All Episodes

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

Contact ProfitLed

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.

This podcast was brought to you by eWebinar.

Learn more at ewebinar.com and find out how you can turn pre-recorded videos into automated webinars that perform better than a live webinar.

Thanks for listening!

Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
My Favorite Murder with Karen Kilgariff and Georgia Hardstark

My Favorite Murder with Karen Kilgariff and Georgia Hardstark

My Favorite Murder is a true crime comedy podcast hosted by Karen Kilgariff and Georgia Hardstark. Each week, Karen and Georgia share compelling true crimes and hometown stories from friends and listeners. Since MFM launched in January of 2016, Karen and Georgia have shared their lifelong interest in true crime and have covered stories of infamous serial killers like the Night Stalker, mysterious cold cases, captivating cults, incredible survivor stories and important events from history like the Tulsa race massacre of 1921. My Favorite Murder is part of the Exactly Right podcast network that provides a platform for bold, creative voices to bring to life provocative, entertaining and relatable stories for audiences everywhere. The Exactly Right roster of podcasts covers a variety of topics including historic true crime, comedic interviews and news, science, pop culture and more. Podcasts on the network include Buried Bones with Kate Winkler Dawson and Paul Holes, That's Messed Up: An SVU Podcast, This Podcast Will Kill You, Bananas and more.

The Joe Rogan Experience

The Joe Rogan Experience

The official podcast of comedian Joe Rogan.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.