When Pineapple Financial decided to make history and become the first Canadian mortgage brokerage to list on the NYSE and go public, they needed a stellar IPO campaign to draw attention and accelerate their stock price. As Creative Director, I was responsible for developing the campaign strategy, creative theme, copywriting, and tasking my team with deliverables and deadlines to execute on the creative strategy.

As Creative Director, I led the development of Pineapple Financials' IPO campaign as the company prepared to become the first Canadian mortgage brokerage to list on the NYSE. I developed the overarching visual identity, campaign theme, and messaging platform, while overseeing a cross-functional creative team of designers, videographers, and editors in partnership with marketing leadership. From concept to rollout, I directed the full creative strategy, including copywriting, website investor updates, and brand system expansion, ensuring the IPO moment felt bold, credible, and industry-defining.

The Challenge

Make a Canadian Disruptor Visible on a Global Stage

While Pineapple had strong brand recognition within Canada’s mortgage industry, its visibility in the U.S. market was limited. The IPO represented more than a financial milestone, it signaled a strategic shift toward becoming a technology-first, solutions-driven platform in an industry that had remained largely unchanged for decades.

The campaign needed to build investor confidence, attract new brokerages, and elevate Pineapple’s perception from a growing brokerage to a scalable, innovation-led public company. At stake was not just a listing, but a repositioning of the brand on an international stage.

The Insight

Momentum Builds Confidence

The IPO announcement followed Pineapple’s recognition as one of The Globe & Mail’s Canada’s Top Growing Companies of 2023, giving us an opportunity to frame the listing as the next chapter in an accelerating growth story. Rather than treat the IPO as a transactional event, we positioned it as a collective industry milestone.

The campaign tagline, “Let’s Make History,” transformed the listing into a rallying call for investors, agents, and partners alike, inviting them to be part of a defining moment for the mortgage industry.

Over a two-month period leading up to and following the IPO, we executed a fully integrated communications takeover designed to dominate visibility within the mortgage and investor ecosystem. The campaign spanned social media, digital ads, website landing pages, paid media, press releases, and national billboard placements, all unified under a bold and future-focused visual system. Investor decks and departmental presentations were redesigned to align with the IPO narrative, ensuring that shareholder communications, recruitment efforts, and public messaging spoke with one cohesive voice.

The Execution

Designing a Market Moment

The IPO visual identity was developed to signal innovation, confidence, and forward momentum, aligning typography, color, and motion to reflect Pineapple’s evolution into a publicly traded, tech-enabled brand. Working closely with my team, we produced launch countdown assets, social-first video content, announcement graphics, investor materials, and internal communications that carried the campaign narrative across every platform. The result was a synchronized brand moment that unified internal teams while projecting credibility and ambition to investors and industry partners.

The Launch & Impact

A Historic First

Pineapple Financial (PAPL) launched at approximately $9.60 per share, officially becoming the first Canadian mortgage brokerage to list on the NYSE. The announcement was amplified through coordinated media outreach, paid promotion, and social rollout, generating significant attention within both the Canadian and U.S. markets. The IPO marked a defining milestone in Pineapple’s evolution and established a foundation for its next phase of growth as a publicly traded company.

Significant increase in brand awareness across Canadian and U.S. markets during the IPO window

Approximately 150% increase in website traffic compared to pre-campaign benchmarks

Increased brokerage recruitment and investor engagement following the launch

Capital raised enabled further investment into proprietary AI technologies,
including development of Pineapple’s Smart AI tools for mortgage agents

To comply with non-disclosure agreements, I have omitted and obfuscated confidential information in this case study.
All information in this case study is my own and does not necessarily reflect the views of Pineapple Financial.