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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 securing significant funding, fostering team growth, and achieving remarkable adoption and satisfaction rates. This multidisciplinary approach, fueled by a relentless curiosity and a commitment to excellence, positions Raj as a catalyst for transformative change in every endeavor.
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Raj R.

Experience

Sep 2025 — Present
Showbie

Showbie

Product Manager

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.
Apr 2025 — Present
Ihsan Labs

Ihsan Labs

Founder & Managing Director

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

Feb 2022 — Present
Flourishing Systems

Flourishing Systems

Head of Product / Director of Innovation

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

Nov 2022 — Sep 2025
CIO Strategy Council | Conseil Stratégique des DPI

CIO Strategy Council | Conseil Stratégique des DPI

Advisor

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

Feb 2022 — Sep 2025
IslamicFamily

IslamicFamily

Director of Product Management

  • 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.
Jan 2022 — Dec 2022
On Deck

On Deck

Fellow

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

Oct 2019 — Oct 2019
Youthful Cities

Youthful Cities

Delegate

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

May 2018 — Sep 2019
Alberta's Industrial Heartland Association

Alberta's Industrial Heartland Association

Project Manager (Transportation & Infrastructure)

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.
Jan 2018 — Jan 2022
Spontivly

Spontivly

Chief Product Officer

  • 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
Jan 2018 — Jan 2022
Spontivly

Spontivly

Head of Product

  • 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.
Aug 2017 — Apr 2018
Edmonton Public Schools

Edmonton Public Schools

Project Manager (Planner)

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.
Jul 2017 — Jul 2017
Bridging Lanka Ltd (Australia)

Bridging Lanka Ltd (Australia)

Project Manager

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

  • Led public revitalization project from concept to construction completion.
Feb 2016 — Jun 2017
City of Lloydminster

City of Lloydminster

Project Manager (Planner)

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.
Sep 2015 — Jan 2016
Ontario Ministry of Municipal Affairs

Ontario Ministry of Municipal Affairs

Project Manager (Planner)

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

Jun 2015 — Sep 2015
Ontario Ministry of Municipal Affairs

Ontario Ministry of Municipal Affairs

Land Use Planning Assistant

Sep 2014 — Dec 2014

Canadian Urban Institute (CUI)

Planning Intern

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

Jan 2014 — Apr 2014

Bay Cloverhill Community Association

Planning Intern (Retail Development)

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

Sep 2013 — Dec 2013
City of Markham

City of Markham

Site Planner

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