Member Spotlight: Anna Koenig, CoS at Starship

Scott Amenta

January 21, 2021

We are lucky to have a growing community of Chiefs of Staff from a variety of backgrounds and industries. We believe it's important to share our member’s journey as a Chief of Staff. Every shared individual experience contributes to the evolving understanding of this position.

We love to highlight members from the Chief of Staff Network and share their story and goals through this Member Spotlight series.

This week Anna Koenig shared her path from a finance & accounting background to landing her Chief of Staff role at Starship through.. a Twitter DM! Anna has had a varied and incredible career path and we're excited to watch her take these new experiences & learnings as a Chief of Staff to the next level.

How did you get into your CoS role at Starship?

This is actually a funny story. My job came out of a Twitter DM! An investor of the company reached out and told me he enjoyed my tweets. We got to chatting and I told him I am looking to make a change in my career. At the time I was working at a different fin-tech company doing accounting and finance work. After telling him what I believe my strengths are, he suggested I apply to Starship for their CoS opening at his portfolio company and it ended up being a really good fit in terms of both job responsibilities and culture. 


What are you working on right now?

Right now I am deep in wrapping up 2020 financials (finance has a way of following me!) I am working with our VP of Partnerships to scale out Salesforce as we bring on a BD team this year. I am also gearing up to plan a full day virtual employee off site in February, and I want to make sure this is a really fun and productive experience for our whole team. 


What’s your professional goal in the next ~10 years? 

You know, this is a question I have a hard time with. I really connect with Steve Jobs saying, “You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.” My career path hasn’t been the most straightforward and it had some interesting pivots (read: I opened a yoga studio for 4 years!) Yet, looking backward everything has made sense and has built to this very moment. I think the key thing is to align your values with your work. I am doing that right now because I think the healthcare industry in the US is really broken, and Starship is making things better.


What’s something that you’re sneaky good at or that people wouldn’t expect about you?

Some of my friends joke I should work for the FBI. I am really good at finding out information online. When Facebook suddenly disabled Graph Search, I found myself deep in Reddit with other professional investigators trying to figure out what happened. I am definitely one of those people holding back info I have figured out on first dates like “When you say Aunt, do you mean your Aunt Melanie with the 4 kids?”


What’s the best professional advice that you’ve ever been given?

Oh my God, I’ve got so much amazing advice over time, but I actually want to credit two people. In 2011, my friend Harry gave me some advice on interviewing. He helped me master how to tell my story - always start at the beginning so people don’t wonder how far back this is going to go. He also suggested asking the hiring manager what their current priority is and how I can help. I found this really makes the conversation much more tangible instead of pie in the sky.

Another piece of advice actually came from a friend of the family in 2012. She was a CEO of a tech co, and I met with her because I was still having a hard time interviewing. I think there was definitely some insecurity and imposter syndrome at play because of my lack of job experience. She told me to go into an interview and pretend I already work there. I was so confident at my next interview for a Business Analyst position at Wells Fargo that I got the job!


What do you like to do outside of work (hobbies, sports, activities)?

I got really into improv right before the pandemic and took 21 weeks of classes. I made so many amazing friends through that and I am sad that I can’t go to shows anymore right now. Also sad like so many others that we can’t go to music shows now. I also really like to stay active and get outdoors (read: camping, hiking, biking, yoga). Last weekend I went totally outside of my comfort zone and took a paragliding class. It was incredible. Other than that I love to cook and am really into juicing. These days, you can find me thinking about OKRs while sipping on a fresh turmeric shot. 


What’s something that you want to learn? (professional or not!)

I ordered a knitting kit off Etsy to make this wool scarf and I am not going to lie, I haven’t gotten very far. But, I am going to get back to it...next weekend. I have this fantasy that I knit on planes and trains and people are like oh that woman must be SO crafty look at her go. I also joined the sourdough baking trend last year. Quarantine is making me into a 1950s single housewife. 

What’s something that you’d like help with?

I think the real answer to that question as a CoS is “No no, help me help you!”

What Pro Tip would you offer to other CoS?

You have to ask the right questions to get to a place where change can happen.

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