Be the CEO, Stay Hungry & Speak Up: What I Learned From a Fireside Chat with Karen Kaplan

Earlier this week,  I had the opportunity to bring together our female leaders (Director level and above) for a Fireside chat with Karen Kaplan, Chairman, and CEO of Hill Holiday. We started with introductions and as I looked around the room I was so proud to hear the names and see the faces of the women in leadership at HubSpot, from our to our VP of Marketing Meghan Keany Anderson to our CFO Kate Bueker and our Director of Engineering Elenora Ludin, it was one hell of a way to start the week.

Our guest Karen needed no introduction, her accomplishments at Hill Holiday span 36 years from the receptionist to CEO and every job in between. She spoke about her career journey, motherhood, her accomplishments, failures and best pieces of advice for carving out the career you want. Karen’s insights were transparent, humble and told a story of curiosity and resilience that I believe resonated with all of us. The time I spent with this group gave me a renewed sense of gratitude and I wanted to share three pieces of advice from Karen that really stuck with me.

1. Consider yourself the CEO of everything you do

No matter if you’re the receptionist or a team lead, consider yourself the CEO and manage your projects, meetings, and people as if the business was your own. Create space for those around you to share their ideas, engage in healthy debates and problem solve with an inclusive mindset. No one can do it alone, so ask for help, create a support system and own every piece of your work. At HubSpot, our core values of transparency and autonomy empower our employees to take ownership of their career, learn from leaders across the organization and take those insights to impact their day-to-day. With such autonomy over my work I feel as though my creativity knows no bounds, I worry less about who’s watching and focus more intently on outcome and results for my program and our people.

2. Stay humble and hungry

Curiosity to always be learning can set you apart and lead to new opportunities. Take the time to dig a little deeper and look for a fresh perspective in your work, learn how different areas of the business interconnect and how it leads to organizational growth and most importantly, take a moment to reflect on how far you’ve come, the good times and the bad, it is meant to teach you something. Last year I had the opportunity to take part in HubSpot’s Fellows Program, a mini MBA-style development course that allowed me to hone my skills as a leader though classes like competitive strategy, high-stakes decision making and SaaS economics. I had the opportunity to learn alongside my peers from Berlin, Singapore, and Sydney while thinking critically about the business from an incredibly diverse lens. The opportunity to participate in Fellows reinforced that my career is a marathon, not a sprint and being curious and hungry for more will continue to open doors and present new opportunities.  

3. Speak up and evict the negative voices in your head

We all have them, those voices that tell you that you're not smart enough, the one that deters you from raising your hand in a meeting or overthinking your next three words and, it's time to show them the door. Trust in your abilities and the belief that you’re at the company, in the room and holding the position because you earned it. Believing in yourself shines more brightly than doubt and when you see it, others will, too. Worry less about saying the right thing, failing in front of others and know that your voice matters. You can help open doors for those that come after you and ensure that everyone has an equitable seat at the table.

I am grateful to work at a company that sees the value in representation at every level of leadership and while we still have work to do, I am so inspired by the women whom I see running teams, global initiatives, households and spending time on a Monday afternoon to listen, learn and support one another. I believe we’re building something remarkable at HubSpot, with some truly remarkable people and I look forward to growing better together.