6 Things to Consider Before Making Your First Sales Hire

As CEO, you’re the initial salesperson. You orchestrate the product roadmap, and at the end of the day, you’re involved in closing every customer. Over time the team that helps you bring your solution to market will grow, but knowing where to start and how (and when) to get there can be overwhelming. Here are 6 things to consider as you get ready to introduce the start of your sales organization.

1. Build your hypotheses

Tempting as it may be to hire a sales pro (or a team of them) to scale your sales, it’s important to have a solid answer for some core questions before you take the leap into building and growing your sales organization.

• What problem is your company trying to solve? This will be your customer message — the reason someone needs or should want your product or service.
• What are the traits of the industry and persona you’re solving for? Understanding your customer persona is critical to knowing how you can better connect to your potential customer and the pain point they’re aching to solve.
• Who has that problem? Knowing who to go after will drastically save you time, let you focus on how to correctly message and sell to that audience, and help maximize your sales efforts to increase the probability of closing deals.
• How do you solve that problem for that group? Why do your customers need your product and how does it differentiate from competitors? Explaining the “how” is integral to your sales narrative during customer conversations.

2. Define the desired role for sales

Once you’ve developed your business hypotheses, it’s important to ask whether this is the right time to think about sales in general as a way to get your product to customers. And the sales channel you ultimately choose — inbound, outbound, channel distribution — should be influenced by the customer’s willingness to pay and expected approach.

For example, think through the target ASP of your product. What type of sales numbers would you need to hit to justify the customer acquisition cost? Inability to justify the cost near-term shouldn’t make or break whether you hire a salesperson, but it should be top of mind as you test your sales channel options and figure out how the buyer of your product or service is likely to make their purchase.

Essentially, make sure you have a clear outlook on the “purpose” of sales in your organization (such as gathering product development insights to help you reach your product-market fit, providing better customer service, hitting ARR targets). This will help you figure out who you’re looking for as a hire and how the organization around them will develop and grow.

3. Outline key characteristics for your first sales hire

Before you post a job on LinkedIn or reach out to your network, determine you candidate’s inalienable needs. Industry experience doesn’t always outweigh startup experience here, since startup culture is fast-moving, ever-evolving, and filled with an array of uncertainty — and not everyone is cut out for it.

Personality and style are details not to be overlooked in your search. You could find that person who can sell a hamburger to a vegan, but if they don’t understand what drives your business and can’t mesh your scrappy but driven technical team, it’s going to be hard for them to excel. And if it’s clear early on that it’s not working, be willing to your cut the cord before it poses risk to your team, your processes, or your brand.

A required skill you won’t find on a resume is the candidate’s willingness to have difficult, even probing, conversations. Your sales hire will be doing this with clients and prospects to understand why they won’t buy, determine their willingness to pay, learn what similar offerings they’re considering, and get to the heart of what problem this solves for them — helping you ensure your product is doing what it needs to. Role-play during the interview process to let them show you whether they can probe for the information you need in a way that strengthens a relationship with the customer rather than pushing them away.

At the risk of reading like those ‘impossible dating criteria’ lists, here are some personality traits and characteristics we’ve seen in the best sales reps:

• Agility. In the early stages, people wear many hats and shouldn’t be limited by their role. This person should be willing to jump in when and where they’re needed.
• Comfort with ambiguity. You’ll appreciate having someone who’s okay with the unknown and for whom lack of process doesn’t spark anxiety.
• A love for building processes. Chances are you don’t have a ton of processes right now, so find someone who enjoys creating them and iterating on the ones you do have in place.
• Achievement-oriented. Look for someone who’s motivated by success.
• Team-oriented. At this stage, no role or function can work in a silo. Sales will receive key customer and product feedback, so the ability to work well with technical and non-technical folks matters.

When you are ready to begin your search, lean into your VC network, too. Your investors want you to succeed, and chances are they have a lot of connections, whether it’s a first or second degree, and would be happy to make introductions.

4. Think about opportunities to pair marketing with sales

Agility and the willingness to wear multiple hats is a winning characteristic for your sales hire — and marketing responsibilities are likely to play a considerable role for this first person.

For example, your sales rep will work with you on the right messaging to push the product or service, frequently creating templates and presentation decks or even white papers. When creating the sales narrative, you’ll want them to have a clear philosophy on how to speak about the product and to ensure this matches with your overall ideas on company voice. It’ll be crucial that they interact closely with the technical side of the house as the product develops and evolves.

5. Don’t forget about the importance of customer success

Keeping your current customer happy is just as important as finding new customers and closing deals. Often that responsibility is for you as CEO to handle, but it may also be that your first sales hire — the POC for many early customers — will remain the go-to for their general post-sale needs. If that’s the case, they’ll need to be able to loop in the technical team as they add customer success to their many hats.

Wherever that role falls for your product and company structure, it’s important to have a plan for handling the needs and lifecycle of your early customers and to clearly identify where that fits vis a vis the skills you’re looking for in your first sales hire.

6. Pace yourself on developing a full sales organization

Eventually, the time will come when your all-star sales rep needs to grow into a true sales organization that can cover the range of roles and functions fully, and at scale. Identifying this time is less of a science than you might think, and it’ll vary by business and industry, but one way to think about it is in terms of pain.

Building out a full early-stage sales organization with split roles often becomes the right thing to do when you find you’re encountering pain or inefficiencies that are preventing you from reaching your maximum potential. When those inefficiencies mean that you’re leaving money on the table, it’s time to expand.

Or, another way to think about it: along with the growth of the product itself, the processes and learnings your first sales rep brings to the company drive when and how much you’ll need to scale the team around them. The more successful they are at selling your solution, the sooner you’ll need that expanded team. So as a positive motivator, let them prove the need for scaling the sales org.