The Better Customer–Startups or Big Enterprise? | Summary and Q&A

TL;DR

Selling software to startups can be a successful strategy, as demonstrated by companies like Stripe, PagerDuty, and Gusto, but it is important for founders to understand when it is a good fit for their product and target market.

Key Insights

• 📈 Selling software to startups has been a successful strategy for many top companies, such as Stripe and PagerDuty, who initially focused on selling to other startups in the YC network.
• ⚠️ However, selling to startups may not always be the best move, especially if a company's product is naturally suited for larger enterprises with longer sales cycles.
• 📉 Founders sometimes make the mistake of trying to sell enterprise-grade products to startups that don't actually have the need or resources for them.
• ❌ Founders should be cautious of assumptions that selling to startups will be easier than selling to established enterprises, as startups can still be demanding and not willing to pay large amounts.
• 💔 Churn is a common issue when selling to startups, as their needs may change as they grow and require different products or solutions.
• ✅ However, selling to startups can be a powerful strategy to gain traction and create a bridge to larger enterprises, as startups can serve as evangelists and training grounds for future customers.
• 🚀 Engaging with startups can provide a pathway to penetrate larger enterprise markets, as they introduce the product to their engineers who may later transition to bigger companies and advocate for its adoption.
• 💡 The key is to understand the game you're playing and how selling to startups fits into that strategy, learning from successful companies in similar spaces and tailoring your approach accordingly.

Transcript

i just want to turn my startup into like a real-time strategy game where i can sit at my computer and click on things and watch numbers go up if i can do that and just sit on the couch and have people bring me food and i click things we're in good shape hello this is michael with harjin brad welcome to inside the group partner lounge as y company t... Read More

Questions & Answers

Q: Why do many founders believe that selling to startups is the best approach for their software products?

Many founders believe that selling to startups is the best approach because they see successful companies like Stripe and PagerDuty starting out by serving startups and assume it is a formula for success. They may also perceive selling to startups as easier or less time-consuming than selling to larger companies.

Q: What are some reasons why selling to startups may not be the right strategy for a software product?

Selling to startups may not be the right strategy if the product is naturally suited for larger companies, if the sales cycle is too long for larger customers, or if the product requires enterprise-grade features that startups don't need. It is essential to assess whether startups align with the product's target market and if there are better opportunities elsewhere.

Q: Why is it important for founders to understand the difference between selling to startups and selling to larger companies?

Understanding the difference allows founders to determine which strategy aligns with their product and target market. Selling to startups can be a successful approach, but it may not work for all products. By studying successful companies in their chosen market, founders can learn from their strategies and avoid common pitfalls.

Q: What are some examples of companies that successfully used selling to startups as a strategy?

Companies like Stripe, PagerDuty, and Gusto have successfully employed selling to startups as a strategy. Stripe started as a payments processor for other YC startups, while PagerDuty's early customers were mostly startups. Gusto used startups as a bridge to enter the SMB market. These companies demonstrated the effectiveness of selling to startups in achieving long-term success.

Summary & Key Takeaways

• Selling software to startups has been a successful strategy for many companies, such as Stripe and PagerDuty, who started by serving other startups before expanding to larger markets.

• It is essential for founders to assess whether selling to startups aligns with their product and target market, as some products may be better suited for larger companies.

• Founders should not assume that selling to startups is easier than selling to larger customers and must be prepared for the unique challenges and demands that startups can present.