Defining Your Career Path & Making a Transition Beyond The Role

Defining your career path & making a transition beyond the role event at the Chief of Staff Summit.

Moderated by: Tyler Parris Founder at Tyler Parris Coaching & Chief of Staff Expert

Speakers include:

-Lindsey O'Sullivan Director of People Operations at Nautilus Labs & former Chief of Staff at Sailthru

-Ali Rohde Chief of Staff at Generally Intelligent

-Manika Garg GM of Core Experience & former Chief of Staff at Zola

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Note: please see the following summary of the core ideas from this conversation at the Summit. We did our best to clarify the ideas for you. Please refer to the video for specific details, ideas, and context.

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How did you get your current job: 

Manika: I actually had a background in strategy consulting did that for many years. I joined Zola in kind of a strategic planning role. It was about six months of me being in that role when our CEO approached me with wanting to create a Chief of Staff role… She had heard about it, but she had never had one…  So we figured it out together, we developed you know what we thought this role could be, so I was essentially the first Chief of Staff that we had, and it was a valuable role.

Ali: A friend luckily mentioned to me that this Chief of Staff thing which comes from politics was actually increasingly a role in Tech. I was like, that's an idea. So after working in politics, I ended up pivoting into Tech. I joined an early stage YC startup called Sorceress. They had gone through YC, and then just raise their Series A. So I joined as their Chief of Staff helping them to scale. I was employee number 18 and grew the team to like 35 employees full time, and then a team of like 80 contractors as well. I had a kind of interesting different trajectory. That following year, I helped to shut down that company and help the founder start something new.

I love what you said about where you come often helps determine where you go. 

Lindsey: I left law and went into Tech, which was where I found Sailthru and at Sailthru advocated for the Chief of Staff title as that was the work I was doing… And ultimately, the reason I was pulled into a lot of those conversations was because of my background in law, right, the analytical thinking and written and spoken skills that came across from that previous experience helped me to excel and drive the Chief of Staff roll forward at Sailthru. 

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On thinking about what’s next:

Ali: Once we did decide to shut down that initial company, I helped the founders decide what they wanted to do next. And they decided that what they wanted to do was actually to build an AI research company. Once they decided on that direction, that was kind of the lightbulb moment for me where I was like, okay, AI research is not where my heart lies, what do I want to do? During that time, I was very open with my founders “this isn't really my path. What do you think I should do next? Because I hadn't actually thought about it that much.” I was lucky in that this time, when I was looking for an operations role, I now had tons of connections. And now I had my founders open so many doors for me — they knew everyone in the Valley. They knew which companies were really hot and which were on a good trajectory. I started talking to a lot of other founders about joining their teams, but I actually found myself feeling a little bit, not excited to be super heads down on one company again. And so I started talking to my founders about potentially getting into early stage venture capital, which I think is not a super uncommon next step for Chiefs of Staff. I told them that and they were very supportive. A few days later they came back to me, and they had had been very active angel investors, and they came to me and they were like, instead of you joining another fund, why don't the three of us start a small fund? You can run it full time, and we'll help part time.

Ali: And I think it's kind of like a bit of a Silicon Valley fairy tale — in that joining one of these companies can really change your career. Meeting these founders who are fantastic, and if you build a good relationship with them, that can totally change your career. 

One piece of advice: which is before you even start the role or just the beginning think about what do I want my resume to look like, after I finish this role? 

Manika: I think the Chief of staff Role is a golden opportunity, right? You're deeply plugged into everything that's happening your company or department, wherever it is that you're serving that role. And it's your chance to kind of take that experience and raise your hand and say, this is the experience that I want to make sure I have… I had no idea what I want next which is trying anything and everything to see if I could be, figure out what I liked. I did financial modeling, worked on talent processing, marketing, analytics, just incubating a business, and I think it really helped me figure out what I liked. But it also I think it helped prove to myself and to everyone else. 

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On personal brand building:

Ali: I think when you're a Chief of Staff, you're doing everything in the service of like your CEO and your company. For me now building this fund, it's important that I have a brand of my own, and that I have relationships with my own. That was something that I've really been focusing on this year, in particular, because I had just never thought about it before. And I'm also still relatively new to tech. So I started this newsletter and have been meeting lots of people, and that's been really amazing. That's kind of a skill and experience that I had to build up that I just did not get as a Chief of Staff. 

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Setting up your successor to success:

Manika: We ended up hiring essentially a Deputy Chief of Staff around the time, we knew that I was feeling ready to move on. And so she had the benefit of us overlapping for a while and being able to kind of absorb a lot of what was going on which, if you can swing it, I think is one of the best ways to do it. But I did start what I called “Adopt a doc”, I literally called it Manika's brain dump. It was a Google Doc…. Where are places where that often doesn't work? Where are places where I have made mistakes in the past? What would I say about handling my principal in certain situations? And so it was really just kind of the treasure trove of what I thought were my learnings more so than even processes,

Ali: And so in terms of handing things off, what I really focused on was teaching my successor how to best work with the CEO with the principle because I had learned kind of like all these hacks — basically to work with my CEO. One of them was you have to get Superhuman. Because if my CEO uses Superhuman, and if you use Gmail… If you draft something you can't, she can't see it.. Kind of very specific tactical things like that. 

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What roles do we see people move into most frequently:

Ali: I think you'll see a lot of people continue in these more generalist roles where they get to have a full picture of the organization. GM, Director, People [roles], Founder all of these things are pretty common. In my opinion, I have seen fewer people go back into a specialist role. 

Lindsey: I would say I've had so many conversations with people in the Chief of Staff role where they come and ask what can I do next? Or what should my next step be? And my response is always to probably frustratingly for them to throw it back to them. Because it's a little bit of a blank check —  like well what are you interested in? What did you like doing in the role? 

But they have to know that for themselves and carve out that path. And I don't I think there's no role that I can think of that you can't go into afterwards, right? If you navigate it properly, if you acquire the skills along the way that you need to like you can get that from this role. It's a matter of owning that path and defining it for yourself. No one's going to tell you what you should should do next coming out of this role. If you've proven yourself,

Monika: I think the best part about this role is it just opens doors, it doesn't definitely doesn't close any. 

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Closing thoughts on what’s next:

Ali: I think we alluded to in the last question like this role is great, and that's a blank check. And it's hard and that it's a blank check.

Manika: Don't worry so much about the next step - it will come. You will have opportunities. But take the opportunity that you have in that role to really just raise your hand, to do anything that sounds interesting to you do take on any task role without ego, right? It does. It doesn't matter what title you have, it doesn't matter how big or small it is, 

Lindsey: I think just building on everything everyone said so far and what I was talking about earlier, it really comes down to knowing yourself. So think about what you want, write it down, flesh it out, lean into your network. I firmly believe don't ask, don't get. So ask for the information, ask about others experiences, ask for their time, ask for the cold or warm intros, and advocate for yourself and others in your network will advocate for you. I think the only other piece I'd say is don't be afraid to take the leap. 

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