The Hardest Jobs for Entrepreneurs to Fill Are Also the Most Important

These are the three thing top professionals look for in startups to persuade them to leave their well-paying job.

learn more about John Joseph

By John Joseph • Mar 31, 2014


Opinions expressed by Entrepreneur contributors are their own.

As an entrepreneur or a budding "wantrapreneur," you've likely attended industry events -- whether cocktail parties or seminars -- where most of the guests work for startups and the conversations seemingly fall into one of two kinds. The first being the people eager to tell you how amazing it is to work with the cohesive, creative, collaborative leadership team at their companies. These people will tell you that they are driven to do their best work every day, in large part because the executives leading the way inspire greatness. The other kind of conversation, while harder to hear, is no less important for lessons learned. This one is a less giddy, more gritty view of the startup experience of long hours every day and a leadership team dynamic that can be most gently described as challenging.

These two very different views of life at an emerging company illustrate just how critical every hire is at the senior-leadership level. To make sure you're getting the right mix of executives to inspire greatness in other employees, you need to look for a rare combination of qualities and personalities. For a company that is moving quickly to capture a market opportunity and scale, it's essential to find senior executives who infuse athleticism into their leadership skills. They need not only the raw intellect to think adroitly and pivot when necessary but also the muscle memory and agility required to build so much momentum, they can run through walls -- not just slam into them.

Related: Rules for Hiring a Startup Team That Believes in Your Brand

These are the hardest people to find, but it's worth your time and effort to do so. With the right dynamics at the top of the organizational chart, it's far easier for young companies to fill the rest of their open positions. That said, it isn't easy. The best professionals in their fields will leave secure, well-paying jobs and wager their futures on a startup if they see three things:

1. Founders with compelling success stories behind them. Going to work for a startup founded by newly minted entrepreneurs is a risk. Going to work for a startup founded by entrepreneurs with successful exit stories from their last ventures is an opportunity. If you've already proven yourself in the market, make sure to communicate that to potential employees.

2. The chance to create a product or service from scratch and potentially help reshape a market. The greatest rewards of startup life come from creating something that didn't exist before -- like turning on a light in a room that was dark or introducing Technicolor to a black and white screen. Many talented professionals spend their careers in jobs where they're never allowed to experience that feeling of creation. This is one of the great draws of startup life.

3. A senior-executive team that works well together: Your talent pool has been to the same industry events you have, and they've heard the same stories about the two very different types of leadership teams at startups. Show candidates that your existing senior team is cohesive, creative and collaborative, and you'll turn one of the most common candidate concerns into a recruitment asset for your company.

Related: These 5 Interview Blunders Will Probably Kill Your Job Prospects

These elements are critical in bringing in the talent who will bolster your second or third wave of recruiting. Ambitious professionals will follow good leaders from company to company, and the networks of those people later become invaluable recruitment pools.

At that point, you can begin cherry-picking the best candidates. Working for a startup is not an event, it's a lifestyle choice. You need to find the employees who can turn long hours and risk into adrenaline to fuel success. These ideal employees are willing to sign on for an extended period of time, and they have support networks at home that provide them with the personal infrastructure they'll need to help build the company.

In searching for these ideal hires, it's important to look for people who can be utility players. Every employee needs to be able to succeed in a variety of situations across the organization. There might be multiple functions within your startup but employees have to easily collaborate beyond their own jobs and treat departmental boundaries as if they're made of vapor, not brick.

Your startup leadership team must comprise highly motivated, creative self-starters in every department but most critically, in the executive suite. Then when your company name comes up in conversation at the next industry mixer, guests will be eager to hear more.

Related: How to Hire Someone Aligned With the Company's Mission

John Joseph

President and co-founder, DataGravity

John Joseph is the president and co-founder of DataGravity, a company focused on helping enterprises extract value from data. 

Related Topics

Editor's Pick

Have More Responsibilities at Work, But No Pay Bump? Use This Script to Get the Raise You Deserve.
Black and Asian Founders Face Opposition at All Levels — Here's Why That Has to Change
Business News

The Scam Artist Who Robbed Backstreet Boys and NSYNC Blind. 'Some of the Guys Couldn't Pay Their Car Payment.'

In the 1990s, Lou Pearlman made millions creating the Backstreet Boys and NSYNC. It was all a giant Ponzi scheme.

Thought Leaders

5 Small Daily Habits Self-Made Millionaires Use to Grow Their Wealth

We've all seen what self-made millionaires look like on TV, but it's a lot more subtle than that. Brian Tracy researched what small daily habits these successful entrepreneurs adopted on their journey from rags to riches.

Starting a Business

How To Raise Capital For A New Business Idea

These practical methods and tools are available to entrepreneurs who want to raise money to create their own new businesses.

Business Ideas

55 Small Business Ideas To Start Right Now

To start one of these home-based businesses, you don't need a lot of funding -- just energy, passion and the drive to succeed.

Business News

Mark Cuban's Grocery Store Hack Will Help You Score Cheaper Produce

The billionaire talked about his early days in Dallas when he was strapped for cash.