The transformation of a startup's digital presence

When Flywire (formerly peerTransfer) launched, its website was not just a marketing tool—it was the product itself. Students initiated payments directly through the website, making it a critical part of the user experience. As the company expanded into new verticals beyond education, the website had to evolve into a scalable platform that could support brand growth, lead generation, and multiple business segments.

Explore how I led the website’s transformation, balancing UX/UI improvements, brand evolution, and technical scalability while ensuring it remained a powerful business and marketing tool.

The first version of the homepage design on CraftCMS, following the design and platform updates from the past few years.

Challenge

Flywire’s initial website served as both the interface for its payment solution and a marketing hub for prospective clients. As the company grew, several key challenges emerged:

Scaling for new business verticals – The company expanded beyond education into healthcare, travel, and business/b2b payments. The website needed to reflect these diverse audiences while maintaining a cohesive brand identity.
Evolving brand identity – A major rebrand from peerTransfer to Flywire required a complete overhaul of the website’s design, messaging, and structure.
Enhancing UX/UI for conversions – As Flywire’s business shifted towards a sales-driven model, the website needed to optimize for lead generation while maintaining an intuitive user experience.
Technical scalability – The initial custom-built website became difficult to manage as content demands grew. A transition to a scalable CMS was necessary to empower marketing teams and reduce reliance on engineering.

Challenge

Flywire’s initial website served as both the interface for its payment solution and a marketing hub for prospective clients. As the company grew, several key challenges emerged:

Scaling for new business verticals – The company expanded beyond education into healthcare, travel, and business/b2b payments. The website needed to reflect these diverse audiences while maintaining a cohesive brand identity.
Evolving brand identity – A major rebrand from peerTransfer to Flywire required a complete overhaul of the website’s design, messaging, and structure.
Enhancing UX/UI for conversions – As Flywire’s business shifted towards a sales-driven model, the website needed to optimize for lead generation while maintaining an intuitive user experience.
Technical scalability – The initial custom-built website became difficult to manage as content demands grew. A transition to a scalable CMS was necessary to empower marketing teams and reduce reliance on engineering.

Approach & execution

Phase 1: Launching the initial website (2011-2015)

Designed and developed Flywire’s first website, serving both as a functional product (payment initiation) and a marketing tool.
Created the first UI/UX framework, ensuring seamless transactions for students while maintaining clarity for institutional partners.
Conducted user testing and feedback loops to refine the experience, balancing usability with branding.

Two early homepage designs from when Flywire was still known as peerTransfer.

Phase 2: Rebrand & expansion (2016-2018)

Led the redesign of the website during Flywire’s rebrand, ensuring a smooth transition from peerTransfer to Flywire.
Reorganized the website’s structure to accommodate new business verticals and tailor messaging for different audiences.
Introduced a more robust design system that extended beyond the website to marketing materials, product UI, and brand assets.
Coordinated efforts between designers, marketers, and developers to ensure alignment across brand touchpoints.

Phase 2: Rebrand & expansion (2016-2018)

Led the redesign of the website during Flywire’s rebrand, ensuring a smooth transition from peerTransfer to Flywire.
Reorganized the website’s structure to accommodate new business verticals and tailor messaging for different audiences.
Introduced a more robust design system that extended beyond the website to marketing materials, product UI, and brand assets.
Coordinated efforts between designers, marketers, and developers to ensure alignment across brand touchpoints.

Two homepage designs following the Flywire rebrand, featuring the vertical expansion.

Phase 3: Migrating to a scalable platform (2018-2021)

Transitioned the website from a custom-built framework to DatoCMS, enabling marketing teams to create and manage content with greater flexibility.
Introduced new lead generation capabilities, integrating marketing automation tools like Marketo.
Expanded the website’s resource center, enhancing Flywire’s thought leadership and SEO strategy.
Developed a structured content strategy to support global expansion, including localization for different regions.

Phase 3: Migrating to a scalable platform (2018-2021)

Transitioned the website from a custom-built framework to DatoCMS, enabling marketing teams to create and manage content with greater flexibility.
Introduced new lead generation capabilities, integrating marketing automation tools like Marketo.
Expanded the website’s resource center, enhancing Flywire’s thought leadership and SEO strategy.
Developed a structured content strategy to support global expansion, including localization for different regions.

Two versions of the homepage following the migration to our first CMS, DatoCMS.

Phase 4: Redesigning for growth & performance (2021-2025)

Migrated to CraftCMS for even greater flexibility and scalability.
Implemented a refined UX strategy based on stakeholder research, user testing, and analytics insights.
Developed a dual-site strategy: one website for B2B clients (Flywire.com) and another for B2C users (pay.flywire.com), optimizing navigation and conversion paths for both audiences.
Led accessibility improvements, ensuring compliance with industry standards to meet the needs of global users.
Partnered with external agencies to refresh the brand’s digital presence, then expanded those updates across marketing campaigns, digital assets, and event microsites.

Phase 4: Redesigning for growth & performance (2021-2025)

Migrated to CraftCMS for even greater flexibility and scalability.
Implemented a refined UX strategy based on stakeholder research, user testing, and analytics insights.
Developed a dual-site strategy: one website for B2B clients (Flywire.com) and another for B2C users (pay.flywire.com), optimizing navigation and conversion paths for both audiences.
Led accessibility improvements, ensuring compliance with industry standards to meet the needs of global users.
Partnered with external agencies to refresh the brand’s digital presence, then expanded those updates across marketing campaigns, digital assets, and event microsites.

Homepage designs following the migration to CraftCMS and the separation of the B2B and B2C audiences.

Outcome & impact

Scalable, Lead-Generating Platform – The website evolved from a simple product page to a full-scale marketing platform, driving inbound leads and supporting sales efforts.
Brand Consistency & Evolution – Successfully integrated Flywire’s evolving brand identity across multiple redesigns and business expansions.
Improved UX & Accessibility – Created a seamless, user-friendly experience that balanced marketing goals with user needs.
Empowered Marketing Teams – Migrated to scalable CMS solutions, enabling faster content updates and reducing reliance on engineering.
Global Reach & Expansion – The website became a critical tool in supporting Flywire’s expansion into multiple industries and international markets.