VP of Sales considering new startup gigs… you need to know these 3 things.


They say the only constant in life is change—and if there’s one thing I’ve learned over the years, it’s that this saying is especially true in the sales world of startups.


Whether you’re a rookie salesperson or a VP of Sales, it isn’t unusual to find yourself looking to change things up on the work front. You might be stuck with a soul-sucking sales gig, or maybe you’re simply looking for a new challenge to expand your horizons and grow your career.


For those at the highest ranks in Sales leadership, I’ve found that the desire to make a change generally comes from the latter—and there’s nothing wrong with that! We should strive to work in a place where we feel like we are continuing to grow surrounded by inspiring people that hold us accountable to truly move the needle.


But for all you VPs of Sales out there who are considering greener pastures, I’d like to suggest that you pause for just a minute, and, to bring in another cliché, “look before you leap” as “the grass isn’t always greener on the other side.”


Specifically, you should look at the following dynamics for any new VP, CRO or Head of Sales gig that comes your way. Knowing what you’re getting into could help you find that role of a lifetime—not knowing could land you in a world of hurt and regret.


1) Be smart about comp!


Naturally, one of the first things you should pay attention to when you’re offered a new senior leadership role within sales is the compensation package. This encompasses much more than just the base salary and incentives. In reality, your VP of Sales job at the very minimum should cover these three key components.


* Don’t sign on the dotted line without equity


No VP of Sales should sign a job offer if there isn’t some sort of equity on the table. The savviest of VPs know that they should look at the long game, and subsequently, they’ll negotiate their exit to ensure they’re protected if things don’t work out.


Equity does just that, giving you shares in the company you’re helping to scale.


Most VPs of Sales receive between one and three percent equity on average, which can translate to a large payout as the company’s value increases. Make sure you know what percentage of equity you’re being offered along with outstanding shares, the overall pool, funding and anything else that could potentially dilute what you’d receive in the long run.


Additionally, know the differences between equity, shares, and stock – they’re not all created equal.


* Be smart and savvy about OTE


Achieving on-target earnings is a top priority in the sales world—and adding language to your plan about these milestones will ensure that all parties have skin in the game.  There are many ways to approach this with accelerators, milestones, and performance-based incentives.


Even more importantly, when you blow the doors off the place and the team is completely crushing it, everyone wins. Finding an appropriate and fair base to variable balance for your earnings can yield big financial rewards for you and your sales team.


* Be prepared for an exit


What happens if your fresh startup is bought out by a larger company and the new executive leadership team decides you’re no longer needed or redundant to their existing sales structure? Without a double trigger, you’ll likely be fresh out of luck.


A double trigger protects you from losing the investments you’ve made in your company by ensuring that if someone else acquires your startup and decides to let you go, you’ll still be able to vest your remaining company stock.


These financial considerations should be a top priority, especially when working in the ever-changing startup market. They could mean all the difference between a big payday and table scraps.


2) What kind of team are you inheriting?


Another important factor to consider is the type of team you will inherit. As a new VP of Sales, you’ll likely want (and need) to make the tough calls of adjusting roles in your sales staff, putting the right people in the right places and scaling the team in a way you know will generate maximum results.


Is the executive team and board going to truly allow you to do that? Are they reluctant to let you make these choices that will develop a strong sales team?


It is essential that you truly have a seat at the executive table so that you have the power and influence to make the decisions that are necessary for your team to reach key milestones and exceed expectations. If the executive dynamic doesn’t grant you the ability to make these important decisions, you’ll likely be relegated to little more than a figurehead.


A strong, visionary CEO is also a valuable asset, especially in the startup world. You don’t want your boss to be constantly changing his/her mind because of the latest news article, SaaS trend, a question from the board or misinterpretation of your marketplace.


A CEO who is strong enough to carefully analyze pros and cons before changing course can make it much easier for you to achieve stability and growth; a CEO who bends with every shift in the breeze will only cause disruptions and monumental errors.


3) Be honest… does the product/service get you up in the morning?


Gut-check time: do you really care about what the company is trying to sell?


The simple truth is that in most cases, it doesn’t matter what sort of great equity and compensation options you receive, or whether you inherit a quality team—if you don’t care about the product or service, you probably won’t have the gumption you need to truly succeed or the ability to genuinely inspire the team.


It’s hard to dedicate 100% of your energy and focus on something you honestly don’t care about, and this can dramatically affect your output. So before jumping at that new offer, ask yourself these questions


  • What is it that you’ve loved about your current or past sales roles?
  • Is it pride in helping other companies become more efficient?
  • Is it the relationships that develop between a company and its customers?
  • Or that you cannot wait to sink your teeth into solving problems to transform the business through the product/service you proudly stand behind?
  • Perhaps all of the above and then some?


If you can’t find a tangible reason to become truly fanatical about your new position, you probably won’t be willing to put in the extra effort that is needed to succeed.


You won’t have that drive to innovate.


You’ll have a harder time overcoming obstacles and roadblocks.


Your team will most likely see through this and start working against you versus with you.


On the flip side, when you sincerely care about the product or service you’re selling, these problems will never stand in your way, and you’ll have the drive you need to deliver impressive results.


Final thoughts… 


If you do find yourself searching for a new VP of Sales job, I hope you take these suggestions to heart. Making these factors a priority in your vetting process, you won’t find yourself stuck in a declining company or a soul-sucking gig.


But enough from me! While these factors are certainly important, I know they’re not the only things Sales VPs look for when considering a new position. What factors are at the top of your list? Are there things companies do or say that act as an immediate turnoff for an otherwise attractive job?


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