Should I hire a sales contractor?

Hiring a Sales Contractor: Key Considerations and Expectations

Hiring a Sales Contractor: Key Considerations and Expectations

Hiring a sales contractor can be a strategic move for businesses looking to scale their sales efforts, enter new markets, or enhance their sales capabilities without the commitment of a full-time hire. However, to ensure a successful engagement and achieve the desired return on investment (ROI), there are several important considerations and expectations that need to be addressed.

Key Considerations Before Hiring a Sales Contractor

Experience and Track Record: Look for contractors with a proven track record in your industry or in selling similar products or services. Their experience should align with your business needs, market challenges, and the sales cycle specific to your offerings.

Understanding of Your Business: A good sales contractor should demonstrate a solid understanding of your business model, value proposition, and target market. They should be able to articulate how they can contribute to your objectives and show adaptability to your business culture and processes.

Alignment of Sales Strategy: Ensure that the contractor’s sales approach and techniques align with your overall sales strategy. It's crucial that their methods complement your existing sales efforts and company values to maintain consistency in your market approach.

Clear Contractual Terms: Define clear terms of engagement, including scope of work, duration, compensation structure (fixed, commission-based, or a mix), performance metrics, and termination clauses. This clarity will help manage expectations and reduce potential disputes.

Integration with Your Team: Consider how the contractor will fit into your existing sales structure. They should be able to collaborate effectively with your team, share insights, and contribute to a cohesive sales effort.

Reasonable Expectations for a Sales Contractor

Quick Ramp-Up: Given their experience, sales contractors are expected to have a shorter ramp-up time compared to new full-time employees. They should be able to quickly understand your products or services and start their sales activities within a short timeframe.

Independence and Initiative: Contractors are typically hired for their ability to work independently and bring fresh insights to the table. Expect them to take initiative, identify opportunities, and execute sales strategies with minimal supervision.

Transparent Communication: Regular updates and transparent communication about progress, challenges, and market feedback are essential. Establishing a routine reporting structure can help keep all stakeholders informed and aligned.

Achievement of Agreed Milestones: Set clear performance milestones and expectations from the outset. Whether it's generating leads, closing deals, or achieving specific sales targets, the contractor should meet or exceed these agreed-upon benchmarks.

Compliance and Confidentiality: Ensure that the contractor understands and agrees to comply with your company's policies, procedures, and confidentiality requirements. This is crucial to protect your business interests and maintain professional integrity.

ROI and Payback Period

The ROI from hiring a sales contractor can manifest in various ways, including increased sales revenue, expanded market reach, and enhanced customer relationships. The payback period can vary depending on several factors:

Sales Cycle: Longer sales cycles in industries like enterprise software or B2B services might extend the time to recognize ROI.

Market Conditions: Economic factors and market demand can influence sales outcomes and the time required to see significant results.

Compensation Structure: The contractor's payment terms (upfront fees vs. commission-based) can impact the initial investment and how quickly the engagement pays for itself.

Typically, businesses might start to see a return on their investment within 3 to 6 months, but this can vary widely. Setting realistic expectations, aligned with industry benchmarks and specific engagement terms, is crucial.


Hiring a sales contractor can provide businesses with the agility, expertise, and strategic advantage needed to navigate competitive markets. By carefully considering these factors and setting clear expectations, businesses can forge productive partnerships with sales contractors, driving growth and achieving a favorable ROI within a reasonable timeframe.