Leaving management consulting for an early-stage startup

From 2016–2020, I worked as a management consultant, helping corporations develop strategies to address some of their most pressing needs. The work was fast-paced and full of interesting problems. Best of all, the learning curve for management consultants is phenomenal. For someone like me who is interested in business, learning every day kept me motivated and energized.

Outside of work, I was volunteering with a local nonprofit in Southern California. My volunteer work involved supporting the management team and the board with developing their 3-year strategy. I saw it as a great opportunity to give back to the community and learn more about how a board works.

I never actively looked into joining an early-stage startup. But when COVID hit, everything changed.

Learning the importance of execution — During the early days of COVID lockdown, the local nonprofit I volunteered at needed to take drastic actions to continue serving the local community. While I continued to focus on improving the organization’s 3-year strategy, the CEO began taking decisive measures that kept the nonprofit operational. The CEO made hard HR decisions, reduced expenditure, and found ways to secure key revenue streams. Despite all the challenges, the organization continued serving the local community thanks to those swift actions. It was a humbling experience — I experienced first hand the importance of execution and realized how essential it is to an organization’s success.

Learning what I truly enjoyed — Around the same time, I worked on two different consulting projects for my firm:

• Building a new digital product for operating room surgeons and nurses.

• Helping a large corporation’s C-level executive with analyzing and communicating a major business decision to the rest of the C-Suite/Board.

On sight, one of those may sound dramatically more exciting and influential than the other. But what I discovered surprised me:

When building a new digital product, I spent my days interviewing surgeons and nurses across the world to understand how to improve the existing surgical model. My learnings were turned into features that would improve how surgeries were conducted.

When working on the C-Suite project, I spent my days analyzing the company’s data and preparing it for the C-Suite presentation. To derive our recommendations, I dove deep into millions of rows of data to piece together insights that would help make a $1+bn decision. The work was influential and had a high profile at the customer’s company.

Having done these two projects back to back, I was able to compare and contrast these two completely different worlds of work. One had a smaller dollar implication (in the near term at least) and the other had significant dollar implications. One was more on the ground building and the other was more in the boardroom recommending. Both were important, interesting, and challenging, but these experiences helped me realize that at the end of the day, I am much more energized and inspired by building on the ground, like I’d seen the CEO of the non-profit do earlier.

Putting it all together, I realized I had a passion for product and a strong desire to learn more about execution. Startups suddenly stood out to me as environments where I could learn and grow in the ways I was itching to. With that, my job search began.

🙋🏻‍♂️ Where to start

I began my search by talking to many later-stage startups (Series-C and Series-D). These later stage companies were easier to find online and had a lot more publicity. While I was impressed with the impact these companies had achieved, I found myself most captivated by speaking to early team members who shared stories of growing the team 10x from a sub-50 person company years earlier. Through those interactions and reflections, I concluded that I was more interested in the “0 to 1 experience” than the “1 to 100 experience.” The 0 to 1 experience would allow me to get hands-on and build a good execution habit. I also considered that I’m still in my 20s, and joining an early-stage startup is as risk-free as it will ever be. There’s no better time than now. So with that, I decided to look for startups in the Seed/Series-A stages.

A quick tip: Startups can come in different sizes (less than 20 people, 300 people, or 1K+ people). When thinking about joining a startup, it’s worth asking yourself whether you prefer joining a company and helping build up the initial product/process/strategy or prefer joining a startup to help the company scale. Jeff Bussgang’s book Entering StartUpLand provides an excellent overview of startups at different maturity levels and what you should expect. For someone who’s never worked in a startup, I was missing contexts for what day-to-day could look like. I found speaking with people working at startups to be the best way to get a feel for what company size I prefer.

🧭 Knowing which team to join

Now that I had narrowed my focus on Seed and Series-A startups, my next challenge was to develop a shortlist of companies to target. I found this step to be difficult because:

1. Most early startups don’t have information online beyond their landing page.

2. It’s hard to tell whether the companies need a non-technical hire right now.

I needed to understand the startup and know whether I could add to the team, but it’s time-consuming to get to know every startup well. Before diving into research, I used the following criteria to narrow my list:

• Is the company B2B or B2C? I like B2B because the business problem is concrete. There is a known issue, and others will pay you if you solve the problem.

• Are they solving a technical or business problem? Business problems speak to me and are something that I appreciate.

• Are they solving a problem that I can relate to? This one is obvious :)

• Do they have repeat founders or first-time founders? I’ve never worked for a first-time founder, so I’m biased. I wanted to learn about entrepreneurship, and I thought repeat founders have more experience starting a company (so more opportunity to learn from them).

• Do they have good investors and board members? There are a lot of startups out there. Targeting ones with reputable investors and board allow me to be more focused.

• How are they doing financially? I looked for startups that showed great rationale for how they spend and raise money.

With a shorter list of startups, I could do better research and articulate why I want to ask for peoples’ time to chat and/or apply to a position. I treated each chat, interaction, and interview as an opportunity to collect more data points on the companies and crystalize whether I wanted to work there.

Through this process, I also learned that while folks are busy getting their business off the ground, people are more than happy to chat with you as long as you show genuine interest in their business. Dropping a resume and sharing all the incredible accomplishments you did at XYZ Co probably won’t get you as far as you’d hope.

While it’s important to show respect to startups you interact with, I found it equally important not to waste time with companies/people that don’t respect yours. Here are some of the things I consider as red flags now looking back:

• Wishy-washy response when asked if they are interested in hiring you, but still ask you for more time.

• Taking a long time to progress you through the interview process and/or changing the interview process midway.

• Low-balling salary and/or equity.

• Trash talking other companies or people during conversations with you.

• Showing a limiting belief in the scope of your work (“I need you to do XYZ and XYZ only for the next three years”). Everyone needs to get hands-on early on, but it’s unrealistic to assume that someone’s responsibility will remain constant in a startup environment.

After shortlisting startups that fitted most of my criteria and interviewing there, I was lucky enough to reach the end of my interviewing process with two offers in hand from companies I liked a lot. Deciding between the two turned out to be the most challenging decision I had to make throughout the process.

🎯 The search for the startup — Knowing which team to join

To give you an idea of why it was hard, here are some of the stats about both companies:

• Seed vs. Series A

• Both B2B

• One solving for a business problem, the other solving for a blend of business and technical problem

• Both have repeat founders

• Both have great inventors

• Both are doing well financially

On top of that, I had convictions around both companies’ missions, products, and goals.

At this point, everyone was selling me the dream (“we are going to be [insert company that’s on the news] in X years”), but I didn’t have enough information to know for sure what would happen next year 🤯.

The criteria I had outlined to find these startups failed to help me decide which one to join. It was impossible to compare the upside when all options have unlimited potential. So instead, I turned the question on its head and asked:

“Who would I rather fail with if this doesn’t work out?”

This mental exercise allowed me to surface what mattered to me most:

1. I want to learn and grow so I can be a great operator.

2. I want to work with people I can be friends with (do it for the mems 💯)

Once I knew what my priorities were, the decision to join Dover became clear to me.

🚀 Joining THE STARTUP — Dover!!

Ultimately, I decided to join Dover. For those who are curious, here are some of the reasons why I was super excited to join:

• Dover is solving a business problem (recruiting) that I believe can be made better for everyone. I agree that this problem can be solved with technology, and like the approach Dover is taking. I’ve also personally experienced the product during the recruiting process — it works!

• Dover’s team moved fast. They knew what they were looking for in a candidate and designed each interaction to understand me better. I felt the connection and thought that they knew me well at the end of it. The co-founders’ ability to run a great interview process gave me confidence in how the company operates (very true now that I’m on the inside).

• Dover paid equal attention to learning and having an impact. Early-stage startups typically focus on the latter, so Dover’s ability to demonstrate that they care about both sets them apart in a big way. During the interview, we had a candid discussion about how I can take my work to the next level, and that resonated with me.

• People at Dover are smart, humble, and friendly. Everyone at Dover always talks about how someone else at Dover did a fantastic job and made the company successful.

Right now, I’m 1.5 months into my new job and am loving every minute of it. These days, I split my time between managing accounts, building the Dover product, and pitching in on the company’s strategy whenever I learn something new. I’m getting a ton of hands-on opportunities to develop my execution muscle, but I also get to leverage the consulting toolkit to help build the Dover product.

One of the things that surprised me the most was the amount of feedback I’m getting (still a work in progress 😁). In consulting, receiving feedback is a daily ritual (maybe just for me 🧐). When leaving consulting, I worried about my learning trajectory, but it turned out not to be an issue. At Dover, learning is still part of my day-to-day. My colleagues are inspiring me/pushing me to be better.

For those interested in making the jump into the startup world, I hope my experience helps provide a perspective on making your search successful. If you experienced something different or have a different perspective, please share it with me. I’d love to connect and hear about your story!

For those who have tips on how to be successful at a startup, let’s connect — I’d love to learn from you!

If you’re curious about Dover, please pay our website a visit.

If you want to contact me, feel free to message me through LinkedIn!