Headquarters:
204 Mapleview Dr W, Barrie, ON L4N 4E8
Year founded:
2004
Number of employees:
42
Phone:
705 730 1130
Email:
info@drivewise.com
Website:
drivewise.com
LinkedIn:
linkedin.com/company/drivewise-safety
“Our forward-looking innovation pipeline is engineered entirely in-house, allowing us to pivot quickly in response to shifting market trends and evolving client demands”
Lesley de Repentigny, DriveWise
Lesley de Repentigny
President and CEO
Martin de Repentigny
Chief Operating Officer
Katherine Scharapenko
Vice President of Operations
Leadership
Lesley de Repentigny, CTDP, is the visionary CEO and co-founder of DriveWise, recognized for transforming road safety education through disruptive, simulator-based learning. A former Canadian Armed Forces officer and aerospace training executive with Adacel, where she managed high-stakes simulation contracts for NASA and the FAA, de Repentigny recognized that road safety training lagged decades behind aviation. By bridging this gap, she established DriveWise as an industry benchmark.
De Repentigny’s pioneering leadership has twice earned her a spot on the Profit W100 list of Canada’s top female CEOs, alongside the Women in Business Visionary Award and Brock University’s Alumni of Distinction.
President and CEO
Lesley de Repentigny
Martin de Repentigny, P.Eng., M.Eng., CDS, is the co-founder and chief operating officer of DriveWise, bringing over 30 years of elite expertise to advanced learning and curriculum design. A retired Canadian Armed Forces officer and former aerospace professional services director at Adacel, de Repentigny holds a master’s degree in engineering and has instructed at the university level. He is a highly credentialed pedagogical expert, certified as both a Driving Instructor and a specialist in Teaching and Training Adults. Additionally, his mastery of instructional analytics is backed by a prestigious Kirkpatrick certification in the 4 Levels of Evaluation.
Chief Operating Officer
Martin de Repentigny
Katherine Scharapenko, MBA, is the vice president of operations at DriveWise, bringing over 15 years of elite expertise in adult learning and program management. Her dedication to road safety and student success anchors the company’s signature over 99 percent client recommendation rating. Academically accomplished, she holds a Bachelor of Commerce from Lakehead University and earned her MBA from the Smith School of Business at Queen’s University.
Scharapenko possesses an advanced pedagogical background, having completed Teaching and Training Adults alongside a prestigious Kirkpatrick certification in the 4 Levels of Evaluation, allowing her to effectively align complex organizational strategies with impactful road safety results.
Vice President of Operations
Katherine Scharapenko
Ryan Scharapenko
PMV Manager
Ryan Scharapenko is a key instructional leader and the PMV Manager at DriveWise, where he has been instrumental in advancing road safety education since 2015. He holds a degree in psychology from York University, an educational foundation that uniquely enhances his approach to driver behaviour and adult learning principles.
Scharapenko is a highly qualified classroom and dual-control in-vehicle instructor, specializing in training both novice motorists and professional fleet drivers. Deeply enthusiastic about integrating next-generation virtual reality technologies, he translates complex simulation metrics into actionable, life-saving habits that consistently yield superior road test success rates.
PMV Manager
Ryan Scharapenko
Matt Davis
Director of Product and Services
Matt Davis is the director of products and services at DriveWise, bringing over 15 years of dedicated expertise to the advanced learning solutions sector. A highly skilled product manager and computer programming alumnus from Georgian College in Barrie, Davis has completed formal training in Teaching and Training Adults. He seamlessly bridges technical design with adult learning principles, he led the specialized development teams responsible for pioneering DriveWise’s award-winning air brake simulator and innovative Toolbox simulator.
As an ardent advocate for simulated training environments, he ensures that the company's state-of-the-art virtual reality infrastructures remain optimized, interactive, and aligned with modern corporate fleet needs.
Director of Product and Services
Matt Davis
DriveWise has spent more than 20 years turning professional driver education into measurable risk reduction for the fleets that depend on it. This track record is what earned the Barrie, ON company its 2026 Canadian Occupational Safety Readers’ Choice recognition, an award voted on by the safety professionals who use these solutions every day.
For clients, the value shows up on the bottom line: fewer collisions, better fuel economy, lower onboarding costs, and stronger regulatory compliance, all reflected in a client recommendation rating the company puts at more than 99 percent.
What sets the training apart
DriveWise designs sector-specific programs tailored to distinct occupations, including municipal workers, corporate fleets, and emergency first responders, rather than applying a single curriculum to every operator.
Its driver safety training adapts to local terrain and strict government regulations, keeping fleets aligned with regional transportation standards. DriveWise pairs specialized instructors with advanced driving simulators to mitigate fleet-specific risks, protect capital assets, and handle unique equipment challenges, an approach it says has made it a trusted fleet training provider across Canada.
Rhiannon Penchion
Commercial Programs Manager
Jaime Dugandzic
Business Development and Marketing Manager
Alex Kureekat
National Program Manager
Simon Williams
Chief Strategy & Distribution Officer, Arch Insurance International
and Active Underwriter, Syndicate 1955
Rhiannon Penchion is an award-winning manager with over 20 years of expertise in learning, training, and development, currently acting as manager of commercial programs for DriveWise and KnowledgeSurge. She drives business growth across multiple sectors by building strong relationships with cross-functional teams, clients, and stakeholders.
Known for precision and efficiency, Penchion ensures complex programs are delivered on schedule and within budget, while championing a growth mindset to optimize operations and drive organizational excellence.
Commercial Programs Manager
Rhiannon Penchion
Jaime Dugandzic is the business development and marketing manager at DriveWise, bringing over five years of dedicated experience in B2B account management, strategic marketing, and client relations. Known for her creative mindset and positive approach, she excels at leading sales initiatives and fostering meaningful long-term partnerships across Canada.
Academically accomplished, Dugandzic holds an Honours Bachelor of Business Administration degree with a focus in marketing from the University of Guelph-Humber. Additionally, she is certified as a Bullet Proof Manager by Crestcom International, highlighting her dedication to professional growth, high-level negotiation, and customer-centric problem-solving.
Business Development and Marketing Manager
Jaime Dugandzic
Alex Kurakeet, PMP, is the program manager at DriveWise, where he combines a global media background with elite customer-focused operational execution. Holding a Master of Management Studies from the University of Mumbai, he possesses advanced expertise in managing multimillion-dollar accounts and orchestrating major international campaigns with global powerhouses like FedEx Canada and Samsung.
Kurakeet’s exceptional leadership has earned him the President’s Award of Excellence twice at DriveWise. Known for meticulous attention to detail and precision across both on-site and mobile training environments, he oversees nationwide program delivery, seamlessly driving operational efficiency and organizational growth.
National Program Manager
Alex Kureekat
Kimi leads the Estate Planning and Wealth Protection team and is a member of the Society of Trust and Estate Practitioners. She understands the complex and delicate nature of family estate planning, the technical requirements around probate and estate administration, and the importance of preserving wealth for future generations. Her advice is accurate, commercial, strategic and tailored to each situation.
Partner
Kimi Shah
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“Our programs are tailored to align with our client’s unique learning objectives. No matter their primary focus, our training consistently delivers a high-impact return on investment: elevated driver performance, substantial collision and fuel reductions, and a powerful boost in workforce morale as our client’s team recognizes the client’s active investment in their personal safety”
Lesley de Repentigny, DriveWise
Turnaround time – claims
Turnaround time – new business
Overall
The targeted model treats training as proactive risk mitigation rather than a compliance exercise. By building programs around a client’s own operational data, the company focuses on the specific hazards a fleet faces, equipping operators with cooperative driving skills and sharper situational awareness to lower the frequency and severity of on-road incidents. The result, the company says, is fewer collisions and safety incidents alongside a stronger, more proactive safety culture where safe operation becomes a shared daily practice.
Leadership rooted in high-stakes training
The company’s foundation lies in high-stakes training. Founders Lesley and Martin de Repentigny developed their instructional skills within the Canadian Forces and the aerospace industry, applying that experience with complex, high-risk training to shape DriveWise’s focus on quality.
Operations are now led by their daughter, Katherine Scharapenko, who continues the original vision while driving growth, innovation, and national expansion, joined by Matt Davis leading technology innovation and Rhiannon Penchion managing instructor standards.
Innovation built in-house
The company’s development pipeline runs entirely under its own roof, allowing it to respond quickly to shifting demands in the logistics and corporate fleet sectors. Internal teams build, test, and deploy proprietary learning technologies, including advanced simulation-based programs, so clients always have access to current, relevant safety training.
Building the next generation of drivers
To meet rising demand for skilled commercial operators, DriveWise is pursuing a dual-track growth strategy built on accredited pathways and national reach. It has established a Private Career College offering industry-certified diploma programs that move students directly into transport careers, while expanding a national training consortium with regional partners to scale its corporate driver training and standardized curricula across Canada, bridging regional workforce shortages with consistent, world-class education. For fleets weighing where to send their operators, that record of measurable outcomes is what ranks DriveWise among the best trucking schools in Ontario.