Hiring your first salesperson is momentous for any small business. As our promised economic improvement draws nearer, more of us will be in a position to consider this next step. But if you’re feeling hesitant, you’re not alone. For many of us, operations and support are a walk in the park to hire for, and sales is more like the Tongariro Crossing on a dark night. Considering hiring a salesperson is a sign you’re ready to grow, to delegate, and to bring in someone whose sole focus is generating revenue. But we don’t want to have someone eat up our profits, cause chaos in the office and kill our brand.
Salespeople are often more autonomous, more expressive, and more driven by results than other hires. That can be brilliant, or it can be a disaster. So how do you make a smart, confident first sales hire without losing sleep? Here’s our own thinking as we have supported our clients (and grown our own sales) over the last five years. We’ve written this up in the form of a practical guide to help you navigate the process.
You can thank us later.
Why Sales Hires Feel Riskier
Sales is personal. It’s the voice of your business. When you hire someone to sell for you, you’re trusting them to represent your brand, your values, and your reputation, most often without you in the room (which is the point, after all).
Unlike admin or operational roles, sales doesn’t usually follow a tidy checklist. It requires initiative, resilience, relationships and connection, and a bit of flair. The best salespeople want freedom to do things their way, and that’s where the tension lies. As a business owner, you want results, but you also want control!
This is the almost-impasse: to attract a great salesperson, you need to offer autonomy. But to protect your business, you need structure.
What to Do Before You Hire
So how do we get through the impasse? Fling ourselves at the applicant we like the most? The one who looks the part? Hire someone we know? (Are related to?!) Have seen selling for someone else?
We have all known these impulses, but true to form, great HR is our friend here and none of the above is the best answer! We have three good, solid steps for you, and two things to avoid, to set you up for success.
✅ Do define what success looks like.
Before you even write the job ad, get clear on what you want this person to achieve. Is it new client acquisition? Repeat business? A certain revenue target? Define the outcomes, not just the activities. This will help you decide who will help you achieve your outcomes most effectively.
✅ Do map your sales process.
Even if it’s informal, write down how sales currently happen. What’s the typical client journey? What tools do you use? What tone do you take? This gives your new hire a starting point, and helps you spot gaps. In fact this exercise may help you hold off before you hire as you could create better results without the investment and risk of a salesperson. It doesn’t require fancy analysis, just some time and commitment to do the groundwork well.
✅ Do set realistic expectations.
Remember your very first few sales? They take time! You are the face of your business and sales are easier for you now, but don’t forget what it was like in the beginning. Your first hire won’t transform your revenue overnight. Be honest about what’s achievable in the first 3–6 months, and build in time for learning and adjustment.
❌ Don’t hire based on charm alone.
It’s easy to be wowed by a confident talker. I have had lots more job offers than I have accepted because I interview well (even if I do say so myself!) Make yourself dig deeper. Ask about their process, their follow-up habits, and how they handle rejection. Ask questions relevant to your particular sales cycle, industry and market. Look for substance behind the sparkle.
❌ Don’t skip reference checks.
Always speak to the referees your candidate has listed. Ask probing, well prepared questions about performance, reliability, and how they worked with others. This is not the time for a friendly chat! Salespeople often fly solo, but they still need to play well with the team. In a close-knit country like New Zealand, it’s not unusual to spot mutual connections on LinkedIn. Take the opportunity to check this out. If you do, that can be a helpful nudge to dig a little deeper. Just make sure you’re being respectful and fair. My rule of thumb is to have a conversation you wouldn’t mind published somewhere. The goal isn’t to catch someone out, but to avoid hiring someone you’ll regret.
Structuring the Role for Success
We may yet write a whole blog on onboarding your first salesperson, but at this stage, let’s just touch on the following dos and don’ts:
✅ Do offer autonomy within boundaries.
Set clear goals and brand guidelines, but let them choose how they reach those goals. This balance helps them feel trusted while keeping your business protected.
✅ Do build in regular check-ins.
Weekly (or fortnightly) catch-ups help you stay connected, troubleshoot issues early, and celebrate wins. Salespeople I know love to get together and talk about how well they’ve done! But it’s also an opportunity to support them if the week hasn’t gone as well as they’d hoped. It gives your salesperson a sense of accountability and support which will help them be the best they can be.
✅ Do provide tools and training.
Even experienced salespeople need to understand your product, your market, and your systems. Invest time in onboarding, whether that’s with you or a collection of people in your business; it will pay off.
❌ Don’t expect them to “just figure it out.”
Salespeople aren’t magicians, and even if they appear confident, they can’t magic up reliable information. If your offering isn’t clear, your pricing is fuzzy, or your CRM is a mess, they’ll struggle. Set them up to succeed. Remember the initial few days they will only retain a proportion of your systems and processes, so give them another chance with review training and the support of a buddy they can ask questions of any time.
❌ Don’t ignore cultural fit.
Sales is high-touch. If your hire doesn’t align with your values or tone, it will show to your team and your clients. Make sure you have a valid 90-day trial in their employment agreement, and do not be afraid to use it. Cultural misalignment never corrects itself.
When You’re Not Ready to Hire (Yet)
If you know you need sales support but aren’t quite ready to take on a full-time hire, there are other options:
Think about a part time option. The market is such that you might be able to access someone very experienced and able who is looking for a meaty role, during school hours. Or perhaps they are complimenting another role and have 10 hours available a week? Feel free to give us a call if you would like some guidance on how to set something like this up lawfully and well.
Cold calling or appointment setting support is available. Get yourself in front of more people and set yourself up for success. Our secret weapon (not so secret now!) is Denise Simons of Relate Communications. Give me a call if you would like the inside scoop on how Relate helps FixHR.
Mary Crampton at Magnify Consulting offers outsourced sales and business development services tailored for small businesses. They help you build a healthy sales pipeline and sales system without the risk of hiring too soon. Whether you need help setting up your CRM, refining your sales strategy, or simply getting traction with new leads, Magnify’s by-the-hour model can be a smart steppingstone.
Yash Kapoor at Innovate Now has mind-boggling AI tools that support all your sales efforts, minimising the people involved and maximising slick processes to reduce waste and save time. Yash’s team optimises off-the-shelf IT solutions where possible to save development time and make fantastic solutions much more accessible to small businesses.
Hiring a salesperson is a leap, yes. But it doesn’t have to be a blind one. With the right preparation, the right structure, and the right support, you can make a hire that genuinely moves your business forward. At FixHR, we’ve helped a number of small businesses navigate this exact moment, from role design and employment agreements to onboarding and support managing those critical first few months.
If you’re ready to grow, and want to do it wisely, reach out to us to help you get it right the first time.
