Raj R.

Empowering Innovation & Excellence in Product Leadership

With a trailblazing journey through diverse sectors, Raj Rajakumar stands as a quintessential Product Leader, steering innovations from conception to scale in the education, nonprofit, and tech landscapes. Spearheading strategies that transitioned ideas to impactful solutions, Raj’s expertise encompasses driving product strategy, enhancing user experiences, and leading cross-functional teams to deliver with precision. Leveraging technology to solve complex problems, his journey is marked by secu…
Raj R.

Experience

  • Showbie

    Showbie

    Product Manager

    Sep 2025 - Present

    Showbie is a learning platform that streamlines teaching workflows and supports school improvement.

    • Lead product strategy and delivery for Showbie’s core classroom initiatives, driving scalable teaching and learning workflows impacting millions worldwide.
  • Ihsan Labs

    Ihsan Labs

    Founder & Managing Director

    Apr 2025 - Present

    Ihsan Labs builds custom AI solutions and digital products for non-profits, startups, and public sectors.

  • Flourishing Systems

    Flourishing Systems

    Head of Product / Director of Innovation

    Feb 2022 - Present

    Flourishing Systems develops CRM solutions for social services to enhance efficiency and service delivery.

  • CIO Strategy Council | Conseil Stratégique des DPI

    CIO Strategy Council | Conseil Stratégique des DPI

    Advisor

    Nov 2022 - Sep 2025

    The Digital Governance Council fosters trust in Canada's digital economy by addressing governance challenges.

  • IslamicFamily

    IslamicFamily

    Director of Product Management

    Feb 2022 - Sep 2025

    • I lead the strategy, design, and growth of mission-driven products that scale impact for nonprofits and government. I’ve launched and scaled three flagship platforms—Transform (client management CRM), Amplify (fintech for benefit delivery), and Embark (refugee intake system)—now powering operations for 50+ agencies and improving service equity.
    • Delivered 90%+ adoption within 60 days and reduced manual workflows by 40–70% through automation and intuitive UX.
    • Built and scaled a distributed product team of 10+ (engineering, design, QA) shipping weekly with 95% on-time delivery across time zones and regulatory environments.
    • Secured $1M+ in non-dilutive funding and closed $400K in SaaS contracts, aligning product strategy with ROI for partners.
    • Drove data instrumentation and reporting innovations that cut reporting time by 75% while enabling funder-grade insights for stakeholders.
    • Recognized with the 2022 Edmonton Startup Award for innovation in civic technology.
    • I thrive at the intersection of product, strategy, and impact—navigating complex stakeholder environments, scaling teams, and turning ambitious ideas into market-ready solutions that deliver measurable outcomes.
  • On Deck

    On Deck

    Fellow

    Jan 2022 - Dec 2022

    ODF supports entrepreneurs at the pre-seed stage and helps transform ideas into startups.

  • Youthful Cities

    Youthful Cities

    Delegate

    Oct 2019 - Oct 2019

    Youthful Cities creates data-driven solutions for better urban living for young people worldwide.

  • Alberta's Industrial Heartland Association

    Alberta's Industrial Heartland Association

    Project Manager (Transportation & Infrastructure)

    May 2018 - Sep 2019

    Alberta’s Industrial Heartland is a key region for chemical, petrochemical, oil, and gas investments.

    • Managed long range planning initiatives and regional infrastructure projects to attract oil and gas companies.
  • Spontivly

    Spontivly

    Chief Product Officer

    Jan 2018 - Jan 2022

    • I led the end-to-end strategy, development, and growth of two high-impact digital products—a hyperlocal discovery mobile app and a SaaS platform—driving rapid adoption and revenue growth across consumer and enterprise markets.
    • Scaled mobile app user base 7x in 3 months, secured $120K USD ARR in municipal contracts, and earned recognition as a Top 20 most-downloaded app in Canada (2020).
    • Redesigned onboarding UX to boost sign-up rates by 60%, helping propel the app to national media coverage, accelerator programs (ATBx, Tampa Bay Wave), and “Top 15 Startup of the Year” honors.
    • Launched a SaaS platform that doubled revenue to $17K USD MRR in one month and expanded the pipeline to 635+ prospects (57% MoM growth) with 150+ organizations on waitlist.
    • Built and led a 6-person engineering and design team, delivering MVP ahead of schedule using agile and scrum practices.
    • Spearheaded integration partnerships (LinkedIn, Eventbrite, Facebook, Zoom, Twitter) while evangelizing the product vision with CEOs and investors.
    • Spoke at 6 industry events across North America, driving brand visibility and partnerships.
    • Backed by:
    • Mark Cuban Companies
    • LOI Ventures
  • Spontivly

    Spontivly

    Head of Product

    Jan 2018 - Jan 2022

    • Designed and launched a SaaS product, doubling revenue within a month and growing the prospect pipeline.
    • Led API integration partnerships with major platforms, enhancing product value and adoption.
  • Edmonton Public Schools

    Edmonton Public Schools

    Project Manager (Planner)

    Aug 2017 - Apr 2018

    Edmonton Public Schools is a major school district in Alberta with over 92,000 students.

    • Led, designed, and managed 10 Year Facilities Plan and 3 Year Infrastructure Plan for Black Gold School Division.
  • Bridging Lanka Ltd (Australia)

    Bridging Lanka Ltd (Australia)

    Project Manager

    Jul 2017 - Jul 2017

    Bridging Lanka connects Sri Lankans by harnessing expertise for community advocacy and development.

    • Led public revitalization project from concept to construction completion.
  • City of Lloydminster

    City of Lloydminster

    Project Manager (Planner)

    Feb 2016 - Jun 2017

    The City of Lloydminster is committed to creating vibrant, welcoming communities with a focus on urban development.

    • Managed multiple long-term capital planning projects, including the Annexation strategy and Downtown Revitalization Project.
  • Ontario Ministry of Municipal Affairs

    Project Manager (Planner)

    Sep 2015 - Jan 2016

    The Ontario Ministry of Municipal Affairs aims to ensure dynamic communities with a high quality of life.

  • Ontario Ministry of Municipal Affairs

    Land Use Planning Assistant

    Jun 2015 - Sep 2015

  • Canadian Urban Institute (CUI)

    Planning Intern

    Sep 2014 - Dec 2014

    The Canadian Urban Institute focuses on urban policy and development solutions.

  • Bay Cloverhill Community Association

    Planning Intern (Retail Development)

    Jan 2014 - Apr 2014

    The Bay Cloverhill Community Association is dedicated to building a great urban neighborhood.

  • City of Markham

    City of Markham

    Site Planner

    Sep 2013 - Dec 2013

    The City of Markham is a diverse community known for its rich heritage and strong economy.

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