Scaling automated outreach for enterprise recruiters

1. Discovery

Personas

The upmarket push was ramping up and several new people were joining. Outside of design, nobody had a clear picture of who we were building for. I did a deep dive into our personas and presented a simple persona framework, which I will summarize below:

The response surprised me. A few people told me they hadn't known design was thinking about this at all, and that it made them more confident in the decisions we were making.

Discovery Findings

We knew of existing customer pain points and product gaps blocking enterprise-readiness, so I conducted research and a lightweight heuristics evaluation to understand which existing UX patterns to build on or rethink.

We heard from stakeholders that products demoing a beautiful, user-friendly experience for recruiters had a competitive edge, so modernizing our design language was one priority.

And, because we were scaling messaging for enterprises with multi-level user hierarchies, the scope of the redesign went beyond simply reskinning components to accommodate higher data volumes. We needed to understand the everyday use cases of a new set of user types, and reconstruct end-to-end flows accordingly.

Design Process

I found the conclusions from discovery most useful once boiled down into a set of guiding principles. They became a checklist I could use to explain a design decision to stakeholders, or rubber-ducky with when working solo.

Sketching at Low-Fidelity

This was a large undertaking with a lot of complex, interdependent sub-features to design from scratch. Some things, like settings and forms, could be taken directly to high-fidelity while others surfaced a lot of complexity at once and needed several rounds of iteration starting from low-fidelity.

Small Feature: Auto-Link Shortening

Long links push a text past the carrier's character limit, which splits it into two messages and breaks the link in half. I sketched a few approaches. The one product liked best shortened links automatically as the recruiter typed. It also needed more engineering than we had, so what shipped was a character count and a pre-send dialog telling the recruiter to shorten the link themselves.

Large Feature: Outbound Attachments

Inbound attachments only had to be displayed or blocked. Outbound meant we needed to surface failed uploads, oversized files, unsupported formats, and accommodate a different set of rules on SMS than on WhatsApp. I sketched every state before anything was built, which gave engineering something concrete to react to, and made it easy to cut the ones that weren't worth it, like a specialized UI I'd proposed for attaching links.

Reflections on the Process

Throughout the design process, creating the UI components was the easiest part. The challenge was that enterprise recruiters experience higher turnover than those at smaller orgs and operate inside permission structures and platform rules that are not obvious and subject to changing.

Almost every design decision here was about surfacing an invisible constraint and informing a user when their message has failed or may fail without blocking their efficiency.

Final Designs

1. Audience selection with live candidate count

Recruiters can select multiple jobs at once and layer stage filters on top. The running total (843 candidates) confirms the audience before sending.

5. Preview and send confirmation

Before a message reaches 1,195 candidates, recruiters confirm the audience and see the message rendered exactly as an individual recipient will. They choose whether the audience stays fixed or updates dynamically until send, with a contextual warning when a dynamic list means recipients aren't final — catching errors before they reach a wide audience, per discovery.