You’ve started a company and are considering hiring your first salesperson. Congrats! It’s taken a ton of dedication, perseverance, and creativity to get this far.
But where to begin? How do you know when it’s the right time? Who should you look for?
In my role helping startup executives within the Amplify portfolio, I get these questions a lot. Personally, I’ve been down this path several times before, building and running sales teams from start-up through exit. Here’s my attempt at packaging the lessons I’ve learned into a short, digestible guide for others on a similar journey.
Caveat: Recognize that every start-up is different – apply my advice with discretion based on your individual situation, company, and industry.
When to hire your first salesperson
“The right time” can vary from one company to the next (per my caveat above). But there are a few indications that could signal you’re ready to formally invest in Sales.
- Funding: Your startup should have some money in the bank, likely funded at the Seed stage or greater. This will give you the necessary foundation and runway to hire and retain Sales talent.
- Product: It’s worth stating (at the risk of sounding obtuse) that a seller needs something to sell. Don’t put the cart before the horse. Before hiring a salesperson, you should have a product that’s beyond beta – something that’s generally available (GA).
- Revenue: To cement the point above, you should have at least a handful of paying customers, thanks to early founder-led sales efforts. Revenue is starting to grow quarter over quarter. This signals stability and gives you the early ability to forecast, which indicates readiness for dedicated Sales.
- Demand: In addition to having existing customers, you should be seeing some market pull, as evidenced by growing web traffic, inbound demand and top of funnel pipeline. I wouldn’t be too quantitative here; rather, look for directional trends that are up and to the right.
With some early customers, demand, and financial footing, you have the baseline to start fleshing out product-market fit. This should be something the founding team is actively working through, and having a customer-facing Seller contributing to this effort can go a long way – which brings me to my next point.
Core responsibilities of your first Sales hire
In the startup world where you often only have a funding runway of years, you’ll need to make some tough choices when you hire. Your first Salesperson will be tasked with more than just closing deals and/or growing a team of hungry sellers. This key role will be a critical member of the team as you work together to hypothesize and experiment to find product-market fit.
If I had to stack-rank the core responsibilities of a first Sales hire in a job req, it would go something like this:
- Collaborate with product leads and executive team to iterate on and define our ideal customer profile (ICP).
- Act as liaison between early customers, prospects, and internal teams to define the minimum viable product (MVP) that serves a distinct market need; Be a critical part of the early team that identifies signal of product-market fit and uses that to define the selling motion.
- Be the face of the company from a Marketing and Sales perspective to establish a brand in the field, generate demand, and execute the Sales pipeline.
- Build a sales funnel and establish run-rate business with reasonably accurate ability to forecast revenues.
- Establish a Sales function from the ground up, starting as a direct seller with the opportunity to build a team.
It’s more important to hire someone who can help you identify product and market fit signals than it is to hire someone with management skills. But with that being said, there are a few key experience-related prerequisites that are worth mentioning before we delve into critical attributes and other “soft skills.” Finding a candidate that fulfills all of the requirements below might be aspirational, but in my opinion serves as a best-case starting point.
- Experience at 2+ early-stage startups, ideally in a similar space. Maybe they haven’t done exactly what you’re doing, but they've done something close. And they should genuinely enjoy the building phase.
- Strong track record of consistently achieving results despite tough circumstances.
- Direct sales rep experience with an interest in management. They might be earlier in their career and look like an IC. Even if the salesperson hasn’t directly managed people before, they have experience acting as a leader, working well cross-functionally, and managing both up and down internally. This correlates and leads us to the Key Attributes to look for in your Sales hire.
Last but most important, in my opinion, are the key attributes and soft skills to look for in your first Sales hire. This person will be in the trenches alongside you and the rest of the founding team, and the position is critical toward long-term success. Here are the critical attributes I’d look for.
- Strong communicator and collaborator: You should look for someone that you, Product, and Marketing will all be able to work closely with as you shape the product and your go-to-market motion together. Your Sales hire should be direct and assertive, while demonstrating respect and positive regard for others, and understanding when to yield to another person’s point of view—whether they’re communicating with customers or internal stakeholders.
- Creative: This person should be an out-of-the-box thinker, since they’ll be on point to develop and iterate on messaging, pitches, sales strategies, and pricing structures from scratch. When a potential customer says “no,” your Sales hire should be skilled at reframing and challenging the way they view the business or product, to see if there’s a way to create value.
- Deeply, conceptually technical with a voracious appetite to learn: They don’t need to code—but they need to get familiar enough with the nuances of your product and your market that you won’t waste a ton of time bringing them up to speed or explaining basic concepts to them over and over again. This understanding will help them match your product with the right market, and then repeat that success at scale. At this stage of your company—when you often have fewer than 50 people—you need everybody to be an input creator.
- Self-aware and honest: They should be open about skills or experience gaps, and capable of accepting and actioning feedback.
- Accountable: Your Sales hire should be willing to take ownership, driven to constantly improve, and show a high tolerance for change and ambiguity.
Knowing when to invest in a formal Sales function or who to hire isn’t always a black-and-white decision, but hopefully the suggestions here are useful to set you off on the right path.
Remember, you’re hiring someone who will work alongside you to find product-market fit. A junior candidate, or even a handful of sales reps, won’t be able to do this work effectively. On the other hand, someone with decades of management experience running enterprise teams will likely be too far removed from what’s needed on the ground floor of a startup. Think critically about what your organization needs, and how that maps to the key requirements, experiences, and attributes you should be looking for. Finding the right person will be worth the investment.