Why a founder should lead (and close) the first ten deals


As a founder, you’re the bedrock of your startup’s sales strategy. This article will make the case for why you should be your startup’s first salesperson, and how to build a powerful sales team after you close your first deals.
Being hands-on in the early stages gives you, the founder, the tools you need to build a strong foundation for your company's growth.
As your company's founder, you need to experience dealing with customers, and to deeply understand your market and help shape the sales strategy. That’s why you should plan to close the first ten deals yourself before you bring a sales team into the picture.
In this article, you’ll learn why acting as your company’s first salesperson is a good idea, and how to stay involved in the sales and marketing processes after you begin to scale.

The five biggest benefits of closing your first ten deals yourself

1. Reducing potential risk

As a founder, the most important thing you can do is de-risk your idea before committing resources to it. It’s critical to validate the demand for your product or service and test it in the real world.
There’s a school of thought that says you can use interviews and market research to de-risk, but you’ll get the highest signal quality and the most useful intelligence by actually going out and trying to sell your product to real people.
Connect with people in your target market and give them your full pitch. When you’re actively trying to sell something, and someone needs to write a check if they want to buy from you, it triggers a set of events that genuinely uncovers whether what you have to sell is valuable or not.
If your initial sales attempts don’t go anywhere, you’ll have the opportunity to course correct before you’ve committed serious resources.

2. Learning how to articulate your idea

The second reason I still practice this process today (and make early sales myself) is that it helps me figure out how to articulate my idea.

This isn’t as easy as it sounds. How do you want to position your product? What are the right words to capture (and hold) a prospect’s attention?

You might have a fantastic idea, but if you can’t position your product in a way that resonates, understand the user’s pain points and connect those pain points to your solution, the chances of closing deals and building a business are low.

I’ve found that selling allows me to make evaluations and corrections in real time, because I get feedback during conversations with prospects.

When you’ve experimented with your positioning and have a message that resonates, you can use that data to build a repeatable process with your future sales team.

3. Debugging sales problems

In the early days, if you’re trying to close deals using a sales team, it’s difficult to know how to debug sales problems and figure out why something isn’t working if you haven’t been in the role of a salesperson.
And if you hire and train an entire sales team before you have the right messaging and positioning, it will be six months or even a full year before you figure out why things aren’t working. That’s a costly problem to unpack and fix.
When you sell as the founder, you can experiment on the fly, iterate on your messaging rapidly in the field and land on a coherent sales strategy. And it makes it so much easier to spot and fix sales problems down the road, because you’ll know what to watch out for.

4. Creating your dream sales team

If you close early sales yourself, you’ll know what skills and strengths to look for in salespeople and sales leaders when it’s time to hire.
By spending time in the trenches, you’ll understand what it takes to convert prospects into customers — not only the words to say, but the personal characteristics it takes to make those conversations successful.
Whether it's the ability to understand customer needs, communicate the value of your product effectively or handle objections, you know what makes a good salesperson — because you've been in that role yourself.
Use your experience as a salesperson to assemble a sales team that can take what you’ve learned from the first few sales and turn that knowledge into a deal-closing dream team.

5. Improving your product strategy

With product strategy, you’re making bets regularly about what to build. Those will be risky bets if you don’t have your finger on the pulse of what the customer wants and needs.
Closing deals and interacting with customers puts you in direct contact with that customer pulse.
When you're intimately familiar with what customers are looking for, you can make product development decisions based on concrete data and interactions rather than theories and opinions. As a founder, your role isn't to dictate every feature, but to ensure that your product team is aligned with actual customer requirements.
Product managers who operate on hypotheses or opinions alone, without customer input, are often off the mark. Your perspective as a founder, informed by real-world sales experience, is invaluable in guiding these team members toward a more customer and market centric approach to product strategy.
Integrating sales insights into product strategy ensures that your team isn't working in a vacuum. You can bring the voice of the customer into every decision, which is essential for developing a product that meets market needs and drives business growth.

The sales-driven founder: Pivotal lessons for startup success

Moving forward, here's some essential advice for founders based on my experiences at Tigera and other companies:

Get firsthand sales experience

As a founder, you should plan to spearhead all the initial sales initiatives and close the first ten deals for your company. This direct engagement adds to your client list and ingrains the core skills and knowledge that will define your business's future.

Leverage founder insight

Use the insight gained from your initial sales to steer product development and team building. Your firsthand experience is irreplaceable, and it provides a benchmark for the qualities and expertise your team will need as you scale and bring on additional talent.

Stay involved in sales once you’ve built a team

Listening to Gong calls is an effective strategy. Gong has features to help you streamline this process and still hear the most important parts of every call. For example, I often set a filter to just listen to what the prospect or user is saying. You will find gaps during these calls and then you can quickly resolve problems with your sales team before they become big issues.

Create a feedback loop with marketing

As the founder, it's your job to ensure marketing messages are practical and that you can use them in sales conversations. If you can't see yourself using the marketing team's positioning to sell to live customers, it's a sign that the messaging might need reevaluation. By doing the sales yourself, you can give the marketing team the direct feedback they need to shape compelling campaigns.

Do a quick impact assessment

Buyers decide quickly if they'll give you their time. Within the first 2 minutes, they're judging whether you understand their main challenges — and there will be some eye-rolling if you don’t. Use what you learn in sales conversations to connect immediately and genuinely with these pain points.
Continually gauge whether your pitch is hitting the mark, or if it’s just filled with impressive sounding but empty phrases. The messaging should always resonate with buyers, not just sound smart.

How to be a sales-savvy founder

Founders who deeply engage in their sales process are often at the heart of a startup's success.
The hands-on expertise you glean from talking to customers directly becomes a reference point for every new hire, product innovation and marketing message — and you can make sure your company evolves with a clear understanding of your market's needs.
To sum up, here’s how to take a sales-driven approach as a founder:
  1. Close the first ten deals yourself.
  2. Use the insight from those sales conversations to steer product development, as well as sales and marketing efforts.
  3. Stay involved in sales once you’ve built a team.
  4. Do a gut check with your marketing messages to ensure they’ll connect with customers in under 2 minutes.
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