How to Hire and Retain Great Salespeople for Your Small Business or Startup | Essential Business Owner Skills

Sean Lund-Brown

Salespeople are crucial to a business's growth and reputation in its field. These employees interact directly with your potential customers or partners, so they are one of the key faces representing your brand. It can also be hard to "sell" your products or services without a salesperson turning qualified leads into happy customers. Without great salespeople, your business will experience less revenue and growth opportunities.

Take the time to vet potential salespeople so they can fit into your company culture. Optimize the job title and provide a clear description of the daily tasks when you advertise for a position. Conduct background checks, and ask specific questions during the interview. To retain great salespeople, offer a variety of incentives and provide professional development opportunities.

Responsibilities of a salesperson

Before we dive into how to hire and retain great salespeople for your small business or startup, let's do a quick overview of what a salesperson is. Different types of responsibilities can fall under this role, depending on the type of business you have.

Salespeople are the bridge that connects customer needs to the product or service your company provides to fulfill this need. They support incoming revenue and are crucial to generating customer loyalty and retention.

While each specific role can differ, the overall responsibilities of a salesperson are:

● Greet, reach out to, or interact with customers

● Provide support to customers who have concerns or questions

● Educate customers on products and services

● Gain insight into customer needs

● Provide feedback on customer complaints

Different types of sales roles

"Salesperson" is an overarching role that can break down into more specific responsibilities depending on your business structure. If you are a startup business, you may be looking to hire your first two foundational salespeople.

However, if you are a growing small business, it may be time to offer specialized roles to different people in your sales team.

Here is an overview of seven different types of sales roles that can exist:

Outside Sales Representatives interact with customers face-to-face outside the office and close leads.

Inside Sales Representatives are responsible for managing and maintaining existing client relationships.

Client Services support the needs of existing customers to ensure retention and company growth.

Sales Support Specialists work behind the scenes to support the sales representatives.

Sales Development Representatives are responsible for researching and networking with potential new customers, working closely with the marketing team, and qualifying new leads that come in before handing them over to closers.

Business Development Managers will actively bring in new customers using door-to-door sales or cold calling to help fill the sales pipeline.

Before you begin the hiring process

Source: Fit Small Business

Before advertising a position or interviewing candidates, there are a few things you need to consider to find a good fit.  

Determine your staffing needs

With the understanding of the responsibilities of a salesperson above, the first crucial step is to analyze and determine your business's staffing needs. What growth stage is your business at, and what specific sales roles do you need to fill? Once you answer these questions, you still need to figure out how many new salespeople you need to hire.

The answer to how many hires you need will generally depend on factors such as:

● Your sales growth targets

● Your previous sales performance

● Changes in the market

● Your strategies for distribution

● Your company's turnover rate

Define what your specific company needs

It's also essential to identify the specific tasks you need to fulfill when analyzing your business situation to hire salespeople. It's true, being able to "effectively sell" is a general trait all salespeople should have. However, the role and the company can require different, more nuanced skills. You'll want to identify:

● The specific tasks relevant to the products and services you are selling

● Your business's growth stage

● The strategies you are implementing and need support

A quick example

For example, let's say you sell products from a physical retail location. Suppose your business plans to open one more location next year and needs retail salespeople in the stores. In that case, you'll need to determine how many salespeople you need per store. You'll also want them to have:

● The ability to educate people on the products you sell

● Communication and people skills to interact with customers face-to-face

● Flexibility for shifts covering all your store open hours

● Experience with retail selling tasks, such as cashiers

Your needs will differ if you are an online business or your business model revolves around providing services at your customers’ location. Knowing what tasks you are hiring for and why will help you identify the right people for the role.

Clearly define job qualifications

Since you will be looking through many applications, it's important to define what you are looking for clearly. For starters, you'll want to identify relevant experience and education. This step will also make it easier for you to write the job listing to attract only candidates that meet your required qualifications.

When deciding what you are looking for, create terms for your minimum qualifications and preferred qualifications of an ideal candidate. Most candidates can easily say they have "selling experience," but what does this really mean?

Revisit the tasks for the role

Take a look at the task and role you are hiring for to define the qualifications and past experiences you want. Identifying qualified candidates will be easier when you are clear on what specific sales experience you are seeking. For example, do you need someone with experience:

● Using a particular technology platform to reduce training costs

● Interacting with a specific demographic that makes up your target audience

● Educating customers about your industry-specific products or services

Writing an effective job listing

Now that you know the specific position you are hiring for, the tasks they will cover, and the qualifications you seek, you can create a job listing. You need to consider some things to ensure your job ad attracts the candidates you want to consider for hire.

Optimize the job title

Your job listing title is crucial to getting your listing in front of the right people. Make sure it's clear what the position is and hit keywords candidates may be searching for.

For example, add the word "Entry Level" to the title if that is the nature of the role. You can also include keywords such as "B2B" or B2C," depending on the position's requirements. While your job title should be concise, you need to make it searchable.

Provide a company overview

An engaging company summary lets people understand your business and attracts them to be part of your bigger mission. While some sales candidates aren't bothered by what they are selling, others value knowing about the company culture and vision. It will be easier to retain someone who supports your mission on top of enjoying the specific role they have.

Avoid copying and pasting an overview from your website. Instead, add points relevant to the job listing. Examples include:

● Insight into your sales team's day-to-day

● Other existing sales team roles and how this new role will fit in

● Company perks and benefit package

Clarify job requirements

The most important section will be the job requirement list. Use the information you gathered so far to populate the qualification section of the requirements. You'll also want to add information on the specific tasks someone in the role can expect to complete.

Make sure the job requirements are realistic, especially for the compensation you are suggesting; you don't want to scare too many people away from an overwhelming list of items or tasks that are confusing. Also, use strong verbs and authoritative language when describing these responsibilities to generate excitement.

Clarify application instructions

Be mindful of what the application will entail. It can be easy to just ask for a resume, so use this as an opportunity to get to know your candidates and weed out anybody who doesn't fit the bill. Things to consider asking for in the application include:

● A cover letter

● Responses to multiple-choice questions

● Responses to open-ended questions

● A task (such as adding a specific word or number to the cover letter) to identify attention to detail

Write a compelling listing

Last but not least, to hire salespeople that fit the role you need to fill, you'll have to attract them with a well-written job listing. You could turn off exceptional candidates with a poorly written job description containing grammatical errors. It goes a long way to get someone to help edit the work or act as a second pair of eyes.

Steps before the interview

Once you have received job applications to your listing, you'll want to make sure you take time to pick suitable candidates. Consider the following steps before reaching out for an interview:

Request a Cover Letter

Cover letters are a great way to tell if a candidate took the time to research your business and if they connect with your mission. You want to gauge how much the opportunity means to them. In contrast, cover letters that are generic forms, copied and pasted for different applications, can indicate they aren't as invested as you would want them to be.

Conduct phone screenings

Quick phone screenings are an excellent initial step before inviting someone to an in-person or virtual face-to-face interview. During the call, ask them questions to determine:

● The legitimacy of their experience

● Whether they took some time to learn about your business

● Their ability to think on the spot

See if the candidates show initiative

You'll want to pay attention to any candidates reaching out before the interview. With a sales position, you want confident people willing to take the extra step to prepare for meaningful interaction (in this case, the interview).

This is an opportunity to see how thoughtful they are when reaching out. If they are too pushy, that can be a red flag. However, if they ask meaningful questions, it can show they are willing to face uncomfortable situations to be thorough and prepared.

Get creative with interviews and beyond

You don't want to ask fundamental, technical questions any salesperson should know. To identify exceptional candidates, get creative during your interview process.

Ask open-ended questions

When you hire salespeople, there are certain traits you may be looking for that only open-ended questions can address. By asking people to provide examples or respond to how they would deal with a specific scenario, you can assess their sales style and identify how quickly they come up with solutions.

It's also important to phrase your open-ended questions in a way that gives you more insight into their methods. For example, when you ask: "How often do you try to convert a lead into a customer?" The answer is most likely to be "Every time" or "I always try to do that."

Instead, ask something like: "What tactic do you take on your first appointment with a potential customer?" Then in their response, you can listen for details on how they handle lead conversions.

Provide opportunities to reflect

While it's typically easy for candidates to talk about how great they are, you want to see how well they can reflect on their weaknesses as well. Make sure to ask a question that lets them reflect on this and see how well they respond. Examples include:

● What is your biggest weakness?

● Tell me about a mistake you made and how you handled it.

● What did you learn when working with your previous company?

You can also ask questions that show skepticism to any of their open-ended responses to see how they react to being questioned. Salespeople will most likely meet skeptical customers and need to know how to reflect on what they just said and turn a situation around.

Consider a personality test

A process businesses are using more and more is asking candidates to take personality assessment tests. You can ask for a general personality test that gives you better insight into what someone will be like in the workplace and how to manage them effectively.

Tests can help identify a candidate’s traits and skills, such as:

● Need for achievement

● Competitiveness

● Optimism

● Confidence

● Persuasiveness

● Relationship skills

● Organization

Consider your company’s culture

When you hire the right person who fits your business's culture, you ensure their success as an employee. If your business doesn't have a well-defined culture or core values, it's best to develop this. Be clear on what makes up your business environment, including values, beliefs, and experiences.

When team members are a good culture fit, they tend to develop better relationships and are more productive. Some questions you can ask during the interview process to determine cultural alignment include:

● Is there a management style that best motivates you?

● What type of work environment are you happiest and most productive in?

● How would you describe your work style?

● What role are you most comfortable taking on in a team?

● How do you manage conflicts with other team members?

● What would you improve in the work environment of your previous job?

● What role does humor play at work?

● Do you work better solo or with a team?

How culture can support retainment

One of the leading causes for turnover is a misaligned cultural fit with your business. When someone feels they don't align with the business culture, it can lead to:

● Toxic environments

● Bad teamwork

● Decreased job satisfaction

● Poor performance and work quality

People need to feel they can thrive in the work environment you offer and align with your company's core values. While this is more important to some than others, it subconsciously impacts every employee and their motivation to perform well. By hiring candidates that fit your culture, you are helping to retain great salespeople.

Tips on hiring your first salespeople

If you are a startup and looking to hire your business's first two salespeople, there are specific things to consider unique to your situation.

Set the tone for your company

Developing a company culture first is crucial as a startup. You want to hire people who will help create the work environment foundations to attract new hires in the future. Be clear on your:

● Mission

● Vision

● Values you live by daily

Hire two salespeople

Yes, you should hire two people to begin. Two people on the team can lead to better productivity when they create camaraderie. They can tweak pitches together, share feedback, and talk about how to improve sales.

Having two salespeople also allows you to understand better what is going on if they aren't bringing in the results you wanted. For example, if both employees are performing poorly, you can ask yourself:

● Is your product priced too high?

● Does your product not have a market fit?

● Are you reaching out to the wrong target audience?

In contrast, if only one person is performing poorly, it may simply be they aren't a good fit for the role.

Recognize characteristics of first hires

While you want to hire top-performing salespeople at every stage of your business growth, there are some unique characteristics your first hires need. They will have more responsibilities than hires further down the line.

For example, you will want people who can:

● Work in an unstructured environment since they will be figuring out the foundations and fundamentals of selling your product or services.

● Wear multiple hats since they will only be a team of two or three.

● Be resourceful with the limited resources available, such as marketing materials.

● Roll with the punches as your startup irons out internal processes.

Consider someone with a healthy network

Since your startup's goal is to grow, hiring salespeople with good networks can be beneficial. Once you are ready to add to the team, look towards your current salespeople to identify potential next hires who are top performers and fit the company culture.

If you target a specific customer base or audience, a salesperson with connections in the relevant area can also be beneficial. Instead of starting all your sales initiatives as cold leads, they might be able to introduce some warm leads or tap into existing connections for references.

Understanding employee turnover

Source: Apollo Technical

Before we jump into strategies to retain your top sales employees, it's important to understand the main reasons they might leave. Employee turnover is expensive. Understanding why employees leave can help you be proactive and avoid high turnover rates.

Compensation is one of the main reasons employees cite for leaving. However, it's usually just the tip of the iceberg. Even if you offer more than a raise, they may leave because of other reasons.

Reasons employees leave a company

The Journal of Applied Psychology notes that employees leave companies due to:

1. A lack of opportunities for advancement

2. Issues with leadership

3. Issues with the work environment

4. A desire for more challenging work

Six strategies to retain great salespeople

Have regular meetings with your sales team

Check in with your salespeople weekly, even with a video conference. These meetings let you stay updated on issues and allow them to report wins in a group setting, providing each other feedback and tips. Since most salespeople are out in the field, a weekly meeting also helps connect them back to your business and feel part of the team.

On top of these weekly meetings, you can also schedule monthly or quarterly one-on-one’s to check in and make sure everything is going well. Give your employee a space to address their concerns or ask for feedback. You can also use this meeting to evaluate their performance. Giving people time to communicate how satisfied they are in their position can prevent unwanted scenarios from escalating.  

Focus on being a great leader

Every employee responds differently to different management styles, and it helps to be a leader who can adapt. For instance, the way you share information or delegate work to one salesperson may differ from another. At the end of the day, salespeople often leave their bosses, not their positions.

While how to be a great leader is a whole article in itself, here is a quick overview of traits to develop:

● Communicate clearly and be mindful of your tone and how you phrase things

● Listen and take your salespeople's contributions seriously

● Create a safe environment for feedback and risk-taking

● Operate with authenticity and integrity

Clearly define opportunities for advancement

Even if you can't offer advancement opportunities right now, having a clear definition of what advancement looks like is still important. Show levels of career trajectories someone can expect in the position you hire them to and what you will be evaluating for them to qualify for advancement.

Perhaps special projects or teams are coming up that someone will get the chance to lead. If you are a startup, share your growth vision and what that will mean for top-performers who stay on.

Provide professional development

Source: Lorman

When your salespeople feel they are growing professionally or personally, it's a great motivator for performance. There are always opportunities to learn new strategies and adapt to new ways to connect with potential customers.

While you can provide sales coaching and mentorship to less experienced hires, there are plenty of other options for employees regardless of how experienced they are. For example:

● Offer a stipend to attend sales conferences.

● Offer reimbursement for training or webinars on insights to current market trends.

● Host internal training where experienced salespeople can learn to become mentors for younger or newer hires.

Get creative about bonuses

Money is still an essential aspect of a job since everyone deals with financial issues daily. If your sales team has a base pay with opportunities for bonuses, get creative with how you structure this incentive. For example:

● You can have larger retention bonuses at different milestones, such as after two years with the company rather than four years, etc.

● Offering to pay student loans once salespeople hit certain intervals

● Extra vacation time after two years, four years, etc.

● Opportunity to receive company shares

● Support well-being through gym membership stipends

Go beyond monetary motivation

You can't expect to motivate your employees solely with monetary incentives. As the statistics previously showed, compensation is not the top reason salespeople leave. Most of the top-performing salespeople are more motivated when they know they positively impact their customers and business.

Here are some other ways to intrinsically motivate employees:

● Provide support and guidance on time management and maintaining a healthy work-life balance.

● Offer opportunities for team members to receive recognition for their accomplishments.

● Allow autonomy so that salespeople feel trusted and independent, not micromanaged.

Continuously assess talent

Even after hiring your sales employees, you should continue to conduct talent assessments, especially to keep up with the ever-changing market. Skills relevant years ago might not be as important today, especially as in-person communication takes a back seat to online communication. By conducting a skills inventory, you can better understand your team’s strengths and weaknesses.

Assess an employee’s talent to identify how their strengths can serve your organization. As the statistics previously mentioned, turnover occurs when employees feel they haven't advanced or need more challenging work.

Continuously evaluating your employees and gathering feedback allows you to determine what else they can be doing to increase job satisfaction. This helps you effectively restructure as you grow and retain talent in the process.  

Always have a backup plan

Even with retention strategies in place, someone can still leave. This may be for personal reasons, such as a family emergency or relocation. Since turnover is a natural part of running a business, don't be blindsided when it occurs. The best way to prevent resulting issues is to have a backup plan.

Ask yourself:

● What is your plan for recruiting and replacing valuable salespeople?

● Can you create a network of potential candidates you can update when an opening becomes available?

● Are there people within your organization you can cross-train for support during turnover?

● Are there people within your organization that can cross over completely and be a new full-time salesperson?

● How efficient is your recruitment and training process to onboard new hires quickly?

Consider our company’s live agents to support your business

You can use a virtual receptionist for your startup or small business. Smith.ai offers a 24/7 call service with live agents that can handle multiple sales-related tasks to help you level up your business. Additionally, the service is available immediately with trained specialists, so you don't have to worry about recruitment and training costs.

A Smith.ai sales development representative can benefit your business by:

● Providing after-hour support, so you aren't overworking your employees to catch leads

● Initiating conversations with potential customers when they arrive on your website

● Providing lead qualifying services and improving the effectiveness of the process

● Completing new customer intake forms

● Communicating with leads from different communication mediums, including text, calls, 24/7 website chat, and Facebook messages

You can also choose to use a 24/7 live agent to supplement your in-house salespeople. Whichever option you choose, Smith.ai will ensure your customer support and lead conversions won't take a hit during a shortage of great salespeople.

Explore our services through a free 30-minute consultation

You do not have to hassle with the hiring process to meet your productivity needs. Instead, our virtual receptionist service can handle the work for you.

You can book a free 30-minute consultation with Smith.ai to learn more about our virtual receptionist service. Take a look at our pricing and sign up with a 14-day money-back guarantee. You can email us at hello@smith.ai, call us at (650) 727-6484, or chat with us live, 24/7, right here on the site.

Sean Lund-Brown

Sean Lund-Brown is a current Marketing Assistant for Smith.ai. A graduate from Metropolitan State University of Denver, Sean graduated with a BA in Music and an individualized degree in Teaching Vocal Pedagogy.

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