Kirsten Bay | CEO & Co-Founder | Cysurance

The current business world is defined by complexity, disruption, and change and desperately needs leaders with holistic approaches and diverse skill sets, perspectives and experiences. Women are taking charge to change the world to be a better place for human kind and the corporate world. One such female leader is Kirsten Bay, CEO and Co-Founder of Cysurance, who is transforming the Cyber security industry and exemplifying leadership with her innovative ideas.

She created Cysurance with the concept to change how small businesses think about and mitigate against cyber threats. Since the inception of her company, Kirsten and her team took its concept from pitch deck to launch in 7 months, and signed distribution partners who will begin co-marketing to over 200k customers.

Kirsten brings more than 25 years of experience in risk intelligence, information management, and policy expertise across a variety of sectors. She leveraged her experience in financial services and cyber security in order to negotiate a best-in-class policy in partnership with Chubb. Chubb is one of the leading insurance carriers in the world which creates a volume driven risk model that is completely new to the market.

In her career, Kirsten has been appointed to congressional committees developing cyber policies, initiatives and recommendations for the intelligence community. She has developed recommendations in partnership with the Center for North American Studies (CNAS) and Center for Strategic and International Studies (CSIS) for The White House energy policy, and collaborated on information studies for MIT-Harvard and several federal agencies. She has also spoken on applied economics and its relationship to both cyber and national security around the world.

First Initiative 

Kirsten developed a Renaissance Faire as a fundraiser for her Shakespeare Club in high school, which was her first entrepreneurial venture. The idea originated from the need to help fundraise for an annual trip to the Ashland Shakespeare Festival, and she also wanted to do something different than the usual way high school students raised money for projects. It was also an opportunity to include the student community in the endeavor in a more engaging way while showing them that the Shakespearian era could be interesting and fun. The initiative became successful and from that point on she started to find innovative and inclusive ways of solving problems.

Self Confidence is Requisite for Success 

Kirsten’s biggest challenge as a businesswoman came when she first transitioned to being a CEO in 2012, as she had to find her footing with the board of directors in establishing herself as the company visionary and leader. This transition was not without conflict, as she often experienced unconscious bias. She worked to overcome these issues by being confident in her expertise, which was the reason for being in this leadership role. Additionally, Kirsten led with proper knowledge of the marketplace, operational proficiency, and vision for the future which helped her to act with the authority that she needed to be successful.

Attaining Balance 

The key to being an entrepreneur and finding a balance is accepting that one can’t do everything, and that there will be times when a specific work or life event must take precedence. That said, understanding how to prioritize is an essential factor, especially when it comes to achieving some semblance of equilibrium, which includes the ability to say no. Entrepreneurs often believe they need to be everywhere at all times evangelizing for their company, but the fact is not every event or meeting is equally important to the success of a business. According to Kirsten “Taking time to engage in life also helps me be better in my role, as it gives me time to reflect on the work I am doing. My passion for my work and vision is what gets me up every

Creating a Balance between Vision, Execution, and Leadership 

Kirsten believes her biggest learning experience is understanding the intersection between vision, execution, and leadership. It is about having the ability to clearly define direction and ideas to a team so that they develop ownership and passion for the journey. Kirsten’s role as an entrepreneur is to create a balance of these three points so that the team understands their role in creating success. Kirsten’s experience with many entrepreneurs is that they believe vision alone will carry them, and do not provide their team with the process and tools to execute on the business plan.

A Break is Needed 

According to Kirsten, “My life is as busy outside of work as it is during the week with family and other endeavors, but I do try to make a concerted effort to decompress and focus on other things in order to clear my mind.” She thinks taking time out is very important to perform at her best. One of her hobbies is golf, which challenges her to work on constant improvement by giving her a place where she can quiet her mind. Beyond that, she enjoys traveling and reading.

Continuing to Improve Innovations 

In this challenging technological era, one of the benefits of rapid technological change is the opportunity to improve on what has been created. The use of technology is incorporated into products and services so quickly that the user experience and benefit is often less than optimal, which presents the opening for new companies to improve these innovations. Kirsten opines, “Naturally, however, as an entrepreneur it means that I must be constantly engaged in understanding how the world around us is changing both inside and outside my industry so that I can continue to learn about the intersections of products and technology.”

Being Open Minded 

Kirsten believes that being calm and flexible in hearing feedback and ideas while remaining focused on the vision is the core to a business concept. She undertakes this exercise every day in terms of temperament. These concepts can be quite challenging when interfacing with investors, customers, and colleagues, but remaining open-minded is the key given that running a start-up company is a fluid process.

A Culture of Clear Communication and Collaboration 

Kirsten’s primary strategy in keeping employees resourceful is creating a culture of clear communication and collaboration. She believes “It is not my role to have all of the answers but, rather, to know the right questions and to have the right people to answer them.” She has found that people most often will go the extra mile if they clearly understand how their role creates success for a company, as well as understanding how their collaboration with their team can benefit their own growth. In short, the team is the greatest resource if they believe that they can trust each other in supporting the growth of the business. Remaining consistent and clear in communicating the goals and path of an organization is critical to maintaining cohesion, as she has seen team bonds begin to fail when there is ambiguity of role or expectation. As teams grow, it is essential that senior management is in sync with that philosophy so that new hires can benefit from consistency in culture

Patience is Vital 

“For Kirsten Patience is the most vital attribute – patience with oneself, patience with the process, patience when people don’t understand your vision. Patience is what enables the calmness that helps one remain focused on the most important tasks that will move a company forward.

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