Derrick Reimer — From Co-founding Drip to Running a Small SaaS at SavvyCal

Derrick Reimer is the technical co-founder of Drip, an email marketing automation service, and the founder of SavvyCal, a scheduling service. While he personally handles development and design to build products, he has also used the help of co-founders, investors, and small teams depending on the business. His career shows not only the process of growing small products but also how his criteria for choosing his next business changed after a sale.

Drip: How a Small Email Tool Grew Into an Automation Business

Drip began in late 2012 with HitTail, a search keyword tool run by Rob Walling. Walling wanted to capture website visitors' email addresses, send educational emails, and connect that to free trial signups. Reimer, then working as a contract developer, implemented this feature, and even connecting a small popup with an email-sending function took considerable effort. The two began turning this process into an independent SaaS, began accepting users in 2013, and officially launched in November of that year.

Reimer did not join under the title of co-founder from the beginning. As his role in product development grew, he was recognized as a co-founder as a key person who had contributed from the early days. A division of labor formed in which Reimer focused on development and design while Walling handled customer interviews and marketing, and Drip grew without outside investment.

Early Drip was closer to a product for collecting email addresses and sending automated responses, but customers wanted more specific automation. A representative example was the ability to tag subscribers who clicked a specific link in an email or move them to a different campaign. As these requests were incorporated, customer churn decreased, and by 2014 Drip began to establish itself as an email marketing automation service beyond a simple sending tool.

In 2016, Drip was acquired by Leadpages, a landing page creation service. The two products connected naturally in that Leadpages collected visitors' email addresses and Drip handled the email marketing that followed. Walling described it not as a deal to buy technology or some personnel, but as a strategic deal that acquired the entire growing business. The specific deal terms at the time were subject to a confidentiality agreement, and the sale amount was not disclosed in public interviews either.

Level: The Gap Between Attracting Interest and Actual Adoption

Derrick Reimer did not leave immediately after the sale; he stayed on after the acquisition and left Drip in early March 2018. According to his recollection, as Drip's nine-person team joined Leadpages, which was about 150 people, the way they collaborated changed dramatically. He especially felt that Slack's culture of real-time conversation and expectations of quick responses eroded his time to focus. This experience became the starting point for his next product, Level.

Level was a Slack alternative meant to reduce work interruptions and handle conversations more systematically. Reimer published an article laying out the problem, interviewed about 40 people, and gathered interest from more than 6,000 people by letting them reserve usernames in advance. When he pre-sold early access for $49, about 50 people bought it. In the actual adoption phase, however, only some buyers attended an introductory meeting, and far fewer had an entire team try the product.

The problems revealed by follow-up research differed depending on customer size. Small teams did not find Slack's inconveniences severe enough to switch tools, while larger teams demanded a much more mature product before moving their existing work. Reimer confirmed that there is a big difference between sympathy for the inconvenience and an organization's actual willingness to switch. After investing about a year, he announced in May 2019 that he was stopping development of Level as a standalone Slack alternative.

Afterward, he redefined the criteria for choosing his next business from the start. It needed to be a market where customers were already paying, the initial product had to be buildable within a few months, and there had to be few decision-makers involved in purchasing. He also considered it important that he could start without dedicated mobile and desktop apps and whether he could reach people to whom he was already connected. The goal was to find a business that matched the product's potential with his own capital, time, and operating preferences.

SavvyCal: Focusing on the Booking Link Recipient's Experience

There was also a change in how he funded the business. Reimer participated in TinySeed's first accelerator cohort in 2019 and received investment, and he explained that this investment came before he created SavvyCal. SavvyCal's current official company description also states that it received small-scale funding from TinySeed and several angel investors. Therefore, Drip's growth without outside investment and SavvyCal's funding history need to be viewed separately by product.

Reimer wrote SavvyCal's first code in March 2020, refined the product with early users, and then launched it publicly on Product Hunt in January 2021. The field he chose was the scheduling market, where existing services including Calendly already existed. He judged that there was room in this market to improve the booking experience more carefully.

At the center of the problem was the person receiving the booking link. The person sending the link could finish coordinating schedules easily, but the other party had to look back and forth between their own calendar and the booking page to find a time. SavvyCal's signature feature was a calendar overlay that let the other party choose available times while seeing their own schedule overlaid on the booking screen. When explaining the product's differentiation, he also addressed both the convenience of the link sender and the burden on the recipient.

For the person offering availability, he added features to protect working hours. These included prioritizing preferred times, leaving buffer time between meetings, and limiting the number of meetings received during a given period. The structure reduced situations where meetings filled every open slot while still showing the other party selectable times.

There was also a difference from Level in its business structure. Switching a collaboration messenger requires organizational consensus and migrating work, but a scheduling tool is easy for one individual to adopt first. In a 2020 interview, Reimer cited this individual-level use and relatively low switching costs as important reasons for the choice. In effect, he had found an entry approach that allowed a small company to acquire customers even in a highly competitive market.

The first customers came from people who had been watching his development process and from his existing network. Reimer asked potential customers about their scheduling difficulties, determined the essential features for an early version, and then, once the product was ready, contacted them again to ask them to use it. He started by directly connecting the early product he had built over several months to previous interview participants.

Marketing was also treated as a separate function from the beginning. When monthly recurring revenue was about USD 1,000, he began working part-time on contract with marketer Corey Haines. After that, he used a Product Hunt launch, podcast appearances, sharing the development process on Twitter, comparison pages against competing products, and affiliate and referral programs as customer acquisition channels.

Revenue and Operating Model: Build It Yourself, but Don’t Do Everything Alone

The result Reimer disclosed in a 2021 public Q&A was surpassing USD 10,000 in monthly recurring revenue (MRR) about one year after writing the first code. Measured from the start of development, this corresponds to roughly spring 2021, and it is a business metric the founder himself published at the time. In the same post, he explained that he was running a three-person team consisting of himself, a marketer, and a customer support person.

SavvyCal’s meeting scheduling service is a subscription model that charges based on the number of users. In the official pricing page reviewed in October 2026, the monthly equivalent price when billed annually is listed as USD 10 per user for Basic and USD 17 per user for Premium. The basic plan provides multiple calendar connections and booking link and team scheduling features, while the higher-tier plan adds a custom domain, the ability to delegate administrative permissions to an assistant, and paid booking features.

His approach to managing product polish does not stop at making screens look good. In a 2024 interview, he explained that it is important to standardize common elements such as buttons, input fields, and tables, and to observe the screen flows customers actually move through. For example, if a customer wants to propose a time from the preview screen of a booking link but that feature exists only on another screen, the repeated small inconvenience gives the impression that the product is hard to use. Reimer continued to take on the role of designing these usage flows and interface consistency himself.

On its official careers page reviewed in October 2026, SavvyCal introduces itself as a profitable independent software company and states that it prioritizes sustainable growth and autonomy over rapid organizational expansion. Its product has also expanded into SavvyCal Meetings for meeting scheduling and SavvyCal Appointments, booking infrastructure for service businesses. In a September 2026 interview, Reimer explained that Appointments is particularly focused on customized booking flows for telehealth services. Building on its existing scheduling experience, it is broadening its scope to more complex business booking problems.

Reimer is best classified as a serial founder who draws on co-founding and exit experience and a small amount of outside investment while remaining at the center of product development. At Drip, he divided roles with a co-founder; at SavvyCal, he started as a solo founder and then used investment and a team. The notable choice in this case is that he reflected a preference for keeping the organization small not only in product development but also in how customers adopt the product, financing, and hiring.