5 Must-Have Qualities of your First Sales Rep

You’ve spent countless hours talking to customers, proving Product/Market Fit, and developing and testing your product. You have paying customers (where the economics make sense) and now it’s time to start the next phase.

This is an exciting time for entrepreneurs. There’s only one problem: you can’t do everything. As your company grows, so will your role as CEO. Hiring a sales rep can propel your growth to the next level, but can also be daunting. Here’s five must-have qualities to look for in your first sales rep

  1. Collaboration

Even if you’re lucky enough to capture a veteran sales leader with 20+ years of experience selling software, you will want to be involved in helping your first hire create a sales strategy. Every product is different, and transferring/sharing your breadth of knowledge about your product and the problem it’s solving will help your rep figure out what sales strategy works best. Hire with onboarding in mind: you want to find some who can take your guidance on how the sales process could run and create/test a few different campaigns to see what really works.

When you’re interviewing, look for someone who is excited to do two things: experiment and collaborate. Ask questions about how they’ve reported to their CEO in the past and how much value they place on teamwork. Be clear in the interview process about how involved you’ll be in creating and implementing a sales process. This helps them to understand how much freedom they will have. Finding a salesperson who’s used to collaborating with peers and superiors will make it easier to establish a good process and then teach that process to new additions down the road.

Sample Interview Question: What do you think the best pitch for our product would be, based on your current knowledge of the product?

2. Buy-In

The first time you hire foundational roles will be the scariest. After all, these people, like you, are going to have to be willing to wear a lot of hats. They are your cheerleaders, your evangelists, and your growth hackers. You need to hire people who believe in your product as strongly as you do. Luckily, buy-in doesn’t require any type of technical skill. You don’t need people who understand the underlying code like you do. Instead, you need to look for people who understand two things: the problem and the vision.

Understanding the problem is the foundation of buy-in. It turns an employee into an evangelist. It helps you evaluate during the hiring process whether a candidate will be excited about work every day. It will also make it easier for your new salesperson to create pitches that speak directly to your target market’s pain points.

More importantly, what separates a great SaaS salesperson from the masses is their grit and an unrelenting belief in the company’s vision. Don’t ask a candidate why they want to work for you. Instead, ask how they think they’ll help you grow the company.

Sample Interview Question: One of our Core Values is “[insert Core Value]” How do you think this will direct your sales process, especially as we grow?

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3. Coachability

Whether you’re looking for a seasoned sales professional or taking the leap with a new college graduate, your first sales lead needs to be able to understand and implement the ideas and strategies that you throw their way. Like we mentioned above, even the most successful veteran reps will have to learn something in order to successfully sell a new product.

Even with that in mind, it can be challenging to find someone who can accept and apply criticism well. Fortunately, a relatively easy thing to test for in an interview: Offer a piece of criticism during your first round of interview and see if they act on it as they move through the process.

Sample Interview Question: How have you changed your sales process to meet the demands of new products and teams?

4. Extroversion

Sales reps have to talk. A lot. That’s true even in this digital age. Your first few reps will probably have to be responsible for the entire sales cycle—from cold outreach to demo to close. They will have to use a variety of emails, calls, and meetings to capture your first clients. Check out a few helpful tips from the Simply SaaS University: SDR 101 class with Morgan Ingram. I’m sure you’ve realized by now that it’s a lot of work. You want to find a rep that thrives on making connections and reaching prospects.

It’s pretty easy to notice an extrovert in an interview, but also check a candidate’s resume to ensure they are harnessing their full extroverted potential. Does their work experience revolve around other people? You want to hire someone who considers working and connecting with other people an asset of their previous work. Skim the resume for phrases like “collaborated with a team” and “worked with clients to…” Don’t be afraid to ask about what types of connections they have in your target market and if they’d be willing to reach out to their network to sell. An extrovert will give a resounding, “Yes!”

Sample Interview Question: What is your dream sales process?

5. Thick Skin

Sales reps have to deal with a ton of rejection. That can be pretty off-putting to both new hires who have never had to cold call and seasoned veterans who are accustomed to management roles. Don’t be afraid to ask candidates how they balance their work-life-rejection with the real world. You don’t want someone who will take the rejection too personally or crack under pressure.

Further, be upfront about cold-calling duties. Mention it in the job description, in your interviews, and in your offer letter. Chances are, your first hire’s title will be higher-level like “Business Development Manager” or “Sales Lead,” so you want to make sure people know exactly what they’re getting into as you develop a sales process and scale up. Try to find someone who is genuinely excited to make “one more call”.

Sample Interview Question: What’s a time that you didn’t meet a goal? How did you handle it?

Hiring your first salesperson can be a daunting task. It can be hard to organize everything necessary for rockstar rep into one job description, but have no fear! Follow these  5 must-haves for your first salesperson so you can hire confidently.


Jesse Grossman is the CEO of 1H Recruiting. As a founder and community builder for more than 6 years, he has learned firsthand how strongly relationships can transform the success of any new business. Telling a compelling story will motivate talented people to join your quest, but many founders tend to think about hiring in a more traditional, transactional sense. It’s almost never to early to plan ahead for the type of team you envision building.