Digital Enablement Director

1 week ago

Toronto, Ontario, Canada Henderson Drake Full time

Digital Enablement Director – Post-Implementation Advisory

Base Salary: $200,000 CAD

Location: Canada (flexible / hybrid depending on client)

We are working with a client who is building out a senior Digital Enablement capability and is looking for a Director-level leader to take ownership of post-implementation outcomes.

This role is not about selling software or running initial rollouts. It is about making technology actually work inside the business once it is live.

Our client needs someone who understands how systems land in real organisations, how people adopt them, and how digital platforms support growth, change, and transaction events.

What the role looks like

This is a senior, hands-on advisory position focused on:

  • Leading digital enablement after implementation, ensuring systems deliver measurable value
  • Driving user adoption across finance and operational teams
  • Applying Six Sigma principles to process optimisation, governance, and continuous improvement
  • Acting as a trusted advisor to clients during acquisitions, integrations, divestments, and major business changes
  • Supporting finance leadership through technology-enabled transformation
  • Translating between technical teams, finance, and executive stakeholders

You will be brought in when things matter most. After go-live. During change. When the business landscape shifts.

What we are looking for

We are looking for someone with depth, not buzzwords.

  • Director-level experience in Digital Enablement, Business Transformation, or Finance Systems
  • Six Sigma qualification (Green Belt or above)
  • Strong user adoption mindset with a track record of making systems stick
  • Background in accounting or finance, with the credibility to advise at CFO and controller level
  • Experience supporting M&A activity, integrations, or complex organisational change
  • Comfortable working in advisory capacity with senior clients

This role suits someone who understands both process and people, and who can operate confidently in boardroom conversations as well as hands-on delivery.

Compensation

  • Base salary of up to
    $200,000 CAD
  • Additional incentives and benefits depending on experience and engagement model

  • Technology Director

    2 weeks ago

    Toronto, Ontario, Canada Apply Digital Full time

    ABOUT APPLY DIGITAL Apply Digital is a global experience transformation partner. We drive AI-powered change and measurable impact across complex, multi-brand ecosystems. Leveraging expertise that spans across the customer experience lifecycle from strategy, design to engineering and beyond, we enable our clients to modernize their organizations and maximize...

  • Director, Digital Onboarding

    2 weeks ago

    Toronto, Ontario, Canada Mastercard Full time

    Our Purpose Mastercard powers economies and empowers people in 200 countries and territories worldwide. Together with our customers, we're helping build a sustainable economy where everyone can prosper. We support a wide range of digital payments choices, making transactions secure, simple, smart and accessible. Our technology and innovation,...

  • Director, Omnichannel Enablement

    2 weeks ago

    Toronto, Ontario, Canada Klick Full time $150,000 - $170,000

    Company Description The Klick Group—comprising Klick Health (including Klick Katalyst and btwelve), Klick Media Group, Klick Applied Sciences (including Klick Labs), Klick Consulting, and Klick Ventures—is an ecosystem dedicated to realizing the full potential of our people and clients in life sciences. Founded in 1997, we have offices in New York,...

  • Director, Omnichannel Enablement

    2 weeks ago

    Toronto, Ontario, Canada Klick Full time $150,000 - $170,000

    Company Description The Klick Group—comprising Klick Health (including Klick Katalyst and btwelve), Klick Media Group, Klick Applied Sciences (including Klick Labs), Klick Consulting, and Klick Ventures—is an ecosystem dedicated to realizing the full potential of our people and clients in life sciences. Founded in 1997, we have offices in New York,...

  • Director, Omnichannel Enablement

    4 days ago

    Toronto, Ontario, Canada Klick Full time

    Company Description The Klick Group—comprising Klick Health (including Klick Katalyst and btwelve), Klick Media Group, Klick Applied Sciences (including Klick Labs), Klick Consulting, and Klick Ventures—is an ecosystem dedicated to realizing the full potential of our people and clients in life sciences. Founded in 1997, we have offices in New York,...

  • Director, Digital Onboarding

    1 week ago

    Toronto, Ontario, Canada Mastercard Full time

    Our PurposeMastercard powers economies and empowers people in 200+ countries and territories worldwide. Together with our customers, we're helping build a sustainable economy where everyone can prosper. We support a wide range of digital payments choices, making transactions secure, simple, smart and accessible. Our technology and innovation, partnerships...

  • Director, Product Enablement

    2 weeks ago

    Toronto, Ontario, Canada Questrade Financial Group Full time

    Questrade Financial Group (QFG), through its companies - Questrade, Inc., Questrade Wealth Management Inc., Community Trust Company, Zolo, and Flexiti Financial Inc., provides securities and foreign currency investment, professionally managed investment portfolios, mortgages, real estate services, financial services and more. Questrade uses cutting-edge...

  • Director, Product Enablement

    1 week ago

    Toronto, Ontario, Canada Questrade Financial Group Full time

    Questrade Financial Group (QFG), through its companies - Questrade, Inc., Questrade Wealth Management Inc., Community Trust Company, Zolo, and Flexiti Financial Inc., provides securities and foreign currency investment, professionally managed investment portfolios, mortgages, real estate services, financial services and more. Questrade uses cutting-edge...

  • Director, Growth Enablement

    2 weeks ago

    Toronto, Ontario, Canada League Full time

    About LeagueFounded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League's platform to deliver...

  • Director, Digital Onboarding

    2 weeks ago

    Toronto, Ontario, Canada Mastercard Full time

    Our PurposeMastercard powers economies and empowers people in 200+ countries and territories worldwide. Together with our customers, we're helping build a sustainable economy where everyone can prosper. We support a wide range of digital payments choices, making transactions secure, simple, smart and accessible. Our technology and innovation, partnerships...