Goodbye and thank you to Context
Friends,
Boy has it been a wild ride. Joining an educational travel company during the heart of a global pandemic was definitely not the safe choice. But now that I can reflect back on 18 months at Context, I can happily say that following my heart and passions has yet again led me down the right path.
I joined Context looking to strengthen my executive leadership skills at a mission-driven organization trying to make the world a better place. Over the course of my tenure, I grew from overseeing one function with two full time reports, to leading three functions with a total of 28 full timers and over a dozen part time staff. I got to participate in board meetings, help set company strategy, procure key SaaS tools, and lead strategic conversations.
Perhaps most importantly, I worked with the directors and senior managers reporting to me to think bigger about what our teams could do. Together we set ambitious OKRs and then worked hard to achieve them. We hired and trained, established new processes, implemented new systems, and aggressively executed. Over the course of this journey I internalized a few leadership principles that I’ve reflected on below.
First and foremost, setting ambitious goals that are simple and clear, so that everyone knows what they are and what success looks like, is critical. But once those are in place, you have to hold your team and yourself accountable to those goals. That accountability means doing everything in your power to make sure you and your team as a unit successfully achieve what you set out to do. Unblocking and supporting each player (whether directly, through a manager, or through a manager of managers), advocating for your team needs, and especially leaning in anywhere that’s needed, whenever it’s needed, is all part of the game.
For me that could mean having a difficult cross functional conversation to advocate for my team’s needs. Or it could mean spending the week before my wedding working until 1am answering client emails because our support team was still staffing up and it would have been wrong to ask my team to work late if I wasn’t willing to work even later. Coaching, motivating, and cheerleading are all core parts of the job. So is actually doing the work that needs to get done, particularly if it’s not happening and there’s no one else to do it. Every challenge is an opportunity to step up and prove yourself as a leader and a teammate. This is true regardless of your title or your job description.
But with that I realized something else — just how much joy I get celebrating the hard work that goes into successfully achieving a set of ambitious goals. There’s nothing better than celebrating wins at the end of a quarter where people acknowledge that at first they didn’t think it was possible. Better yet, is the impact this makes on the following quarter, when you see the transformation in the “what’s possible” perspective start to shift and goals that were once thought of as herculean become a little more commonplace.
Over the course of my time at Context, and particularly over the last year, we worked hard to actively capture the nearly overwhelming demand for our tours and experiences as travel rebounded post-covid. And our hard work paid off. We saw partner sales grow >4500% from 5 to 7 figures quarterly alongside a 38% AOV growth YoY. More importantly, that meant that we let tens of thousands of people discover what everyone at Context knows to be true; that there’s nothing like exploring a city with a world class expert, who can change your perspective and show you connections between people, places, history, and culture that you didn’t know existed.
Even though my tour of duty at Context has come to an end, it’s this mission of bridging cultural divides and showing our shared humanity that makes Context a company that I will continue to support long into the future. The fact that I still have many people I consider friends to be working at the company is just a cherry on top.
Thank you to all my teammates and colleagues for making this professional time in my life so fulfilling, educational, and generally fun. And thank you to Context’s fearless CEO, June. Your honesty, transparency, empathy, and dedication have taught me a lot about leadership. I feel lucky to have had the chance to work so closely with you and know our relationship will continue long into the future. Thank you for taking a bet on me and for giving me this opportunity. I wish you and the Context team every success and triumph imaginable.
With love,
Elon
P.S. One journey ends, but another begins — more to come…
