This guide is for founders of early-stage B2B tech companies employing a direct sales model as they move from founder-led sales to hiring their first sales professionals. Different companies make that transition at different times, which means that knowing who to hire, and what to look for, varies. But there are broad patterns and this guide is here to help founders understand where they are today, and what type of sales hire will help them achieve their future revenue goals.
Introduction
Making your first sales hire is a significant, company-altering decision. And if you don’t have a go-to-market (GTM) background or haven’t built a startup before, it can feel like a black box. And here’s the thing: Your first sales hire might be the most important GTM hire you’ll ever make. If you want to build a business that grows to hundreds of millions or billions in revenue, you first need to get to $5M, then $10M, and so on.
Let’s say you’ve decided it’s time to hire for sales. Maybe you no longer have the bandwidth to run sales yourself. Or maybe you’ve hit a ceiling on how much more you can mature your GTM motion and strategy without help. Either way, you face a tough question: Who should you hire?
At this stage, many founders are told to “hire a salesperson who’s seen your revenue ramp.” It’s the right advice, but for reasons that aren’t usually explained. Here’s the logic: Every company must answer four critical questions to build a repeatable, scalable GTM motion. Typically, the more mature your GTM, the clearer your answers. The less mature, the more you’re still figuring things out.
So as your company transitions from founder-led to sales-led GTM, you need a clear view of how mature your motion really is and where the gaps are. Only then will you know what kind of salesperson to hire, the type of person who will build on what you’ve started and set your business up for sustained commercial success.
The four questions:
- What are we selling? This is a question about your product. What exactly are you offering, and what problem(s) does it solve?
- Who are we selling to? This is a question about your Ideal Customer Profile (ICP). What kinds of companies are you targeting? And within those companies, who are the users and/or buyers?
- Why should the customer buy now? This is both a sales and marketing question. How do you tell your story, position your product, highlight customer pain, and drive urgency?
- How are deals sold? This is a question about your sales process. How do you consistently and predictably move potential customers through each step of the sale, from first conversation to close?
It’s important to remember that at early-stage companies, small teams mean broad roles. The less mature your company is, the more you need someone who can flex across sales, product, and marketing in real time which is a very different skill set from being just an A+ closer.
With that in mind, let’s get into the specifics of what your first sales hire should look like depending on your GTM maturity.
Stage #1 – Pre-Revenue
At this stage, you’re pre-revenue and likely pre-seed. Your primary focus is on answering the first two questions: What are we selling? and Who are we selling it to? Because right now, all you have is a theory. You think you see an unmet need in the market and you think you can build the technology to match it.
You either need to validate that theory or disprove it and pivot. Because if you can’t build a real product that solves real problems for real customers, your company will never scale.
But the only way to get those answers is by talking to customers, which takes some sales skills. You need to get onto customers’ calendars, ask sharp discovery questions that uncover customer pain and priorities, and feed those insights back to the product organization.
Typically, this role is filled by you, the founder. But there have been exceptions – Snowflake is a famous one – so it’s worth understanding what it looks like when a salesperson is hired this early. (More on the Snowflake story here.)
Just know this: If you hire for sales now, it’s not to hit a number…yet. It’s to embed in the market, identify buyer pain, test your narrative, and translate those insights into product and GTM strategy. The foundation is built now so you can go to market with confidence later
Key Deliverables:
- Conduct dozens or hundreds of discovery calls with potential customers.
- Develop a point of view on which companies and personas are most likely to purchase, and why.
- Document and synthesize recurring pain points, use cases, and objections.
- Act as a translator between market insights and the product org.
- Identify signals that a customer is ready to buy with urgency.
- Test and iterate early messaging and positioning with customers.
- Begin sketching the outlines of a future GTM motion and playbook.
Ideal Qualities & Experience:
- Strong discovery instincts. Listens deeply, asks smart/probing questions.
- Comfortable with 0 → 1 builds. Thrives in ambiguous environments and doesn’t need structure to start producing results.
- Strong outbound skills. Able to get on customer calendars without support from Sales Development Reps (SDRs), marketing, etc.
- Excellent communicator. Clearly conveys market learnings back to founders, product, and the board.
- Long-term mindset. Takes ownership of the product and business like a founder would.
What title is right? This person is probably a Director or Head of Sales. You might need to top this person in the future and it’s easier to do that if they don’t have a VP or C-level title. Given the strategic and cross-functional nature of this role, and the fact it’s not about driving revenue (yet), it’s unlikely this person is an Account Executive (AE).
Stage #2 – Early Revenue, Pre-Repeatability
If you’ve made it this far via founder-led sales, you’ve closed some deals and are likely in the $100K–$1M revenue range, probably with seed funding. Your product is maturing, and your ICP is starting to take shape. In other words, you have early but incomplete answers to the What are we selling? and Who are we selling it to? questions.
You’re also developing a point of view on the other two questions: Why should the customer buy now? and How are deals sold? But to build a repeatable motion and unlock real growth, you need more at bats in the market. It’s the only way to uncover what messaging and process actually works, over and over again.
This means finding someone who can sell and build. Not a top-down Chief Revenue Officer (CRO) who needs a big team or a junior AE who needs a finished playbook. You’re looking for an autonomous salesperson who can sell without a perfect playbook, while contributing to that playbook.
The right person won’t wait for clarity. They’ll create it. They’ll close deals, shape your GTM motion, and lay the groundwork for repeatability and scale.
Key Deliverables:
- Act as a translator between market insights and product decisions.
- Collaborate with founders and product to sharpen ICP and prioritize roadmap.
- Pipeline generator capable of sourcing deals independent of marketing or SDRs.
- Meet or exceed quota, while capturing what’s working and what’s not.
- Define and document the key steps in the sales process, from qualification to close, so early wins can be repeated.
- Test variations of qualification and discovery questions, pitch, and pricing. Find what works.
- Track objections and map which ones kill deals versus which ones are fixable.
- Create the first basic sales materials and collateral like email templates and pitch decks.
Ideal Qualities & Experience:
- Comfortable with 0 → 1 builds. Thrives in ambiguous environments and doesn’t wait for structure to start producing results.
- Full-cycle salesperson. Can generate pipeline independently and manage the process all the way through to close.
- Tactical and strategic. Hands on enough to sell but strategic enough to zoom out and shape GTM strategy.
- Efficient builder. Able to build lightweight but effective systems and processes quickly.
- Strong communicator. Distills customer insights into actionable input for founders and product.
- Resilient and reflective. Learns quickly from lost deals and adapts.
What title is right? It depends on your skill set. If you need help shaping your GTM strategy and motion, hiring a Head of Sales with some strategic range can make sense. But if you’re comfortable owning that yourself, you’re better off hiring two AEs who report directly to you.
Two AEs give you a baseline for comparison, gives you more at bats in the market, and makes it easier to spot what’s working and what’s not. The AEs can share insights and sharpen messaging together. If both fail, you may have a product or ICP problem. But if at least one succeeds, you’ve got real signal to build on.
Stage #3 – Meaningful Revenue, Ready to Scale
If you’ve made it this far without hiring a salesperson, you are probably over $1M in ARR with Series A funding, have real and referenceable customers, and functional answers to all four GTM questions. You’re not done answering them, but you have real market validation.
You’re also stretched thin. And now, lack of sales headcount and repeatability is the major bottleneck in the business. You’re not scaling yet, but you’re ready to.
This is when you bring in someone to professionalize your sales motion – a playbook-writing sales leader who can still sell, but whose primary job is to codify what’s working, build and mentor a world-class team, and lay the foundation for scale.
Key Deliverables
- Write the company’s first formal sales playbook.
- Create a simple, consistent process for tracking deals and projecting revenue. Set clear targets, regularly review active deals, and spot risks early so you can plan with confidence.
- Build a world-class sales team from scratch. Recruit top performers, onboard them quickly and effectively, and coach them into consistent revenue contributors.
- Design and implement a simple and motivating comp plan.
- Establish the revenue operations function and set up the foundational sales tech stack.
- Ensure tight feedback loops across product and marketing. Act as the connective tissue between sales and the rest of the org by turning market feedback into company strategy.
- Look at sales data to see what’s working and what’s not. Track how leads move through the process, why deals are won or lost, and where things get stuck. Then use those insights to improve how you sell.
Ideal Qualities & Experience:
- Comfortable with 1 → 10 builds. Thrives in ambiguous environments and doesn’t wait for structure to start producing results.
- Experience building and scaling early sales teams from scratch. Knows what to look for, how to interview and hire, and how to make great AEs even better.
- Player-coach mindset. Equally comfortable setting strategy and rolling up sleeves to execute.
- Data-driven without analysis paralysis. Understands how to work with incomplete data to forecast, identify and resolve bottlenecks, etc.
- Leads and motivates from the front. Willing to jump into deals and model what excellent looks like.
- Highly cross-functional. Collaborates well with founders, product, marketing, and post-sales.
What title is right? This person is likely a Head of Sales or VP Sales, though in the right scenario, it could even be a CRO. You are looking for someone with the seniority, experience, and strategic skills to build a true sales function. Ideally, they bring both a strong network and the gravitas to quickly recruit top AEs to your company.
A Few Parting Thoughts
First, I believe founders should lead sales for as long as possible. If you can’t sell your product with all of your knowledge and passion, no salesperson is going to come in from the outside and save you. And the more revenue you generate on your own, the more you’re proving you have a great product solving a real problem, and the easier it becomes to recruit a world-class salesperson. Top sales talent loves to sell a winning product. But not every founder will or can manage sales into the millions of revenue, so it’s worth exploring what the different sales hires should look like at different stages.
Second, as you’ve probably noticed, each stage reads like a mini job spec. That was intentional. If you’re a founder or hiring manager and want to copy or paste any of it for your own role, please do.
Third, while I hope this was helpful to a broad audience, I wrote it specifically with early-stage founders in mind who are hiring, or thinking about hiring, sales for the first time. I also tried to make it useful for the investors and advisors helping guide those decisions. So if you found this valuable and think it could help someone else, I’d be grateful if you passed it along, especially to someone in one of those groups.
And finally, if you’re hiring for sales and want to make sure you get it right, I’d love to help. I specialize in helping B2B tech startups with GTM hiring. Feel free to reach out at: rkim@spmb.com or https://www.linkedin.com/in/ross-j-kim/
