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Empowering Perspectives: Five9 Female Executives Share the Career Advice that Impacted Them Most

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Andy Dignan Chief Operating Officer

Andy Dignan has spent the majority of his career in the contact center and collaboration space.  From consulting, to implementing, to designing, and selling solutions, his strength lies in his ability to bridge the gap between technical and business level conversations.  Whether it’s meeting with a CIO or whiteboarding with a CTO, Andy is skilled at developing solutions that create positive business outcomes.  He has a deep understating of the technology landscape and is considered an industry expert in the contact center & collaboration industry.

March is Women’s History Month, which we kicked off earlier with a partnership announcement with Alliance of Channel Women for International Women’s Day (IWD). Put simply, Five9 wouldn’t be what it is without the contributions of so many strong women –internally, as partners, and as customers. The unique experiences of each have undoubtedly pushed Five9 to be one of the leaders in our space, but beyond that, it has created an environment where women are recognized and celebrated. What I’m particularly proud of is how many strong female leaders we get to engage with every day, especially within the Five9 organization and in all parts of business, from engineering to customer advocacy, to HR and marketing, among others.  

I’ve experienced firsthand the impact of having female representation in technology and the ripple effect it can have on personal aspirations and success. My mother was in IT in the education space for over 20 years and was the person who pushed me to pursue this path in college. Growing up, I thought I was destined to be either a lawyer or a Zamboni driver (a kid can dream!) but I owe my current passion for exploring how technology transforms our lives to her influence. 

In addition to honoring my mom, I wanted to continue our month-long celebration of Women’s History Month by asking other strong female leaders within Five9 and beyond to reflect on one of the most important pieces of advice they’ve received. What they shared provides a glimpse of why they are so great at what they do, and more importantly, is advice we can all benefit from, regardless of who you are or what you do.  

Some highlights:  

  • Niki Hall, CMO: Recognize the success of others

  • Gail Mahan, Director, Contact Center Ops & Tech at Alaska Airlines: Focus your energy on work that will impact the business   

  • Kimberly Lytikainen, Chief Legal and Compliance Officer and Secretary: Be tough on business, but kind to people

  • Kelly Burke, Sr. Director, Product Management: Share your experiences with others

  • Stacey Cole, Senior Director of Global Partner Marketing: Have a strong point of view and be accountable for results

  • Mary T. Kass-Muckey, Vice President and Chief Information Officer at Omaha Steaks: seek depth and understanding that lies beneath the surface

  • Tricia Yankovich, Chief People Officer: trust your gut and ask the necessary questions to understand the situation in its entirety

  • Jenn Maciver Edwards, VP of Customer Experience: pursuing a life outside of work  

I believe diversity in ideas and insights makes us all better, as individuals and as a collective team forging Five9’s path forward.  

Happy Women’s History Month!

-Andy  

 

Niki Hall, Chief Marketing Officer

“Recognize others’ success. For many women, success isn't always recognized unless there's outside validation that makes people pay attention. As a female leader, I try to be that 'outside validation,' actively looking for opportunities to acknowledge and celebrate another person's contributions. Being a champion for someone is helping them amplify what makes them great. 

Second, don't just celebrate, reward. While talk isn't cheap, there are other valuable ways to celebrate women beyond a nice email to management or a shoutout during a team meeting. Promotions, providing opportunities to have a seat at the table, giving career-defining guidance – these actions can further close workplace gaps women often face. This also provides longer-term value in up-leveling a person, not only within the workplace but also for their career. This champions someone in both material and immaterial ways, and we need to do both.” 

 

Gail Mahan, Director, Contact Center Ops & Tech at Alaska Airlines 

"There’s never enough hours in the day to do everything that comes your way. It’s always going to be a challenge to keep up with all the work that’s on ‘your plate.’ It’s okay that you cannot accomplish it all. Instead, focus your time and effort towards the work that will move the business forward and make the biggest impact. Over the years, I have learned that I need to let the small things go, which has allowed me to implement creative solutions that boost productivity and helped me focus on delivering value to both Alaska Airlines and our customers."  

 

Kimberly Lytikainen, Chief Legal and Compliance Officer and Secretary

“'Tough on business, Kind to people.' My mentor, the late David Shannon, who was the first General Counsel at NVIDIA and a giant among legal leaders, gave me this advice when I was mid-career and I watched him live it every day!  He helped me learn how to balance being a go-getter and being focused on driving business results while also really seeing people and prioritizing being kind to each other. We can lift each other up even as we course correct as a team. Today, I make sure our team makes time to celebrate our wins -- big or small. Five9 leadership takes our responsibility as role models seriously by first always looking for what’s working great, in addition to identifying opportunities to make an even more significant impact for the company. This motivates every person to show up as their best self, confident they are supported in their fearlessness to do great things! 

 

Kelly Burke, Sr. Director, Product Management

"Never underestimate the value of your experience and how it can help others. We all have a unique career path and can often forget how that unique knowledge and insight can inspire or advance others along their own paths. I often encourage women to share their knowledge and experiences as much as possible. By being open and present when connecting with others, you can really impact how someone approaches work and life in general. I also find that the more I practice sharing my journey, the more inspired I feel in return!“ 

 

Stacey Cole, Senior Director of Global Partner Marketing

One of the best pieces of advice I was given came from a previous boss. She said always to have a strong point of view and be willing to take full accountability for the results. In our ever-changing world of technology, having a clear vision and perspective on what you want to achieve and how you plan to get there is essential. This means being proactive, taking initiative, and being confident in your decisions. However, it's equally important to take responsibility for any positive or negative outcomes and learn from them. This advice enabled me to lead confidently, take risks, and grow my mutual trust with the teams I work with. 

 

Mary T. Kass-Muckey, Vice President and Chief Information Officer at Omaha Steaks 

“Growing up, my mother often shared a Portuguese saying: “Quem vê cara não vê coração,” which loosely translates to ‘Whoever sees a face does not see a heart.’ Her intuition allowed her to see beyond appearances and delve into people’s true needs. 

Throughout my 35-year career, I’ve carried this wisdom with me. When faced with complex problems or challenging team dynamics, I’ve learned to resist the urge to jump straight to surface-level solutions. Instead, I allocate time to understand the core of the issue. By doing so, I’ve successfully navigated tense situations with colleagues and tackled development projects that come with their own preconceived solutions. I genuinely believe my marriage is stronger, and my advancement in my career accelerated because I followed her advice.    

In a world often focused on outward appearances, my mother’s wisdom remains a guiding light—a reminder to seek depth and understanding beneath the surface.”  

 

Tricia Yankovich, Chief People Officer

“One piece of advice that was given to me by a mentor of mine, a Chief People Officer, was to trust my gut and also seek to learn more about each and every situation in which I’m asked to help solve or action. This has been invaluable to me over the years, in realizing my ability to assess a business matter, and trust that I have valuable input and insights to use in addressing the issue. I loved that my mentor always pushed me to learn more, ask questions, get to know the people, and try to really understand the problem. In doing these things over time, I’ve been able to help align the business with great solutions while doing the right thing by people with care and thoughtfulness. In dealing with people each day in my role, trusting my gut and learning more have never failed me. In fact, when I don’t trust my gut and I take another person’s perspective instead of learning on my own by asking questions and leaning in, is when I’ve made mistakes. 

I try to encourage my team to operate in this way too, asking them what they would do or what they think which empowers them to use their gut and learn more by leaning in.” 

 

Jenn Maciver Edwards, VP of Customer Experience

"A former boss shared the importance of recognizing that there is a season for everything. This same leader encouraged us not to confuse our careers with our lives. Make sure your life gets as much attention as your career does. I was mostly focused on my career and work for a long time. In doing so, I was hyper-focused only on the next objective.  It resulted in less engagement with things outside work -- people and experiences. This advice helped me realize that when we aren’t fully engaged, we miss opportunities that can and do make us more effective, creative, and better able to lead. When we have a “life” outside of work, we are better able to build and create both the career and specific business outcomes we seek. Now, I prioritize and actively take time out for my family, myself, and my community.  For me, public art and storytelling are an important part of how I spend my time outside of work. I have found that it energizes me and when I return to work, I am a more engaged and productive leader."   

 

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Andy Dignan Chief Operating Officer

Andy Dignan has spent the majority of his career in the contact center and collaboration space.  From consulting, to implementing, to designing, and selling solutions, his strength lies in his ability to bridge the gap between technical and business level conversations.  Whether it’s meeting with a CIO or whiteboarding with a CTO, Andy is skilled at developing solutions that create positive business outcomes.  He has a deep understating of the technology landscape and is considered an industry expert in the contact center & collaboration industry.

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