I was once on a call with a marketing agency owner... let’s call her Linda. On this call, I discovered that she was successful in company sales as an inside rep. She was a well trained and successful sales person previously, with a well-known brand.

Sales shouldn’t be a problem. So why did she need to talk to me?

After Linda started her own business, she started suffering from equilibrium imbalance. Linda shared a few things with me, such as:

• She can’t afford to hire a better and more experienced team with industry specific experience.

• Most people know her and her reputation, so they only want to deal with her.

• She doesn’t have as much time to do sales and manage the business, interact with clients, and train her team.

• In the past, key team members have been “stolen” away for higher salaries and more benefits than she can offer.

I knew just how she felt- been there, done that.

When I asked Linda why not just raise the prices and sell more so she could share profits with employees and keep key team members, her answer was a hard learned lesson.

“Selling for a well known brand is much different (and easier) than having to sell for your own company.”

Why is that?

She is the sales person, and it’s her name on the door, so in reality she has to sell herself and her team. It’s also harder to sell retainer work rather than project work, especially with a junior team. It’s very much like a startup trying to get their first sales. The team, process (machine) will not be where you want it to be. It's the salesperson's job to understand the context of the client's business and construct the vision on how you can help as opposed to showing a slick presentation or having the perfect machine.

Entrepreneurial sales skills extends beyond just finding new business and closing new clients. The ability to dig deeper, ask tough questions, understand context, and empathize are all skills that entrepreneurs will need to hire as well. Past success selling for a company doesn’t guarantee success selling as an entrepreneur.

Have you made the transition from selling as an employee to selling as an entrepreneur? What challenges did you have to overcome and what hard lessons did you learn? Can a sales coach help you be more effective with what selling time you have?