E11 w/ Mariya Delano: How to Fix a SaaS Trial-to-Paid Conversion Problem

Jason Cohen introduces Jane Portman and Benedikt Deicke, the co-founders of Userlist, an email-automation platform they have built for nine years for SaaS product marketers. Userlist’s homepage describes it as “email automation for sophisticated product marketers.” Benedikt explains that it supports lifecycle and transactional email, but differentiates itself through advanced, SaaS-specific functionality and a deliberately “super nerdy” feature set. Simple newsletter users can find tools that cost five times less, he says. The central problem is that trial conversions have fallen by half and previously sticky customers are beginning to cancel. Benedikt says some customers never properly integrate Userlist because setup requires work; others eventually decide it is too expensive, especially when they use only its newsletter capabilities. Cancellations sometimes lead to cheaper tools such as Mailchimp, ActiveCampaign, SendGrid, or an in-house system. Jason repeatedly challenges the apparent contradiction: Userlist says it is for sophisticated marketers, yet many customers cannot measure email ROI, cannot complete implementation, or use only basic newsletter features. He suggests these may simply be the wrong customers rather than evidence that the product lacks value.

Jason questions why growing companies would cancel as they gain more users and presumably receive more value from Userlist. Benedikt explains that the return on investment from SaaS email marketing can be difficult to prove when customers do not invest enough time in the program. Jason and Mariya push back: Mariya describes email as one of the most measurable marketing channels because teams can connect opens, clicks, upgrades, seat expansion, feature adoption, and churn to specific people or company domains. The discussion then turns to accounts where the one person who understood Userlist’s value left. Jason says Userlist should not treat this as entirely unavoidable. If only one champion sees the reports and understands what the product does, the rest of the company has no reason to preserve the subscription. He compares this with New Relic, whose performance reports can reach the CTO, infrastructure lead, and other stakeholders. Userlist could similarly expose reports to multiple people, add its logo to exported charts or screenshots, and prompt customers to involve colleagues. Benedikt realizes that the team has historically followed up with customers mainly to provide training and encourage more usage, not to review results and make the value visible internally.

Benedikt estimates that about 40% of non-spam sign-ups activate, while roughly 50% of paying customers who remain are using Userlist as intended. That means many people never connect multiple data sources, configure rules, or build the integrated email program that justifies the product. Jason says this is a major opportunity: the people who begin a trial or become customers are already expressing interest, but Userlist’s optional onboarding does not reliably get them to value. Jason cites an example from another software company where customers who completed an hour of one-on-one training retained at four or five times the rate of customers who did not. He suggests requiring the training rather than merely sending automated nudges. Mariya recommends making the product itself demonstrate what becomes possible after integration: show unavailable features in the interface, display a sample report, and prompt the user to connect a data source at the moment they try to use a dependent feature. Jason adds that the click can trigger a highly relevant email offering help, instructions, or a booking link. Jason then proposes charging for implementation—perhaps $10,000 or more—rather than offering substantial consulting for free. Benedikt had imagined a $1,000 guided-onboarding fee, but Jason says it “needs to hurt” so that the customer and the customer’s boss have a clear consequence and incentive to complete the work. Serious buyers will budget for it; unserious customers will self-select out.

Jason argues that Userlist’s claimed customer is not simply a large company. A small company can still be ideal if it has a sophisticated marketer, understands lifecycle email, can secure engineering help, and sees a substantial financial outcome from the program. Mariya gives an example of a one-person business with freelancers and an email list in the five figures that spent $20,000 on consulting and more than $2,000 on email-marketing tools. In her view, a $1,000 implementation fee would be trivial for this kind of buyer. Jason says the perfect customer should be described operationally: they need to connect several data sources, combine transactional and lifecycle emails, create rules and flows, understand metrics, and have enough authority or internal access to get the implementation completed. Userlist is not currently finding and selling effectively to these people. Jane acknowledges that they have not succeeded in selling to companies with larger budgets or slightly larger teams, while Benedikt says he is personally underqualified for enterprise sales. The founders debate whether the product’s remaining feature gaps are the main problem. Jason responds that Userlist already contains the capabilities a sophisticated SaaS marketer needs; the deeper issue is that its selling process, pricing, and customer acquisition have not caught up with the product’s evolution.

The group examines Userlist’s $149 lower tier and its apparently generous allowance of up to 500,000 emails per month. Jane says the tier should probably be eliminated because it does not match the ideal customer profile. Mariya compares email tools and says that 500,000 emails commonly costs $1,000 or more per month, making Userlist’s price look unusually low. Jason notes that Userlist is cheaper than tools such as ConvertKit even for much simpler newsletter use, which makes the pricing inconsistent with its sophisticated positioning. Benedikt explains that the 500,000-email baseline is intended to prevent customers from worrying about message limits, and that the real calculation is based on users multiplied by five. Mariya says the issue is not merely the number itself; the allowance signals that Userlist is thinking like a generic, low-cost email tool rather than a specialized product for serious marketers. She suggests lower limits on entry plans—possibly around 1,000 to 5,000 contacts, depending on the metric—and pricing that reflects how sophisticated email marketers actually evaluate tools. Jason cautions against randomly changing one price or volume limit. Userlist should interview its intended customers to learn whether they value pricing by contacts, messages, users, or another usage measure. The price should reflect the value of advanced functionality and help fund the high-touch implementation those customers need.

Benedikt asks whether Userlist should abandon its geeky positioning and simplify into a cheaper SaaS-marketing tool. He says the mid-market customers they have often lack the resources to use the product properly, and supporting them is painful. The founders consider a $29 plan and a return to the simpler product they offered earlier, but Jason rejects the idea because it would put them into a crowded market against established incumbents without a compelling advantage. Benedikt describes Userlist’s deeper differentiation: its data model reflects the fact that users can belong to multiple companies and have different roles in each account; events can contain properties; arrays can represent a customer’s integrations and their states; and marketers can query that information to build highly targeted messages. Jason agrees that these are genuinely sophisticated capabilities, even though most marketers would not immediately understand them. He argues that Userlist should keep the product and homepage focused on sophisticated SaaS marketers, rather than allowing basic, legacy customers to determine the roadmap. The missing piece is demand generation. Userlist has relied on SEO, social posts, its email list, and occasional community activity, including a TinySeed lecture, but the founders cannot name a podcast their target buyers listen to. Jason says they need to find where these technical marketers gather, attend the relevant events and communities, and speak directly to them. Mariya adds that the right conversations are technical—deliverability, integrations, data criteria, automations, and reporting—not generic marketing discussions.

By the end of the working session, Jason frames Userlist’s situation as a partial alignment problem rather than a failed product. The product, support, and homepage have evolved toward sophisticated SaaS marketers, but marketing still reflects the older audience, pricing has only partly changed, and sales has not been designed for higher-budget technical buyers. Userlist should interview ideal customers, understand how they define value and budgets, test a substantial paid onboarding program, and rebuild acquisition around the places those buyers actually spend time. Jason suggests selling an onboarding package that includes weekly calls, implementation guidance, and unusually responsive technical support. The initial anchor might be $20,000, $10,000, or even $30,000 depending on the account. If a buyer cannot pay the full amount, Userlist could trade a discount for an annual prepayment, a logo, or a testimonial. The point is not merely to collect a fee; it is to establish that implementation is valuable and create reciprocal commitment. The founders leave with a clearer direction: do not interpret basic customers’ churn as proof that the sophisticated market does not exist. Benedikt says they have reached a point where the product no longer resembles the community they originally served, so they must learn where the new audience is. Jason also reminds them that their employees clearly care about the company and that their nine-year path produced a distinctive product. When Jane describes feeling like an impostor, Jason and Mariya argue that her experience makes her more qualified than many target customers. Jason connects the feeling to perfectionism: the same dissatisfaction that drives excellent work can falsely become the belief that the work is never good enough.