Joel Esguerra
Joel Esguerra
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About Me

Joel Esguerra

Joel Esguerra

Senior Product Designer with 10 years of experience building B2B SaaS products from 0 to 1 — twice contributing to acquisitions — and scaling them at enterprise level. Deep experience designing complex operational software across AgTech, ChildcareTech, EduTech, and Real Estate CRM.

Education

B.B.A. Information Systems

York University | Toronto, Ontario

SEP 2007 - APR 2012

UX Design Course, UX/UI

Springboard | springboard.com

SEP 2016

AI Design & Design Systems

Memorisely | memorisely.com

MAR 2026

Skills

Design

Product Design

Design Systems

Native Mobile (iOS/Android)

Information Architecture

Interaction Design

Visual Design

AI Prototyping

Accessibility (WCAG)

Development

Agentic AI Workflows

AI-Assisted Development

Front-End Development

Strategy

0-1 Product Design

PRD Writing

Cross-Functional Collaboration

Stakeholder Storytelling

User Research

Requirements Gathering

Tools

Figma

Claude Code

Storybook

Cursor

GitHub

Pendo

Datadog

Notion

Jira

Confluence

Experience

Milk Moovement

Senior Product Designer

Oct 2022 - Present

Milk Moovement

Halifax, NS — Remote

  • Redesigned platform navigation across 20+ pages for 4 distinct user types — delivering a 40% NPS lift, 15-25% productivity gain per user, and a 50% reduction in sales demo time
  • Designed Moove an AI-driven scheduling optimization engine that reduced Coop transportation costs by 30%; built transparent criteria-setting UI to drive user trust in AI-generated outputs
  • Shipped MooRules, a conversational AI invoice builder that interprets plain-language input into configurable, rules-based billing logic for Coop finance teams
  • Designed Driver and Producer mobile apps for real-time load tracking, pickup logging, quality scores, and payment visibility — replacing manual and paper-based field workflows
  • Launched a Webflow-integrated Member Bulletin Board replacing physical newsletters; increased Coop member engagement by 80%+ and contributed to 3 new enterprise deals in year one
  • Conducted 170+ stakeholder interviews across Producers, Drivers, Coop Admins, and Finance teams to ground every major product decision in validated user research
Procare Solutions

Senior Product Designer

Jan 2020 - Oct 2022

Procare Solutions

Denver, CO. — Remote

  • Led full redesign of Procare's parent-teacher communication mobile app — rebuilding age-specific child dashboards (Infants, Toddlers, Pre-K) and secure sign-in/out flows for iOS and Android
  • Designed 0-to-1 EduTech curriculum feature enabling childcare owners to source, license, and deploy 3rd-party lesson plans in-app, directly reducing teacher workload and staff turnover
  • Launched in-app content marketplace with Marco Polo and Learning Beyond — giving Procare a competitive differentiator no rival childcare platform had at the time
  • Contributed to Procare's design system component library; created brand illustration assets still active across marketing and product today
Sandbox Software

Product Designer

Acquired by Procare - 2020

Sep 2017 - Jan 2020

Sandbox Software

Hamilton, ON.

  • Designed entire product from 0-to-1 as sole designer: child and staff CRM, payment processing, classroom scheduling, parent sign-in kiosks, and a teacher-to-parent communication app
  • Grew platform from 20 to 1,200 schools across North America in under 2 years, contributing to 94% YoY revenue growth and a $12M acquisition by Procare Solutions in 2020
  • Redesigned new-user onboarding flow — reduced support load by 40% and improved 30-day trial retention by guiding users to their first activated classroom and enrolled child
  • Rebuilt company website in Webflow, tripling inbound sales leads for the commercial team
  • Conducted 80+ school visits and interviews with owners, teachers, and parents to validate every major product release
Team Leads - Keller Williams

Product Designer

Acquired by Keller Williams - 2017

Jul 2016 - Aug 2017

Team Leads - Keller Williams

Milton, ON.

  • Designed a B2B real estate CRM platform from 0-to-1 as the sole designer alongside a 7-person engineering team, serving Keller Williams agents across North America
  • Platform contributed to a $6M acquisition by Keller Williams within 8 months of product launch

Recommendations

★★★★★

Joel poses an incredible affinity for understanding problems. While Joel can output screens, mocks, and flows with the best of them - Joel's true value lies in his endless hunger to understand customers, problems, and why. This affinity for deeply researching (and understanding) users then translates into all his design work. Which in turn yields world class UX and UI. Joel would be an invaluable asset to any team. One of the skills Joel possesses that sets him apart from other design leaders I have worked with is his ability to seamlessly transition between Micro and Macro Context. Enabling him to work both at the IC and executive level flawlessly.

Miles Rand

Miles Rand

Head of Product

★★★★★

Joel is an exceptional product designer and was an absolute force at Milk Moovement. He was incredibly helpful when it came time to prototype thoughtful, credible solutions for marquee prospective customers, often on tight timelines and with real commercial stakes. Beyond pure design, Joel brought a strong go-to-market mindset. He was invaluable in creating sales enablement materials and collateral that actually reflected the product accurately while telling a compelling story for customers. Joel combines strong design taste with pragmatism and speed; a rare mix. Any team building and selling a serious product would be lucky to have him.

Kenny Harris

Kenny Harris

Sr. Enterprise Account Executive

★★★★★

What separates Joel is how he operates at the intersection of product and design. He doesn't wait to be handed a problem statement — he helps shape it. Joel consistently surfaces the actual problem underneath the one being debated, articulates it clearly enough that engineers and stakeholders align faster, and moves into execution without losing that clarity. Most designers translate requirements. Joel challenges them. His collaboration style creates alignment, not just agreement — and his work lands with less friction because the people who need to build it were part of understanding why it matters.

Stephen Anastasi

Stephen Anastasi

Dir. of Product Management