Sales Tips for Entrepreneurs. How to Build Confidence and Close More Deals

If the word “sales” makes your palms sweat—you’re not alone. In a recent VEST Tables discussion, women founders and professionals openly shared their struggles with sales: fear of rejection, discomfort with self-promotion, and not knowing how to start (or close) a sales conversation.

Whether you're launching a startup, building a consultancy, or growing your career, sales is an essential skill. This guide is here to help you shift your mindset, understand your selling style, and become a more confident, effective salesperson.

What Is Sales Anxiety—and Why Do So Many Women Experience It?

Sales anxiety is a real and valid experience. It often stems from internalized beliefs—like the fear of being “too aggressive,” the worry of coming across as inauthentic, or the pressure to be perfect. Many women are taught to be helpers, not closers. But that narrative is changing.

Here’s the truth: Sales is not about pressure—it’s about connection and value. When done with intention, it becomes one of the most empowering parts of your business journey.

Understanding the 4 Main Types of Sales

To sell confidently, it helps to know what kind of sale you’re making. Each one has different rhythms, tactics, and expectations.

1. Direct-to-Consumer (DTC) Sales

You’re selling directly to an individual—often online or in person.

• Focus on emotional storytelling and personal connection.

• Common in ecommerce, coaching, and lifestyle brands.

• Strong visual branding and clear messaging matter most.

  
  

2. Enterprise or B2B Sales

You’re selling to another business, often with multiple decision-makers and longer timelines.

• Focus on solving a business problem and demonstrating ROI.

• Trust and relationship-building are crucial.

• Expect formal pitches, contracts, and follow-ups.

  
  

3. Product Sales

This can be a physical or digital product—something people can use, hold, or download.

• Focus on functionality, differentiation, and ease of use.

• Demonstrations, samples, or user stories can drive conversion.

• Requires clarity in features and pricing.

  
  

4. Service-Based Sales

You’re offering your time or expertise—consulting, design, coaching, legal advice, etc.

• Focus on trust, track record, and transformation.

• Testimonials and case studies help potential clients say yes.

• Often involves calls, proposals, and custom packages.

5 Tips to Sell With Confidence (Even if You’re New)

1. Reframe Sales as Service

Sales isn’t about talking someone into something. It’s about helping someone get what they need. This perspective turns anxiety into empathy and puts you in the mindset of a trusted guide, not a pushy closer.

2. Craft a Powerful, Simple Pitch

If you can’t clearly articulate what you do and why it matters, your audience won’t feel confident either. Ask yourself:

• What do I offer?

• Who is it for?

• What results can they expect?

Clarity builds confidence—both for you and the buyer.

3. Practice, Don’t Perfect

The more you practice your pitch, the less scary it becomes. Role-play with a friend, record yourself, or rehearse answers to common objections. Remember: you don’t need to be flawless—you just need to be clear and grounded.

4. Follow Up Without Guilt

Many women hesitate to follow up, fearing they’re annoying or pushy. But sales rarely close on the first touchpoint. A thoughtful follow-up is not just okay—it’s often expected and respected.

5. Track Your Wins and Lessons

Each sales conversation is a learning opportunity. Keep a record of what worked, what didn’t, and how you felt. Over time, these notes become a personal playbook that builds resilience and growth.

You’re Not Bad at Sales—You’re Just New at It

Sales is a learned skill—not a personality trait or something you’re born with. Every successful entrepreneur, coach, or consultant you admire once fumbled their first pitch too. What matters is your willingness to learn, to listen, and to keep showing up.

Selling doesn’t require you to become someone you’re not. It asks you to own the value you already bring. By reframing sales as service, practicing your pitch, and staying grounded in your purpose, you can transform the process from intimidating to empowering. Remember, confidence is built one conversation at a time. You’re not behind. You’re just beginning. And the more you show up with intention, the more natural it will feel to close deals with clarity, integrity, and impact.