Beating the Odds to Land a Startup Opportunity

start-up-sign.From the outside, the startup world appears flush with opportunities. New companies are formed daily, raising huge sums of venture capital to take on the incumbents and put your company out of business. The game is massive and dynamic. So why do proven executives find it so hard to crack into the startup world?

The entrepreneurs founding these startups are by and large young and inexperienced business leaders. They may know technology, or markets, or strategy, but chances are they would never have qualified for a leadership position at your company, let alone have been your boss.

They favor doers over managers. There is almost a disdain for professionals and experience… it ties you to the past, not the future. They want “talent” not “executives”. They will take a “10X” engineer any day over an engineering manager.

And they are more comfortable with people who look, talk and act like them. Sh*t stirrers and glass breakers. There is little room for order and process in their “disruptive” world.

Add to the unconscious biases against women and minorities, a very real bias against age, and you see the problem. If they are successful they will need you, and people like you, to build the tracks and make the trains run, but for now, they are suspicious.

So how do you get into the game? First, it’s important to respect what makes startups so different. They are not businesses per se, not yet anyway. They are products or services, they are engineering or marketing, they are equity or debt, but they are not yet businesses. And they move quickly. Frankly, that is there primary competitive advantage. They travel light and fast.

Process is seen as the antithesis of disruption-scale creativity. So you need to appreciate that management in a startup is not what is commonly viewed as management in a scaled operating company. Forget what they taught you in business school.

Large companies win by managing complicated organizations and processes to achieve results; startups win by taking leaps of faith and sticking the landing. When modern management techniques were invented in the early 20th Century, hierarchical leadership was the ideal. To translate the vision and ambitions of a leader or set of leaders down through the organization so even the lowliest production worker could contribute to success.

But in startups people are not the means of production, they are the means of creation. Minimally Invasive Management focuses on serving the creative talent by helping them set goals, resolve conflicts, communicate across functions and develop skills. A Minimally Invasive Manager is not the old boss; they are a new servant leader. Critical to success, but not the top of the food chain.

So where do you fit? First, look for opportunities where you can add value in the creation of the business, not simply the running of the company. Demonstrate that you are talent, not just a suit. Show them that you can operate lean and mean. That you have a passion for what they are doing and where they are going. And that you are willing to take a step back; in title, in compensation, in status, whatever; in order to take two steps forward after you prove yourself.

Whatever you do, don’t directly import your old methods and tactics. They don’t want to hear about how you did it at your old job, they want you to apply your experience to their situation and arrive at a bespoke approach to their challenges.

Where to start? There is an infinite amount of media covering every new startup and venture capital investment. Pour through it. Look for products or services that excite you, because you will need to communicate that excitement to win them over.

Use your network to reach out to founders, leadership, investors and/or board members. These are small, clannish organizations so don’t worry about tripping over formality.

Don’t just tell them about your qualifications, tell them why you want to work for them and what you bring to the table. Show them you will make a real difference to their success. Be prepared to explain why your experience will benefit them and not be an impediment. Convince them that you won’t need a staff or a big budget, but rather that you can roll up your sleeves and work the long days and nights to get where they are going. And of course, when the time comes, remind them that you have the proven ability to scale.

Don’t wait for a job posting to make contact. Be proactive. And then be respectfully persistent. If there is nothing for you at the moment, offer to advise or train their people, for free. Startups like to “try before they buy” so use that to your advantage. While they are scoping you out, you are making sure that this merry gang is right for you. If not, no harm no foul, and no explaining away a mistake on your resume.

And the roles inside a startup change rapidly. As the company scales and business takes off there are plenty of opportunities to assume more responsibility. Don’t over-think the company’s prospects or the job specification; you can’t know the former and the latter will change rapidly. Just make sure the role is one you can crush, and that it will lead to more opportunities down the road when you do.

The good news is that more and more startups are savvy to providing “game changers”, people whose experience can accelerate or amplify their success, with flexible and short-term roles. So you can test the waters and not encumber yourself with a commitment you may regret later. There are recruiting firms who specialize in filling such roles, particularly for finance, marketing and sales executives.

If you have the skills, perhaps you could volunteer to be a coach or mentor to their junior people already working in your area. And if you are qualified, maybe you can join as an independent board member. There are many ways to get your foot in the door.

In our book, Straight Talk for Startups, 100 Insider Rules for Beating the Odds, we present a broad set of entrepreneurial best practices that will further help you appreciate the differences between startups and operating businesses. As Elaine Paul, CFO of Hulu said:

“This book accelerates your learning with advice from experts who’ve been there and done that. Read it cover to cover to save yourself from making rookie mistakes that upend all too many big ideas.” 

© Randy Komisar 2018, All Rights Reserved


Randy Komisar Jantoon Reigersman

Randy Komisar Jantoon Reigersman

Randy Komisar is the co-author of Straight Talk for Startups (HarperBusiness; June 2018). He is a venture capitalist with decades of experience with startups. He is the author of the best-selling book The Monk and the Riddle, about the heart and soul of entrepreneurship, as well as numerous articles on leadership and startups. He is also the co-author of Getting to Plan B, on managing innovation, and I F**king Love that Company, on building consumer brands. He taught entrepreneurship at Stanford University and is a frequent lecturer at universities, as well as a regular keynote speaker on entrepreneurship, innovation and leadership. He joined Kleiner Perkins Caufield & Byers in 2005 to focus on early-stage ventures. Prior to that, he created the role of “Virtual CEO” to partner with entrepreneurs to help them and their businesses achieve their potential, serving as Virtual CEO for such startups as WebTV and GlobalGiving. He was a co-founder of Claris Corp. and served as CEO for LucasArts Entertainment and Crystal Dynamics. Randy was a founding director of TiVo and Nest. He served as CFO of GO Corp. and as senior counsel for Apple, following a private practice in technology law. He has also served on dozens of private and public company boards and advises such organizations as Road Trip Nation and the Orrick Women’s Leadership Board. Jantoon Reigersman is the co-author of Straight Talk for Startups (HarperBusiness; June 2018). He’s a seasoned financial operator with extensive experience in startups and growth companies. He serves as Chief Financial Officer of publicly traded Leaf Group (NYSE: LFGR), a diversified consumer internet company. Earlier in his career, he served as CFO of Ogin Inc., investor and member of Goldman Sachs’ European Special Situations Group and investment banker at Morgan Stanley in their mergers and acquisitions team. He also initiated and led the 9000METER expedition, the first expedition to attempt 9000 vertical meters on human power by diving over 152 meters below sea level and by climbing the summit of Mount Everest at 8848 meters. He is a Fellow of the inaugural class of the Finance Leaders Fellowship and a member of the Aspen Global Leadership Network. For more information, please visit http://straighttalkforstartups.com

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