Carolyn CrandallCarolyn Crandall currently holds the dual roles of Chief Deception Officer and CMO at Attivo Networks. 

She is a high-impact technology executive with over 30 years of experience building new markets and successful enterprise infrastructure companies such as Cisco, Juniper Networks, Nimble Storage, Riverbed, and Seagate. Her current focus is on breach risk mitigation by teaching organizations how to shift from a prevention-based cybersecurity infrastructure to one of an active security defense based on cyber deception.

Carolyn is an active evangelist, blogger, byline contributor, author, speaker on industry trends and security innovation, and mentor for women.  She has spoken at industry events around the world, been a guest on Fox News, been profiled by the San Jose Mercury News, and received many industry recognitions including Top 25 Women in Cybersecurity 2019 by Cyber Defense Magazine, Reboot Leadership Honoree (CIO/C-Suite) 2018 by SC Media, Marketing Hall of Femme Honoree 2018 by DMN, Business Woman of the Year 2018 by CEO Today Magazine, Cyber Security Marketer of the Year 2020 by CyberDojo (RSA), and for 9 years a Power Woman by Everything Channel (CRN). Additionally, Carolyn serves as an Advisory Board Member for the Santa Clara University Executive MBA program and in 2019 co-authored the book, Deception-based Threat Detection, Shifting Power to the Defenders.

Did you ever sit down and plan your career?

Honestly, I can’t say that I have formally planned my career. What I do, however, is actively track hot companies and technology that I find interesting, as well as follow trend-setting CEOs and venture firms associated with companies I might want to work for next. I also stay in regular communication with executive search firms so that when I am ready to make a move, I have a relationship so if something really hot comes up, I’m on their radar. I also use these discussions to help others by making introductions when I know a company is seeking and someone is looking. Although, most people cite word of mouth or relationships as a reason for securing their job positions, I think I am tracking about 70% of my placements based on working with an executive search firm.

Have you faced any career challenges along the way and how did you overcome these?

I have had my share of career challenges and setbacks.  This often occurs when leadership changes are made at a company and a new CEO or department leader wants to bring in their own team. It was particularly difficult when this occurred during the 2009 recession when new roles were not being created and people were not actively shifting out of their current ones.  What I did during these times to get not only what was available but what I wanted was to be patient and to network like crazy — not in the form of calling people to ask for a job, but more to check in and see how they were doing, what projects their companies were working on, and if they needed any contract help. This often opened a dialogue when they or colleagues had an opening that matched my skills. I expect during these COVID-19 times, many people will be feeling dejected and want to give up.  I encourage you not to. Be smart and don’t fixate on filling out mass applications. Seek out the positions you want, be as patient as your needs will allow, and come prepared to stand out with your resume and your interview. Also, I must admit, unless it was very early in my career, I have never had any traction submitting a resume online and would not count on this as a way to get noticed.

What has been your biggest career achievement to date?

My biggest career advancement so far has been making it to the C-level. My biggest personal career achievements are better recognized in two ways. First, I have been able to take new companies into market leadership positions and second, I have had the opportunity to create new jobs for college hires and watch them flourish as they grow and gain new skills. It is extremely fulfilling to see members of my team hit their stride and do things in remarkable ways.

What one thing do you believe has been a major factor in you achieving success?

The biggest factor is in not holding back and not restricting myself to only doing things that I have done before. I constantly try to learn, and I’m willing to try new things and risk small setbacks along the way. I have also forced myself to keep a stiff upper lip when it comes to the criticism of those who don’t feel I am credible or deserving of what I have achieved or am trying to do. Living in world where I present myself in both a technical and marketing role has definitely had its challenges as all too many people dismiss you immediately for having a marketing title, even if you carry the technical chops required.

What top tips would you give to an individual who is trying to excel in their career in technology?

Never stop learning. On-the job experience, self-learning, and certifications can all be incredibly useful in advancing your career.

Don’t be afraid of what you don’t know. If you don’t know something, find a way to learn it. Surround yourself with people that do know — whether colleagues, mentors, or outside advisors.

Don’t be afraid to say you don’t know and to ask others for their opinions and support. Leadership is not based on telling people what to do. It is based on setting a vision and then utilizing your team and resources to best accomplish that vision.

Be visible and build your reputation. Celebrate your successes and don’t be ashamed to communicate your achievements. Don’t forget to share your knowledge with others.

Measure your success not only on what you achieve but also on what you help others achieve.

Remember, when looking to advance, it is always tempting to ask for a title, but the request will often get brushed off if you’re just asking for it for the sake of a title. It is much better to ask what traits a person with a certain title needs to possess, where your skills are compared to those required, and what actions you could take to close any gaps. It is then fair to ask, if I possessed these skills, would I be able to advance to the next level. In some cases, for whatever reason, a company won’t be able to accommodate your growth even if you achieve these things. It’s best to fully understand the reality of the situation and to know when it is time to move on.

Do you believe there are still barriers for success for women working in tech, if so, how can these barriers be overcome?

Yes, there are still barriers for women working in tech. These barriers will be overcome with time and grit. Women need to not give up and not get disheartened by being a part of a team or sitting in meetings where no one around them looks like them. Over time it will get better and as women have more time in cyber, they will also rise in roles, which will make way for the power to hire more women and drive momentum in diversity. Throughout this growth, women also need to take the time to help each other. Sometimes we fight so hard that we don’t realize the impact of our actions. Women in leadership roles can often be viewed as “aggressive” – I’ll refrain from using the b word. I have found that women often have to work harder than men to be heard and taken seriously. Men appear to more automatically gain respect with their given title, whereas women with the same title often have to fight for or be pushed to prove themselves to garner that same respect.

As we seek to fit in and advance our careers, please be mindful to have a positive effect on other others and to not intentionally or accidentally create “road kill” of other women along the way. As the saying goes, be careful of who you burn on the way up as you might see them again on your way down.

What do you think companies can do to support and progress the careers of women working in technology?

Companies can help support women in cybersecurity by making sure to offer support programs so that they don’t end up feeling isolated, ignored, or alone. This can include creating strong support networks and a culture that welcomes women and the different views they bring to the table. This can be as simple as helping create social situations so that leadership and colleagues can get to know these new team members, offering mentoring, or creating online groups of like-minded people to learn how they cope with similar circumstances.

The tech industry has a lot to offer women, and women have a lot to offer the tech industry.  By being welcoming and supportive, we can attract incredible talent and be a better workforce for it.

There is currently only 17% of women working in tech, if you could wave a magic wand, what is the one thing you would do to accelerate the pace of change for women in the industry?

If I had a magic wand, I would create a subsidy program that would cover the payroll of new graduates and women looking to change careers for their first year, offering shadowing and career advancement opportunities. This would create new opportunities that would not be there otherwise, and after one year, these women would have gained valuable experience and proven their value, which will help them in establishing required skills and experiences needed for advancement.

What resources do you recommend for women working in tech?

Podcasts and webinars are fantastic ways to continue to learn and access to them is often free. I would try to listen to one podcast a week while exercising or driving or watch a webinar over lunch.  Vendors provide access to free training, and these can be great sources of education and information. I also think every individual should attend at least one conference a year for learning and networking. I would negotiate being financially supported by the company to do this into any final offer. Also, when you are at the event, as tired as you may get, make sure to attend as many sessions and meetings as you can.  The last thing I would do is to blog at least once a month. It will drive you to learn and make sure that you really understand the concepts. Writing it down and adding your perspectives will make you think through how well you really learned the material.


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