Don't Fail

Instant tutoring and structured study resources - scaling a mobile learning platform to 400,000+ users.

Mobile App

Start-up

Industry

EduTech

Roles

Co-founder

Product Lead

UI & UX Design

Date

2017-2024

Introduction & Summary

Don't Fail was a mobile learning platform I co-founded, designed and built over a 5-year period. I led the product direction, UX, UI, and feature strategy across two full product versions - from our early tutor-Q&A marketplace to a more advanced on-demand tutoring and study companion app. This case study highlights the evolution of the product and the reasoning behind our major pivot.

The idea began just after high school, when two close friends and I realised how privileged we were to have access to great tutors and strong learning resources. We wanted to make that same support accessible to students across South Africa. Shortly after, two angel investors backed us, giving us a 12-person development team - which is where my journey into product design began.

What I Owned

Product direction, UX strategy & feature architecture

UI design system & interaction design

User flows, research insights & usability testing

Messaging, app store materials & marketing touchpoints

Outcomes

R2m+

R2m+

Investments Secured

20,000+

20,000+

Monthly Active Users (peak)

400,000+

400,000+

Total Users

The Problem

Students across South Africa were struggling with access to high-quality study support. Tutors were available, but hard to reach, inconsistent, and often unaffordable. Students needed quick help, verified explanations, and reliable study material in a single place.

V1 - The Learning Phase

What we built

A tutor Q&A marketplace where students posted questions and tutors responded.

Browsing, answering, and filtering questions.

Basic tutor profiles and lightweight matching.

Early subject library.

What we learned

Students needed real-time, face-to-face help, not asynchronous Q&A.

Tutors wanted predictable income, not ad-hoc question answering.

Engagement plateaued because value didn’t feel immediate enough.

Version 1 – Early Marketplace Model (2019–2021)

The Pivot

After analysing usage data, tutor behaviour, and high-intent student flows, we realised the Q&A model wasn’t delivering consistent value. We pivoted to a real-time tutoring experience with scheduled and emergency sessions, a deeper study library, and stronger personalisation. This required a full redesign of the product experience.

V2 - The Final Product

A cohesive, end-to-end learning experience designed to support students across preparation, practice, and live tutoring.

Every feature was designed to work together - fast access to tutors, a structured study library, reliable scheduling, and a visual planning system. The goal was to remove friction at every step of the learning journey while meeting the unique needs of South African students.

Key Goals

Enable students to get a tutor instantly.

Support scheduled sessions with transparent pricing.

Build a full study library structured by grade, subject, and exam board.

Improve trust with richer tutor profiles and ratings.

Easy Onboarding

A fast, low-friction onboarding that clearly communicates the app’s value, personalises the experience, and guides students with smooth, delightful micro-interactions.

The onboarding introduces the core value quickly, collects only essential details, and personalises the experience with minimal friction. Micro-interactions keep the flow light, clear, and welcoming - helping students reach value in under a minute.

Emergency Tutor Flow

Instant, on-demand tutoring - a streamlined flow that connects students to the best available tutor within minutes.

Students often need help immediately, so the Emergency Flow captures only key context and auto-matches them to the best available tutor. The streamlined steps and concise summaries create a fast, confident, no-decision experience.

Schedule A Session

A simple, predictable scheduling experience that makes booking single or recurring sessions effortless.

The scheduling system allows students to book ahead, set up repeat sessions, and manage all upcoming lessons in one place. The design focuses on predictability and trust, helping students and tutors build consistent learning relationships.

Calendar View

A clear, visual schedule that helps students manage study time, track sessions, and stay organised around exams.

The calendar presents upcoming sessions, study blocks, and key tasks in a simple, colour-coded layout. It becomes a central planning tool that supports exam preparation and builds long-term learning habits.

Study Library & Past Paper Viewer

Past papers, memos, and notes - cleanly organised for quick navigation and fast revision.

Past papers and memos are structured by grade, subject, and year for quick, intuitive access. The layout mirrors real studying habits, helping students find the right resource in seconds.

Cellphone data is precious to low-income students in South Africa - we made sure to make resources available even when offline.

Impact

400,000+

400,000+

Total users

20,000+

20,000+

Monthly active users (peak)

8,000+

8,000+

Questions answered

50+

50+

Tutors onboarded

+24%

+24%

Average session duration

-18%

-18%

decreased customer churn rate

Reflection

Don’t Fail was where my career in product design began. After two angel investors backed us and gave us a 12-person development team, I quickly realised we needed clear product direction - and no one else was going to provide it. I taught myself UX, UI, product thinking, research, and how to work with engineers by necessity.

Over five years, I went from a founder with an idea to a product designer capable of shipping complex flows, leading strategy, and building systems used by hundreds of thousands of people. It shaped how I think about design, decision-making, and the responsibility we have when building tools for real users.

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Made with strong coffee and banging tunes.

© 2025 Portfolio by Ross Bentley

Made with strong coffee and banging tunes.

© 2025 Portfolio by Ross Bentley

Made with strong coffee and banging tunes.

© 2025 Portfolio by Ross Bentley

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