For over 25 years, Paul Donald has been at the forefront of solving complex productivity challenges through innovative technology. A seasoned entrepreneur and senior technology executive, Paul’s career has been defined by a single driving force: bridging gaps in communication, trust, and transparency—especially in industries that desperately need it.
Today, as CEO and co-founder of Encircle, Paul is leading the charge to transform how the property insurance ecosystem functions—bringing credibility, clarity, and confidence to an industry long burdened by skepticism and inefficiency.
But Encircle is more than just another tech company. It’s the realization of Paul’s personal mission to eliminate the disconnect between restoration contractors, insurance adjusters, and policyholders—three parties that, historically, have rarely seen eye-to-eye.
From Living Room Code to Industry-Wide Impact
Paul’s relationship with the property insurance industry began in a rather unexpected way—in the late 1980s, sitting in his living room, watching his college roommate develop policy management software. It was his first glimpse into the intricate and often misunderstood world of insurance, and it planted a seed that would take root years later.
Fast forward to Paul’s time on the senior executive team at BlackBerry, where he worked for over a decade helping to bring mobile technology to enterprise markets. It was there that he reconnected with the insurance space—this time from the inside. Working directly with major insurers, Paul helped develop mobile apps that connected carriers with their third-party contractors and policyholders.
What he saw from the inside was staggering.
Mistrust was rampant. Communication was broken. Adjusters were skeptical of contractors’ reports. Restorers felt their work was constantly challenged. Policyholders were left out of the loop—and often left unsatisfied.
That front-row seat to the industry’s dysfunction revealed a massive opportunity: to create a platform that would serve as a single, shared source of truth for everyone involved in a property claim.
That’s when Encircle was born.
A Founder Driven by Purpose
Paul didn’t build Encircle because the market needed another software tool. He built it because the industry needed trust—and trust had to start with better communication and indisputable data.
From the start, his vision was bold: to align field teams, office staff, insurers, and homeowners through one platform that would document and tell the entire story of a property loss from beginning to end. And not just tell the story—but do it with clarity, credibility, and speed.
Encircle was engineered to do just that—by enabling field teams to capture rich documentation (photos, videos, notes, sketches, and forms) on-site, and syncing that data instantly to office teams, adjusters, and clients. This created a level of transparency and real-time collaboration that had simply never existed in the industry.
Paul’s goal was never to force any party to “bend” to the other’s way of working. It was to give each stakeholder what they need to do their jobs well—while operating from the same set of facts.
Tech Innovator with a Track Record
Encircle isn’t Paul’s first successful venture.
Before launching Encircle in 2012, Paul had already earned a strong reputation as a high-impact technology leader. He was the COO at PushLife, a mobile entertainment startup acquired by Google in 2011. Prior to that, he founded and led PeerDirect, which was sold to Progress Software in 1999.
His decade at BlackBerry saw him help scale one of Canada’s most influential tech companies, where he led enterprise initiatives across multiple verticals—including insurance. He’s also a dedicated angel investor, mentor, and active contributor to Canada’s Technology Triangle, helping nurture the next generation of tech talent.
What’s common across all of Paul’s roles is a relentless focus on solving real problems through smart, intuitive technology. With Encircle, he’s applied that same focus to one of the most friction-filled sectors in North America—property restoration and insurance claims.
A Leader Shaped by Industry Insight
Paul’s leadership style is grounded in understanding—not assumption.
He’s spent years listening to restoration contractors, understanding their boots-on-the-ground challenges: chaotic job sites, unclear expectations, constant documentation demands, and a constant fight to get paid for completed work.
He’s also talked extensively with adjusters, who struggle to make decisions based on incomplete or inconsistent documentation, often under pressure to close claims quickly and cost-effectively.
Then there are policyholders, who are often left in the dark—confused by the process and resigned to the belief that they won’t be made whole.
Paul has always believed that technology can humanize a process, not just automate it. And that belief guides every decision he makes—from how Encircle is built to how the team engages with customers.
Advocating for Choice and Openness
One of Paul’s most steadfast beliefs is that restorers deserve freedom in how they work.
While some industry players attempt to lock users into a specific software ecosystem, Paul has led Encircle with an open approach. Through open APIs and integration-friendly tools, Encircle allows customers to use the platforms that work best for their unique needs—without compromise.
This commitment to openness has helped Encircle grow into one of the most trusted brands in the restoration industry, often recommended organically in contractor groups, social media forums, and industry events.
Investing in Industry Education
Paul also believes that knowledge shouldn’t be gatekept. Under his leadership, Encircle launched Encircle University (EncircleU)—a free, on-demand learning management system where restoration contractors can not only learn the platform but also earn continuing education (CE) credits.
It’s one of many examples where Paul has gone beyond the product to support the broader industry ecosystem.
What’s Next: AI, Automation & Real-Time Intelligence
Paul’s long-term vision is to make Encircle the strategic operating system for property claims—one that helps adjusters, contractors, TPAs, and carriers all operate from the same verified source of data.
The company is already working to integrate cutting-edge AI technologies, including:
- Visual AI for automated documentation verification
- Speech-to-text tools for faster note capture
- Smart recommendations to assist in report creation
But at the heart of every innovation is the same goal: to make life easier for the people doing the hard work of restoring homes and settling claims.
Leadership with a Human Touch
Inside the company, Paul is known not just as a visionary, but as a transparent, approachable, and empowering leader. He’s created a culture where:
- Team members can work where they work best
- There’s no multi-layered hierarchy
- Feedback flows freely
- Wins are celebrated—and failures are learned from
Encircle’s rapid growth is a direct result of the culture Paul has cultivated: one of purpose, agility, and constant improvement.
Paul Donald’s Legacy: Rebuilding Trust, One Claim at a Time
In a world where property losses often create tension, confusion, and mistrust, Paul Donald is building something different.
Through his leadership, Encircle isn’t just changing how restoration documentation works—it’s reshaping the relationships that make up the property insurance ecosystem. His mission isn’t about technology alone. It’s about restoring trust, simplifying complexity, and making the industry better for everyone it serves.
And for Paul, this is just the beginning.
🔗 To learn more about Encircle and Paul’s mission, visit: www.getencircle.com
