TIFFANY CARRELL

Systems That Stick:
‍Square Case Study

Square logo image

Design learning ecosystems for real-world complexity.

‍Most onboarding tries to force behavior through a funnel. It’s reactive, fragmented, and focused on getting users to click the “right” button. But real behavior isn’t linear, especially when you’re a small business owner juggling risk, regulation, emotion, and survival.
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I was Head of Scaled/Self-Serve Onboarding at Square. My team wasn’t just creating digital onboarding for self-serve users, we were re-architecting how people meet the product. Across multiple surfaces, channels, and user types, we built a system that aimed to meet users in context, support behavior change, and scale with the messiness of real businesses. Our overall goal was to reduce time-to-value, increase user confidence, and turn education from an afterthought into an engine for long-term engagement.

Why It Matters

What actually is onboarding? Everyone seems define it differently. Is it time bound? Action bound? Something else entirely? Starting a business isn’t just a cognitive task, it’s an existential leap. Our job was to lower that cognitive load, support identity transformation, and earn the user’s trust through clarity and care.

When you get that right, you’re not just teaching someone how to use a tool. You’re helping them get going so that they can focus on building their business. That the platform they chose sees them, supports them, and will grow with them. That’s what sticks.

The Challenge

How might we build a coherent, high-signal customer education system that scales across dozens of entry points, user types, and lifecycle moments… without turning it into a bloated soup (or would it be a stew?) of monotonous articles, PDFs, and broken flows?
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The Big Idea

A coordinated system of moments, messages, and media that responds to what users are doing and feeling, not just what we want them to do next. It wasn’t about making more stuff. It was about making the right stuff work together - at the right moment, on the right surface, and with as little friction as possible.

My Role

I led the development and execution of a customer-centric, systems-based onboarding strategy spanning product education, content design, media, data, and learning systems. I also built and led a high-performing cross-disciplinary team, and partnered across product, design, engineering, support, and marketing to create frameworks and experiences that work across every stage of the customer journey.

Guiding Principles

Learning Without the Hustle : No logins, no walls, just seamless, contextual onboarding guidance designed around real workflows.
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Design for Emotion, Not Just Tasks : Build content to respond to mapped moments of user uncertainty, excitement, and frustration.
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Multiproduct ≠ Multimess : Orchestrate a unified experience across Square’s product suite, avoiding the trap of siloed onboarding.
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Data-Informed, Human-Led : Analytics gives us the what. Research gives us the why. We design from both.
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Content as Infrastructure : From information architecture to tone to strategy, every content piece is a building block and serves a purpose.

Deliverables

Customer-Centric Onboarding Strategy

Mapped the end-to-end onboarding experience across channels and products, optimizing for emotional and cognitive load. This meant everything from help docs to video to live support got considered as part of a unified experience.


Bespoke LMS Built on CDP Integrations

Designed and launched a no-login learning system that used customer data to deliver seamless, journey-tracked experiences. Designed and built from scratch to meet real user behavior. (See image below)


Analytics Strategy & Dashboarding

Partnered with analysts to develop a robust measurement framework, including dashboards, behavioral funnels, and outcome metrics tied to activation, retention, and NPS.


Multimodal Media Experiences

Led a cross-functional team to produce high-impact learning content, including video, animation, and interactive guides. This media brought the product to life and met learners across cognitive styles.


Team & Culture Building

Built and nurtured a multidisciplinary team of content strategists, producers, and learning designers. Created a culture of psychological safety, creative risk-taking, and user obsession.

A screenshot of Square Academy

Screenshot of course info on the Square Academy homepage we built, captured via the Wayback Machine.

Contact Me

I'm excited to keep diving into:

Adaptive systems as scaffolding for confidence

Building real-time, behavior-aware learning experiences that meet users where they are. The goal is to turn uncertainty into momentum and friction into flow.

Designing for emotion as a core system function

Shaping emotional journeys, not just completing tasks. Trust, clarity, and retention live in how people feel, not just what they know.

AI as anticipatory guide, not just assistant

Using machine learning to surface the right content at the right moment. Support becomes presence when it arrives before the user even asks.

Content design as a systemic layer, not an afterthought

Elevating content to the level of product, experience, and data. Communication is design, and clarity should be part of the foundation.

Learning as a catalyst for identity and belonging

Creating systems where education reinforces self-belief, especially in high-stakes contexts. To truly learn is to feel seen, capable, and connected.

Orchestration over overload

Designing interconnected systems of content, context, and timing that act more like a system than a megaphone. The goal isn’t just clarity, it’s coherence. A whole that learns, adapts, and supports in real time.
Copyright Ⓒ 2025 Tiffany Carrell ♡ All rights reserved.