A common organization problem – your sales are a bit flat and the concern is meeting the expansion objectives for your company. As you evaluate new sales talent, consider the pros and cons of hiring a former successful entrepreneur.

Hiring a successful entrepreneur can offer benefits to getting the company back on track. Most entrepreneurs have unique story telling skills and understand how to sell. They can be a unique alternative for many organizations. They can disrupt the corporate culture – positively or negatively.

Most entrepreneurs with previous success will understand the moving parts of launching a product or service to marketplace with speed and a “vision” mentality. They will be risk takers and know what it takes to have grit when times are tough. With previous successful ventures, they will understand cash flow and how to become creative when times are difficult especially when hearing those dreaded words from the accountant or internal finance leader “There is not enough cash to cover payroll, what do you suggest we do?”

Previous successful entrepreneurs normally will bring two key attributes:

  1. They are good communicators
  2. They have existing relationships


One question to ask yourself is how the unique characteristics of an entrepreneur can fit within the current corporate culture. Many entrepreneurs might have serious difficulties not being the “leader of the ship”. Since they come from a solo mentality, working within a team may be difficult from the onset. Consider implementing a collaboration methodology into the organization through the use of an accountability system, where everyone has specific roles, responsibilities and project timelines.

Previous entrepreneurs know how to bootstrap a company, but they can be difficult to manage with respect to change. Entrepreneurs can become stagnant quickly without new challenges and retention issues can become a problem. You may want to have a pipeline of projects and innovation opportunities, which will reduce their “drifting” effect. Always consider the ramifications of a non-compete agreement and employment contract to reduce the risk that the entrepreneur uses your business as a learning space to launch a competing organization. I have seen this happen many times!

When you are evaluating talent to increase sales, focus on how they can help to reach the short and long-term goals of the company. The entrepreneurial “hard-work” mindset and drive are hard to find in many team members and might be a unique fit for your organization.

If you are looking to hire an Entrepreneur to help grow your business, READ our “Entrepreneur Interviewing Process – 10 Key Consideration Steps”.