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January 28, 2025 57 mins

Most companies think the answer to more revenue is to sell enterprise, but they aren't aware of the massive hassle and costs that come with going upmarket.

There's no such thing as free money. The bigger the deal, the more attention you need to give your customer. The more customizations you offer, the more versions of your product you have to maintain.

Many founders think the air is better up there because they think it'll solve their money problems. Spoiler alert: It won’t.

On this episode, Melissa and Todd discuss all things enterprise sales and why they stayed away from it, and why they think you should too if you have a good thing going with self-serve SaaS


Takeaways:
• What we learned from spending a decade selling to big companies
• The not-so-hidden costs of enterprise: sales, operations, product
• Why going upmarket is not always a path to more revenue
• Things you should consider before going upmarket

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Connect with our host

  • Follow Melissa Kwan on LinkedIn where she share stories & lessons from her founder journey weekly.
  • Subscribe to 'your founder next door', Melissa's bi-monthly newsletter on how to build a company without an abundance of resources and friends in high places.
  • Follow @themelissakwan on Instagram and YouTube where she shares short videos of business advice and other truth-bomb sound bites.

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