Jessi Contreras

Benchmark: Leading without the title

Role: Senior Product Designer, Acting Lead

Tools: Figma, FigJam, Jira, Confluence, Useberry, Intercom, FullStory, AI-assisted workflows (Claude, MCPs, ChatGPT, and more)

Impact: Built and shipped a full SaaS product while establishing the design practice, research process, and cross-functional operating model from scratch. Across 20+ user flows, 8 research studies, a complete billing system, and an active legacy migration.

About Benchmark

  • Benchmark is a privately held email marketing platform founded in 2004, serving small and mid-sized businesses globally. The company launched a fully reimagined product in October 2025, built on modern architecture and a contact-centric model, with a goal of 3,000 paid users by end of 2026 through new acquisition and migration from Benchmark Classic.

Read Benchmark: Creating the Design Practice for the story on design system, accessibility, documentation hub and AI tooling.

Joining Mid-Flight


I joined Benchmark in October 2023 as a Senior Product Designer on a brand new platform, while development already had a three-month head start. No PM operating model. No research practice. No design system. One designer. Full product, spanning 20+ user flows from authentication and onboarding to contact management, campaigns, billing, settings, and account lifecycle.


The first call I made was to not design a single screen. Without shared infrastructure, every future change would cost more. I built the design system foundation first. What became a 300+ component system that underpinned every flow that shipped.


  • The challenge was never just designing a product. It was building the conditions for design to work while simultaneously shipping it.

How I Operated


With no PM layer, I set my own direction, wrote my own requirements, flagged problems before they were assigned, and built relationships that gave me influence without formal authority.


Changing how engineering and design worked together:

Early on, backend development was happening without design input, features were being scoped and built before design had a seat at the table. I raised the pattern directly with the CPO, who took it to the VP of Engineering. The result was a structural process change: BE now initiates design conversations before FE begins work. When new FE developers joined, I extended that same operating model from day one so it held.


  • I integrated AI-assisted workflows into my daily process to move faster without sacrificing quality. When a second designer joined after I had operated alone for over a year, I brought them into the practice I had built, not just handing over documentation, but working through real problems together until the standards were theirs.

The full story of the design system, research practice, documentation, and AI tooling lives here.

The First Year


By the time Benchmark launched in October 2025, design was driving development rather than following it. Getting there meant two years of identifying what needed to change, making the case for fixing it, and navigating a team still learning how design and engineering work together.


  • Filters were one of the hardest challenges. The logic was technically complex, and early designs had to be tested and revised to balance what the backend could support with what users could actually understand. Research and testing drove both UI and logic changes. The filters that shipped are meaningfully different from where they started, and more coherent for it.

Research as a Decision Tool


There was no research practice when I joined. No templates, no process for connecting findings to decisions. I built that process and ran it across two years.


  • Before designing solutions, I ran discovery with real users, structured methods, and documented findings that fed directly into product decisions.

  • All 8 self-initiated studies produced changes to the product, across contact management, feature validation, email builder evaluation, and accessibility compliance. Methods ranged from moderated discovery sessions and unmoderated usability tests to surveys, heuristic evaluations, and structured WCAG audits.

Setting Up Contact Management


The new Benchmark is contact-centric. Every contact exists once, with a complete unified profile, and can belong to multiple lists without duplication. For users who had managed separate, overlapping lists for years, this was a fundamental shift. If they couldn’t navigate it, the new platform had no foundation to stand on.


Before this model shipped, I validated it through a three-part discovery study covering interviews, usability testing, and a filter preference test. Seven sessions, 45 to 50 minutes each, with real Benchmark users who had been on the legacy platform for up to 15 years.


  • During the bulk actions task, the first two users could not find the actions button. I redesigned the placement mid-session, validated it with the remaining participants, and it held. Four UX fixes shipped before MVP as a direct result of the study.

Sending The Best Campaign


Sending an email campaign is the core action in any email marketing platform. I designed the end-to-end campaign flow, from multiple entry points including the dashboard, email section, contact page, and lists, through template selection and into the campaign checklist.


Leadership envisioned a single-form approach, but a form would fail on incomplete required fields and create errors at the point of sending. I reframed it as a preview-style checklist where users see what their email looks like in the inbox while completing each required detail, then send, schedule, or test without hitting a wall.


  • 67% of campaigns created reach send or schedule. Behavioral data pinpoints the main friction point in the schedule time picker modal, not the checklist itself, giving the team a clear next target.

The Billing System


Billing is where product complexity and business decisions collide. I designed the complete billing system for Benchmark, covering every plan state a user can encounter across free, paid, and multi-user tiers, including upgrades, downgrades, payment failures, and account management.


Every flow was designed under one-month timelines with incomplete backend specifications and pricing decisions still being finalized. Edge cases surfaced post-launch were corrected without disrupting the live product.


  • The billing system grew after launch. Annual billing was designed and added as a new flow, building on established system patterns rather than starting from scratch.

Mailing Lists


Benchmark supports two list types: Static Lists for manually curated audiences and Dynamic Lists that update automatically based on contact criteria.


Before committing engineering to both, I validated the need through a two-study research sequence. The business wanted Dynamic Lists, but I ran the research to confirm users did too, independent of internal assumptions. 86% of participants rated Dynamic Lists 4 or 5 out of 5 for usefulness, and both list types showed strong weekly usage intent, confirming neither was a niche feature worth skipping.


  • I designed the full flows for both list types. In usability testing, 15 of 16 participants completed all tasks, finishing in under 5 minutes on average.

Benchmark Classic Migration


Migrating users from a legacy platform is one of the highest-stakes design challenges in a product transition. Benchmark Classic users have up to 15 years of data, established workflows, and no immediate obligation to move. But Classic will sunset, making early migration critical for the business.


I designed the contact and template migration flows that allow Classic users to bring their existing data into the new platform. Contact migration deduplicates years of overlapping lists into unified profiles and maps custom fields through a guided four-step wizard. Template migration brings existing email designs into the new builder, preserving years of content without requiring users to start from scratch.


Three migration epics delivered solo across six weeks. The goal throughout: make the transition feel like a continuation, not a disruption.

Outcomes

Product shipped

  • Sole designer across a full SaaS platform, 20+ user flows from first screen to shipped product
  • Product launched October 2025, actively growing toward 3,000 paid users by end of 2026
  • Three migration epics delivered solo across six weeks


Research impact

  • All 8 self-initiated studies produced direct changes to the product
  • 4 UX fixes shipped pre-MVP from a single discovery session, including a component redesigned and validated mid-study
  • 86% of participants validated Dynamic Lists before engineering committed to the build
  • 67% of campaigns created reach send or schedule


Organizational impact

  • Structural process change: BE now initiates design conversations before FE, driven by design advocacy
  • Second designer onboarded and operating independently after one year of solo practice-building
  • AI-assisted workflows adopted across the team, reducing ticket writing from hours to minutes per cycle

The Product Today

Benchmark's new platform is live, growing, and actively adding new features and users. Built from the ground up to replace a decade-old legacy product, it is now in the hands of real customers including enterprise names like FedEx, Panasonic, and Samsung.


The migration from Benchmark Classic is underway, bringing years of user history into a platform built to serve them better. Visit benchmarkemail.com to see it in action.