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Sept. 2, 2022

4 questions to figure out if you are at the right company

The cybersecurity sales world is in a period of profound change. 


First, we had a salesperson's market where it seemed that salespeople were jumping from job to job for bigger OTEs. Good salespeople were in short supply, and companies were dangling the carrot of big OTEs and getting people to change companies.


Then the world turned as recession loomed, and there was a panic among VCs and the public markets. Hiring freezes started in March, and before we knew it, layoffs began happening. Companies were no longer desperate for sales talent; even if they were hiring, they were unwilling to pay over the market.


This turmoil is now an opportunity for us all to take stock of our situation and decide if we are at the right company and doing the right job. But instead of chasing big OTEs, we should have a more thoughtful view of where we are and what we want to do.


I was coaching a cyber security sales executive a few years ago, and he had some questions he used to assess what he was doing. I took his questions and added my own relevant to startups, especially now.


Question 1: Am I working with an interesting product that has a meaningful impact on my customers?

Do I find the things it does and the problems it solves interesting? Cybersecurity sales is often a grind with many setbacks and lows. It is just a little better if you are interested in what it is you are selling!

Does it have a meaningful impact on my customers? There is so much about this aspect of the question for salespeople. If significant impact results in big business outcomes, this often means you can build large deals. Prospects also like working with people who help them achieve great things. People who drive significant transformations get accolades, pay raises, and promotions. You want to be the person that helps your prospect accomplish these things.


Question 2: Do I get to work with great people I can learn from and who challenge me to get better?

Let's face it, there can be chaos, frayed nerves, and less than polished leaders at startups. Has anyone else worked for a 28-year-old founder with no enterprise or leadership experience?!

But can you look beyond these and find ways to grow in your role? Are you learning from those around you? Are they challenging you to get better and develop yourself?


Question 3: Does this company have longevity?

Many startups have been able to raise funding whenever they need it for the last few years. But now, suddenly they can't. This has pressured the company to slow its burn rate and ride out the next 18-24 months.

But are they in a position where they can ride it out? Have they been getting the traction to suggest a real business that is worth sticking with? Can they still fund the sales team, so it has a chance of success? Suppose the product roadmap is being reigned back. Is there enough to compete in the market and deliver customer value?


Question 4: Is the gain in alignment with the pain? 

This is where the rubber hits the road. Selling at startups is hard! There is definitely pain that we sellers need to work through. But is the comp package worth it? Is my PCR high enough to get a decent chunk of the deal in commission when I close business?

I wouldn't recommend to anyone to join a startup just for a stock package. There is a slight chance that your stock will be worth anything. But... if an exit does happen, will it be life-changing for me? Am I going for a nice vacation, or am I paying off my mortgage?


I encourage you to look at these questions and honestly assess your situation. Think through each question carefully. Some of you will decide that you are in the right place. Some of you will decide you are not.

Use these questions to come to a well-thought-out decision.


You might also like this blog: 4 best practices that will make your sales deck effective


Unstoppable’s sales operating system is designed for cybersecurity startups and removes the random guesswork, provides repeatable sales plays, and enables you to grow more consistently, and faster. Schedule a strategy call