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
Connect with Melissa
Follow Melissa Kwan on LinkedIn where she share stories & lessons from her founder journey weekly.
Find her on @themelissakwan on Instagram, TikTok, Twitter and YouTube where she shares short videos of business advice and other truth-bomb sound bites.
About Melissa Kwan
Melissa Kwan is the Cofounder and CEO of eWebinar, an on-demand video software with chat that lets companies run their demos, onboarding calls, and training sessions without anyone having to be there live. The idea came from her previous SaaS company, where she delivered the same sessions live for years and could only ever reach a fraction of her prospects and customers. She founded eWebinar to help people grow their business without growing their workload.
Melissa is a three-time bootstrapped founder with 15 years of startup experience. Specializing in B2B sales and business development, she has built companies with very few resources by automating what she could, outsourcing wherever possible, and inspiring talented people to join her with shared focus and enthusiasm.
Her previous company, Spacio, was the leading open house lead generation software in real estate, acquired by HomeSpotter in 2019 after four years. Before Spacio, she founded Flat World Apps, which built marketing apps for real estate developers selling residential pre-sales. She started her career selling real estate in Vancouver, then spent time in international trade in Hong Kong before moving into enterprise software. At 27, she left her job as an inside sales executive at SAP to start her first company.
That path through manufacturing, real estate, enterprise sales, and SaaS shapes how she thinks about building businesses. Over the last decade she has come to believe that happiness should be the foundation of a career rather than the result of one, and that it comes from designing your life with intention.
Melissa writes about bootstrapping with limited resources, on-demand delivery, product-led growth, life design, and the founder journey. Her writing has appeared in Forbes and Business Insider. She hosts the ProfitLed Podcast and writes a weekly Substack newsletter, "your founder next door," where she documents building eWebinar without outside funding.
She's a digital nomad who travels 10 months of the year and calls Amsterdam, New York, and Hong Kong home.
About ProfitLed
On Season Two of ProfitLed, Melissa (CEO and Cofounder of eWebinar) and Todd (COO) goes in-depth on one topic per episode on their "Journey to $1M" at eWebinar.
They share war stories, mistakes, and lessons learned as they grew the company to a million in ARR over 36 months. Their goal is to demystify bootstrapping by sharing their experience of it, and tell you what it's really like to figure things out as you go.
ProfitLed is a podcast by and for founders brave (and crazy) enough to grow their startups to profitability without venture capital.
Enterprise is not a way to a quick win, even if it seems like it.
