PathPilot Founder Drew Lindsay Wants to Close Canada’s AI Career Confidence Gap

As artificial intelligence reshapes jobs and the skills employers value, many Canadians are struggling to see where they fit in the changing labour market. A national survey commissioned by PathPilot found that 64 per cent of Canadians believe young people will have the skills to compete for Ottawa’s promised AI-related opportunities. Yet only 44 per cent believe they personally have or could develop the skills required for an AI-related job. The divide is especially pronounced among older workers, with confidence falling from 62 per cent among Gen Z respondents to 28 per cent among Boomers. Canadian entrepreneur Drew Lindsay believes the problem is not simply a shortage of training. It is a lack of clear, personalized career navigation. After more than 20 years in recruitment and building GuruLink into an eight-figure business, Lindsay has officially launched PathPilot, a platform that helps job seekers explore career options, identify skills, find relevant jobs, prepare resumes and practise for interviews. It also helps career professionals manage caseloads, reduce administrative work and track outcomes. Built within GuruLink, PathPilot has already engaged more than 2,000 users and 100 career practitioners. An independent evaluation found that 82.9 per cent of participants considered its recommendations relevant, while 63.9 per cent discovered career options they had not previously considered. Techtalent.ca spoke with Lindsay about the opportunity behind PathPilot, the appropriate role of AI in career guidance and what employers, educators and governments must do to close Canada’s AI-readiness gap.

After more than 20 years in recruitment and building GuruLink into an eight-figure business, what convinced you that career navigation was the next problem worth tackling?

DL: Over more than two decades in recruitment, I saw the same issue repeatedly: most people make major career decisions reactively and with very little support. They often seek help only after losing a job, becoming frustrated in a role, or discovering that their skills no longer align with the market. At the same time, career professionals are stretched thin and spend too much of their week on administrative work rather than counselling, up to and beyond 60% if you can believe that. That problem becomes more urgent as AI changes jobs and skills faster than traditional career-support professionals and systems can respond. GuruLink gave us a strong understanding of how employers evaluate talent and where candidates tend to struggle. PathPilot grew from the belief that we could apply that experience earlier in the process and at scale, helping people understand where they are, where the market is moving, and what practical steps they can take next. In today’s changing landscape, career navigation should be continuous, not something people access only when they are in crisis or transition.

PathPilot serves both job seekers and the professionals who support them. How does that two-sided model work, and where do you see the largest commercial opportunity?

DL: On one side, PathPilot gives job seekers personalized support with career exploration, skill development, labour market data, job matching, resumes, and interview preparation. It is available when people actually need it, including outside the operating hours of a traditional career centre. On the other side, it gives practitioners a clearer view of their caseloads, the actions clients are taking, and the outcomes that follow. By reducing repetitive administrative work, PathPilot allows practitioners to leverage that shared context to spend more time on the conversations where their experience and judgment matter most. The opportunity is primarily with the organizations responsible for supporting large groups of people through career transitions: educational institutions, employers, workforce-development organizations, and publicly funded employment programs. These organizations already invest heavily in career services, but they often lack the capacity, coordination, and outcome data needed to serve everyone effectively. Our opportunity is to help them extend the reach and impact of the professionals they already have.

More than 2,000 users and 100 career practitioners have already engaged with PathPilot. What have these early users taught you, and how has their feedback shaped the platform?

DL: One of the clearest lessons is that people rarely need more generic information. They need help determining what is relevant to them specifically, and what they should do next. Working with PathPilot, career practitioners have also reinforced that AI is most valuable when it removes friction rather than trying to replicate the entire counselling relationship. That has kept us focused on practical tasks such as organizing information, identifying possible career paths, preparing materials and tracking progress. The early results are encouraging. In DARO’s independent evaluation of PathPilot, 82.9 per cent of participants found the recommendations relevant, while 63.9 per cent identified career options they had not previously considered. That second finding is especially meaningful because effective career guidance should expand someone’s field of view, not simply confirm what they already know. Feedback from users and practitioners continues to shape the platform. We are building around real workflows and real decisions, rather than assuming that engagement alone is evidence of value.

You describe a coordination gap between job seekers, practitioners, employers and funding organizations. How does PathPilot create a shared view without compromising users’ privacy or control over their information?

DL: A shared view does not mean unrestricted access to someone’s personal information. It means ensuring that the professionals involved in supporting an individual are working from relevant, consistent information rather than disconnected spreadsheets, systems, and conversations. Responsible data governance is part of PathPilot’s foundation, not something added after the product was built. PathPilot is ISO 42001 certified, the first international standard for responsible AI management, and we are working toward ISO 27001 certification and SOC 2 compliance, which would further strengthen our information-security practices and give partners greater confidence in how we protect their data. One of PathPilot’s core principles is that individuals should retain appropriate control over their information, while institutions and practitioners receive the visibility necessary to provide support and evaluate outcomes. The goal is to make coordination possible while limiting access to what is appropriate for each role. Trust is essential in career guidance. If people do not understand how their information is being used or do not feel comfortable sharing it, the platform cannot achieve its purpose.

PathPilot is intended to extend rather than replace career professionals. Which parts of career guidance can AI handle effectively, and where does human judgment remain essential?

DL: Human touch will always be crucial. AI is effective at tasks that involve processing large amounts of information, finding patterns, and producing a useful starting point. It can help someone explore possible occupations, identify transferable skills, compare their experience with job requirements, prepare a resume or practise for an interview. It can also handle administrative work that consumes practitioners’ time. Human judgment remains essential when the issue is not simply what someone could do, but what they should do given their circumstances, motivations and priorities. Career decisions can involve confidence, identity, family responsibilities, financial risk, and major life transitions. Those factors require empathy, context, and accountability; something AI can’t accomplish We view AI as a way to make practitioners more effective and career support more accessible. It can help a person arrive at a conversation better informed and better prepared, while giving the practitioner more time to focus on the difficult, high-value parts of that conversation.

Your survey found that 64 per cent of Canadians believe young people will qualify for new AI-related opportunities, yet only 44 per cent believe they personally have or could develop the necessary skills. What explains that confidence gap?

DL: It is much easier to feel optimistic about a national goal in the abstract than to see a credible path for yourself. Canadians hear that AI will create new opportunities and assume younger people will receive the education and training required to pursue them. But when people assess their own position, they may not know which skills matter, where to learn them, or how their existing experience translates into an AI-shaped workplace. Age also plays a role. Sixty-two per cent of Gen Z respondents believe they have or could develop the necessary skills, compared with 55 per cent of Millennials, 43 per cent of Gen X and 28 per cent of Boomers. That suggests many experienced workers view the transition as something happening around them rather than an opportunity they can participate in. This is not simply a training gap. It is a navigation and confidence gap. People need to understand the specific capabilities relevant to their career and the practical next step they can take, which is the whole goal of why we launched PathPilot

Canadians identify uncertainty about which skills matter, fear of AI and doubts about its relevance as bigger barriers than cost. What should employers, educators and governments do differently to make AI readiness feel practical and attainable?

DL: The first step is to stop talking about “AI skills” as though they are a single, highly technical qualification. Most people do not need to become machine-learning engineers. They need to understand how AI is changing their job or field and how to use relevant tools effectively, responsibly, and in context. Employers should be clearer about how roles are changing, which skills they value, and how existing employees can develop them through practical experience. Educators need to be empowered to connect AI learning to specific occupations and real workplace problems rather than offering only broad awareness or highly technical programs. Governments should make it easier for people to understand which training leads to genuine labour-market opportunities. The survey points directly to this need: 50 per cent of Canadians said clearer information about which skills are worth building would help most, compared with 33 per cent who prioritized more AI training in colleges and universities, and 17 per cent who selected additional government funding. At PathPilot, we also believe that while AI skills are important, honing other “soft skills” like curiosity, communication, collaboration, creativity and critical thinking are where people really need to focus their energy. People need a visible path from where they are today to an attainable next step.

PathPilot is available in 84 languages and is targeting institutions, employers and workforce organizations. How large could this business become, and what outcomes will tell you that it is improving Canadians’ career prospects rather than simply increasing platform usage?

DL: The need PathPilot is addressing is much larger than any single segment. Students, displaced workers, newcomers, experienced professionals, and people considering a career change all face versions of the same navigation problem. The institutions supporting them also need better ways to serve more people and understand what happens after that support is delivered. Because those challenges exist well beyond Canada, the long-term opportunity is significant. However, we do not want to define success by log-ins, time spent on the platform or the volume of AI-generated recommendations. Those figures can describe activity, but they do not necessarily demonstrate impact. The outcomes that matter are whether users identify relevant opportunities, build useful skills, take meaningful next steps, and ultimately improve their employment prospects. For practitioners and institutions, we will look at whether they can support larger caseloads, spend more time on higher-value guidance, and better track the results of their programs. PathPilot succeeds by helping people make better-informed career decisions and being the backbone for the organizations supporting them.