Jessi Craig: One Partner Away from A New Career Trajectory

As an editor at First Round Capital, Jessi Craig has found her niche – but it wasn’t easy to carve out. Equipped with sharp marketing skills and a knack for writing, she could have taken on any number of other careers. Like so many fresh college grads in Washington, she found herself caught in the “DC bubble” while finding her professional footing. 

Jessi launched full throttle from Georgetown’s School of Forensic Science into the private sector. Swept along a traditional path paved with Hill and embassy internships, she carved out a unique space for herself within the world of consulting, that familiar destination where so many successful DC professionals find themselves at one point or another.

How Jessi Craig Tried on Many Hats Before Finding One That Fit

As she tried on a variety of hats in positions everywhere from Evernote to the Department of Commerce and even the Russia Desk, Jessi Craig honed a robust range of skills. Equipped with proficiencies in marketing, editing, copywriting, and research, her biggest hurdle was pinpointing the right way to use them in synergy and achieve the most significant impact.

As her college years came to a close, she met the person who would change everything: fellow Georgetown alum, Will Smith, from McChrystal Group. Despite her initial assumptions, she joined the team not as a consultant, but as a research assistant for General McChrystal’s New York Times bestselling book, Team of Teams: New Rules of Engagement for a Complex World. 

“Even though my roommates were telling me it was a big mistake to take this leap on an unknown horse, I ultimately went for it. Spending several years with McChrystal Group got me deeper into writing, content, and book publicity that I had never imagined.”

Jessi’s tenure at McChrystal Group gave her formative opportunities, like ghostwriting senior leaders’ notable bylines everywhere from Forbes and Entrepreneur to the Harvard Business Review. Serving as a research assistant for the book project rather than joining the sales or business development team put her on an ambiguous career path, and she had a lot of doubt at first. Jessi had to tap into her resilience and trust her path. In retrospect, this unique jumping-off point was the differentiator she needed to stand out. Pivoting into content marketing, a significant part of her current role, was a natural next step:

“After a book comes out, you want it to be evergreen. You want to keep the momentum going. How can you extend the book and the themes? Content marketing is the natural answer. If we continue to offer several articles that tie into current events or themes we’re seeing, then tie them back to the book, we can extend its shelf life.”

Backed by such a wide range of credentials, she smoothly transitioned to a new chapter at venture capital firm First Round Capital.

Top 5 Takeaways from Jessi Craig

1. Words matter. They are incredibly important in both your personal and professional relationships. 

2. It’s okay if your college major ends up having nothing to do with your career path. Even though she had a different background than most content marketers who study English or Communications, Jessi found her place in that space and has continuously excelled.

3. Keep an open mind, and challenge any biases, stereotypes, or assumptions you’ve held onto. You have so much to gain from being open to meeting new people, exploring new opportunities, and going in different directions than you ever saw yourself heading.

4. Find opportunities on credible platforms to establish your own credibility and credentials, just like Jessi did at the McChrystal group.

5. Always say yes to opportunities that come your way and get your hands dirty. Do the work no one else is doing and pay your dues. So many times, showing you’re willing to take one for the team like Jessi did with the initial book project will pay countless dividends. Being a team player is a rock-solid way to demonstrate your potential worth as a longtime employee. 

In her current role, Jessi oversees the marketing team and heads up the First Round Review. The company’s digital magazine publishes long-form profiles of innovators in the tech and startup sector. Through this platform, thought leaders share groundbreaking insights from the startup space that inspire entrepreneurs to reimagine what it means to build a company and expand their conception of how they can. 

As Jessi navigated the initial steps in her career, a passionate desire to make a difference, one that so many of us hold close to our hearts, was her guiding light. This sense of purpose and a little creativity led her to a vibrant opportunity that’s the perfect fit. I hope that hearing about how her path took shape and the challenges she overcame will help you find your way a little easier. Hear her full story in the episode and follow along by reading the transcript below!

Tune into Jessi’s episode by watching on YouTube up above, on Spotify, or on Apple Podcasts. Please subscribe, rate, and review! 

Transcript

BRYAN WISH: Welcome to the One Away Show with Jessi Craig.  I was just re-reading your One Away experience. Tell us a little bit about how it happened.

JESSI CRAIG: It all goes back to when I was finishing up college in Georgetown. I was very much in this sort of D.C. bubble. There’s a running joke that everyone who goes to Georgetown thinks they’re going to be the next Madeline Albright. I was definitely in that camp. I’d done a lot of internships. I interned at our embassy in Hungary and in St. Petersburg. I worked on The Hill, at the Department of Commerce, and for the Russian Desk. I was trying to plot my trajectory towards this bigger move into public service and start focusing specifically on formulations. 

This thought occurred to me that I was getting pretty lopsided. I’d only had public sector experience. At that point, I’d never really worked for a company or held the kind of job my dad had always had. I picked my head up a little bit and decided that during my senior year, I should get some internships working in the private sector. 

I happened upon management consulting and banking, the classic east coast school options that every new guard starts considering when you need a job and money. None of those really felt perfect. It felt like being a small cog in a big machine; not super inspiring work, but something steady and reliable that my parents had heard of and would be excited about.  

I was doing all these interviews on campus before I got a couple of offers. As I was weighing my options, I ended up getting an offer from the McChrystal Group, a small boutique consulting shop that had just started a couple years ago. No one had really heard of it. You might have heard of General McChrystal, who founded it start applying his experience with running special operations to the business world. I thought this was a super interesting proposition, so I met up with an employee named Will Smith. We had some time overlapping in our time at Georgetown. As a fellow alum, he agreed to meet with me. He offered to walk me through the McChrystal Group and what they were doing. He suggested that I apply, not to be a consultant as I’d been envisioning, but to work on a new book project. The General had already published the typical post-war memoir of what he learned. Now, he was writing a business book on management and leadership and what people could learn from his experiences. 

When I got the offer for this temporary position, I dove in headfirst. I got paid to read books, research, and think deeply about all these management and leadership concepts. Eventually, it came to a point where I needed to make a decision. I could continue doing this work full-time, or go back to consider other offers I had on the table.  Even though my roommates were telling me it was a big mistake to take this leap on an unknown horse, I ultimately went for it. Spending a number of years with McChrystal Group got me deeper into writing, content, and book publicity that I had never ever imagined. Now I work in tech doing content and editorial and narrative and all these things that are a world away from foreign service and the Madeline Albright life I was considering previously. 

BRYAN WISH: What were you feeling? What were the pressures? What did your parents say? Evoke the emotions at that time or any relevant stories. Maybe provide guidance to other people who are considering something different for themselves. 

JESSI CRAIG: At least at the school I went to, there was a ton of pressure to lock down a job, no matter what. It could honestly be anything as long as you had one. Pretty much all the people I knew had a job by October of our senior year which was pretty crazy because you’re so many months away from graduating and this idea you’re supposed to have it all figured out and know exactly what you want to do. There’s a real pressure there that leads some people to stumble into something take it just for the sake of having a job.

Obviously, there’s a huge amount of privilege and opportunities that must intersect to make those choices difficult or easier for some people. I was very lucky that my parents supported me, so I probably would have been okay if I didn’t have a job lined up. That’s not the case for everyone.

It’s more that it’s easy to just get yourself started on this track when you’re running down this path and not really questioning why. What I wish I’d done a better job with was picking my head up earlier. For example, if you went to school on the west coast and you emerged in tech, that seems like the natural path. Can you pick your head up and look at see what other opportunities there are in other industries or other places in the country? Similarly, where I was,  banking, consulting, government, and law were the main tracks that you think of. How can you get involved in tech or something that’s more outside of your comfort zone when you’re coming from a different world? The main takeaway I have is that I wish I had cultivated those diverse experiences more intentionally. 

BRYAN WISH: When you were making this decision, did you feel off-base going into the consulting side of things? Deep down, did you question it internally? 

JESSI CRAIG: No one dreams of being a management consultant when they’re a little kid. You start having these feelings of maybe you’re selling out. Georgetown was a Jesuit school, so being men and women for others was a big theme they kind of instilled in you. That’s not really how you feel when your main client is the post office, and you’re recommending layoffs to save taxpayer money. It doesn’t feel very connected to the skills you want to cultivate and the mission you want to track towards. I had a lot of hesitation around that.

I also think I’m naturally a person who works better in smaller team settings. Being part of a 100,000-person company just didn’t appeal to me and just having more of an opportunity to make an impact. When I joined McChrystal Group, it was pretty small. They probably had about 35 people. That’s the sweet spot for me, I’ve discovered over time. There’s enough people where you know everyone, can get really close, and have a huge opportunity to make an impact, but it’s also not like three people in a room.

BRYAN WISH: Share some tidbits about meeting Will Smith where you walked away after you said it sounded great to you.

JESSI CRAIG: I had some options when I was joining. I could have been a consulting intern and working on all sorts of projects, or I could have joined him on the business development team in sales and trying to earn new clients. In retrospect, it felt obvious to pick the book project. When else would I have had a chance to get to work on that? At the time, I was the only person besides the other ghostwriter who was working on a project. It was a differentiator, and one that seemed like an advantage. 

On the flip side, sometimes I felt a little lonely. It was usually just the two of us in a room working on the book. I wasn’t having the same sort of experiences that other people were having. It was a more ambiguous career path. Like, what do you do after you work on someone’s book? It’s not like there’s a clear next rung to place your phone on. In retrospect, that’s a strength. It was a huge, unique differentiating factor. It’s the thing people always bring up when they looked at my LinkedIn.  They say “Wow, that’s crazy that you did that.” At the time, I was more insecure. I was like, “It does sound crazy. Why did I do that?” I felt more the hesitation around it at the beginning, but it was such a singular opportunity that I felt like I couldn’t not do it. 

Ultimately, I learned so much more than I would have at a more standard experience. Even if it seems a little unorthodox or you’re not really clear what you’re going to get out of it or what the next step will be, you still have to put yourself out there sometimes.

BRYAN WISH: Compared to the experience you would have had if you went another route versus what you got in the McChrystal Group because of the conversations you had with Will, what were some of the things you look back on now that you can point out? Which frameworks and things you learned do you still apply to your life today?

JESSI CRAIG: One of the biggest things I gained in that experience was work ethic, learning to be scrappy, and hustling. When you’re in a less proven environment than a brand name like McKinsey, you have to hustle a lot more. You don’t have those big resources, so you have to become “full-stack” and do everything yourself. The biggest lesson I learned as a marketer was that I had to learn everything. I needed to know how to run social media, put together an email campaign, write sales collateral, and figure out how to get it printed. You’re doing everything, soup to nuts. When you’re in a bigger environment, your role is more constrained, and you have a smaller slice of the pie. It’s not that it’s easy to coast, but you’re not stretched in the same sort of way. There are skills you would gain around cross-functional team navigation, working in big settings, and probably presenting to big groups that would be really valuable. You don’t have that same drive and hustle to figure things out on your own and get things out there. It’s a much slower moving iceberg.

BRYAN WISH: Were you given a roadmap to say what they’re doing and how to do it or was it more of a blank slate?      

JESSI CRAIG: When I started the book project, they had an abstract and a couple early drafts. That was basically it. It was the beginning of the project. The first part I was tasked with doing all the underlying research. I read a lot of books, summarized them, wrote first drafts, fact checked everything, and did all the end notes. It was a really fun process; being heavily sarcastic there. 

Afterwards, once we had more of a substantial book on our hands, we had to figure out the narrative and how it flowed together. That’s where I worked on those sorts of skillsets with the co-authors and with the main person who was undertaking the bulk of the writing. I was sort of his assistant. I really got to learn a lot from him.

The next phase focused on launching the book, which is kind of classic marketing. You’re marketing yourself. You’re marketing a book. You’re trying to get people to pay attention and care, and most importantly, buy it. It involved everything from publicity to media training. 

John McChrystal got to go on all the shows just because of who he was. It was fun to tag along for those things. He was even on the last week of The Daily Showwith Jon Stewart. I helped prepare talking points and social media campaigns, things like that. It was all about getting people interested, like “let’s get people talking about the book to their teams.” Becoming a best seller had been discussed recently. There’s a lot of work you can do to make it a better chance that you’ll land at the top of the list. That was also a really interesting learning curve.

After a book comes out, you want it to be evergreen. You want to keep the momentum going. How can you extend the book and the themes? Content marketing is the natural answer. If we continue to offer a number of articles that tie into current events or themes we’re seeing, and tie them back to the book, we can extend its shelf life. From there, it started from the ground up with content mapping:

• What are the big themes we can hit on? 
• What are the other things we can tie to? 
• What should our editorial strategy be? 

Then going out and doing it. Just doing both the high level and then in the actual lower level execution stuff. Interviewing all the leaders, ghostwriting posts for them, putting them together, shipping them, promoting them; just the whole life cycle of a piece. That’s where I worked on those skills for the first time. 

This is  kind of what we do at First Round, too. The review is a very small team. We’re only two people. We put out about 50 promos a year. It’s a lot of managing a high-level strategy and also the execution at the same time, which I really enjoy. 

BRYAN WISH: You went from research to carrying all the nitpicky things to the whole marketing and strategy and all the pieces because you took a very entrepreneurial dive after college. While you were at McChrystal Group, how do your relationships evolve or improve? What was that like with Will who gave you the opportunity? What is your take on working with Stanley McChrystal directly on certain things?  

JESSI CRAIG: Will Smith, we’re still friends. We were texting the other day. He’s been such a great resource to have. It was always nice because while he was the one who brought me in, I was never really on his team. It was that third-party view of how things are going, getting feedback, and having a sounding board. 

Even after I left the McChrystal Group, staying in touch and meeting up whenever we’re in the same place. That was super valuable to me to have that. He’s still there. He has that long lens perspective and has built such a great career there.

The other person I would point to is Kathleen Hatfield, who joined as the head of marketing. I had a real world-class expert to learn from. She had been at Prophet, Lippincott, and some really great marketing and branding firms. She has a super strong foundation. I got to learn a lot. That was sort of the best of both worlds. When you’re learning and doing a lot, but you’re also in the more junior position at the start of your career. You can learn a lot from other people too. I really enjoyed that.

As for General McChrystal, he has almost a cult following within the military of people who really revere him. It’s very evident when you interact with him. He’s going out and doing speaking engagements and writing, but he’s incredibly thoughtful. He would always joke that if he didn’t become a general, he would have become a writer. At West Point, they have a collection of his poetry or writings that he did when he was there in the 70s. It’s kind of interesting. He definitely has this intensely thoughtful characteristic that is incredible. 

Just leading by example is sort of the biggest thing I picked up from him. How he left the military was much publicized. There was a lot of to-do about that, but he was very straightforward and taking responsibility for that. The way he talked about it everywhere afterwards was incredibly classy and everything you want to see in a leader. That was the biggest takeaway; leading from the top and responsibility ending up on you was the biggest thing I got from working with him.

BRYAN WISH: Talk about the foundational experience and how it’s guiding specific decisions and is helping you think about things you’re doing at First Round and maybe even in your own life beyond work.

JESSI CRAIG: Joining a venture capital firm is not something I had ever considered especially when I was starting out in my career. What’s so special about First Round is that the brand that’s been cultivated over the years is really about the firm as a while. It’s not one partner that’s developed their own personal thought leadership. It’s really the collective and it’s about giving back to this community founders and company builders. It’s really content forward. That was what was so exciting to me. Content is the star of what we’re doing in marketing and building our brand. That’s really exciting and it’s pretty rare. They’ve also been doing it for a long time. Camille Regan started the review seven years ago and she’s been a wonderful resource. I still talk to her all the time. She sort of set something out and had a vision. Being able to continue that and grow it for where we are now in 2020 is really exciting. 

We are really trying to cultivate a brand of First Round being an incredibly helpful early stage investor. Whether you’re starting a company, whether you’re working at an early stage company, whether you’re thinking about starting a company one day, we hope you view First Round and specifically The Review, our content arm, as being a really  helpful resource and your first call, the first place you go when you’re looking for information on how to do that. That’s the main overarching goal. Content has been the best way we found to achieve that. With The Review, we interview the top leaders in tech; not necessarily the big CEOs or the people you’ve heard of. It’s probably people you’ve never heard of. 

The director at this fast growing startup who is in the trenches doing things and has incredible wisdom to share. The thesis has been that they are too busy to stop and write things down and do a blog post a carefully curated Tweet storm. They’re really the people you should be hearing from. By interviewing them and writing up their lessons in a profile, more people can get access to their wisdom. Traditionally, you’d only get that if you were being one-on-one mentored by that person. Really trying to democratize access, expand, and build a bigger tent of people who can build strong companies. That’s the goal from a macro level. 

Every day, what that looks like is identifying people to interview, crafting those questions, and crafting the narrative for the piece, writing it, editing, and then promoting. That top level strategy and bottom down execution has been the biggest thing that has served me well from what I’ve done in the past. 

BRYAN WISH: On your profile, you write that words matter. The ones we choose, the way we order them, and most of all, how we add them up to create stories. Explain that to bring us home. 

JESSI CRAIG: From all these experiences, words and writing have been kind of the through line for me. When people ask what I do. I joke and say, “All the words.” It’s not just as simple as The Review. It’s any tweet. It’s things partners put out. It’s how we communicate internally. 

There are so many ways words show up in our businesses and in our lives. Being really intentional about the way we choose them, the messages we’re trying to convey, and how other people will interpret them is such a huge part of my job and should be a bigger part of everyone’s lives. A lot of snafus and public fiascos might be averted if people were more careful about how they strung their words together. That’s an important skill. 

Even if you’re not in marketing, it’s so critical to work on. Writing crisper emails. Building your own personal brand on Twitter. There’s a lot of ways it shows up and I think it’s a skill we need to explicitly call out and work on. It’s something I honed unwittingly in college. I wasn’t an English major or that traditional path you might think for someone who ends up in content. I was in a Russian studies major; working actively on another language. 

I did a lot of research and writing papers on political theory and things like that where I was building those skills, but I hadn’t made the connection for myself that that was a passion for me, that was something I was interested in, and that it would be super important for working in the tech world. Just calling that out more explicitly and everyone, whether they’re in marketing or not, having a goal to get better at that is something that I would encourage.