Sell Me This Pen by Brian CalifanoSmall business owners and colleagues often debate about whether or not it’s wise to hire a salesperson. 

Now I know that all the salespeople reading this are saying: But hey, how do you make money without sales?

It’s true — you need sales to make money. However, the question is not whether or not you sell, but how

The most common concern about an outside salesperson is that he or she may not fully understand the business or service. Investing in an employee requires strategy, thought, and faith — not to mention time spent navigating labor law complexities.

Here is a simple yet powerful statement: without cash flow, there is no business. Salespeople promote your name and organization, thereby ensuring an ongoing revenue stream to sustain the business. Businesses can either outsource sales, hire an internal salesperson, or hire a business development person with an extensive rolodex that connects your business with the right people. The third option, while not quite sales, comes at a lower overall expense to your business, but is still an effective way to generate leads. 

So if you’re thinking of outsourcing sales, here are some things to consider: 

Ask him or her about process. Many people who don’t know sales think it’s all about turning on the charm. As Jordan Belfort once said, “Sell me this pen.” All successful salespeople know how to target their intended audience and market the strengths of the product to the end user. Sales are accomplished through a series of communications, meetings, and “getting out there.” It’s important to make sure you understand the salesperson’s process to determine if it fits with your company’s processes and procedures.

See if there is a good fit. This individual will represent your company. This person will attend trade shows, meetings, and be the face of the company — conveying your mission and values. You don’t want someone out there contradicting the company’s message to the outside world. And if geographically possible, it’s best to meet the potential salesperson in-person —  you can better understand somebody when you’re in the same room as him or her. 

Determine if he or she will be an advocate for your company. Enthusiasm is critical. You will want a rep who will go beyond just selling product or service — you need a cheerleader. As a real simple example, you don’t want to hire a vegetarian if you own a meat processing company. Your best bet is to hire someone who lives the product and is a customer as well. 

So is there a magic formula for hiring a salesperson? Unfortunately, no. As a business owner, you must first decide whether or not you want to focus on sales to drive business or if you want to be focused on the day-to-day operations of your company. You can’t do it alone. Delegate as needed. Sales is a unique skill that not everyone has, but those that do are very successful and can bring much wealth and prosperity to the companies and owners that they work for. 

Takeaway: If you’re a company that is seeking to grow, a fractional CFO will help you determine what your expected ROI is on an outside salesperson or how this will impact your topline. For a free diagnostic on whether you should hire within vs. outsource your sales process, reach out to Brian or Scott at

Brian Califano & Scott MargolinBrian Califano

Scott Margolin

Co-founders & Managing Partners


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