Join us for our installment of the Pacesetters Doing Business series featuring Mass General Brigham on August 7, 2025.
08/07/2025
1:00pm - 2:00pm
Virtual
The BIMA Summer Sizzler is a chance to network with your digital media industry peers from the agency, publisher, and adtech community!
08/14/2025
6:00pm - 9:00pm
Fenway Park
Enjoy networking with fellow members and hear from Chamber Staff on how to best leverage your Membership to achieve your business goals.
09/09/2025
3:00pm - 4:30pm
Greater Boston Chamber of Commerce
This program is in redevelopment. Click this page for DEI resources.
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Owners of small businesses are naturally attached to their companies on a personal level, a dynamic that is often compounded when the owner is also its founder. While it’s critical for them to remain involved in growth strategy and execution, they need to know when it’s time to seek help in the form of hiring a sales manager and/or representatives. The decision to do so or not can represent the difference between successfully scaling a business and flat growth or even declining revenue.
As sales is the lifeblood of any company, handing over primary responsibility to others is as much an emotional decision as a logical one. It is thus totally understandable why owners are often reluctant to do so. “No one knows the business as well as me, so how could anyone else do a better job selling than I?” is a question that many owners ask themselves, their employees, and outside advisors. While it’s generally the case that few employees, if any, understand all aspects of the business better than the owner, that does not mean that the owner is the most capable person at each function. For example, owners/Chief Executives commonly hire a Chief Financial Officer to bring financial and accounting expertise to the company, or someone with Human Resources expertise to handle personnel issues, and generally don’t question their decisions to do so. So why is it so difficult for owners to give up control of selling?
While healthy profit margins are generally the key metric for business owners, and effective operational and cost controls can be as critical as topline revenue, the positive feeling that comes from acquiring new customers or expanding relationships with existing ones can often generate unparalleled optimism for a business owner. Particularly if the viability of the business as a going concern is tied to a handful of key accounts or finding new ones, it can feel more risky to transfer responsibility for sales to someone else than it is for other functions, and it very well may be. At the same time, it is often more of a question of to whom rather than if.
Business owners should thus ask themselves the following questions before finding the right person or people to lead sales efforts:
If you are an employee or outside consultant helping a business owner make the decision to build a professional sales organization, help them get over the emotional barrier first before attempting to persuade them with logical arguments about the aforementioned and related questions. Let them know that they can still be involved with customers and building the strategy that the sales team will implement on their behalf. Also help them envision positive emotional payoffs beyond simply more revenue. For example, do they really enjoy all of those sales trips and time away from business operations and their loved ones and hobbies? Once they can envision the positive personal benefits they can begin to evaluate the business issues with an open mind.
If the decision is made to move forward, the next steps involve assessing the specific jobs required and sourcing the talent to fill them. In many cases, particularly if the owner wants to continue to stay involved with sales in some capacity, a prudent first step is to hire an experienced individual contributor sales representative. Hiring someone from a competitor or with industry experience is important. Invest in training this person both in terms of product training and addressing any skills gaps they may have. Once the new hire is onboarded and productive, owners can determine if they need to hire a full-time sales manager and/or more sales representatives. Alternately, if the company only needs to hire one person initially, a “player-coach” model can work in which the new hire handles not online frontline selling but also the sales management function in terms of reporting, working with marketing, etc.
Regardless of what specific tactical approach is the best for a particular business, owners should realize that it’s okay to both stay involved and seek help. Outside advisors like sales consultants, trainers, and coaches can serve as valuable, unbiased advisors. While hiring a sales team is not always necessary for all small businesses, considering doing so—and developing a thoughtful plan to make a determination—is the right path for most.
Founder & Principal,
SalesOrg Solutions LLC
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