Why and How I Switched from Investment Banking to the Start-up / Tech World

After having countless conversations with recent grads in IBD or consulting, thinking about a career switch and finding their current jobs unfulfilling, I put together a high level guide for making the switch based on frequently asked questions.

Note that this is only based on my own experience and perspective, but hopefully you find it helpful. If you still feel lost and confused, feel free to hit me up!

First, let’s start with the why.

Q: Why did I want to leave investment banking?

• I found the actual job of being an investment banking analyst to be unfulfilling, not intellectually challenging enough, and culturally oppressive. (The caveat here is that some people do have significantly better experiences depending on the bank, group, and even the projects they get staffed on.)
• I knew I can’t see myself waking up 10 years from now being excited about finance. I decided that I don’t see myself in private equity or any kind of finance long term. This is where you do the soul searching (see this post) first, and then decide if this is really the path you want to take.
• Get rid of your sunk cost fallacy. Even though I dedicated my entire college to getting the perfect finance job and was well-positioned to stay in the industry, I also know living and breathing that life everyday is the reality. I did not want that reality. What’s the point of working your a** off on the wrong thing?

I think for most people who have done banking and are thinking of the switch, you don’t really need that much more convincing from me to understand why I’m an advocate of leaving. The main thing I urge you to do is to get out earlier than later. The sooner you get on the right path for you, the sooner you can reach career fulfillment and earning potential doing what you love.

Now moving on to how exactly you can go about this very scary (but rewarding) journey of figuring out what you actually want and can do.

Q: There are way too many opportunities within “tech” and “start-up” where do you even begin with the job search?

Follow the steps below while browsing on LinkedIn and Angelist for jobs.

Step 1: Is there a specific industry that you are drawn to?

Once you start browsing jobs, you will notice that you are probably drawn to certain industries more than others (SaaS, Consumer, E-Commerce, Robotics, etc.). If you are truly industry-agnostic, that’s fine too.

Step 2: Figure out what stage of company you want to join

Early vs. Mid-Stage vs. Late-Stage vs. public companies will give you a VERY different experience. This is arguably one of the most important steps.

Early Stage:

I joined Senreve as employee no.4, and got to work across different functions from business operations, to marketing, to analytics, to international expansions. I am not exaggerating when I say I literally did a bit of everything.

• Pros: You get a lot of ownership, a very broad scope, and work directly with leadership if not a leader yourself. You can get a real “start-up experience” where you can see and experience how a company is started from scratch.
• Cons: Everything you want to do, you will most likely be the one to execute it. It’s sometimes hard to think strategically when you are in the weeds all the time, and you are also perpetually overcapacity. The early-stage life is not glamorous, and most early stage companies do not succeed. Compensation is also likely to be lower.

This is best for people who love a fast paced environment, want to pivot away from finance, truly believe in the company that they are joining, and willing to hustle and sacrifice a bit of work-life-balance. Even though the career risk is low for someone who is starting out, the likelihood of financial upside is also low. It’s critical to do your research on the people starting the company. I was lucky to have found Senreve through a college friend.

Mid Stage: No personal experience here, but based on observations it’s a great balance of being able to move through the ranks quickly, have ownership within your scope, and a network of mentors and peers. Compensation varies but it can be very comparable to large companies if you take into account of equity.

Late Stage / IPO: I recently joined Dropbox in Product Growth so this is still an evolving experience for me, but so far I’ve enjoyed the big company life a lot more than I expected.

• Pros: You get a lot more resources and support, such that you can really focus on doing whatever job you signed up for. Even though your area of scope is a lot narrower, you can be more strategic and still have a lot of ownership if you have a great manager (as is in my case). You will also have a much bigger network of mentors and peers. Compensation is likely to be higher.
• Cons: Because there are so many processes in place and so many stakeholders within the company, things definitely move a lot slower. If you are impatient for change, then you might hit a few more blockers here. That being said, it is still possible to make a tangible impact if you join the right team.

It’s difficult to join a large company in a non-finance role if your goal is to pivot away from finance after banking. These companies are usually looking for people with a bit more experience unless you are willing to take a step back and start at true entry level in product, marketing, operations, etc.

Step 3: The role

If your ultimate goal is to pivot away from a finance role, then there are two ways typically:

1. Start at a mid-stage or late-stage company in a finance role (finance strategy, corporate development, etc.), and pivot to other roles internally after a few months / year.
2. Start at an early-stage company and jump directly into business operations or any other analytical functions that can leverage some of your banking skills. You will end up wearing multiple hats anyway, so you can always shift your focus towards a function that you like over time.

Within tech, engineering and product tend to drive the company. Within E-Commerce, it’s marketing and product. For most people, it’s going to feel more rewarding to be as close to the revenue-driving function as possible, aka what the company prioritizes the most. This is why within a bank, most people want to be on the investment banking side.

If you have the technical background, try switching into engineering or product management. If you don’t (which I did not), then try to leverage your analytical abilities to switch into growth, business operations, and/or product.

How to Actually Job Search:

1. Talk to people within your network! Referral is the most effective and the easiest way to get a job, so start browsing LinkedIn heavily.
2. Set job search alert on LinkedIn and AngelList.
3. Subscribe to a few newsletters. My favorite one for recent grads is the Accelerated newsletter by CRV — they always have a job section at the end. StartupLadder, OneJob, and some female-focused ones include Elpha, AllRaise are also good.
4. Another source is to subscribe to VC portfolio job alerts (GSV, NEA, First Round, etc.). If there is an industry you are particularly interested in, then subscribe to VCs that tend to invest in that industry (e.g. GSV for education).
5. I do see a lot of people looking to hire, so if you want to ping me directly I’d be happy to matchmake.

Other Frequently Asked Questions:

Did you have to take a huge pay cut?

• Most likely yes — how much depends on the company and your role. I’ve heard of friends who have not had to take a pay cut (even though that’s rare).
• However, my view is that you should be investing your time in maximizing long-term outcomes earlier in your career. It’s much easier to take the pay cut now than later. I also believe that if you are doing something you truly enjoy and are passionate about, the money will most likely follow.

What tangible skills did you have to offer from banking to tech?

• To be honest I had no idea how to pitch my skillset at the time, outside of my ability to use PowerPoints, Excel, and hustle a LOT. The struggle was that I felt like I can do most of the jobs I saw, but I had no relevant experiences to back it up.
• I found that the most tangible thing that people cared about on my resume was my analytical skills. And the case study phase was my opportunity to put in the work and show my strategic thinking and presentation skills (with plenty of attention to details and a beautiful PowerPoint of course.)
• The soft skills do matter a lot in every job, but you have to be proactive in convincing people of that during the interviews.
• Show a lot of passion and do your homework — it really does go a long way.

Did you consider VC?

• I have a lot of thoughts here but the short answer is yes. If you are looking to get into early-stage VC though, most people will tell you to get more operational experience in order to 1. be better at your job and add more values, and 2. gain more credibility and ultimately move up the ranks to become a partner.
• If you are more interested in growth equity, then it’s a natural step from finance.