Kimberly Lytikainen is the General Counsel, Chief Compliance Officer and Secretary of Five9, a leading provider of cloud software for the enterprise contact center market. Kimberly is a seasoned legal executive with an impressive background that includes tenure in Big Law and leadership roles in marquee companies. After earning her JD with honors, Kimberly began her legal career as an IP associate with Baker & McKenzie and then Graham & James (now Squire Patton Boggs). Her superb law firm training prepared her for her next challenge: the inhouse world. Kimberly joined Sun Microsystems and then graduated to VP status with NVIDIA and Pivotal where she led world-class transactions teams. Her General Counsel breakthrough came with a move to MINDBODY, where she led the company through a successful IPO. Kimberly retuned to the Bay Area and joined online retail favorite Poshmark as its CLO before landing at Five9.

Kimberly possesses a thirst for knowledge and strives to hone all facets of her professionalism. Her style incorporates a mix of a dedication to excellence, thoughtfulness and business savvy…with a high dose of positive disposition, all of which has made Kimberly one of the most sought after legal leaders in the profession.

Kimberly was kind enough to provide her wonderful insights and advice on the current pandemic and the professional landscape. I’m excited to share them with you!

Thank you Kimberly!

From an executive’s perspective, how can an employee increase his/her value to the organization during these challenging times?

Now more than ever we have an opportunity to bring our business acumen to the table by showing we can prioritize based on what’s most important to the company during this pandemic.  For example, right now at Five9, given the types of customers who rely upon our platform, we’re focused on reliability, and every day each employee strives to live the promise of our name (to deliver 99.999% uptime).  To us in Legal & Compliance, that means that we are not just executing daily tasks that may be great to do from a regulatory perspective but rather asking ourselves, will this task move the needle to help our customers trust even more that Five9 is the best choice to… power a call center used for delivering the long awaited vaccine for COVID-19, contact tracing, or connect a small business owner to the help they need to apply for a financial life line for their employees?

Amp up creativity. Now is the time to take a chance on doing things differently, especially where many companies are reluctant to add expensive headcount in G&A given macro-economic uncertainty.  Sure, we’d all love to hire several twenty-year veterans who can get things done independently but maybe we can recast a lawyer role into an operational role.  Perhaps there is a front desk person who would love to bring their passion for technology and organization to bear by filling a legal ops role.  One such role could be an automated self-help site stood up on a platform like Confluence which business partners can access for checklists, playbooks and do it yourself NDAs or other template agreements.  Maybe this candidate is a member of an under-represented group who would love to cross-over to a new career and is looking for someone to believe they can!

Be authentic.  Back in March, I shared with friends that I believe COVID-19 will be an authenticity accelerator.  It’s turned out to be true.  We can infuse compassion into our everyday life with our team by opening up and sharing what’s really going on.  I have found that the more real I am with my team the more we are connected.  It’s soothing to appreciate that we’re all facing similar challenges whether it’s as a parent, partner, friend or caretaker of an elderly parent.  Our Legal & Compliance team meets weekly on Fridays to share wins and “not yets” from the week.  Lately, I’ve been sharing funny as well as frustrating moments from home with my team while stewarding three kids, the ages of 8, 16 and 17, through distance learning and applying to colleges during the pandemic.

       Kimberly Lytikainen

What is your management philosophy during this pandemic and how are you keeping your team mentally healthy, motivated and positive?

I believe it’s all about connection.  Us legal folk in particular tend to “suck it up” and just go heads down getting our work done every day.  I challenge myself and the team to resist that temptation by mindfully paying attention to those around us.  Every day, I intentionally reach out to at least two colleagues to check-in by phone if possible or by DM via Slack.  I ask, “what’s on your mind?” “How can I be of help to you today?”  I try to make sure my team feels seen by me and knows that I truly care about them, not just about getting things done for the business.

Workshop – leadership as an activity.  Enrolling the team in a professional development project that helps them think big is another great way to keep the team healthy especially during these trying times with multiple outside stressors, such as the most recent, incredible fires in California which make it even more challenging to go outside for exercise or even to see others in your community.  Our team is engaging in a project I’ve called, “leadership as an activity.”  Together we’ve defined 3 different areas that embody how we can be leaders, regardless of our title or particular level we may happen to be at in the company.  One area is “own the message.”  If a business partner does not understand our advice or follow a recommendation, why is that?  I often find lawyers get discouraged by such an event and ultimately the joy goes out of in-house practice when we feel unheard or ignored.  Our team is digging deep into this question and why this may happen, ultimately understanding that it’s our job to land our advice in a way that our business partner understands, finds actionable and truly helpful to solve their problem in that moment.

What is your advice for staying nimble and managing change through Covid-19?

Pause.  Breathe.  Smile.  It’s usually easy to go fast for most of us.   For me at least, pausing, first slowing down when I’m confronted with change for a long time was like writing with my left hand.  Since studying yoga beginning twelve years ago, I’ve learned the power of taking time first to breathe.  There is always more time than we may think there is.  From there, I’ve found we can much better assess the situation, then take impactful action.

For example, my team and I remind each other to practice every day putting our attention out to the business, and listening.  We can often pick up through facial expression, tone (thank goodness for Zoom) and word choice what’s really important for that business partner.

Finding humor is also very helpful.  Our small team is supporting an extremely fast moving, high growth SaaS company.  Right at the moment when we fully digest that there is more to be done that can physically be accomplished in a day, is when we cheer each other on with a dose of humor.  Whether an unexpected virtual background, a joke or just contagious laughter, we can count on each other to lighten the mood!

Black Lives Matter is a movement that has impacted the world more meaningfully than ever. How is your company/team “walking the talk’ and making a difference?

Our overall objective at Five9 is to improve the number of underrepresented employees and provide career opportunities and development for all our employees, enabling us to attract and retain diverse talent. With recent events that have unfolded and the national awareness of injustice and inequality, we have taken a fresh look at our company culture and our Diversity and Equity plans.

We have listened to our underrepresented employees, especially the BlatinX employee resource group (comprised of members of underrepresented minority groups and non-minority supporters and allies of inclusion and diversity at Five9), and we’ve created a plan that focuses on 4 areas: Awareness, Education, Hiring and Immediate Support.

Within these 4 focus areas we are doing the work collectively and individually.  In this effort, we created our first Diversity and Inclusion Statement:

• We value diversity
• We embrace authenticity and trust
• We are committed to learning, empowering, advocating, allying and supporting each other

Through all of this, we’ve learned that a diverse and inclusive culture helps us achieve the company’s mission to revolutionize the contact center and make customer support a more human experience.

The legal profession is one of the least diverse professions. In the wake of the Black Lives Matter movement, what is your advice to the legal community and its leaders on how it can approach diversity and inclusion to effect real and positive change for people of color?

Reach out to the community, start with our youngest humans.  For example, it’s been a joy to go to local elementary schools in East Palo Alto and East Menlo Park to share a little bit about all the different career paths you can take with a law degree.  It’s important to share with those who may not think of it that this is a profession available to them, and that they can do it!  My own parents did not graduate from college, and barely earned enough to cover the household bills while I was growing up.  A mentor through an internship in high school helped me consider the possibility of a legal career.  That spark changed my life.  It is my privilege to be able to light up others to pursue this profession.

Look for ways to bring in diverse people to the legal org, proactively and creatively make it happen.