A Guide to Hiring and Onboarding Top Outside Sales Representatives

According to Xactly, companies that experience a 5% increase in sales rep attrition can see a 4–6% rise in selling costs, with revenues potentially dropping by 20%. This underscores the critical importance of hiring the right outside sales representatives.

The role of an outside sales rep is pivotal: they are the face of your company, engaging directly with clients, closing deals, and fostering long-term relationships. 

However, the challenge lies not just in filling the position, but in attracting and retaining top-tier talent who align with your company's goals and culture.

In this guide, we'll discuss the best practices for hiring outside sales reps, highlight common pitfalls to avoid, and share expert strategies for building a high-performing sales team that drives sustainable growth.

What Does an Outside Sales Representative Do?

An outside sales representative plays a critical role in your business by directly interacting with potential clients and driving sales. 

Unlike inside sales reps who usually work from an office, outside sales reps spend much of their time on the road. They meet clients face-to-face, attend events, and build relationships crucial for closing deals.

Their primary responsibility is to generate new business, but they also maintain and strengthen relationships with existing clients. 

A well-rounded outside sales rep acts as your company's face, delivering personalized presentations, demonstrating products, and negotiating terms to secure sales.

Inside Sales vs. Outside Sales

When it comes to sales strategies, businesses often decide whether to hire inside sales representatives or outside sales representatives. 

Both roles are integral to a company’s sales process, but they have distinct functions and suit different business models. 

Understanding the key differences between inside and outside sales can help you determine which is best suited to your needs.

Also Read: Inside Sales Compensation Plans and Commission Structures

Key Responsibilities of an Outside Sales Representative:

Prospecting and Lead Generation:

• Identify new leads through research, networking, and cold-calling.
• Build a strong pipeline by consistently seeking out potential customers.

Client Meetings and Presentations:

• Conduct in-person or virtual meetings with prospects to showcase your products or services.
• Tailor presentations to meet the unique needs of each client, demonstrating how your solution solves their problems.

Relationship Building:

• Develop long-term relationships with clients, ensuring their satisfaction and encouraging repeat business.
• Act as the main point of contact for clients, resolving issues and maintaining a positive relationship.

Negotiating and Closing Deals:

• Present and negotiate pricing, terms, and contracts.
• Work with clients to close deals while ensuring both parties are satisfied with the terms.

Market Research and Competitor Analysis:

• To stay ahead of the curve, stay informed on market trends, competitor activities, and potential new products or services.
• Continuously monitor customer feedback and adjust sales strategies accordingly.

Sales Reporting and Administration:

• Document activities, progress, and outcomes in a CRM system.
• Report regularly on sales metrics, lead generation, and other relevant KPIs to track performance and adjust strategies as needed.

The Scope of an Outside Sales Rep's Role:

• Autonomy: Outside sales reps typically have more independence than inside reps, as they manage their schedules, meetings, and territories. This freedom allows them to engage clients in a more personalized way.
• Travel: They often travel to meet clients in person, whether that means attending trade shows, visiting business offices, or traveling within a designated geographic area.
• Results-Oriented: The role is largely performance-driven, with reps expected to meet or exceed set quotas in terms of revenue generated, new clients, or deals closed.

Steps in Hiring and Onboarding a Successful Outside Sales Representative

Hiring and onboarding the right outside sales representatives is essential to driving revenue growth and ensuring a high-performing sales team. 

This section covers the key steps in the process. It starts with identifying the skills and qualifications needed, then moves to finding the best talent, crafting effective job descriptions, conducting interviews, offering competitive compensation, and setting clear expectations. 

It also emphasizes the importance of onboarding and training to ensure your new sales rep succeeds from day one.

1. Skills and Qualifications to Look For

When hiring an outside sales rep, identifying the right skills and qualifications is crucial. A successful sales rep needs to balance technical sales expertise with interpersonal skills. Here's what to look for:

Core Sales Skills

• Prospecting: Look for candidates who can effectively generate new leads and maintain a full sales pipeline.
• Negotiation: Ability to negotiate terms, pricing, and contracts while ensuring both the client and company benefit.
• Closing: Experience in successfully closing deals, especially in complex sales environments.
• Communication: Clear and effective communication is essential, both for conveying product value and building client relationships.

Industry Knowledge

• Market Understanding: The ideal candidate should know industry trends, challenges, and competitor offerings.
• Product Expertise: A deep understanding of your products or services ensures that the sales rep can answer client questions and provide relevant solutions.

Soft Skills

• Relationship Building: Strong interpersonal skills and the ability to develop long-term client relationships.
• Self-Motivation: The outside sales role requires a high degree of autonomy. Look for candidates who are self-driven and have a history of meeting targets.
• Adaptability: Sales reps must adapt to changing market conditions, client needs, and evolving sales strategies.

Technical Skills

• CRM Proficiency: Familiarity with CRM systems like Salesforce or HubSpot to track leads, manage opportunities, and report on sales activities.
• Sales Tools: Competence in using tools for prospecting, communication, and analytics.

2. Where to Find Candidates

Once you’ve determined the qualifications for your outside sales rep, it’s time to find the right candidates. There are several avenues to explore:

Job Boards and Recruiting Platforms

• General Job Sites: Platforms like LinkedIn are essential for posting job openings and reaching a large pool of potential candidates.
• Recruitment Agencies: Partner with agencies that specialize in recruiting sales talent. They can help you find candidates with the specific skills and experience needed for your industry.
• Referrals and Networking: Tap into your existing network or ask your team members for recommendations. Employee referrals can help identify highly-qualified candidates who are familiar with your company culture.
• Sales Outsourcing Platforms: Consider using sales outsourcing services or platforms, which can connect you with seasoned professionals for flexible, short-term needs or to scale your sales team quickly.

If you’re looking for a seamless way to scale your sales team with contract-to-hire options or fractional sales leadership, platforms like Activated Scale provide tailored solutions to match the pace and needs of your business.

3. Crafting an Effective Job Description

A clear, well-structured job description is the first step to attracting the right candidates. Your job description should provide clarity on expectations, responsibilities, and qualifications.

Key Elements to Include

• Job Responsibilities: Clearly outline the daily tasks and objectives, such as prospecting, meeting clients, and managing relationships.
• Required Skills and Qualifications: List the must-have sales skills, industry experience, and educational background.
• Performance Goals: Include measurable targets, such as sales quotas, new client acquisition, or revenue generation.
• Compensation and Benefits: Detail the salary structure, commission model, bonuses, and any other incentives or benefits.

Company Culture

Share what it’s like to work at your company, including values, team dynamics, and career development opportunities. This helps attract candidates who align with your company’s mission and culture.

4. Interviewing and Evaluating Candidates

Interviewing is a crucial step in identifying the right candidate. Use structured interviews and evaluations to ensure you're hiring someone who can succeed in the role.

• Behavioral and Situational Questions

Ask candidates to provide examples from their past experience that demonstrate their problem-solving, client handling, and negotiation skills.

Example: "Can you tell us about a time when you turned a difficult lead into a successful sale?"

• Assessing Past Performance

Look for candidates who can share specific metrics, such as sales quotas met, new clients secured, or revenue growth achieved.

• Evaluating Cultural Fit

Determine if the candidate's values, work ethic, and approach to sales align with your company’s culture and goals. Ask questions about their preferred working style, teamwork, and how they handle rejection.

5. Compensation and Incentives

Offering competitive compensation is essential for attracting and retaining top sales talent.

Salary vs. Commission

Determine the balance between base salary and commission. A typical model involves a base salary with performance-based incentives to encourage top performance.

Bonuses and Incentives

• Include bonuses for exceeding sales targets, signing large clients, or hitting key performance indicators (KPIs).
• Non-monetary incentives, such as recognition awards or career development opportunities, can also motivate reps.

Equity or Profit Sharing

Offering stock options or profit-sharing programs can attract high performers who are invested in your company's long-term success.

6. Onboarding and Training Your Sales Rep

Once you’ve selected the right candidate, effective onboarding and training are essential for ensuring their success in the role.

Onboarding Process

• Introduce the new sales rep to the company, its products or services, and its culture. Provide them with a thorough understanding of expectations, company policies, and the sales process.
• Assign a mentor or team lead to guide them through the first few weeks.

Sales Training

• Provide in-depth training on your products, sales tools, CRM systems, and the sales methodology your team uses.
• Offer training on handling objections, closing techniques, and how to track performance through CRM.

Mentorship and Support

• Set up regular one-on-one check-ins to monitor progress, answer questions, and provide ongoing guidance.

7. Setting Expectations and KPIs

Setting clear expectations and KPIs (Key Performance Indicators) helps keep your sales rep focused and motivated.

Defining Sales Goals

• Set clear sales targets, including monthly or quarterly sales quotas, new client acquisition, and revenue targets.
• Break down goals into manageable tasks and milestones to ensure continuous progress.

Tracking Performance

• Use CRM systems to monitor sales activities, track client interactions, and measure progress against goals.

Regular Check-ins and Feedback

• Schedule regular performance reviews to evaluate results, offer feedback, and discuss ways to improve.
• Provide constructive feedback on successes and areas for improvement.

Simplifying How to Hire Outside Sales Reps with Activated Scale

Finding the right outside sales rep can be challenging, especially when you need experienced professionals who can hit the ground running. 

Activated Scale offers flexible solutions that help you hire outside sales talent efficiently, whether you’re looking for contract-to-hire options, fractional sales leadership, or specialized sales support.

Activated Scale Services:

• Contract-to-Hire: Try out candidates on a contract basis before making a full-time commitment.
• Fractional Selling: Access skilled sales reps for short-term or project-based needs without the overhead of full-time hires.
• Fractional Sales Leadership: Gain experienced sales leaders to guide your team and strategy on a part-time basis.

With Activated Scale, you can scale your outside sales team quickly and effectively while minimizing risk and maximizing flexibility. 

Conclusion 

Building a successful outside sales team requires more than just finding the right people; it’s about ensuring they have the skills, support, and motivation to thrive. From identifying key qualifications to crafting job descriptions and setting clear expectations, each step in the hiring and onboarding process is essential for long-term success.

However, flexibility is often just as important. As your business grows, your needs will evolve, and having adaptable hiring options can help you scale effectively. Whether through contract-to-hire roles, fractional sales solutions, or fractional sales leadership, you can bring in top-tier talent without the long-term commitment.

For businesses looking to grow quickly and efficiently, Activated Scale offers these flexible solutions, allowing you to access experienced sales professionals and leaders when you need them most. 

Book a demo call with Activated Scale today!