From Entrepreneur
to Enterprise
How startup skills can make you happy
and successful at an enterprise company
When I left an eight-person Peter Thiel-backed startup for Salesforce, people thought I was crazy.
Transitioning to a large company from a fast-paced startup can be a serious culture shock, and we all know entrepreneur-types simply aren’t built to be happy and effective in the enterprise space. Or are they?
Whether your startup is getting acquired or you simply need a change of pace, you can thrive at an enterprise by applying the same skills you developed at a startup.
Keep up your momentum
In startup-land you got accustomed to a relentless go-go-go pace. There were constant meetings and frequent releases. Late-night triple-shot lattes became your new best friend. Now you’re not only used to this speed, you need it. Going any slower than lightspeed feels like sitting in stop-and-go traffic on the Autobahn.
It’s a simple fact that a 14,000 person company is less nimble than an eight-person company — and for good reason — but just because larger companies move slower doesn’t mean you need to. Brief moments of calm exist within large companies as work changes hands. Take advantage of this time to get extra things done. Right now my team is busy building designs I submitted earlier this week, giving me the perfect window of opportunity to write this post.
Even if you left a startup to find better work-life balance you can take on a lot at an enterprise company before it even remotely resembles the pace of your former life. Your ability to turn out great work and make it seem effortless will make you a phenom at your new gig.
Don’t stop wearing all those hats
Being dropped into a silo with a narrow focus and limited responsibilities was so commonplace in the traditional enterprises of yesteryear that many of us are skeptical of large companies as a viable career path. However, a new generation of enterprise companies has been redefining the corporate workplace by providing the culture, opportunities, and resources to keep even the most hungry startup veteran satisfied.
As an entrepreneur-type you naturally change the world around you to suit your needs, making you especially capable of getting what you want out of a corporate gig. One way to do this is to actively seek out side projects that fuel passions not satisfied by your core responsibilities. There’s no lack of opportunity in a large company, and accommodating side-projects is easier than you’d imagine if you keep up some of that startup momentum you’re accustomed to.
Not only will side projects keep you engaged and prevent you from getting siloed, not acquiescing to a well-defined corporate role will give you opportunities to help others, build your network, and help you discover and develop new skills.
Keep seeking constant feedback
Startups are barraged by a relentless stream of market feedback. It’s easy to tie your role to tangible metrics like number of new signups, funnel conversion rate, or closed service requests — all of which make it obvious whether or not you and your team are succeeding.
It’s more difficult to define the results of your efforts within a larger organization. Instead of relying on clear-cut metrics to know how you’re doing, try applying lean and agile methodologies to your career.
Waiting for a quarterly performance review is as old-school as getting an AOL CD-ROM in the mail. Actively seek out regular reviews from management with the same tenacity you would getting customer feedback on a product. Bluntly ask, “How am I doing?” or “What could I be doing better?” If everything is going well, you can move forward with confidence. If something is going wrong or could be more efficient, you want to find out so you can define the problem and iterate on solutions as quickly as possible.
Never stop searching for your Big Idea
The most underrated benefit of an enterprise is the frequency and depth to which you’ll be exposed to highly complex new problems. Many entrepreneur-types I’ve encountered are reluctant to join large companies for fear of slowing down or losing their edge, but let’s be clear: the career stagnation we associate with large companies isn’t inevitable — it’s a choice. Your ability to learn and solve problems won’t suddenly evaporate because the size of your company has changed.
Simply put, the best (and most successful) business ideas come from personal exposure to an existing inefficient system. Brian Chesky and Joe Gebbia founded Airbnb because they couldn’t afford their San Francisco loft. Travis Kalanick thought up Uber when he couldn’t get a cab. Marc Benioff experienced the pains of the traditional software model and left a high-paying corporate job to found Salesforce and pioneer the SaaS model.
Learning about the operations, scale, and pain-points of a large company is invaluable if you one day hope to go back to the startup pool and create a successful company. Experiencing these challenges firsthand won’t only help you grow as an entrepreneur, they may eventually spark your big idea.
Continue challenging the status quo
At first glance it may not seem like startups and enterprise companies have much in common, but the skills each require to be successful are incredibly connected. Both need visionaries who can move quickly, adapt constantly, tackle a wide variety of responsibilities, and see beyond an initial problem set and plan for the future.
So when looking for your next gig, don’t limit your career path to only one type of company because of what you’ve been told. If you can succeed at a startup, you have what it takes to excel and thrive at an enterprise.
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