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Derrick Reimer

Founder and CEO · SavvyCal

Scheduling Indie SaaS

Why watch

Reimer is testing whether a small, craft-focused software company can still win a crowded horizontal market like scheduling against much larger rivals.

Derrick Reimer is the founder and CEO of SavvyCal, a scheduling tool he started in 2020 in Minneapolis, Minnesota, to take the friction out of finding a time to meet. A programmer and designer, he earlier co-founded the email marketing company Drip with Rob Walling and co-hosted The Art of Product podcast with Ben Orenstein for years.

From Drip to a failed Slack rival

Reimer and Walling built Drip into a marketing automation product for small businesses, and Leadpages bought it in 2016 in that company’s first acquisition. He maintained what he calls “a really large rails application for 8 years” there.

After Drip he built Level, a team chat product meant to compete with Slack. It did not take off, and he has described on the Indie Hackers podcast how he bounced back from it with SavvyCal.

Building SavvyCal as an indie company

SavvyCal launched with a small amount of backing from TinySeed and a few angel investors, and Reimer wrote much of it himself in Elixir and the Phoenix framework. “Elixir has been fantastic,” he said on The Tuple Podcast in 2024. He started from the observation that scheduling links save time, yet many people resist sending or receiving them, and he called it “both a product problem and a people problem” because of the etiquette involved.

On craft and small customers

Reimer describes himself as “predominantly a craftsperson” and has said openly that he is unsure how far a carefully made, low-priced product for small teams can grow when many founders now move to enterprise sales. Faced with the usual choice between raising prices to sell to enterprises and staying a small lifestyle business, his answer on the Tuple podcast was “how about neither?”

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