Founders and early-stage startup employees wear a lot of hats.
It can also be overwhelming.
But because sustained growth is so critical to your early success, it’s hard to know when is the right time to make your first sales hire.
If you work hard and your clients love your offering, operational concerns (service delivery, technical ops, marketing, accounting, HR, and so forth) should take up more and more of your time and attention.
But founders and small business owners can get so caught up chasing new business that those operational requirements in mission-critical departments start to get placed on the back-burner.
Executives are always key influencers in the sales process—even at Fortune 500 companies. But you’re only one person. You can’t do it all alone. Unfortunately, founder-led sales processes rarely scale. The institutional knowledge and personal guarantees that a founder brings to clients can’t be replicated by new reps.
So don’t get tunnel-vision! Even if you had the time to catch all of your inbound leads, you would be wasting opportunities if you didn’t also hire sales reps to go to market and hunt for new business.
Like at all growing companies, you will eventually need to delegate business development tasks to a coordinated sales organization. After all, marketing can’t sign contracts with enterprise buyers.
But starting from scratch is hard. You’ll need to collect stories and strategies, develop playbooks, implement tech solutions, create management structures, and document training processes.
Your first sales hire can make or break your company’s growth trajectory. If you’re successful, the fruits of your labor will multiply quickly. If you mess it up, you’ll have burned precious time, wasted crucial energy, and probably spent a pretty penny for the privilege of landing right back where you started.
So before you start drafting that first all-important job posting, consider these two very important questions:
- Is your company ready to grow? Timing is everything. Below, we look at three different factors that will help you determine if now is the right time to hire.
- What traits should you look for in your first sales hire? Startups move fast. How can you be confident that your first hire will be resilient enough to handle the changes you’ll inevitably throw at them? Keep reading to learn six important indicators of hiring success.
If you already feel overwhelmed, don’t worry. Every new sales organization has faced down these same two questions. With the benefit of their experience, and access to the right support networks, you’re well on your way to nailing your first sales hire!
How to Know If Your Sales Org is Ready to Grow
There are three main criteria to consider when determining whether or not your company is ready to start a sales organization:
1. You Have Product-Market Fit
The first thing you should ask yourself is if you have product-market fit. Don’t trust your gut. You need to test your assumptions. Can you close perfect-fit opportunities? Can you reliably go out and find them?
If you don’t have product-market fit, you won’t be able to generate future demand for your services. Hiring sales reps won’t help. You’ll burn cash and destroy goodwill. Focus on improving your product and studying your buyer.
You don’t want to set up your first sales hire for failure.
2. You Have An Existing Client Base
Your first sales hire will report to you. You need to have some experience finding prospects, closing business, and retaining customers. You need to have compelling customer stories that you can offer as social proof, and you may even need customer references who can advocate on your behalf.
Once you have an understanding of your unique sales cycle, you’ll be able to build a repeatable process for your new sales team. And with a repeatable process, you’ll be able to hire and grow successfully.
3. You Understand Your Strengths and Weaknesses
Founders are a bottleneck. When you’re responsible for everything, you can’t be trusted to be responsible for anything.
What and when do you contribute? When do you get in the way? What sets you off? If you don’t understand how you fit into your own business, you’re not in a position to hire effectively.
If you’re a technical founder, you should aim to bring on a strong first sales hire who can grow that aspect of the business pretty independently. Leave sales to the sales pro, and focus on where you contribute the most.
But if you already have a great technical team in place, consider being your company’s first Sales Manager, and have the first few hires report directly to you.
Pro Tip: Plan for the future! You don’t have an existing recruiting brand or a pre-existing sales talent pipeline. So don’t rush your first hire. Protect your reputation: It will take a while to organize your incentive compensation plans, set realistic quotas, and find a good fit. Don’t make promises you can’t keep, and don’t burn any bridges! The rep who isn’t right as your first hire might be perfect as your fifth hire.
What to Look For in Your First Sales Hire
So, you’re ready to grow your business. Congratulations! You have product-market fit, you’ve secured a good number of existing customers, and you’ve decided to focus on your strengths as a business owner.
Your first sales hire can’t be just anyone. They will be directly responsible for your company’s growth trajectory. Fit is critical:
1. Comfort With Ambiguity
Your first sales hire will need to fill in with other areas of the business to drive their own sales success. Will they be comfortable stepping into this role?
Can they help solve bugs? Can they resolve billing issues? Will they write their own sales collateral? Will they plan for a scalable CRM? They don’t need to be experts in these areas, but the extra effort needed shouldn’t scare them away either.
Top performers from top companies usually operate within a specific set of parameters. But what happens if you take those away? Your first sales hire needs to be comfortable building their own processes, without losing sight of their goal: Close more deals.
2. A Player, Not a Coach
Your first sales hire can’t be afraid to get their hands dirty. Can they run a demo? Are they willing to work the phones? When was the last time they cold-called someone?
Hunger far outweighs experience for this hire.
You don’t need a strategist or a paper-pusher. You need a go-getter. So don’t get bamboozled by fancy titles: Sales Directors or Regional VPs may have useful experience, but if they’re not eager to be front-line contributors, they’re not right for you.
3. A Technical Talker
Your buyers aren’t dumb. No matter how polished your brand is, they will recognize that you have a young company with an unproven offering. Your first sales hire needs to be able to lean into this perspective.
What your organization lacks in experience, it needs to make up for in expertise. Your first sales hire should have industry-specific knowledge, be able to learn the product, and be able to speak to the buyer’s needs.
It will probably be a while before you have dedicated sales engineers and solution consultants to support your front-line reps. So your first sales hire needs to be somewhat comfortable talking through technical implementations. They probably don’t need to be able to code, but being involved in code-related conversations shouldn’t make them panic, either.
4. Relevant Past Experience
Very few applicants will have direct experience being the first sales hire. So you’ll have to read between the lines.
Your recruit should be a go-getter and be able to solve problems on their own. If their past experience highlights these traits, that’s a good sign! Look for previous roles that required them to document their process, test new hypotheses, reflect on their experiences, and build on their failures.
A great first sales hire will be able to help train your second, third, and fourth sales hire, too.
Not sure what to ask? Check out our list of common sales interview questions, and use them to help design an interview process that meets your unique needs.
5. Skills, Not Stories
Experienced sales reps will tell you about their performance metrics. But numbers don’t tell the whole story. Weak reps can get shielded by hot products, effective marketing, or lucky territories. You need to dig deeper. Get qualitative data, too.
Don’t be shy about asking for samples. Can they run you through a live demo? What’s their current product’s elevator pitch? You can even hand them a script and a phone number, and ask them to call a prospect.
If your job candidate is effective even without advance preparation, it’s a good indicator of their potential after you’ve given them proper training.
6. Cross-Functional Fluency
Your first sales hire will effectively be a one-person department. Even if they’re not in a management position, you’ll want to pull them into cross-functional meetings and have them represent the voice of the sales “team.”
The ideal candidate should be eager to do more than “just their job.” They will have to collaborate with developers, customer support, product management, marketing, finance, and more. Can they argue a point to these groups? Can they keep the peace? Will they fit in with the team? Can they bring a fresh perspective?
How to Get Help with Sales Hiring
If you’re thinking about hiring your first sales rep, Uvaro can help. Our recruits graduate with more than 200 hours of dedicated digital sales training. Our career coaches can make tailored introductions to recruits who fit your “first hire profile”. And our sales residencies are an affordable way to “try before you hire.”