Dates in automation & segmentation
My role on this project
Owner: All UX & Design assets & decision, prototypes, design thinking
Partner: Problem definition, competitive analysis, and scope with Engineering & Product Manager
Overview
In marketing automation, dates are everywhere — birthdays, renewals, anniversaries — yet Drip customers couldn’t use them without writing complex liquid code.
Designing this capability meant tackling more than just a new field type. Dates carry nuance: absolute vs. recurring, relative timeframes, timezones, and import formats. Customers expected the flexibility they’d seen in other platforms but wanted it to feel simple and predictable. Through early research and customer sessions, it became clear that users didn’t want complexity — they wanted clarity. My goal was to make date logic feel conversational, not computational: flexible enough for power users, but intuitive for everyone else.
Date triggers in workflows
We added the ability to have date trigger people into automated workflows.
Date delays in workflows
We added the ability to use dates as delay in a workflow. Allowing the ability to chose a specific date or dynamic dates that are set in custom fields.
Dates for segmentation
I mapped existing segment date operators to extend date logic while maintaining usability and technical consistency. Introduced new operators (in the next, in the last, not in the next, not in the last) with a contextual calendar picker for absolute and recurring dates. Reused familiar UI patterns to reduce friction and speed adoption.
Defined parsing rules, data formatting, and timezone behavior in partnership with engineering; tested early prototypes. Used AI tools for grammar exploration, copy validation, and rapid interaction prototyping to accelerate iteration and decision-making.
AI assisted Prototype
Built a prototype, AI-assisted in v0, translating early design concepts into a working tool within days of defining constraints and assumptions. The prototype was vibe-coded from lightweight Figma explorations and tested with customers to validate operator logic and interaction flow. This rapid approach confirmed usability early and shaped key design decisions before engineering investment.
Collaboration and Decision-Making
This project was as much about partnership as it was about pixels.
I worked with product leadership to define what belonged in V1 versus later releases, balancing ambition with feasibility. Engineering contributed heavily to operator behavior and timezone logic; customer success helped frame messaging for migrations and imports.
We also ran early validation calls with existing customers whose automation strategies relied on date logic. Their feedback clarified both terminology and the real-world use cases we needed to serve.