How First-Time Founders Can Develop Sales Skills

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“As a founder, what must you have to be successful?”

I’ve asked a lot of entrepreneurs this question—22, to be exact. And out of those 22 people, all but four answered:


At first, this answer surprised me. Wasn’t it more important to have a great idea, or a great team, or a great work ethic? But it started to make sense.

After all, entrepreneurs are constantly selling—they pitch investors, they pitch clients, they pitch potential employees, they pitch influencers and journalists, and so forth.

If you’re just starting out, and you’ve never sold before, check out these four strategies for learning how to sell.

Shadow a Salesperson

Watching a great salesperson work is hugely informative: you’ll get insight into their best practices, routines, responses to common questions and objections, and more.

But you shouldn’t follow just one salesperson around. As a general rule, shadow one salesperson from every “segment” you’ll be approaching.

For example, to learn how to sell to VCs, you should shadow a fellow startup founder. To learn how to sell to journalists, shadow a PR rep. To learn how to sell to your clients, shadow a salesperson in your industry.

You should call upon your network to get these opportunities. But let’s say you don’t know any PR reps or industry salespeople–in that case, I recommend finding relevant groups on MeetUp and leveraging the contacts you make there. For example, if you’ve founded a SaaS company, going to a meetup for SaaS entrepreneurs, salespeople, or enthusiasts would give you tons of potential connections.

Once you’ve identified some people you want to shadow, here’s how to frame your request:

Hey name,

I hope you’re doing well! I have a semi-unusual request for you: Could I follow you around for a day (or a half-day) while you work? You’re an amazing job title, and I’d love to learn how you communicate with clients and leads, talk to investors, pitch to influencers, etc. Lunch on me.

I’d be happy to work with your schedule, but if you’re too busy, absolutely no worries.


Your name

If you get a positive response, ask to shadow the person on a day where they’ve got a variety of tasks and meetings.

Here are a couple things I recommend watching for:

  • What language the person uses
  • How they tailor their approach to the individual lead or client
  • Which communication formats they use (email, phone, Skype, in-person meetings, etc.) and for what purposes (following up, answering questions, explaining the product, introducing themselves, etc.)
  • How they prepare

Once you notice an effective technique or strategy, you can incorporate it into your own sales methods.

Build a Sales Process

Pablo Picasso allegedly said, “Learn the rules so you can break them like an artist.”

And this maxim definitely holds true when it comes to selling. Once you’ve become a more experienced salesperson, you can go rogue.

But up until that point, establishing a sales process will give you consistency and direction—as well as a baseline for tracking your progress.

First, figure out how the typical sales process unfolds. This step will take a couple weeks, at minimum: You’ll need to be getting out there and doing lots of outreach so you can gather first-hand data.

Maybe you find that the average customer requires three phone-calls and one face-to-face meeting before deciding to buy. Or that it’s much easier to close deals with clients when you’ve given them a live demo. Or that rather than reaching out to the CEO of the company about your payroll software, you should contact their human resources decision.

Take what’s most effective, and create a formal plan. This plan should have distinct stages; so, Stage 1 might be “Establish contact with manager of human resources,” whereas Stage 2 could be, “Schedule product consultation.”

While it’s most important to set up a process for traditional selling, you’ll also find it helpful to set up processes for pitching to VCs, the media, and anyone else you’re informally selling to.

Identify Your Sales Personality

Everyone has a different sales personality. Some people are hyper-confident and almost aggressive, while others are more reserved and quiet. Some people are fantastic at creating long-term connections with customers; others are instantly charismatic.

Why is your sales personality important? Well, it’s going to dictate how you sell when you’re not trying to consciously alter your behavior.

There’s a seemingly infinite number of tests, quizzes, and charts online to help you discover your “sales type,” but the easiest (and most authentic) way doesn’t require any external tools. Just think about your networking personality.

If you find it easy to enter a room and strike up a conversation with a stranger, then you’ll likely default to a confident, energetic sales approach. On the flip side, if you find making small talk exhausting and boring, then your sales approach will probably focus on really getting to know the customer and identifying their pain points.

Recognizing how you naturally sell will help you play up your strengths. Choose situations that work with your sales personality–to use the previous example, if you hate small talk, then don’t chase leads at a big conference. Instead, go to an industry dinner or laid-back get-together.

Pitch All the Time

The more practice you get, the better you’ll be. With that in mind, you should try to pitch constantly.

That’s easier than you’d think. If you’re open to selling opportunities, you’ll find them everywhere.

To give you an idea, let’s pretend that a friend asks you which movie you’d like to see on Friday. Make it your mission to “sell” her on your movie of choice.

The next time someone asks you about your company, recognize it as a chance to practice your elevator pitch and sell him your startup.

If you’re in the office, interviewing a job candidate, you should absolutely be focused on selling the position, the team, the culture, and so forth.

Basically, not a day should go by where you don’t try to sell someone something.

As you do this, I suggest writing down what works and what doesn’t. Having a detailed log will show you which strategies to keep and which to throw out.

Most startup founders don’t come to the table knowing how to sell. But by following these four strategies, you can learn how to close like a pro.

Frequently Asked Questions (FAQs) on Developing Sales Skills for First-Time Founders

How can I develop my sales skills as a first-time founder?

As a first-time founder, developing your sales skills is crucial. Start by understanding your product or service inside out. This will help you to confidently explain its benefits to potential customers. Next, learn about your target market. Understand their needs, preferences, and pain points. This will enable you to tailor your sales pitch to address their specific needs. Practice active listening and effective communication. These skills will help you to build strong relationships with your customers. Lastly, always seek feedback and be open to learning. This will help you to continuously improve your sales skills.

What are some common mistakes first-time founders make when selling?

Some common mistakes include not understanding the customer’s needs, focusing too much on the product features rather than the benefits, not effectively communicating the value proposition, and not following up with potential customers. Avoid these mistakes by taking the time to understand your customers, focusing on benefits, clearly communicating your value proposition, and maintaining regular contact with potential customers.

How can I improve my negotiation skills?

Improving your negotiation skills involves understanding the needs and interests of the other party, being prepared, and being willing to compromise. Practice active listening to understand the other party’s needs. Prepare thoroughly by researching and understanding all aspects of the negotiation. Be willing to compromise and find a solution that benefits both parties.

How can I build strong relationships with my customers?

Building strong relationships with customers involves understanding their needs, providing excellent customer service, and maintaining regular contact. Understand your customers’ needs by asking questions and listening to their responses. Provide excellent customer service by being responsive, helpful, and professional. Maintain regular contact with your customers through follow-up calls, emails, or meetings.

How can I effectively communicate my value proposition?

Effectively communicating your value proposition involves clearly explaining the benefits of your product or service, how it solves a problem, and why it’s better than the competition. Use simple, clear language and focus on the benefits that are most relevant to your target market.

How can I handle objections from potential customers?

Handling objections involves understanding the objection, addressing it directly, and providing a solution. Listen carefully to the objection, ask questions to understand it fully, and then address it directly with facts, examples, or testimonials. Provide a solution that resolves the objection and benefits the customer.

How can I improve my closing skills?

Improving your closing skills involves understanding the buying signals, creating a sense of urgency, and asking for the sale. Look for buying signals such as questions about pricing or delivery. Create a sense of urgency by explaining the benefits of acting now. Ask for the sale directly and confidently.

How can I improve my follow-up skills?

Improving your follow-up skills involves being organized, being persistent, and providing value. Keep track of all your follow-ups in a CRM or spreadsheet. Be persistent but respectful in your follow-ups. Provide value in your follow-ups by sharing useful information or insights.

How can I improve my presentation skills?

Improving your presentation skills involves practicing, getting feedback, and continuously learning. Practice your presentation multiple times to become comfortable with the material. Get feedback from others and use it to improve. Continuously learn by reading books, taking courses, or watching videos on presentation skills.

How can I improve my prospecting skills?

Improving your prospecting skills involves understanding your target market, using multiple channels, and being persistent. Understand your target market so you can identify potential customers. Use multiple channels such as email, social media, and networking events to reach potential customers. Be persistent but respectful in your prospecting efforts.

Aja FrostAja Frost
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Aja Frost is a writer, tech/design geek, and podcast addict. Check out her site or say hi on Twitter.

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