When to hire your first salesperson


As a founder, you should validate sales yourself, then hire a sales leader. Don’t rush hiring based on pressure from investors, or you may end up regretting it.
As a seasoned founder with multiple startups under my belt — including my latest venture, Vimaan — I've come to recognize that bringing in your first startup sales hire requires careful timing and strategy.

This article explores this pivotal decision and shows you how to align your vision with market signals, manage investor expectations and steer your startup through this important time.

The founder should make the first few sales 

In the early days, your founding team is the beating heart of your company's vision. That’s why I recommend that founders lead the charge in sales. You’re the one who can best articulate the unique value proposition of your product or service. 

But beyond communicating passion and vision, you’re also the right person to establish a sales motion — a repeatable sales process that proves the business can scale.

Before bringing on dedicated sales personnel, founders need to demonstrate that the sales process can be replicated and is not reliant on their individual charisma or networks. During this process, you’ll fine-tune the pitch, identify key customer pain points, determine if the product features support a repeatable and scalable business model and streamline the sales cycle.

While you’re out selling as a founder, you’ll also be honing in on product-market fit (PMF), which is one of the most challenging things about this period of your startup. You’re looking for a consistent demand and a clear customer profile that you’ve engaged with multiple times. During this process, you can get support from a sales rep or a sales professional, but you should be leading the charge.

Once these elements are in place — when you can see a clear pattern of why and how customers are buying, and you're confident in the repeatability of your success — that’s the perfect time to bring in a sales leader.

At that point, your salesperson can focus on scaling up the established sales motion rather than creating it from scratch. Their role is to multiply the success you achieved when you were driving sales, and apply the proven sales process to a broader market to drive the company's growth.

Which path are you on? Existing market vs creating a brand new category

Introducing a product into a well-established market is a whole different story from creating a brand-new category. Each scenario requires specific sales strategies and decisions from founders.

Let’s examine the distinct approaches required for each path.

Hiring a salesperson when you’re entering an existing market

In an established market, the playbook for sales and hiring is relatively clear. You generally know what you need to do first and what sales motion you’ll use, so you know what kind of personality to recruit as your first sales hire.

In one of my previous startups, we were enhancing an existing product in the magnetic disk drive industry. We knew our customer base and their needs, which meant we had PMF from the outset, so we could focus on perfecting the technology.

We looked for salespeople who were passionate about building the business from the ground up, not just interested in quotas and commissions.

If this is your situation as a founder, you can and should hire salespeople quickly, sometimes even before the product is fully ready. Especially if:
  • You understand the market and anticipate a lengthy sales cycle. This necessitates an early start to your selling process.
  • The sales motion is familiar — which means you’ll be able to integrate new hires quickly and effectively.

When to hire if you’re creating a new category 

When venturing into the uncharted territory of creating a new market category, the timing of expanding your team — particularly in sales — is completely different.

In a new market, the ideal salesperson is not just a seller but an explorer and educator. This person must have the tenacity to navigate untested waters and the insight to help shape both the market and the product.

It's tempting to rush into hiring a salesperson after early positive signs, but early positive feedback is not always indicative of true PMF. If you misinterpret these signals, you could end up throwing resources and commitment behind a direction that might not be right.

Rushing this decision can have serious consequences, including:
  • Wasted time and money: Investing in a sales direction without confirmed PMF might mean you squander significant resources. The financial hit you take might be difficult to recover from.
  • Broken trust: Entering the market too soon and having to retract or pivot publicly isn’t a good look, and it can harm your market credibility.
In this situation, it’s often safer to err on the side of hiring too late rather than too early. The cost of hiring too soon, both in financial and reputational terms, often outweighs the risks of delaying the hire.

I know the drive to grow fast is compelling — but have patience. Getting strategic validation of your market fit will pay dividends in establishing a sustainable and credible presence in a new category.

Which comes first: Sales rep or leader?

There’s a lot of debate about whether to hire a sales representative or a sales leader first. I know others advocate for starting with a rep who can nail down sales processes, but I firmly believe that hiring a leader first is essential. 

A leader comes with a vision for institutionalizing and standardizing the sales motion, so you can ensure that it’s optimized and ready to scale. Sales leaders are the architects of the team, and they will put down the foundation you’ll build on as you scale.

After your sales leader ramps up and puts processes in place, they can multiply their efforts by hiring a team.

Don’t cave to pressure

Navigating the pressures of VC or private equity demands is a common challenge for entrepreneurs, especially when it comes to hiring decisions. Investors, driven by their own metrics and timelines, might assume your startup is prepared to expand its sales force and could pressure you to accelerate at a pace that doesn't match your current readiness.

This push to hire a salesperson can stem from a gap in understanding about whether you truly have PMF — investors and board members may believe you’ve nailed down PMF, but you might have a different assessment of the situation. As the founder, you’ll need to maintain your internal gauge of whether you are truly ready to scale your sales efforts. 

If you’re not ready to hire, don’t just give in — have honest conversations with investors and board members and express your concerns.

Trust your instincts and knowledge of your business, and above all, be intellectually honest.  Make sure any move to expand the team is made with conviction and not just in response to investor impatience.

It's better to proceed with caution and hire when the time is right, rather than rush to hire and risk your company’s future on a foundation that isn't secure.

Navigating your startup’s first sales hire

Deciding when to hire your first salesperson is a critical part of the early days of your startup.  Here are the most important takeaways to guide your startup's sales strategy:
  • Founders should initially lead sales to establish a replicable sales motion and ensure PMF.
  • Understanding market nuances is key — different strategies apply for existing categories vs. new market creation.
  • Hiring a leader first lays a solid foundation for sales, as opposed to starting with a sales rep.
  • Open, honest communication with investors is essential for resisting premature hiring and safeguarding the company’s trajectory.
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