Why You Should Leave Your Corporate Job for an Enterprise Tech Startup


Everything you wanted to know about leaving your corporate job for a(n enterprise) startup but were too afraid to ask

A common discussion I’ve had since leaving Morgan Stanley IT a couple years ago is with people in IT at big banks wondering what it’s like to join an enterprise startup and whether it could possibly be for them.

With the holiday season upon us (and many people contemplating career moves or unhappy with their year-end bonuses at their corporate jobs), there’s no better time than now to consider joining an enterprise startup. In this post I’ll cover the why and how of leaving your corporate job, and break the process down into 3 phases.

In terms of some context, regardless of whether you’ve been working at your corporate job for 2 years, 5 years, or even 20+ years, this post is for you. I’ve had so many conversations on this topic lately that I figured it makes sense to share it so that hopefully folks outside my 2nd degree network can learn from this and potentially make the leap!

Phase 1 – What are the benefits of joining a startup?

In short, there are a ton of benefits. But coming from the context of working at a large corporation, the below 4 are most relevant to the conversation.

Quickly make an impact

No matter your role in a large corporation, it’s easy to feel like a cog in the wheel. I’ve spoken with the full spectrum: analysts two years out of school doing grunt work, to Managing Directors with 25 years of experience who spend their days in endless meetings that often feel pointless and too far removed from the action.

The nature of a startup is that it’s all hands on deck all the time. Especially in the early days, there’s no room for surplus. There’s always so much to get done, and strong founders show how your work enables the overall goals of the company to ship and sell product. That recognition and impact makes it all feel very satisfying.

Be judged by your ability to execute

One of the best parts about startup culture is being judged on what you accomplish, versus the corporate game of being judged on politics and lip service. By necessity, startups tend to be more action oriented with less bureaucracy, so there will be less hurdles in your way to get your job done than in a corporate context.

Granted some startups do face their own organizational issues, but generally they move faster, are more merit driven, and individuals are more likely to end up empowered to accomplish more and learn more along the way.

Less risk

This one may come as a surprise, but given struggles that so many of the Fortune 1000 are facing these days, joining the right stage enterprise startup can be a lot less risky of a career move than staying in your job.

Whether you’re in financial services, advertising, media, manufacturing, retail, or so many other industries, traditional Fortune 1000 companies are contracting and trying to do more with less staff. This means more RIFs (reductions in force) and more risk to the consistency of your job. Even if you’re a star performer, sometimes if you’ve been at a company too long, you end up “too expensive for your role” and can get axed in a mass downsizing.

While on the whole startups are a risky proposition, within the context of enterprise tech, if you find a company with product/market fit, the risk comes down to execution rather than other miscellaneous factors. As will be described further below, if you take the time to properly vet an opportunity and join a fast growing company in an attractive market, you can end up in a way less risky situation than you currently are.

Have fun

Joining the right enterprise startup can be a terrifically rewarding experience intellectually. It isn’t a pie in the sky aspiration to want to enjoy coming in to work every day. By finding a company tackling a mission that you’re passionate about with a driven team of solid people, you can truly have fun. This is amazingly rewarding given how many hours we spend at work every week. Contrast that with folks I’ve spoken to who are tasked with “cutting edge” projects at their companies…only to find themselves figuring out a 2 year deployment cycle for implementing a clunky piece of legacy software.

Put simply, startups (and the people who work at them) are fun. There are less corporate rules dictating your every action, so yes you can enjoy a beer at your desk at 4pm (but just make sure to get your work done). People bond over the camaraderie of being in the trenches together fighting the good fight, meeting fast looming deadlines, and often taking on massive incumbents with far greater resources.

Phase 2 – Evaluation Criteria

Great. So I’ve sold you on the virtues of joining an enterprise startup. But how do you survey the landscape to know which companies to even look at, and what type roles you’d be a fit for? See below for the key factors to consider.

What stage? (i.e. What’s your risk tolerance and your desired work/life balance?)

First things first. Stage is a function of your risk tolerance. How much funding has the company raised. How many employees do they have? Where are they in terms of product/market fit for earlier stage companies, and revenue and profitability for later stage companies?

These elements will dictate the inherent risk in the opportunity. Stage also dictates what sort of work/life balance and role you can expect, because, frankly, the earlier the company, the less “balance” you’ll have and the more hands on you’ll need to be.

What salary mix between cash vs. stock are you seeking?

Stage will also impact compensation, so you need to figure out what you’re seeking to optimize for based on your financial needs. If you’re much later in your career and are relatively comfortable financially, then optimizing for equity makes sense because you won’t be a financial burden on the startup from a salary perspective and you can have a greater share of the upside should the company succeed. If you’re earlier in your career and need money coming in for near-term and mid-term needs, then focusing on a stable salary with less upside is the right way to go.

Based on your needs, you should evaluate what a startup can offer and make sure you’re aligned. While most people assume you need to take a massive haircut from your corporate paycheck to join a startup, in the enterprise context if you go to a later stage company, they can often afford to pay competitive market salaries.

What sectors do you have experience in, and what role aligns to your skillset?

You may not realize it, but coming from a Fortune 1000 company gives you two skills that are both highly valuable traits for enterprise startups:

  • Understanding the inner workings of big company life and their inherent processes

  • Having deep domain expertise in a specific industry

After all, enterprise startups are building companies to solve large scale pain points, and then need to sell their product, implement it, and keep their customers happy. Oftentimes today in enterprise startups you have founders with webscale backgrounds (coming from Google, LinkedIn, Twitter, etc.), so bringing your know-how to the table can complement their experience really well. The later stage in your career that you are, the more it makes sense to target a startup selling into an industry you come from.

From a role perspective, you need to think about where you’d be able to add value. Some of the core roles for early companies like Developers (e.g. here & here) and Sales People (e.g. here and here) are pretty easy to figure out if you align with. As companies get a bit later stage, they then need Product Managers, Marketing, Data Scientists, and People Ops hires, among many other roles.

It gets a bit more difficult (but certainly not impossible) if you’re in a senior management role, which would perhaps necessitate going to a later stage company where you could manage a team and help set strategy. Recently though, I’ve seen lots of senior folks take on COO roles at early stage enterprise startups because they can help with implementing processes that will be important as the company grows, provide big picture thinking and relevant insights during strategy discussions, and grow/manage teams. For instance, the COO of our portfolio company, Socure, joined the company after being a two-time customer at his previous corporate jobs. For those of you good with Finance and Excel, being a company’s first CFO is an exciting opportunity too.

If you’re coming from a business function that doesn’t nicely align to a Developer or Sales function, think creatively about how your experience can help. For instance, one role that I’ve seen grow tremendously in the last few years and where domain expertise can be critical, is in Customer Success. Many of my friends from financial services have seen great success in Customer Success roles where they’ve brought skills to the startup around navigating customers, understanding pain points, knowing what drives budgets, and even just “speaking the same language” to end customers who are usually former colleagues.

Phase 3 – How to Engage

Engaging with your local enterprise tech ecosystem requires some effort, but if you follow the below steps then over a few months you can learn the lay of the land, meet interesting founders, and build relationships that could potentially lead to your next gig.

Get to know the ecosystem and attend meetups

Step one is exploring your local ecosystem to learn about what enterprise startups are present. The best and most authentic way to do this is through attending meetups. In New York for instance, you can check out the NY Enterprise Tech Meetup*, which is a monthly tech forum dedicated to showcasing new startup technologies to an audience of corporate buyers, enterprise entrepreneurs, investors of all stages, and grad students. Through meeting the presenting companies each month and networking with the crowd, you can get a feel for what’s going on in the community and learn about companies that may be of interest. *(shameless plug, I founded the NYETM and you can join here.)

You can also be more specific and attend meetups on topics ranging from Spark to Scala to R to Containers. At these meetups you can meet fellow practitioners who come from big companies and startups alike, and often can point you to highly relevant other people to connect with based on your shared interest.

Help startups of interest

Once you’ve gotten to know the lay of the land and some companies stand out that may be of interest, reach out to see if they’re open to grabbing a coffee. Don’t just reach out cold and ask for time though. Startup founders are running at a million miles a minute, so make sure that in your note you have a reason why they should take the time – perhaps you have interesting feedback on their product, or market insights from your job that could be helpful to them.

Once you sit down with them, see if there’s a way that you can be helpful with something, and try to make it tangible. Can you make some relevant introductions? Can you do a few whiteboarding sessions to share feedback on their product architecture or go-to-market strategy? By leading with help and mentioning some specific actions, you can begin building a relationship with the company. As the relationship grows, you can then explore the possibility of being a formal Advisor or informal mentor to the company.

I highly recommend taking this route because it’s a way to build deep relationships with a few companies in parallel, you can determine if any of them are places where you could see yourself working full time from a culture, mission, and traction perspective, and you can do this all while still keeping your day job (which is a plus given that you don’t make a drastic move and accidentally join the wrong company).

Work-Bench can also help here, given that we have over 35 enterprise startups in our extended NYC-based community. Jessica Lin and Stephanie Manning from our Community team are always eager to connect great talent to our startup founders (feel free to shoot us an email).

Make the leap!

As mentioned above, by this point you’ve hopefully built up some real relationships with some founders and not only gotten to know their companies in more depth, but actually helped them over a several month period.

If the conversation hasn’t come up yet about your longer term plan of leaving your corporate day job for a full time role at a startup, you should bring it up with the founders you most likely see yourself joining to see if there’s a path to getting there. Just keep in mind the Phase 2 evaluation criteria above, because even though you may be mentoring and advising startups of various stages, for the one you join full-time you need to make sure that there’s the right role for you, and that you can create the right compensation structure.

And like we said before, if you’re interested in connecting with any of our 35+ member or portfolio companies, don’t hesitate to reach out to our recruiting team!

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