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Sydna Kelley of Alert Logic: “Your failures will define you more than your successes”

Make leadership organic; Allow people to lead in a way that feels genuine to them and they will be much happier and productive in their leadership roles. Everyone has special talents that they bring to the task at hand and allowing each person to demonstrate their own unique value allows them to fulfill their purpose. As […]

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Make leadership organic; Allow people to lead in a way that feels genuine to them and they will be much happier and productive in their leadership roles. Everyone has special talents that they bring to the task at hand and allowing each person to demonstrate their own unique value allows them to fulfill their purpose.


As a part of our series about strong women leaders, I had the pleasure of interviewing Alert Logic’s Sydna Kelley, Chief Services Officer.

Sydna Kelley has spent 20+ years streamlining operational efficiencies, eliminating waste and creating scalable business models for disruptive and emerging companies, resulting in exponential valuation increases and acquisition.

As Chief Services Officer, she applies her passion for operational excellence, cultivating a “customer-obsessed” culture and enabling 360-degree visibility into customer deployments to ensure industry-leading cyber attack protection.

Cyber attackers are more relentless than ever and technology alone cannot stop destructive attacks. It’s for this reason that Alert Logic’s Security Operations Center (SOC) is in many ways the heart of its business — spanning continents and employing 24/7 security analysts who analyze network traffic and 60 billion+ log messages daily. Sydna has reimagined the SOC and Alert Logic’s approach to customer success.

Sydna has been responsible for 85M dollars security operations budgets in some of the most heavily regulated industries.


Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I started as a business major in college and took a computer engineering class and was instantly hooked! I love puzzles and process challenges, and computer science engineering was fun and logical. After graduation, I worked as a computer engineer in highly-regulated industries such as banking and pharmaceuticals and loved the transformational change these industries were going through at the time. There are special complexities with highly-regulated industries; the supporting processes that are needed for security and structure are both challenging and rewarding to create. I also learned throughout the years that I’m fanatical about customer service, especially when linked with technical operations, security and compliance. My love of the security industry grew out of dealing with dynamic change and complexity, and the desire to help people be successful with security technologies and protection.

Can you share the most interesting story that happened to you since you began leading your company?

Although there have been many interesting challenges I’ve faced over the years, the most relevant story is how the cybersecurity industry and my company (and team) responded to the COVID-19 challenges by creating a collaborative and productive virtual workspace that also allows for work/life balance and emotional support during this stressful time.

The experience over the last year has been unprecedented. I’m delighted to see how people can rise above the daily stress and challenges and reach out to each other for support. My entire global team has embraced the challenge to make sure everyone stays happy, healthy and connected during these potential times of isolation. We have utilized creative ways to stay aligned such as daily scrums, weekly round table discussions, virtual town halls and several other strategies creating enhanced levels of communication. There have also been fun events including virtual happy hours and a virtual house party — so the team has not lost its penchant for fun!

The combination of these virtual events and heightened collaboration has brought the cross-functional and multi-national teams closer in many regards including enhanced personal relationships as well as objective and priority alignment. It has been a ray of hope for me to see how we have seamlessly banded together across the globe through this shared challenge.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Early on in my career, I had to orchestrate an end-of-year computer processing run at a bank where I was leading the Consumer Loans computer platform. The amount of time I spent preparing, coding and orchestrating this for the company had topped anything I had ever done to that point in my career. One of the steps involved an operator in the data center. Their job was to load tapes in a certain way throughout the beginning of the processing (yes, that sentence just dated me). As the end-of-year process began, the operator mistakenly began loading tapes incorrectly and everything I had planned started to fail miserably. I didn’t keep my cool and needless to say, the operator began to cry and break down. I took a breath, apologized and we eventually figured it out together and saved the day so that everyone saw correct bank statements on January 1. The two lessons I learned were: 1) respect for people is always the first step to mobilizing a team and creating successful outcomes, and 2) automation always has an element of human intervention that we have to plan for.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I had several wonderful mentors along my journey and each one has provided lessons and examples of leadership across many different scenarios. One influential leader and mentor I worked with for 10+ years faced challenges with an element of laughter and I remember how effective that was. Keeping perspective even in the most critical situations was a huge leadership lesson for me.

My parents also had a huge influence on me and pushed me to never give up and do my best in every situation. Perseverance is one of the core competencies past mentors have teased me about!

I have also seen how strong personal ethics can influence leadership and build strong organizations with aligned purpose. I try to be selfless when I think through problems and make decisions. If you can put aside personal agendas for the good of the collective community, you will always do the right thing for the company and people on your team.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

I believe keeping perspective in life is the key to dealing with challenges and stress. If you have the right perspective, even the most challenging day can have a silver lining. I’m happy to see more and more people creating work/life balance in their lives and I believe this creates a higher level of happiness and productivity.

My happy place is sailing and being on the water, so I always go back to that feeling when dealing with a stressful situation. I urge all of my leaders to spend time away from work to gain that perspective and then bring that energy and balance to their jobs and decision making. This has been especially important in the last several months as we’ve been exclusively working remotely due to the pandemic. This has created a strong need for everyone to establish their own work/life balance even in the most trying of times.

As you know, the United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

I have always found that a diverse team with different perspectives and experiences creates the best overall solutions. Every team I have led has had diverse representation and I take great pride in that fact. I want to make sure I do anything I can to give everyone a voice, especially people who struggle to be heard based on old ways of thinking. Voices with new ideas create transformational change for the betterment of the organization and collective culture and hold the key to our future.

As a business leader, can you please share a few steps we must take to truly create an inclusive, representative, and equitable society? Kindly share a story or example for each.

Respect everyone, always. Everyone deserves to be respected and trusted and their input needs to count. Each individual has something unique to contribute and differences can be celebrated.

Make leadership organic. Allow people to lead in a way that feels genuine to them and they will be much happier and productive in their leadership roles. Everyone has special talents that they bring to the task at hand and allowing each person to demonstrate their own unique value allows them to fulfill their purpose.

Make every job a high-profile job. People need to see how their job contributes to the overall objective and each unique piece allows the group to be more successful.

Demonstrate your worth. I work to craft a vision to inspire my team so that they can see a better future, a better process, enhanced services, and overall improvements that will delight our customers. Ultimately, I know I’m doing a good job when they become the creative force and explore their own path to reach their unique potential.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

In my opinion, decision making and accountability are the two most important and most challenging aspects of being an executive. Experience inherently provides you situations where you will win or lose, so trial-and-error learning is part of developing into an effective executive. When it comes to tough decisions, experience trumps education and relevant decisions come from relevant experience. A huge part of executive leadership is making the tough decisions and owning the outcomes regardless of what unfolds.

What are the “myths” that you would like to dispel about being a CEO or executive. Can you explain what you mean?

— One myth about being a C-level executive is that you have ultimate power through the decisions that you make and don’t worry about building support or ramifications for your decisions. Key decision making is a big part of being an executive but making hard decisions is challenging and extremely stressful due to the amount of people impacted by these decisions. When it comes to tough decisions, experience and education are both critical — relevant decisions come from relevant experience.

I believe the best executive leadership comes from people who want to serve first. This servant leadership mindset and leading an organization well, serving it as a good steward, can only benefit you, your company and ultimately the customers. Due to the importance of this, most leaders agonize over each decision that impacts the ability to do business more effectively and ultimately enhance employee and customer satisfaction. If you don’t like to serve and you aren’t ready to take ownership for key decision making, you probably won’t enjoy being an executive.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

One thing I have noticed recently during that last couple of months of quarantine and while working from home, women tend to be pulled more frequently into the challenges of work/life balance. During this time of less separation between work and family, there is a natural gravitation between women and their children and although they enjoy being home with their families, it is a challenge to switch off. It is certainly a labor of love but also a balancing act.

What is the most striking difference between your actual job and how you thought the job would be?

I’m always surprised at how invested I become in the outcome of my company and teams and it doesn’t feel like a job but more like a passionate pursuit! I’ve always been loyal to the companies I’ve worked for but over the last several months I feel extremely invested in seeing my company and all of our team members reach their potential. I’m happy to feel so invested about security outcomes but it’s something that continues to surprise me.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive? Can you explain what you mean?

I think the best executive leadership comes from people who want to serve first. This servant leadership mindset and leading an organization well, serving it as a good steward, can only benefit you, your company and ultimately the customers. Do business more effectively, more ethically, and in ways that create and enhance customers’ satisfaction and you gain success for your company. If you don’t like to serve, you probably won’t enjoy being an executive.

What advice would you give to other women leaders to help their team to thrive?

Keep moving forward. You can’t let others and their opinions impact your ability to succeed. Don’t listen to negative remarks. I remember a situation where remarks were made about a female executive who was a role model for me at the company. Someone made the statement that “she’s was in the twilight of her career”. That seemed odd to me considering she was younger than her male executive counterparts. We can no longer listen to the negative voices of the past and have to be confident and proud of our experience and our unique contributions as women.

How have you used your success to make the world a better place?

Day to day, I try to make small positive impacts by lifting up my team and taking the time to interact with customers. Hear what they need and how we can help. I love the quote from Mahatma Gandhi that says: “Be the change that you want to see in the world” and I try to remember that every morning. I think grass-roots efforts make a difference in a company and in a community, and the small positive interactions that make each day worth living and ultimately make the world a better place.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

1. Mistakes should be expected and tracked to create a dynamic process for learning and improvement.

To achieve top performance, we must first recognize and learn from our mistakes. And for that to happen within the workplace, for employees to willingly acknowledge errors, they need an environment in which it feels safe to have honest dialogue.

Early on in my career as a manager, I managed two operational teams. Consistently one team on average would have 0 or very few reported incidents per month while the other team would consistently show a higher number of specific incidents with a specific root cause identified. After digging into examples on both teams, I realized that the team reporting the higher incidents weren’t less effective or less careful, they were simply more comfortable admitting mistakes when they happened. This was an early lesson for me at allowing people to make mistakes and feel comfortable reporting them so we could track resolution and create a continuous improvement cycle. It also helped me think through creating metrics that supported the right behaviors.

2. Women add a much-needed perspective in technology and in the security industry.

STEM was not something I was encouraged to pursue in high school. I was lucky enough to have a supportive professor in college that observed my aptitude for computer science and process engineering. With the right opportunity, I excelled and that opened up my eyes to the challenges and opportunities in cybersecurity.

Supporting STEM across all genders early on and through creative outreach can provide the necessary talent we need for the future in key areas of technology and cybersecurity. I have always found that a diverse team with different perspectives and experiences create the best overall solutions. Every team I have led has had diverse representation and I take great pride in that fact.

3. Extroverts and introverts can both be highly successful and impactful leaders.

Extroverts are more likely to network and seek out opportunities which lead to the misconception that introverts are less desirable candidates for leadership or C-level positions. Introverts tend to be introspective and observant, naturally making them thoughtful listeners and strong leaders.

Don’t let any preconceived notions dissuade you from identifying your unique talents that create an advantage for you and allow yourself time to develop your leadership presence. There are many traits, including conflict resolution and high emotional intelligence that are equally or more important to being able to capture the limelight.

4. Your failures will define you more than your successes.

My favorite Winston Churchill life lesson quote is “Success is the ability to go from one failure to another with no loss of enthusiasm.” It’s a wonderful way to look at life and anything that feels like a defeat.

I’m a competitive person and like most people, I don’t like to fail. It helps me to recharge when I remember that every lesson I have learned has made me a better person and leader. Challenges teach valuable lessons that help you grow and the important thing to remember is don’t give up and keep moving forward.

5. People are always the most important resource.

The most important lesson I’ve learned throughout the years is the importance of having happy, healthy, engaged people as part of your team and company. This is not just a stretch goal but a daily imperative. A few key elements to creating this engaged and inclusive team include the following:

. Respect everyone, always; Everyone deserves to be respected and trusted and their input needs to count. Everyone has something unique to contribute and differences can be celebrated.

. Make leadership organic; Allow people to lead in a way that feels genuine to them and they will be much happier and productive in their leadership roles. Everyone has special talents that they bring to the task at hand and allowing each person to demonstrate their own unique value allows them to fulfill their purpose.

. Make every job a high-profile job; People need to see how their job contributes to the overall objective and each unique piece allows the group to be more successful.

. Inspire people through your vision; I work to craft a vision that inspires my team to image a better future, better processes and improved services that will delight our customers. Ultimately, I know I’m going a good job when my team becomes the creative force behind change that allows them to reach their unique potential.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I’d like to inspire more people to become aware of the fact that human trafficking is an industry of 32 billion dollars in the U.S. and 150 billion dollars worldwide that is causing untold heartache and tragedy. One major misconception is that this crime doesn’t happen in the U.S. and doesn’t pose a risk to U.S. businesses. It also can affect any individual of any age, race, gender and nationality. Everyone should be aware that this is something that is happening right now to someone in our country and unless we all admit that and become involved, it is not going away any time soon. The first step to eradicating this atrocity is to recognize that it exists, and then we can stop it.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

I love the Winston Churchill life lesson quote that says: “Success is the ability to go from one failure to another with no loss of enthusiasm.” I just think that is a wonderful way to look at life and anything that feels like a defeat. I’m a competitive person and I don’t like failing so it helps me to recharge and remember that every lesson I learn makes me a better person and a better leader. Anything that is worth the effort will be hard. When you’re in the middle of something difficult it can look like you’re failing, when, in reality, you’re probably learning a valuable lesson that can help you grow. I think every role I’ve ever had has elements of this as an undercurrent and the important thing is to not give up and keep moving forward.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

Anne Hidalgo. Hidalgo is the first female Mayor of Paris and ran for re-election on what is considered the “third rail” of urban politics in France — car parking on city streets. She didn’t shy away from this hot button political issue and decisively won a second term. This decision to stick to her guns in the face of “conventional” or “prevailing” wisdom, achieve success against the odds and remain committed to her vision of ecological transformation for the city has applications for business and cybersecurity leaders.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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