How to Hire a Salesperson for a Startup: Key Steps and Tips

A sales team can make or break a startup. 

At Artisan, our salespeople have been the primary drivers of our incredible growth. 

To quote our CEO, Jaspar, they took Artisan from an “idea in a Figma file” to a market leader in one of the world’s hottest new categories. 

We believe any startup can find exceptional talent. But it’s all about having the right process. 

Key Qualities to Look For in a Salesperson for Your Startup

There is no perfect salesperson. However, top-performing sellers of all stripes are almost always adaptable team players and excellent communicators. And don’t forget to look for a proven track record, too. 

Adaptability and Resilience

Running a startup is easy, said nobody, ever. 

There are regular setbacks, restarts, and pivots. This rough terrain demands that new hires roll with the punches. 

Research from Grand Valley State University found that resilient sales reps do the following:

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  Initiate more calls to potential customers

  
  
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  Consistently put in extra effort

  
  
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  Generate more revenue

  
  

All sales reps have hard days. But they must be able to bounce back. 

Look for the following resilience indicators:

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  Open-mindedness

  
  
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  Emotional intelligence

  
  
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  Willingness to learn 

  
  
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  Ability to shift approach

  
  
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  Tolerance for criticism

  
  

The key is to assess whether candidates have experience in fast-paced, challenging environments. Questions like “Can you tell me about a time when you faced a significant challenge?” are helpful. 

Always encourage answers with concrete examples and clear explanations of problems and solutions. And watch out for the red flags of blaming others, not learning from the challenge, or giving up. 

These questions are especially important if you’re an early-stage startup hiring a sales manager to take on multiple duties.

Strong Communication and Persuasion Skills

Social skills are a salesperson’s superpower. Developing relationships, understanding customers, and building trust are essential for closing deals.

It’s best to seek sales reps who persuade through good communication rather than underhand tactics like overpromising. More often than not, these backfire and increase churn. 

A good salesperson will have the following communication skills:

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  Active listening

  
  
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  Empathy

  
  
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  Clarity

  
  
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  Confidence

  
  
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  Negotiation 

  
  
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  Self-awareness

  
  
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  Adaptiveness

  
  
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  Written communication

  
  

Focus on communication skills that best fit your customers and channels. For instance, if you primarily cold call, prioritize tone, clarity, and active listening. 

And remember that a sales rep who wins over Gen Z consumers may not get similar results with the C-suite. 

Proven Track Record or Demonstrated Potential

Seasoned salespeople have great intuition and know the right path to take to close deals. 

Here’s a checklist for putting together a picture of past performance: 

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  Average deal size in past sales roles

  
  
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  Industry knowledge

  
  
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  Number of years working in sales

  
  
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  Previous responsibilities and position (sales manager, assistant, or account executive)

  
  
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  CRM knowledge and tech stack (HubSpot, Salesforce, etc.)

  
  
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  Preferred sales frameworks

  
  
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  Inbound or outbound sales strategy

  
  
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  Sales experience with your ideal customer

  
  

In addition, compare their past results to industry benchmarks. Research from HubSpot found that the overall average win rate is 21%, while the close rate is 29%. 

Also give weight to the types of companies a candidate has worked for. A sales manager who spent ten years in an enterprise organization with set-in-stone processes may not be a good fit for startups. 

What’s more, keep in mind that some of the best hires may not have the most extravagant resumes.

Startups benefit from hiring passionate salespeople who:

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  Resonate with the mission

  
  
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  Want to learn

  
  
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  Enjoy challenges

  
  

These candidates may lack experience, but they will grow with your company. That said, experience tends to be preferable with your first sales rep, who will be responsible for shaping your entire sales process. 

Where to Find the Right Sales Talent for Startups

Where you search for talent affects candidate quality and relevance. Let’s look at some of the best places to find skilled employees. 

Explore AI-Driven Solutions

Hybrid teams are the future of sales. Implementing an AI solution from the get-go—alongside your human hires—is a direct route to lower costs and greater efficiency. 

Research from Hinge Marketing found that high-growth firms are 58% more likely to have integrated automation processes for marketing and sales. 

Introducing technology early means that you’ll see these benefits from the get-go. Plus, you’ll keep up with competitors. The capabilities of these solutions are improving at lightspeed. 

AI tools automate and speed up the following tasks:

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  Lead generation

  
  
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  Data enrichment

  
  
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  Personalized outreach

  
  
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  Follow-ups

  
  
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  Multi-channel sequences

  
  

For example, Artisan’s AI BDR Ava handles all parts of the early and middle stages of the outbound sales cycle. She finds and scores new leads, sends personalized outreach, tracks pipeline progress, and optimizes campaigns in the background.

Tap Into Your Network

Word of mouth is a tested way of finding a new sales hire. 

The likelihood is that salespeople and entrepreneurs in your network are well connected with other salespeople. 

Asking colleagues you know and trust to recommend sales reps leads to:

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  Higher-quality candidates

  
  
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  Better cultural fit

  
  
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  Lower risk of poor performance

  
  

In addition, networking events where you can meet potential candidates in a relaxed, social environment can be great places for finding talent. 

Use Niche Job Boards and Platforms

Don’t skip the general sites. But startup-only recruitment platforms like Wellfound (formerly AngelList Talent) connect you with people seeking work in early-stage businesses. These candidates likely understand and enjoy the risks, rewards, and challenges of selling for a startup. 

In addition, stay up-to-date with postings on niche-specific platforms. Dice, for example, is a job board for tech companies. Creatively is dedicated to creative people. And Toptal focuses specifically on the top 3% of global freelance talent. 

Keeping specific helps you find salespeople who understand the nuances of your customers and industry challenges.

Leverage Social Media

Today, everyone and their recruiter has a social media account. Research by Content Stadium found that 98% of employer branding and recruitment teams use social media in some way. 

LinkedIn currently has over one billion users and is the most popular platform for branded content, with Facebook taking the silver medal. These platforms allow you to access a wide network, talk about your role, and build connections. 

Regularly posting on social channels builds a bank of followers who align with your values and company culture.

Take a long-term approach and post content that reveals insights into your startup, such as:

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  Behind-the-scenes videos

  
  
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  Infographics

  
  
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  Funny skits

  
  
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  Employee stories

  
  
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  Updates and reflections

  
  

When an opportunity crops up, you can post your opening and immediately connect with people aligned with your mission and values. 

In addition, many candidates are job hunting on social media. An active profile acts as an invite for job hunters to research your company and reach out if appropriate. 

Consider Outsourcing or Freelance Sales Talent

Perhaps it’s too early for full-timers? Or maybe your business is growing, but you’re unsure exactly how fast.

There’s no need to restrict yourself to traditional employment styles. Freelancers and outsourced services are cost-effective options when you don't know your exact needs. 

Here’s why businesses choose freelancers and outsourcing:

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  Lack of in-house skills 

  
  
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  Suitable for part-time roles

  
  
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  Cost flexibility

  
  
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  Hire salespeople in any location

  
  
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  No complex onboarding process

  
  
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  High level of expertise

  
  

Platforms like Upwork and Fiverr are good places for finding freelancers. Simply search by role or post an ad. Pay particular attention to candidates’ profiles, reviews, and past experiences. 

The one downside of this approach is that hiring many disparate parties can make your team feel somewhat disconnected. One way of circumventing this is to build a team of freelancers and employ the best workers full-time. 

Freelancing acts as a trial period, allowing you to follow a framework like early Facebook’s "hire fast, fire faster" strategy—although perhaps slightly less intensely. 

How to Create a Job Description That Attracts Top Talent

As a startup, you can’t necessarily compete with the high wages of Fortune 500 companies. However, you have a unique power—to inspire talent. Startups offer opportunities that established enterprises don’t.

1. Focus On the Startup's Vision and Mission

A company with strong values and exciting goals can be more enticing than a hefty paycheck. 

According to Textio’s analysis of around a billion job listings and recruiting messages, using the first person, such as “we,” tends to perform better than “you” or impersonal language like “the ideal candidate.” Gong also found that 25% of sales reps stay in their jobs because of a strong future outlook. 

Create a value-driven pitch for your startup and share it in job descriptions. Also consider adding a video explaining your company and vision for extra engagement.

To form your story, ask yourself the following questions about your mission:

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  What makes you different? 

  
  
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  What are your long and short-term goals?

  
  
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  How is your product improving the world?

  
  

Your job description should inspire people with the same approach to growth and disruption as you. 

2. Be Clear About Expectations and Goals

Honesty is key to finding the right person. Be truthful about work hours, payment, and the role. 

Don’t overemphasize the negatives. But mention critical challenges and, if you have any, explain the difficulties you’re experiencing establishing yourself in a competitive market.

Spell out the following key responsibilities:

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  Cold calling 

  
  
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  Technology use

  
  
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  Building pipeline

  
  
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  Management

  
  
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  Email follow-up

  
  
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  Pitching

  
  
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  Negotiating

  
  

State where the candidate's role starts and ends, and give them your metrics for success. 

In addition, highlight opportunities for sales development. Textio’s research found that language promoting a growth mindset encourages more applicants than strict requirements. This includes phrases like “opportunity to grow,” “work hard,” “persevere,” and “forward thinker.” 

3. Include Perks and Benefits 

For many employees, perks are as important as pay. 

In the job description, share the following benefits if you offer them: 

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  Flexible working hours

  
  
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  Equity options

  
  
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  Good work culture

  
  
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  Growth opportunities

  
  
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  Gym memberships and wellness experiences

  
  
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  Health insurance

  
  
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  Paid sick days 

  
  
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  Childcare

  
  
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  Travel perks

  
  

You can also offer incentivized salaries with elements of a pay-by-commission structure. However, check that you have the correct processes in place to handle this system. There’s a shocking story of Wells Fargo employees who opened millions of fake accounts between 2002 and 2016 to hit unrealistic sales targets. 

How to Assess Sales Candidates Effectively

When hiring for a sales job, you need a thorough interview process to properly vet potential employees. It’s also vital to test skills in the session and ensure a solid cultural fit. 

1. Design a Startup-Relevant Interview Process

Research from Aptitude found that 50% of companies have lost top talent due to a poor interview process. Top performers always have a choice. Take too long or give a bad impression, and there’s every likelihood they’ll go elsewhere.

Here’s a sample interview process you can replicate in your startup:

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   Begin with a 30-minute phone call to assess suitability and screen candidates

   
   
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   Conduct an in-depth interview via video call or in person

   
   
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   Have the candidate complete a test or practical roleplay

   
   
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   Conduct a final interview with additional team members

   
   

Following a structured approach makes it easier to compare candidates. Often, you’ll know someone isn’t a good fit within the first ten minutes of meeting. So, keep the first step short to save time. 

Conversely, when you’re feeling positive about a candidate, show your excitement to maintain momentum. Aptitude’s research also found that four out of five candidates like to receive feedback throughout the interview process. 

2. Test Practical Skills With Role-Play Scenarios

Can the candidate do what they need to? The best way to find out is through tests and roleplaying. 

Practical tests assess the following skills:

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  Planning

  
  
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  Problem-solving

  
  
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  Communication

  
  
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  Handling feedback

  
  
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  Sales ability, like pitching and closing

  
  
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  Conflict resolution

  
  

Adjust the scenario to the position. For example, if your sales pipeline prioritizes email, role-play the candidate’s written communication skills. 

You should also recreate common scenarios that your salespeople face, including challenges and obstacles. 

For example, a SaaS CEO may ask the candidate to take part in a simulated sales call while they act as a customer unsure about their budget and the ROI of the company’s product. 

However, Goodhart's law states that when you observe someone who knows they’re being assessed, it ceases to be a good measure. With that in mind, go a little deeper and ask the candidate to share their logic and the reasons why they made certain decisions. Don’t seek perfection. Instead, try to understand their approach and skill set. 

3. Look for Cultural Fit

During Apple’s early hiring process, Steve Jobs and Senior Design Officer Jony Ive prioritized cultural fit over technical knowledge. They oversaw all recruitment and chose creative candidates who resonated with Apple’s values and mission.

Skills can be taught, but character can’t. Does the candidate understand your mission and values? These shared values will keep them motivated through setbacks. 

For example, as Airbnb expanded, the founders only hired employees who were passionate about hospitality and the customer experience. This kept the team aligned and working cohesively. 

However, there’s a common pitfall. When focusing on cultural fit, it’s easy to hire only employees with similar backgrounds. McKinsey’s “Diversity” report found that ethnically and racially diverse companies perform 26% better. In addition, Textio also found that jobs with simple statements about equal opportunities fill 6% faster.  

So, assess cultural fit while maintaining strong diversity principles. 

Empower Your Startup Sales Team With Smart Solutions

During the early stages of a company’s growth, you should look for people who can keep pace with fast changes, handle uncertainty, and slot smoothly into your company’s culture.

However, expanding your team is expensive. An AI tool like Artisan takes care of all the early and middle stages of the sales cycle, freeing up your new hires to focus on cultivating human connections with the highest-value leads.