Selling at a Startup, and Why I Joined Stackdriver


Sometimes it’s the simplest advice that sticks with you the longest. Years ago a colleague offered me a piece of advice to evaluate career opportunities, specifically the type of teams you want to work with. He explained how few companies can attract and retain smart people with the right attitude, people who are “smart and cool”.  This is a simple benchmark, but I’ve thought of the “smart and cool” test when thinking through every career move I’ve made since, several of which have been at startups.

If you’re in sales, or just getting started in your sales career, technology startups provide a great opportunity to accelerate your work experience and personal development. Challenges and problems arise frequently and unexpectedly, requiring you to think quickly and come up with creative solutions.  Most importantly, you can help build something (a product, company, team, or all three) by testing techniques and processes and working towards a challenging, sometimes seemingly impossible, team goal.

But what makes startups most interesting is how they attract a different personality type than those at big companies.  A different set of values — overcoming challenges at all costs, a strong drive to create, appetite for risk and change, high work output – these all set the company culture.

There are lots of startups to choose from, so how do you evaluate what type of environment would be best for your career?  Even if you’re not personally investing your money in the company, you’re investing a lot of time, and putting this logo on your resume.  You need to think through more than just compensation and your direct responsibilities.

Coming from a sales perspective, I like to look at several things to assess an opportunity:

Market Opportunity

Just like a venture capitalist, you should think about working in a big market with lots of potential for growth.  It’s perfectly okay if there are competitors, because it means you won’t have to evangelize a new approach before you can start selling.

“Cool solution. Now what was the problem?”   If this quote seems fitting, run away!

Personal Interest

In sales, you need to be passionate in what you sell.  It’s less a love for the product as much as a desire to work with the problems your clients face and helping to solve them.


You can identify the culture based on the personality types of the leadership team who help set the culture.  We spend so much time at work if you don’t enjoy being with your colleagues, this should raise a concern.  What is the attitude of those you met from the company?


What is the leadership style of the executive team?  Would you describe them as authoritarian, visionary, scientific, or maybe lead-by-example types?  Do they impress you?  What are their backgrounds, what is their plan, how do they respond to tough questions?

Ask yourself if you would feel comfortable asking them for help, and pay notice to how they answer your questions, even if they seem basic.  Great leaders are good teachers, and if they can’t communicate effectively with you they won’t be successful spreading the message to prospects, partners, investors, and attracting more talent.

Career Growth

In the role you’re evaluating, can you take on a level of responsibility that will continue to challenge your skills?  Typically in startups there’s more problems to solve than time to solve them, and you should be able to discuss a path to grow into additional responsibility.

I joined Stackdriver because it met all of these criteria.  I wanted to be part of creating a successful company, test my leadership skills, and help build and coach a sales team.

In past sales roles, I learned about the growth of cloud computing by talking to my counterparts at Amazon Web Services and was surprised by the names of the companies who had migrated.  This is a space with massive growth potential, however, the flexibility of the cloud brings new challenges Stackdriver is in a great position to solve.

Stackdriver presents a tremendous growth opportunity to my career and I’m excited to find out what we can achieve.  In this new role I would like to replicate elements I’ve seen from other successful teams, and to eliminate some of the barriers novice sales professionals face when advancing their sales career.

Are you interested in joining an exciting startup to accelerate your sales career?  Check out our jobs page for updates on hiring, and get in touch!

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