From consumer to vendor: security career advice and lessons learned

As the co-founder of a cybersecurity talent community, I’ve heard just about every piece of career advice out there. And ever since I left a large financial institution to become chief strategy officer at Flashpoint last year, I’ve received no shortage of questions from other cybersecurity professionals considering similar career moves. Making the jump from the operational side to the vendor side can be a big decision, which is why I’d like to reflect on my own experience and share some of my lessons learned and advice picked up along the way.

Be adaptable 

When joining a startup, things tend to move quickly. The environment is typically less structured and with few formal workflows or processes. But as the company grows, captures more market share, raises capital, increases its headcount, and develops new products, the structure, order, and processes that were once lacking will emerge and become more prominent—and often very quickly.

Case in point: when I joined Flashpoint roughly 18 months ago, the company had just closed its Series B round of funding. We’ve since more than doubled our headcount, opened a new corporate headquarters, launched multiple new offerings, and closed our Series C round of funding. Having so many milestones and developments in such a short period of time not only gave us no choice but to keep up with the fast pace, it also required us to adapt and embrace the numerous new processes and structures that were implemented as a result of our rapid growth.

But as someone who spent many years working for a large and highly structured enterprise, I’ve actually found a sense of comfort and familiarity in many of the new processes and organized workflows Flashpoint continues to adopt. If upon joining a startup you struggle to adapt to the pace, structure, (or lack thereof), keep in mind that these aspects of the company will likely become more developed, organized, and sustainable over time.

Be a team player 

 Starting a new role at a new company means joining a team of individuals who might have different backgrounds, skill sets, and perspectives. Recognize they might also use different tools, have different workflows and processes, and operate under a different dynamic than what you’re used to. Especially during your first few months at a new company, go out of your way to be open-minded, willing to learning from and collaborate with your new team, and above all else, listen!

Even though you might have done something one way at a previous company, what worked for you in the past might not be best for your new team and company. While bringing fresh ideas to your new role is certainly encouraged, don’t come in trying to rock the boat right away. Seeking to change well-established processes without first learning about the company, establishing yourself in your new role, and considering whether any changes you want to make will add value can be counterproductive and even detrimental in many cases.

Understand work-life balance is what you make of it

As I mentioned, most startups are fast-paced. But while we move quickly, we have to make sure we’re doing things correctly. At Flashpoint, we refer to this as GSDR: getting stuff done right. Mastering this combination of speed and precision can be tricky and may require longer work days at first. Keep in mind that until a company reaches its growth phase and can afford to expand its headcount, you might be required to wear more hats than you’re used to. For some people, this could mean supporting sales efforts, developing marketing collateral, or addressing customer inquiries. If certain components of your role are unfamiliar or challenging to you, then naturally, you might need to put in more time to accomplish the desired outcome.

I always tell myself that if I work 12-hour days, then I’m going to earn the visibility of a company that puts in 12-hour days. While this type of schedule and commitment can take some adjusting among those of us who came from large enterprises, it’s important to remember that because startups tend to grow faster, they also create new positions and hire new employees faster. As such, it’s likely that your role, responsibilities, and work-life-balance will become more manageable over time.

Be willing to take risks

Going from a large enterprise to a budding startup is neither a decision to be taken lightly nor is it one without risk. This might seem scary or daunting, but recognize that any big career move—regardless of company, industry, or role—will always carry a certain degree of risk. While you can minimize it, you can’t avoid it entirely—which is why it’s best to embrace it.

The worst thing you can do in a new role is be hesitant or anxious about the countless “what-ifs” you’re worried you might face. Having this type of mindset not only prevents you from excelling, it can hinder the morale, progress, and productivity of those around you. If you aren’t fully committed to your role and company, how can you expect your teammates to be? Rather than get bogged down by your hesitations, fears, or uncertainties, focus instead on the new culture, opportunities, or whatever else excites you about this new step in your career.

In my experience, being successful—especially if you’re moving from a large enterprise to a startup—requires going “all-in” and not being afraid to embrace all of the new risks and challenges you’re likely to encounter along the way.

Find the right company

This is by far the most important piece of career advice I’ve ever received. Especially today, you see so many people jumping from enterprises to startups because they think it’s very buzzy or cool. While it may very well be buzzy and cool, if you don’t love the company and what it stands for, you’re neither going to be happy, nor successful. If you’re unsure whether a company is right for you, it might help to ask yourself the following questions:

• Do you believe in the company’s mission?
• How will your experience and skills support the company’s mission?
• Will joining the company enable you to develop new skills and progress in your career?
• Have you ever been a consumer of the company’s offerings? How was that experience?
• Is the company’s culture a good fit for you?

As one of Flashpoint’s first customers, I had been following the company since its earliest days. This perspective enabled me to gain invaluable insight into numerous aspects of the company long before I become an employee. I recognize not everyone has the opportunity to become so well-acquainted with their prospective employer, but it’s crucial to do your due diligence and make sure you’re honest with yourself about why you want to work there. Everyone has their reasons, but for me at Flashpoint, it was the company’s collaborative approach with customers, the real-world problems it was (and still is) committed to solving, and the incredibly smart and welcoming people.