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Pitching in the Sales Process

In sales, narratives are critical to connecting with potential customers. Whether it’s a 1-sentence elevator pitch or a 40-minute sales presentation, this guide will provide you with actionable strategies to strengthen your pitch, create impactful discovery questions, and integrate them seamlessly into your founder-led sales process.

Special thanks to Sales expert and advisor, Peter Wooster, for his collaboration in creating this resource.

About Peter Wooster

Peter has 25 years of Tech Sales and Executive Management experience. 

He founded Wooster Advisors 8 years ago to help early-stage and growth-stage technology companies with setting up and growing Sales and Customer Success. He has advised over 85 venture-backed companies to date. 

Prior to Wooster Advisors, Peter was the Chief Revenue Officer for Marin Software, where he grew revenue from $0-$80 mill and was part of the Executive Management Team that completed a successful initial public offering (MRIN). Joining in 1999, he was the founding member of the sales organization (15th employee overall). Peter was responsible for Strategic Accounts as well as building the first ever SaaS sales team. He was at for 4+ years and was a member of the sales organization during the IPO.

If you'd like to learn more about partnering with Peter Wooster, please contact the Lighthouse team at

Why Your Pitch Matters

Your pitch can be thought of as a powerful storytelling tool that enables you to share the story of your product and the reasons behind its creation. It serves as the backbone for all your outreach efforts, including email campaigns, live conversations, and product demonstrations.

But why is this so crucial? Essentially, your pitch sets the tone for your entire sales journey. It helps form the foundation for your research, identify the right companies to approach, prepare effective discovery questions, and lay the groundwork for successful prospecting and outreach.

Crafting Your Pitch

In order to create your pitch, you need to understand your product category, hook the potential customer with your background, and link your product benefits to the customer’s needs. 

Understanding Your Category

Before crafting your pitch, you must first identify the category your product falls into. There are 2 main categories to consider:

  1. The Disruptor: Disrupter products involve selling in an existing marketplace with competitors. Prospects are aware of the problem you're solving, and they are actively seeking better solutions. Think of Salesforce — when they entered the scene, they addressed a problem everyone was already familiar with. In this scenario, your discovery process often flows smoothly because prospects know the problem and are actively looking for a better solution.
  1. The Evangelist: If your product introduces something new to the market, you fall into this category. Here, you're educating potential customers about a problem they might not even know they have. Your sales process is more about creating awareness and showing the value of your solution.
Case Study: Marketo
In the case of Marketo, a company that entered the scene with groundbreaking marketing automation solutions, many businesses didn't understand the full spectrum of what Marketo's solutions could offer. Terms like "marketing qualified leads" and "sales qualified leads" were unfamiliar, and the idea of breaking down the marketing pipeline into specific categories was a foreign concept. Most businesses simply thought of leads, opportunities, and prospects.

To succeed in such a scenario, Marketo had to educate potential customers about the challenges they might not even realize they had and then convince them to evaluate the products and processes. It was almost like having two sales cycles right from the start: first, making businesses aware of their hidden challenges and then persuading them to go through a full sales cycle.

Pitch Framework 

While there’s no universal approach to your pitch, here are some essential steps to consider: 

  1. Build Your Origin Story: Your origin story is the narrative behind what you've created and why you've created it. Why did your team decide to build this product or service? Were you solving a challenge that you personally faced? Or did you see an opportunity in the market that others might not have noticed? It's about articulating the "what" and the "why."
  2. Connect with the “Why”:  When prospects understand why you've built your product, they want to know that you're not just another company looking to make a sale. They want to know that you genuinely believe in what you're offering.
  3. Explain Universal Benefits: Highlight what your prospects can expect when they become your customers. Will they save money, generate more revenue, save time, or operate more efficiently? These universal benefits should be woven into your narrative. They help prospects envision your value and how it aligns with their goals.
  4. Clarify the Process: Once you've framed the "what" and the "why," it's essential to explain how the process works. How do prospects go from being aware of your product to becoming satisfied customers? Is it a short-term project or a long-term commitment? By outlining the process, you make it easier for prospects to grasp the journey they're about to embark on.
Pitch Example

Here’s an example we've created using the company, Tome and their 43 million series B funding announcement

“Hi, [Name], 

Great to meet you. I’m the founder of Tome, an AI-powered storytelling tool that lets anyone create compelling stories. 

My co-founder and I realized that the current methods of creating and delivering presentations were outdated and hard to maneuver. Creators and teams often spend countless hours tinkering with their presentations only to make them look marginally better, and, ultimately, these creators are unable to achieve the desired impact on their audience. 

Through our work at Instagram and Messenger, we realized there was a better and faster way to tell stories. Tome has beautiful, modern creation tools that are powerful and easy-to-use for anyone. For example, our text tool automatically beautifies text, saving you the time to search for the perfect font or adjust letter spacing and shadows. Our table feature is also simple, useful, and powerful.

Tome is seamless to incorporate into your team's workflow, and we have a dedicated Customer Success team to help you onboard. 

Can I ask you some questions about your current presentation workflow and learn how Tome can make it more seamless for you?

Tailoring Your Message for Engagement

Your pitch should be adaptable to different stakeholders and buyer types. Consider who you're talking to and what their role is. Are they a user champion, a leader, or in an operational or financial role? 

Typically, there are 5 key stakeholders you may want to tailor your base story to: 

  • User/Champion: Your direct user and advocate
  • Leadership: Owns the budget and strategic outcomes
  • Operations: May own the implementation and/or administration
  • Financial: Manages the budget and procurement process
  • Technical: Defines and evaluates technical requirements 

If you're speaking with someone who is typically in an operations role, for example, you can highlight the ease-of-use. If there are multiple decision-makers on the call, you may want to dedicate a little extra time to make sure everyone understands the key points and how they’re relevant to their role. 

Additionally, you should consider where they are in the buying process. Here are the main buyer types to focus on: 

When in doubt, refer back to your Customer Personas.

Best Practices: Making Your Pitch Work 

Here are some key takeaways to keep in mind when crafting and delivering your pitch:

  • Keep it concise and specific, avoiding industry jargon: Limit your pitch to a maximum of 2 minutes and tailor your pitch to the customer persona, explaining why it will exceed their expectations.
  • Verbally deliver your pitch; use slides and visuals to validate it: This allows you to further build and maintain a personal and emotional connection with the potential customer. Use slides to showcase relevant customer success stories and product features that may benefit the customer. 
  • Include facts only after mentioning your product concept and personal background: Begin your pitch with your personal background and what inspired you to create the company. Unless the customer gets hooked on the concept of what you built, they’re going to be skeptical. Once they’re intrigued, you can discuss benefits like ROI, costs, etc. 
  • Avoid too much personal background: Avoid getting too personal or including too much information on how the product should be assessed. You must earn the customers interest before you get the right to sell or qualify them. Use the majority of the time to explain how your product can help them.
When to mention competitors

Generally, you shouldn’t mention competitors in your pitch. However, if there's a dominant player in your industry, you can mention them to showcase your product's unique selling points. For instance, if 97% of the people that use Excel only use 15% of its features, and you built a product that focuses on those core features in a more streamlined experience, mentioning Excel would be warranted. 

Bringing up competitors should be done with caution and only if necessary, as it can detract from the impact of your own product story. 

Determining Pitch Success

Gauging the success of your pitch can be challenging, but you can often determine its impact through 2 measures:

  1. Emotions towards the product: The audience's response to the pitch should give you a clear indication of their interest. A positive reaction may result in a request to continue the conversation, while a negative reaction could mean that the product does not align with their needs or budget.
  1. Understanding the product: More importantly, at the end of the call, the customer should have a clear understanding of the product. They may love it and want to proceed to the next step, or may determine that it is not a fit for them and choose not to move forward. 

If there is uncertainty, the pitch was not successful, and it’s best to clarify any points before ending the call. 

The goal for both you and the customer is to have a mutual understanding of the potential for a future relationship, and as a result, avoid wasting your or their time. 

Discovery Questions

To maximize the impact of your pitch, use discovery questions to learn more about the customer, their challenges, and how to meet their needs.

Note: discovery questions are not qualifying questions. The goal of discovery questions is to understand the customers’ pain points (focus is on their needs), not if they qualify for a sale (focus is on your needs). 

Setting the Stage

Before delving into the essential discovery questions, it's crucial to set the stage for the conversation. Take a moment to establish a rapport with your prospect. This can be a brief introduction or a 30-second version of what you do. The goal here is to create a foundation for a meaningful conversation. Remember, you should be prepared to share a more detailed version of your story if your prospect expresses interest.

Creating Effective Discovery Questions

To create discovery questions, there are 3 steps: 

  1. Determine practice blockers: The first set of questions in the discovery process should focus on clarifying technical blockers. These are not budget-related or decision-making questions; they are about determining whether there are any fundamental issues that might hinder the prospect's ability to benefit from your product or service.
  2. Define Product Competencies: Clearly define the value your product can provide, either unique to you or better than a competitor.
  3. Decide Strong / Weak Answers: Hold yourself accountable by deciding what a strong or weak response is before talking to prospects.

Discovery Question Examples

Using the company Square as an example, here are some questions you can ask after your pitch to help tailor your discussion or presentation:

Tailoring Your Pitch

Once you've gathered preliminary information and ruled out any technical obstacles, it's time to shape your pitch to be as bespoke as possible. A generic presentation is rarely effective; your sales presentation should always address the unique needs and challenges of the prospect. 

To craft a personalized pitch, you should ask questions that reveal:

  • The prospect's specific pain points and challenges.
  • The aspects of your product or service that would be most beneficial to them.
  • Whether they are currently facing the problem you aim to solve.

Align and Agree

The final step in the discovery process is to align with your prospect and mutually agree on whether there's potential for further engagement. It's not the stage to discuss budget and timing, but rather to confirm that both parties see value in moving forward. If there is alignment, you can proceed to the next steps of the sales process.


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