Last week at Klaviyo HQ we assembled an all star panel to share their lessons on Going Long to Build an Enduring Career. Thank you to..
- Lily Lyman, GP @ Underscore VC
- Stephanie Furfaro, Chief Business Officer @ Rapid7
- Jen Kessler, VP of Product @ Klaviyo
…for sharing their wisdom & insights. And a special thank you to Jason Jones from Klaviyo & their team alongside Daria Marmer & Women in Product for helping pull the evening together.
Follow Your Interests to Find Your Path
For anyone out there unsure of their path.. neither Jen, Lily or Stephanie started their career in startups. They explored their curiosity and their careers eventually arced toward their interests. Paired with some leaps of faith!
Lily left Facebook in the Bay Area to move across the country to Boston while pregnant for a career switch into investing at Underscore. Stephanie joined a growing, unproven startup named Rapid7 in 2011 from a stable job because it felt “right in her gut” and later took on their Support function without having any experience leading that department before. Jen started a company with her best friend right after business school and went through Y Combinator’s accelerator program before being acquired just three years later.
On Mentors
Jen shared that she hasn’t explicitly asked people to be her mentors but instead seeks out their expertise so it feels natural to build a relationship together through their specific knowledge which, in turn, helps her grow.
Lily shared that there is a difference between a mentor and a sponsor. You really want to try to find sponsors who will champion and advocate for you when you’re not in the room or pull you into rooms. She’s very thankful for the people in her career that have pulled her up.
Stephanie shared that the people who were willing to have tough conversations with her were the most meaningful mentors, not just those who might tell her what she wanted to hear as she has nurtured her network of sponsors and coaches over time.
Some Things Change. Some Things Stay the Same
Stephanie espoused the enduring value of building a strong team. At the end of the day, even in technology, there are core human elements needed to invest and build a strong team to solve hard problems together. It’s always about great people and really good teams.
Jen said the truth never changes. Whenever she gets stuck she asks herself “what do I know is true? What are the goals for the company? How do I go from there?”
Lily talked about how she has learned the benefit of making a decision outweighs the risk of being wrong vs. waiting, agonizing, and experiencing paralysis by analysis. Just keep moving!
On Maintaining Energy
Lily shared that setting boundaries commands respect. She loves what she does and seeing what drives people, makes them tick, and gets them excited. It’s all about the team at Underscore and working with great people. She’s also tried to screen out “Just & Sorry” – two trigger words – from her vocabulary.
Stephanie loves being in front of customers helping them solve problems. Unpacking those problems to achieve goals as a conduit for engagement gives her energy. Also, she found it easy earlier in her career to push really hard and “do all the things”. She’s learned to value her boundaries and go to a book club, meet up, or just go for a walk to be her best self over the long term. And to stop apologizing for things!
Jen has never met a product she hasn’t tested. She loves seeing where innovation is headed and using things every day to see how they’re changing, experimenting with new products. There’s so much more we can do and use cases to explore! Also, as a perfectionist, she’s had to learn that if you can get to 80% or 90% by the end of the day, just stop. She’s had to learn that perfectionism holds her back from “getting stuff done”.
On Business School
*All three of our panelists went to business school*
Jen found business school to be a transformational experience. It changed the types of people she knew and the opportunities available to her. The world was smaller to her beforehand and after school she felt like she could do anything, learning about the great big world of different industries and motivated people helped her dream bigger.
For Lily, business school helped her get over imposter syndrome and figure out that she could learn anything if she got out of her own way. She’s still consistently in touch with a cohort of friends from her class. There is a famous course at Stanford Business School called “Touchy Feely” that she still uses every day to become a better leader (more from Lenny’s Newsletter here).
Stephanie was the first person in her family to go to college. It was another big investment to go get her MBA but she valued the people she met and exposure to different ideas through professors and experts. Her guidance is not that getting an MBA was important but how you apply it being most critical.
What should a Mentee be thinking about?
When it comes to mentees and how they should approach Stephanie, Lily, or Jen (or another well accomplished senior leader), here are some of the attributes they look for in mentees when thinking about paying it forward:
- Our leaders are looking for coachable, curious leaders who really want feedback
- Leaders who have attitude, aptitude, and ability
- Attitude and aptitude for learning, paired with humility, are superpowers
- A “can do” mindset, both in work and in life, is a secret for success
Thank you for sharing! We only scratched the surface! If you want to learn more about Lily, Stephanie, or Jen you can find them on LinkedIn or operating a leading company / investment firm around town! Thank you so much for sharing your time & wisdom and to Klaviyo for hosting us!