Sales / Founders make the best salespeople: Overcome the sales stereotype and get your startup on a winning path

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When it comes to sales, who better to represent your business than the person who started it all? Drawing from my own journey with Tigera, I've come to realize that founders possess a unique set of skills and knowledge that naturally lend themselves to the art of selling. This guide will dive into the reasons why founders are naturally effective salespeople, the pitfalls to avoid when selling, and practical tips to improve your sales game. It's a blend of personal experience and actionable advice aimed at helping you transition from founder to sales strategist seamlessly.Why do founders make good salespeople?As a founder, your grasp of your business is extensive. You’ve created your company and product, so you hit the starting line with a wealth of knowledge and insights. It's this depth of knowledge that sets founders apart and can make them great salespeople. Buyers, users and customers also have a unique level of respect for founders, stemming from an acknowledgment of the journey and expertise a founder brings to the table. They assess you on very specific criteria: Do you understand their domain? Can you empathize with their daily challenges? Do you understand what it's like to spend a day in their shoes? How well do you grasp technology and your products? I’ve discovered that most founders also have a remarkable ability to learn and apply new knowledge rapidly. This skill is crucial in sales. Adapting the same approach of quick learning and implementing it in sales strategies can be a game changer. You have an innate ability to absorb and react to new information and use it to enhance sales techniques in real-time.Sales traps to watch out forHere are some common pitfalls founders need to look out for when taking on a sales role for the first time: ● Underestimating your own knowledge: Many founders believe what they know is common knowledge. It's easy to fall into the belief that everyone knows what you do — but that's not the case. Your knowledge — whether it's about the domain, the product or your market — is vital. It’s not easy for someone new to replicate this understanding, and it’s essential for successful deals.● Buying into sales stereotypes: Many people believe salespeople are slick and fast-talking, but the real skill in sales is found in two practices: listening and asking questions. Top salespeople excel at these. They know that to understand and serve their clients better, they need to listen intently and inquire deeply. Don’t believe the stereotypes. When it comes to successful sales, there’s more than meets the eye.● Thinking you have to pretend to be someone else: Authenticity is crucial in sales. There are countless ways to be successful, and the most effective path is the one that’s true to your own style. Pretending to be someone you're not is a mistake — and it will affect your connection to your customer. Authenticity resonates with people, so staying true is crucial.How to get over the discomfort of sellingIf you have hesitations about selling, how do you get over them? Start by reframing your approach to the process. It’s okay to fail. In fact, falling flat is part of the learning process. Embrace uncomfortable situations and look at them as opportunities for experiential learning. Selling can be an exciting challenge for you. It’s about stretching your capabilities and stepping up to meet new goals. It might be daunting at first, but each effort is a step towards improvement. If possible, I recommend shadowing an experienced salesperson and observing their tactics. I learned a great deal by observing the best salesperson on my team early in my career. Their expertise was invaluable, and by paying close attention, I picked up the skills needed to lead effectively. And keep in mind: You can learn this. Sales, like any other skill, can be learned and mastered. It's not a mystical art or a trait that only a few are naturally born with. Break it down into components and study it analytically. Many founders are analytical by nature, and that's a strength. Use that strength to dissect the sales process, understand it and innovate from there. Look for the best examples around you, replicate what works and adapt it to fit your style. With this mindset, anyone can become a highly successful salesperson.So you’re selling — now what?As you start selling, take note of what works and what doesn’t, and use that information to continuously improve your playbook. Each interaction is a chance to refine your approach. Learn from each pitch. What resonated with the client? What fell flat? Take these lessons, adjust your strategy and try again. Think about small changes. Fine-tuning is better than a complete overhaul of your sales process. With every iteration, your playbook will get sharper, and your confidence will grow. Selling isn't static — it evolves as you do. Keep learning and iterating. That’s how you’ll find sustained success in sales.

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Founders make the best salespeople: Overcome the sales stereotype and get your startup on a winning path

TLDR

As a founder, you likely make the best salesperson for your company, due to your deep understanding and authentic connection to your business. This post outlines practical steps for founders to refine their sales strategy and close deals.

When it comes to sales, who better to represent your business than the person who started it all?

Drawing from my own journey with Tigera, I've come to realize that founders possess a unique set of skills and knowledge that naturally lend themselves to the art of selling.

This guide will dive into the reasons why founders are naturally effective salespeople, the pitfalls to avoid when selling, and practical tips to improve your sales game. It's a blend of personal experience and actionable advice aimed at helping you transition from founder to sales strategist seamlessly.

Why do founders make good salespeople?

As a founder, your grasp of your business is extensive. You’ve created your company and product, so you hit the starting line with a wealth of knowledge and insights. It's this depth of knowledge that sets founders apart and can make them great salespeople.

Buyers, users and customers also have a unique level of respect for founders, stemming from an acknowledgment of the journey and expertise a founder brings to the table. They assess you on very specific criteria: Do you understand their domain? Can you empathize with their daily challenges? Do you understand what it's like to spend a day in their shoes? How well do you grasp technology and your products?

I’ve discovered that most founders also have a remarkable ability to learn and apply new knowledge rapidly. This skill is crucial in sales. Adapting the same approach of quick learning and implementing it in sales strategies can be a game changer. You have an innate ability to absorb and react to new information and use it to enhance sales techniques in real-time.

Sales traps to watch out for

Here are some common pitfalls founders need to look out for when taking on a sales role for the first time:

● Underestimating your own knowledge: Many founders believe what they know is common knowledge. It's easy to fall into the belief that everyone knows what you do — but that's not the case. Your knowledge — whether it's about the domain, the product or your market — is vital. It’s not easy for someone new to replicate this understanding, and it’s essential for successful deals.

● Buying into sales stereotypes: Many people believe salespeople are slick and fast-talking, but the real skill in sales is found in two practices: listening and asking questions. Top salespeople excel at these. They know that to understand and serve their clients better, they need to listen intently and inquire deeply. Don’t believe the stereotypes. When it comes to successful sales, there’s more than meets the eye.

● Thinking you have to pretend to be someone else: Authenticity is crucial in sales. There are countless ways to be successful, and the most effective path is the one that’s true to your own style. Pretending to be someone you're not is a mistake — and it will affect your connection to your customer. Authenticity resonates with people, so staying true is crucial.

How to get over the discomfort of selling

If you have hesitations about selling, how do you get over them?

Start by reframing your approach to the process. It’s okay to fail. In fact, falling flat is part of the learning process. Embrace uncomfortable situations and look at them as opportunities for experiential learning.

Selling can be an exciting challenge for you. It’s about stretching your capabilities and stepping up to meet new goals. It might be daunting at first, but each effort is a step towards improvement.

If possible, I recommend shadowing an experienced salesperson and observing their tactics. I learned a great deal by observing the best salesperson on my team early in my career. Their expertise was invaluable, and by paying close attention, I picked up the skills needed to lead effectively.

And keep in mind: You can learn this. Sales, like any other skill, can be learned and mastered. It's not a mystical art or a trait that only a few are naturally born with. Break it down into components and study it analytically. Many founders are analytical by nature, and that's a strength.

Use that strength to dissect the sales process, understand it and innovate from there. Look for the best examples around you, replicate what works and adapt it to fit your style. With this mindset, anyone can become a highly successful salesperson.

So you’re selling — now what?

As you start selling, take note of what works and what doesn’t, and use that information to continuously improve your playbook. Each interaction is a chance to refine your approach.

Learn from each pitch. What resonated with the client? What fell flat? Take these lessons, adjust your strategy and try again. Think about small changes. Fine-tuning is better than a complete overhaul of your sales process.

With every iteration, your playbook will get sharper, and your confidence will grow. Selling isn't static — it evolves as you do. Keep learning and iterating. That’s how you’ll find sustained success in sales.

The founder factor: Leveraging your inherent strengths for sales success

The bottom line is clear: Founders are naturally predisposed to be effective salespeople because of their depth of knowledge and the respect they command.

Key takeaways to remember are:

● Your deep understanding of your business is a sales asset — use it.

● The best sales strategy involves listening carefully and asking strategic questions.

● Authenticity is a necessity for making genuine connections.

● Sales skills can be learned and mastered with a structured approachIteration is the name of the game. Evolve your sales playbook with each experience.

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