How to Choose a Startup Company to Join

This guest post is from Daniel Stein who graduated from the UW TMMBA program in 2014 and is a product manager at Smartsheet.  Prior to Smartsheet, he worked at Microsoft for four years as a program manager for Office.com and Excel.  In his free time, he performs as a professionally trained classical flutist and appreciates the natural beauty of the Pacific Northwest.

Many of us enrolled in an MBA program with a desire to transition to a smaller company, where we could have a broader role with more challenge, growth, and responsibility.  But it isn’t obvious how to identify the startup that best aligns with our career goals.  In making the transition from program management at Microsoft to product management at Smartsheet, I found it useful to evaluate opportunities in terms of three criteria: role, product, and people.

Your role should be indispensable to the company

It isn’t enough for a company to have the role you are looking for; the company should consider your role to be critical to the business.  I was looking for a product management role where I could work broadly across the company to ship great software that would delight customers and grow the business.  But I knew that I would only be successful at a company that understood product management and valued it as part of the core culture.  At Smartsheet, there are posters on each floor with the names and faces of the product managers, to ensure that everyone in the company knows where to direct product feedback.  Smartsheet’s CEO Mark Mader personally interviews prospective product managers because of the high-profile nature of the role.  Through these signs and others, I could tell that Smartsheet realizes that their product needs to be great for the company to succeed.  This in turn makes it a good place to make an impact as a product manager.  If your company truly understands and values your role, both you and the company will be set up for success.

The product should benefit from your unique expertise

People often talk about working on a product you are passionate about.  Ideally, the product you work on should also use your unique knowledge and experience.  In making a career transition, it’s important to balance what you change versus what you keep constant from your prior job.  Among the factors of role, company size, and product area: shift the factors where you want to grow, and keep some factors constant to hit the ground running and offer a competitive advantage versus other candidates.  In my transition, I shifted role (program management to product management) and company size ( >100k to <200) to gain the experience I wanted.  In choosing Smartsheet, I kept good alignment with my past product experience to make the transition successful.  At Microsoft, I had worked on Office, so I felt right at home at Smartsheet, which focuses on business productivity and also includes a spreadsheet interface.

If you are considering two companies that both have the role and team you are looking for, favor the one where you can offer unique expertise.  It will serve as your bridge to get the job in the first place and be successful once you are there.

The team should be the right size, with the best people you can find

Choosing the right team is the single most important factor in choosing a company.  It goes without saying that you should work with the best people you can possibly find. You should be excited to learn from and work long hours with everyone you meet in your interview loop.

It’s also important to choose a company whose stage matches the experience you want to gain.  This depends on how much “learning through doing” vs. “learning through others” you would like to have.  If you join a very early stage company, you’ll likely be the only person in your role, so most of your growth will be through experience.  If you choose a more established company, there will be at least several others who are experienced in your role.  If the company is too large, you may have less breadth and responsibility than you would like.  I was looking for a company between 100-300 people so that I could work on a small team of strong product managers and still have broad responsibility.  I found this stage to have a good balance of “learning through doing” and “learning through others.”

Of course, financial risk is also an important aspect of choosing a company size.  A smaller company will have greater risk in both compensation and job stability, but it can be worth it if you love the product and team, and you want experience of building a company from scratch.  It’s never a good idea to join a company with the primary expectation of a large financial upside.  That sort of thing is very difficult to predict, so optimize for what you can control: loving the team and the product.  If you consistently choose great people and optimize for your own learning, you’ll do well over the long term of your career.

Getting started: Identifying candidate companies

Once you know your framework for choosing a startup, it’s time to create a specific list of companies to explore.  Many great startup companies are not yet widely known, so it takes some research to identify them.

One of the best ways to identify companies is through the portfolios of top venture capital firms.  Companies that have received funding (especially repeat funding) from well-respected VC firms have already undergone vigorous vetting and have access to resources that will help them to succeed.  In Seattle, Madrona is the largest VC firm, so it is worth researching their portfolio to find companies that meet your size and product criteria.  Some of the Bay area VC firms have also invested in Seattle companies.

Apart from VC firms, it’s also worth following local industry news & networking organizations.  Geekwire is a primary source for tech news in Seattle, and they maintain a list of startup companies on their site.  Local meetups like New Tech Seattle and New Tech Eastside are also great ways to connect with local startups.

Finally, your own network is a good way to identify candidate companies and also the single best way to get your foot in the door at any company.  Once you have identified a startup company of interest, use LinkedIn to see if you have any connections at that company.  Regardless of what department they are in, ask them to meet up for coffee to learn more about the company culture.  If you are intrigued, ask them if they would feel comfortable introducing you to someone in your target role.  It doesn’t matter whether the company currently has openings in your department, because if they are successful, then they will soon!  It’s all about making the connections and keeping in touch.

Happy startup hunting, and I look forward to hearing about what you learn.