Changing gears: making the move from corporate enterprises to startup environments

Say you’ve only ever worked in a mature company – perhaps one that has thousands of employees or has undergone an IPO, start-up environments are an exciting way to change gears for professional growth. From having the freedom (or requirement) to work on a broad range of projects to flattened hierarchies empowering you to make and contribute to decisions, you know there is a lot of impact to make and credit to gain by joining a start-up. You will likely be leaving behind some of the stability and other benefits that come with the more established company infrastructures you’re used to. Yet you’re near enough sure that you want to make the pivot. Questions that linger might include:

• How do enterprises and startups differ?
• Which parts of my corporate training set me up for success in a startup environment?
• What will I have to unlearn?
• What are some tells and healthy signals to look out for in startups?

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So let’s explore them!

Beginning with the facts, startups are risky. In the Corporate vs. Startup debate there is a tendency to only ever sell the upside of the latter. Every startup will change the world. Every startup will mint millionaires of their rockstar operators. Or, so go the ideals! Startup reality is often not so given. Throughout the process of finding an opportunity right through to the first few days in a role, there are ways to de-risk the bet you’d be making on a bright, young company.

One of the more immediate ways to suss a startup out is to look into the leadership. Is the founder prominent in the company? There may be an origin story about how the company came to be and what the founder stands for, found on the website. Dig deeper to find interviews with the founder and get a sense of their history. Some example profiling questions:

• Are they a serial entrepreneur?
• An industry veteran?
• A wunderkindt with limited experience in the industry? Or reframing the question: a young person can bring fresh ideas to a market in need of innovation.

There are advantages and disadvantages to all scenarios, so work them out. If you followed the story of Elizabeth Holmes even a little bit, you know that a lot of experienced people believed in her story as a prodigy. But entering into a field like biotech with little experience is not the same as starting a social media company after dropping out of undergrad. Holmes’ accomplice Sunny Balwani was a serial entrepreneur and helped to get their company to a billion dollar valuation, but he had no experience running a lab. An industry veteran may have close information about the field and product development- a good product is at the heart of every successful business. But it’s possible that the industry vet is not prepared for the scrappiness of a start-up and the fundraising and networking requirements to keep the company going. Leadership extends to the board and the investors, so finding out what you can about the composition of the advisory board and the investors is going to inform how the organization will be directed. 

Check out Gergely Orosz' approach to profiling the founder of the recently topical Fast.

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Researching companies and roles

• Like any position, it’s important that you connect with the mission of the organization or the product developed. If you’re interested in a move to a start-up, it means that you’re looking to be challenged to be a larger part of shaping the future of a company and its output. Make sure you genuinely feel excited about the product. 
• Consider what you may be gaining and losing by leaving a corporate position for a start-up role. You are leaving behind a structured organization that has well established infrastructure with sufficient resources to get done what you need to get done. Start-ups may have fewer processes in place and can require you to work quickly and to tap into your problem-solving resourcefulness.  
• Compensation: consider the risk vs reward scenario. Will taking a lower salary with worse benefits pay off in the long run IF the company is successful? It could be a risk to take this leap, but if the company is the right fit, you will be able to play a role in helping bring that company to success. A corporate position may be more stable but you are less likely to have a role in charting the course to success. 
• As said above, but saying it again for good measure: look for founder interviews and company reviews to get a better sense of the culture and if it would be a good fit. 
• Network! Brene Brown says "courage starts with showing up and letting ourselves be seen," and this applies to networking. Seek out connections to employees and ask for an introduction. Start-ups are often at conferences and events advertising their work- it could be a great time to strike up a conversation with the employee. Your research will come in handy for these encounters. 

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Applying

• Whether or not you were able to network a connection to a hiring manager, a cover letter and resume will likely still be required, as well as some persistence. Tailor your cover letter to the organization you are applying to. Corporate HRs and hiring managers may be focused on your past and how it will apply to your future work, looking to mitigate risk by learning about your performance in similar settings. Start-ups too will want to see a resume with experience that shows that you can handle the work, but they are more focused on finding self-starters who can think creatively and on their toes. Emphasize how you can bring value to the start-up, be as specific as possible. If you can name an actual issue and explain how you would address it, it’s a great way to stand out. 

• Remember: Start-up managers are looking for someone who knows more than they do, so that the work can be confidently passed off. 

• Start-ups may be looking at you beyond your application materials, your online presence should strategically reflect you and your passions. Do you have a blog or portfolio online? It is advertising for you, so be sure it reads like that! 

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Interviewing

• As with any interview, it is an opportunity for you to learn about the company just as much as it is a chance for them to learn about you. Ask lots of questions. Structures that you take for granted in a corporate position are worth asking about when moving to a start-up. You may ask about how your success will be measured and if there are regular opportunities to discuss your future, even if at your previous job professional reviews were built in. 
• Ask about the qualities needed for success at the company and what support is offered. Corporate culture is typically slower paced with multi-functional teams. Start-ups are by nature still building up teams and processes. It’s likely you will be more of an individual contributor or working on a small team. This can be a significant shift in working style so figuring out the support you need to personally succeed is important. Is there a formal or informal mentoring program? Is the CEO available to staff for one-on-ones? What kind of timelines do employees work with- short turnovers, long-term projects, or a mix of both? 
• How do employees connect outside of work? Are there opportunities to get to know people outside of the day-to-day? If you’re someone who thrives working on a team or with colleagues with a shared mission, it will be helpful to know that there are regular karaoke nights and regular staff retreats.  

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Negotiating Employment

• You’ve received an offer- great! Now’s the time to negotiate. Hopefully you’re excited about the company and the opportunity that lies ahead. Start-up positions can be competitive so it’s time to congratulate yourself and to remember the value you are bringing to the table. There is an inherent risk in joining a start-up. Your employment package may include equity, but the value is undetermined and the future of the company may be uncertain. It’s possible you are leaving something with a known value (the salary at a corporate role and maybe even equity- likely a smaller amount but with more certain value). Be sure you are entering your new position with full awareness of the risks you are taking and that you feel comfortable with the trade-offs.  
• This goes beyond salary and equity- start-ups may have limited benefits compared to mature companies. If you anticipate that your position may be intense with a broad scope of work, make sure that your personal and vacation leave is sufficient for what you need to maintain balance. 

• Remember: Voicing your needs at an emerging company has the potential to create systems that will benefit all employees, current and future. If you are the first person to request paid parental leave, negotiating a generous (by corporate standards) paid leave may set a precedent that will support future parents in the company. 

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