Hire Sales Reps

When it comes time to hire sales reps, many companies get stressed out. They believe they should bring on new salespeople because that will be the most straightforward path to growing revenue. But hiring salespeople comes with a lot of challenges. 

One of the biggest challenges is that companies know it’s easy to hire the wrong salesperson. Salespeople are great at faking (read: lying) during interviews. They are in the business of selling and often fool inexperienced Founders and business owners. This poses a serious hurdle for inexperienced leaders.

Additionally, hiring the wrong type of salesperson who interviews well and is honest can be a disaster. The cost of hiring sales reps who fail is substantial.

It will vary based on your company but a simple way to think of it is the salary you paid plus the opportunity cost (time) of missed sales that a better salesperson would have brought in. There’s also the additional cost of your company’s time required to onboard and train the new sales hire.

Something you can’t quantify is the morale decline of your team when making the wrong sales hire. If you’re hiring sales reps, it’s key to read below to make sure you can put yourself in a position to succeed with your next sales hires.

Are You Ready To Hire a Sales Rep?

If you’ve already hired new salespeople with success, you can skip this section. If you’re hiring your sales reps for the first time, keep on reading.

Sales Representative Hiring Checklist	Yes/No
Proven repeatable Sales Process
Sales Playbook
Marketing Support
Churn Issues?
Budget?
Clarity In Type Of Sales Rep Hire
Formalized Interview Process

Transitioning From Founder Led Sales

First off, are you even ready to hire sales reps? If you’re a startup Founder you may be looking to make your first sales hire. Perhaps you think you can hand sales off to someone who is more experienced to fix your current sales issues.

Unfortunately, the Founder has to sell. So if you’re a B2B startup founder who wants to hire a sales rep but hasn’t produced a repeatable sales process, you’re not ready to bring on your first salesperson.  Read this instead.

Getting some sales as a Founder isn’t enough. You need to make sure that you have a repeatable process in place. This means you can document everything from lead to close, including who to target, and how to get meetings with your prospects.

Without that in place, you’re setting yourself up for failure with a new salesperson. 

You also need to consider the segment you sell to. If you’re selling to enterprise clients you need fewer signed deals than if you’re selling to SMBs.

There is no magic formula or number when it comes to moving away from Founder led sales. The key considerations are, is this a repeatable sales process that can be shared with someone else who can clearly and confidently execute on the process.

There is more to say here, you can check this article out on hiring your first salesperson.

Onboarding New Salespeople

Another thing to consider is are you ready from an onboarding perspective? Do you have a sales playbook? Are you using tools like Gong to record sales calls so they know what good looks like and can accelerate their ramp time?

Ensuring you have the onboarding process in place will improve your chances of making a sales rep hire that succeeds. Spend a bit of time on this part before hiring a salesperson and you’ll be in a good spot.

Marketing Support

From a marketing perspective, do you have genuine interest in your product? Are people coming inbound to talk to you? Or do you have a way to generate meetings that that are repeatable?

The worst thing you can do is hire a sales rep and then have them struggle to close deals because they can’t build a pipeline of qualified opportunities.

Churn Issues

Even if you have the above in place, you need to look at your churn honestly. If you’re constantly refilling the bucket of customers because customer churn, you will be wasting the new sales hires time.

Fix your churn issue first before you hire a sales rep.

What Kind of Sales Representative Should You Hire?

Depending on the type of company you are and the stage that you’re at will determine what kind of salesperson you should hire.

For sake of clarification we’ll break this down into three types of stages of companies across three different types of sales. There are of course exceptions and other options but when it comes time to hire a sales rep this should give you some insight.

(the table columns are not related)

Company Stage	Sales Type Hire
Early	SMB
Growth	Mid-Market
Established	Enterprise

Stages

Early

Early stage companies are your typical startup or new SMB. These are companies that are transitioning from Founder led sales.

They may have zero sales reps or a few. It’s unlikely there is a large sales team in place.

Early Stage Sales Rep Hires

For early stage companies, you want to hire someone who deals very well with ambiguity. Someone entrepreneurial in nature is also a strong fit. People who take action without knowing everything tend to be a strong fit.

Hiring a sales rep with a bit of experience is usually a good idea because there’s a lot they’ll need to figure out on their own. 

People who work with urgency are a great fit for this stage. They need to be able to roll up their sleeves and get work done. Most likely you’ll have limited resources so people who require a lot of assistance and hand holding are often a terrible fit.

Growth

Companies that are growing rapidly that usually hire salespeople in batches. This is most commonly you’re venture backed startup. These companies hire sales reps in cohorts to scale training and onboarding.

They deal with similar challenges of the early stage companies but the risk is reduced by quite a bit because the early stage sales reps figured a lot of the unknowns out. 

Growth Sales Hire

Often, these sales reps will be moving up market and taking on enterprise accounts. As the company matures, the product does too. This means the type of salespeople tends to be a little less raw but still shares some characteristics of an early stage hire. The strong sales hires tend to take direction better at this stage than the early ones.

Established

Established companies are the ones you know by name. These are the Salesforce, HubSpot, Zooms of the world.

They have a clear ICP and buyer personas. The playbook is written. They are all about executing. There are very few unknowns for the sales hires. 

Established Sales Hire

Later stage established companies have tons of resources to support any needs a new sales hire might have. From learning and development departments to the best sales tools available.

Sales Rep Types

When hiring sales reps, the types of companies you sell to is critical to know. Selling to Small and Medium sized companies requires a vastly different skill set than selling to Enterprise companies. You want to align the sales hire skills to the type of sales process you have. 

Combining the type of sales process you run, with the stage of the company you’re at will help you zero in on making the right decisions when it comes to hiring salespeople.

	SMB	Mid-Market	Enterprise
Typical Company Revenue	0-$50M	$50-$1B	$1B+
Typical Headcount	1-100	100-1000	1000+
Sales Cycle Length	Fast to Medium	Slow to Medium Speed	Slow
Sales Process	Simple	Simple to Complex	Complex
Deal Size	Small	Medium	Large
Difficulty	Easy	Medium	Hard
Number of Decision Makers	1 to a few	A few	A few to many

• SMB Companies

SMBs typically refer to companies with a limited number of employees and revenue, usually under 100 employees and less than $50 million in annual revenue. These businesses often operate in local or niche markets. 

The decision-making process in SMBs is usually faster due to fewer hierarchical levels and a more centralized leadership. Their budgets for products and services are generally smaller, and they often prioritize cost-effective and straightforward solutions. 

SMBs usually require solutions that are easy to implement and manage, with a strong emphasis on customer support. Sales strategies for SMBs often focus on demonstrating immediate value and return on investment (ROI).

• Mid-Market Companies

Mid-market companies are larger than SMBs but smaller than enterprises, typically with employees ranging from 100 to 1000 and annual revenues between $50 million and $1 billion. These companies often experience rapid growth and are in a phase of scaling their operations. 

The decision-making process can be more complex than in SMBs, with more stakeholders involved. Mid-market companies have larger budgets than SMBs but are still cost-conscious. They seek solutions that offer scalability, efficiency, and integration capabilities. 

Sales strategies for mid-market companies often involve demonstrating how a product or service can support growth and operational efficiency.

• Enterprise Companies

Enterprises are large corporations, usually with more than 1000 employees and exceeding $1 billion in annual revenue. They operate on a global scale and have complex organizational structures with multiple layers of hierarchy. 

Decision-making in enterprises is often slow and involves numerous stakeholders and lengthy procurement processes. Enterprises have substantial budgets but require comprehensive, customizable, and scalable solutions that can integrate seamlessly with their existing systems. 

Sales strategies for enterprises focus on long-term relationships, comprehensive service offerings, and the ability to meet extensive and specific requirements. Enterprises often seek vendors who can provide extensive post-sales support and strategic partnership.

Knowing the above, you want to match the right previous experience with the stage you’re at. An SMB sales rep will make a bad hire if you’re moving into selling to the enterprise. An enterprise salesperson will make a bad sales hire if you have a high volume transactional sales.

• Sales Rep Skills By Type

These stages and companies you sell to, require different skills. It’s not recommended that you hire sales reps who don’t have the past experience. 

Something else to consider is vetting the sales hires for their true experience. Many salespeople will say they have enterprise experience but they sold to one department at an enterprise company. They lack true enterprise experience which is important to flesh out.

If you don’t understand this and you sell a solution that touches various parts of the enterprise organization, they will likely struggle. These sales reps tend to be better suited for mid-market sales.

Common Mistakes When Hiring Sales Reps

If you avoid the most common mistakes when you make your next sales hire, you’ll put yourself in a better position to hire a sales rep that delivers.

These mistakes are based on working with dozens of companies that made bad sales hires while working as a Fractional Sales Manager or a B2B sales consultant.

Hiring Sales Managers

Seeing a sales leader apply when you’re hiring a sales rep often feels like you’re getting a buy one get one free potential hire. Unfortunately, too many companies hire previous sales managers who have been out of the game for too long. They’re used to viewing dashboards and managing teams. 

They lack insight on the latest practices needed to execute. Things like sales prospecting methods that work in 2024 are foreign to them. They simply don’t know what to do.

Companies think they’ll learn the role, do well, then be in a position to hire sales reps underneath them. But this almost never happens.

Another consideration is the “player coach” model which also leads to failure more often than not. The reason for this is the person who is the player/coach will follow their best incentives.

This means either the individual contributor portion of their role or the manager portion of the role is neglected. It’s almost never a good idea.  

Hiring From Big Logos

When companies see well known logos on a potential sales hire resume they think they struck gold. In their eyes, they’ve been prequalified and trained by professional sales departments. While some of that is true, that doesn’t mean they’re going to work for your company.

Here’s why. Placing big company people in small businesses and startups tends to be a culture shock. The environment and resources available to them are totally different. They’ve gone from a place where they have everything they could possibly need.

This person has been following a proven and established playbook. Now they have none of that. You’ll have a playbook but it’s still a work in progress.

There’s also the loss of selling at a company that has brand awareness. A strong brand can automatically put you in a position to be considered. As the old saying goes, “nobody gets fired for buying from IBM.” 

Hiring Based On Past Performance

It’s normal to look at someone’s track record as a way to assess potential future performance. This is reasonable.

However, when hiring sales reps you need to know two things:

• Salespeople lie during interviews and

• Past performance does not guarantee future results

You should be vetting for sales skills when hiring salespeople by making them do role plays and specific skill assessments. When it comes to past performance, evaluate that by considering the nature of the sales environment. 

At an extreme, selling Zoom in 2020 was simply taking orders. There were people who were answering phones, sending contracts, and blowing their quota out of the water.

Obviously, this doesn’t apply to all sales hires but the point stands. You need context around their performance.

Are these inbound leads? Was this a one year performance? Did they back up their performance with multiple years? Have they performed well at a few companies? 

Hiring Reps From Category Leaders

Similar to past performance, you need to be careful to hire sales reps from companies that are category leaders. Not to take anything away from these salespeople but when you’re selling something that is clearly better than what is on the market, it’s substantially easier to close deals.

These people make great hires at established companies. If you’re an early stage startup, you should avoid hiring these sales reps.

How Many Sales Reps Should You Hire

The typical advice is to hire sales reps in batches of at least two or three at a time. The reason for this is simple. It makes onboarding and training easier. You don’t have to have a bunch of individual sessions, you do it in groups. 

The second major reason is it creates a competition of sorts. The sales reps you hire should be competitive. You’ll have an unscientific A/B test to see who is good. It’s possible the two or three are all good. Usually one out of three is not going to be fit though.

It is fine if you can’t hire more than one sales rep at a time. Most early stage companies can’t. Focus on making the best possible sales hire.

Sales Hire Roles

When someone says they need to hire sales reps that may mean different things to different people. Clarifying the sales roles you may be hiring for is important. Let’s take a look at the most popular roles when it comes time to hire sales reps.

Sales Rep (Sales Representative):

A Sales Rep is a general term for a professional who sells products or services. Their responsibilities can vary but typically include identifying potential customers, presenting products, negotiating deals, and closing sales. They aim to meet sales targets and may work in various industries and sales models.

BDR (Business Development Representative):

A BDR focuses on generating new business opportunities. They identify potential clients, initiate contact, and nurture leads to create sales-ready opportunities. BDRs often work on outbound strategies, like cold calling or emailing, to stimulate interest in a company’s products or services.

SDR (Sales Development Representative):

SDRs primarily handle inbound sales leads. They qualify these leads by assessing their potential and readiness for sales conversations. SDRs act as a bridge between marketing and sales, ensuring that only qualified leads are passed on to the sales team.

AE (Account Executive):

An AE manages the entire sales process with potential clients, from initial contact to closing the deal. They conduct product demonstrations, negotiate terms, and ultimately aim to convert leads into customers. AEs are responsible for meeting sales quotas and building client relationships.

There are three types of AEs: SMB, Mid-Market, and Enterprise

Full Cycle AE (Full Cycle Account Executive):

A Full Cycle AE handles all stages of the sales process, from lead generation and qualification to closing deals and managing client accounts. They combine the roles of BDR, SDR, and AE, providing a comprehensive sales approach.

Sales Rep (Sales Representative):

A Sales Rep is a general term for a professional who sells products or services. Their responsibilities can vary but typically include identifying potential customers, presenting products, negotiating deals, and closing sales. They aim to meet sales targets and may work in various industries and sales models.

Other Things To Consider When Hiring Sales Reps

Can You Afford To Hire The Best Sales Reps?

Hiring sales reps is expensive. Here some salary numbers for each of the popular sales roles.

SDR/BDR – The salary for these roles ranges from $45-$65,000 a year and can increase if they’re focused on enterprise sales or a more technical industry

Account Executives – Sales rep salaries range from $65,000-$85,000 a year on the lower end and can easily go over $145,000 a year on the higher end.

The compensation above does not include variable compensation such as commissions and bonus. 

Hiring Sales Reps That Are Commission Only

The dream for businesses is to hire commission only sales reps. These salespeople are only compensated when they close new business. 

The financial risk of these sales hires is as close to zero as it gets. But it’s usually a bad idea. Good B2B salespeople rarely if ever work for only commission.

They can get a guaranteed base while focusing on closing deals to double their total compensation. And companies that want to hire commission-only salespeople are notorious for hiring a bunch of salespeople and hoping they deliver. You get what you pay for and it’s typically a bad idea.

The Sales Rep Hiring Process

You feel confident that you’re ready to hire sales reps. The process can begin. But where do you start?

First, determine who your ideal candidate will be. Think about what would make a good sales hire. List all the skills they will need and characteristics you want them to have to do well as a sales rep in your company. 

Then, put together a job post. Be honest. Don’t sugar coat the role. You want people who want to take the work on. You should be transparent about the position to attract the right applicants.

Now it’s time to get the job posting out there. Post it on the popular job boards, share it on LinkedIn, and make sure to drop it in the many private Slack and Discord sales communities. 

Spend time sourcing new candidates as well. Reach out to dream sales rep hires. You can use a Fractional Sales Recruiter to help you source and recruit salespeople. 

As the applicants role in, you should spend time reviewing their resumes and LinkedIn profiles for fit. You need to have a strict qualification criteria that you follow.

You are better off taking your time to find the right hire than be flexible on your rep qualifications. 

Once you have a pool of qualified candidates, begin the screening process. Your interview screening process should be based on an interview scorecard. Every candidate should be asked the same questions. 

It’s also recommended to make candidates take an aptitude test. For everyone that passes the first round, you can move them on to the next round which should do a deeper dive into their experience and past performance.

You’ll want an experienced sales leader to assist you here. As mentioned above, salespeople are notorious for being good at fooling inexperienced interviewers.  For candidates that pass this round, they should be moved to an additional round to assess their sales skills.

Sales skill assessments vary based on what you’re hiring sales reps for. This may include mock cold calls, cold email tests, sales presentations, and running product demonstrations. 

The key here is to have an experienced sales leader who knows what good looks like to determine if this is a sales rep worth hiring or they don’t meet your standards. You also want to test for coachability.

When running a role play or having the sales rep do a demo, it’s important to give them feedback to see how they react. Some will be obviously coachable. Others will not take kindly to the feedback. The latter is not going to be a fit to hire.

Throughout the entire interview process, you should be using an interview scorecard. Check out this article on How To Hire A Sales Manager to learn more about the interview scorecard and what makes an effective interview process.

The final round of interviews should be with the company founders or senior management. Some companies will incorporate mid-level managers and their future teammates to test for culture fit but it will depend on the organization.

Once you’ve made a decision, you’ll want to move quickly with an offer and run a background check when appropriate.

Congrats, you just hired a sales rep.