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Sales and Marketing + How to Talk to Investors with Tyler Bosmeny and YC Partners (HtSaS 2014: 19)

June 4, 2026
by
Y Combinator
YouTube video player
Sales and Marketing + How to Talk to Investors with Tyler Bosmeny and YC Partners (HtSaS 2014: 19)

TL;DR

In this video, the CEO of Clever shares his insights and strategies on sales for startups, emphasizing the importance of founders taking on the sales role and the unique advantages they have, as well as providing tips for effective prospecting, conducting sales conversations, closing deals, and avoiding common traps.

Transcript

okay so okay great thanks for having me so my name is Tyler I'm the CEO of clever and what I want to talk today is about sales and I have a little bit of insight into this I graduated college I actually studied math and statistics probably like some of you here in this room and thought I was destined for this world of Finance I was about to go star... Read More

Key Insights

  • 💼 Sales: Sales is often seen as a mysterious and intimidating aspect of running a startup, but as a founder, it's important to take on the responsibility of sales yourself.
  • 💼 Passion and industry knowledge: As a founder, your passion for your product and your deep knowledge of the industry can outweigh sales experience, making you uniquely qualified to sell your product.
  • 🏢 Clever: Clever is a software company that builds solutions for schools. They have achieved rapid growth, with one in five schools in America using their app platform.
  • ♂️ Prospecting: Prospecting is the process of identifying potential customers. Clever used personal networks, conferences, and cold emails to successfully prospect and reach potential customers.
  • 📞 Listening in sales: Good salespeople spend more time listening than talking. By asking the right questions and understanding the customer's needs, founders can build strong relationships.
  • 📄 Closing deals: Follow-up and tenacity are key in closing deals. Founders should be prepared to follow up multiple times and move the deal forward even if the customer seems hesitant or non-responsive.
  • 💰 Pricing and negotiations: Founders should be comfortable with negotiations and ensure that they don't get caught up in minor details during the redlining process. The goal is to sign deals and get revenue, so focus on moving forward.
  • 💡 Unique insight and scalability: Founders should highlight their unique insights in their pitch and consider the scalability of their product. Having repeatable aspects in the sales process can help determine the viability of a startup.

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Questions & Answers

Q: Why does the speaker believe that founders should take on the sales role themselves?

The speaker believes that founders have unique advantages, such as passion for the product and industry knowledge, that can make them more successful at sales than experienced salespeople. Founders also have a vested interest in the success of their startup and can convey their vision and commitment effectively to potential customers.

Q: What are some effective strategies for prospecting?

The speaker suggests using personal networks, attending conferences, and sending concise, customized cold emails to reach potential customers. These strategies can help founders identify and connect with potential customers who may be interested in their product.

Q: How does the speaker recommend conducting sales conversations?

The speaker advises founders to focus on listening and asking questions to understand the customer's needs and problems. By demonstrating genuine interest and empathy, founders can gain a better understanding of their customers and their unique challenges, which can help tailor their product offering to meet those needs.

Q: What are some common traps to avoid in the sales process?

The speaker warns against falling into the trap of endless follow-ups and quibbling over minor contract details. While persistence and attention to detail are important, founders should focus on reaching a yes or no decision as quickly as possible to avoid wasting time and resources on potential customers who may not be genuinely interested. Additionally, founders should be cautious of offering free trials, as they can delay the sales process and may not lead to a commitment from the customer.

Summary & Key Takeaways

  • The CEO of Clever shares his experiences and lessons learned from his career in sales and building a successful startup.

  • He emphasizes that founders should take on the sales role themselves, leveraging their passion for the product and industry knowledge to be successful.

  • The speaker provides strategies and tips for prospecting, conducting sales conversations, closing deals, and avoiding common sales traps.


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