better opportunity to make money and progress in our career.

Today, the job market can be a tricky one to navigate, especially during these strange times. Many industries have serious staffing shortages, (cybersecurity for example) while others are laying off (big tech trimming the fat) and preparing for the economic worst. Here’s my Quick guide on some things to consider, self-reflection questions to answer, before you jump ship, and leave a safe and sound position for your next adventure.

1. Why are you leaving?  If you read my blog, you know I’m a big “gut check” guy, and always ask people to look inside before looking outside. Understanding why you feel the impulse to leave is super important. You need to be honest with yourself, and make sure you’re leaving for the right reasons and not the wrong reasons. If you’re truly unhappy, see the product as an issue to attaining your goals, or think you can truly make more money elsewhere and advance your career, those are great reasons. If you’re bailing because you haven’t worked hard and a massive quota is staring you in the face, you’ve got a bigger problem. Changing jobs can have positive, and negative, impacts on your life. Make sure it’s for good reasons.
2. What additional benefits and incentives are being offered by the new company? For the most part, you want to go from good to awesome when you switch jobs. You should be leaving for the promise to make more money, take a step up the corporate ladder, to enjoy a culture that’s a better match, or to get better benefits for a new phase of your life. Do some due diligence and make sure you can achieve your target compensation by talking to current reps within the new company. Open that benefits PDF that they send over, and make sure there’s no hidden bombs. Is health care covered? Do they have 401K matching? Do they cover cell phone usage? Just make sure you take everything into account when analyzing the next step.
3. How secure is the new company’s financial situation?   Be sure and dig deep on the company’s market and financial position. There’s nothing worse then transferring to a new company that gets hit with massive layoffs two months later. Or the case of the startup that’s being called the new Unicorn, that runs out of money and can’t get funding six months after you start, and get bought by a PE firm, and you receive a termination notice. Get out the shovel, and dig deep. I have asked to talk to the CFO of the startup before, and ask some general questions: how much runway do we have? Are we currently looking at raising funds? Do we have a close relationship with our VCs? All questions, especially if you’re going into a management or executive position, that are reasonable to ask.
4. Is the new company’s customer base likely to remain resilient during the recession?  If you know a downturn is looming, or hard times are coming, look at the industry and customer base that both your current company, and new company surface. Are they going to be impacted in a different way during a downturn? Will selling become harder as budgets disappear? This also ties into product. Is the product you sell or are going to sell a necessity, and is there true value, or is it seen as a “nice to have”?  Do your research.
5. What is the company’s reputation in the industry? Always recommend looking at how a company is viewed by both prospects and customers, as well as the rest of the industry. There are a ton of tools on the web to do this, and for many companies, especially in the SaaS/tech world, you can look at Gartner and Forrester reports, and to review sites like G2, to find the company’s status. Do you want somebody that’s been a non-performer, or the new hot company that everyone wants to buy? These services will also typically list weaknesses of all the companies that they track.
6. Are there any potential career advancement opportunities with the new company? You should always ask yourself, where do I want to be in 3,5 or 10 years.  any of the generations today have been job hopping during these hot market times. It’s not uncommon to see people switching jobs every year. But his times harden, you wanna make sure that your next move can accommodate your career aspirations. If you were to stay at the next company are there advancement opportunities? Is there a path to leadership? Or if leadership is not in the cards for you, is there an opportunity to grow your territory and reach personal income goals?
7. Is the company’s sales team well-structured and well-supported? There is nothing worse than being a sales Rep and having absolutely zero support. The image of the lone wolf is cool, but one man is not an army. Asked directed questions about sales support to management, marketing, and other reps in your position. Make sure that their support to help you achieve.
8. What are the terms of the new employment offer or contract? Make sure you review the offer letter or employment contract and review all the details. I cannot tell you how many times in my career I have had reps they have not read the fine details of their offer letter and are surprised to find things out. Understand your compensation plan, the fixed invariable components, the MBOs, details on draw, and expense reimbursement. There is nothing worse than having that sinking feeling, or a misunderstanding that presents itself after the fact. Ask questions and understand everything. and oh yeah, absolutely, positively, get everything in writing.

I hope this provided some value, just some lessons learned from the school of Hard Knocks, and a career of selling, changing companies and managing people.  Go get ‘em!