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Chief Information Officer

LAWPRO is conducting a search for an experienced and highly qualified Chief Information Officer (CIO) accountable for defining and delivering IT strategy and capabilities across the enterprise. This includes infrastructure and operations, development and support, data analytics and business intelligence, regulatory and audit compliance, security and business continuity. Reporting to the CEO, the CIO will be responsible for giving oversight and direction to IT and business leaders on strategy, standards, and opportunities for shared services and economies of scale.

LAWPRO intends to modernize its core IT platforms over the next several years. This complex and exciting project, with multiple stakeholders and significant system interdependencies, will be led by the CIO, who will have a strong grasp of infrastructure transformation, data migration, workflow optimization and change management.

The CIO is a key contributor to the company’s strategy and planning process and will be responsible both for IT operations and for technology innovation. It is critical for the CIO to build strong and productive relationships with all business unit leaders, acting as a true partner and making IT a business enabler.

The CIO will manage 4 direct reports on the IT leadership team; total headcount in the IT organization is approximately 18.



  • As a member of the senior management team, make a key contribution to the formulation of the company’s business, digital and regulatory compliance strategies.
  • Proactively advise the senior management team on the emerging technologies and digital trends that are most relevant to the company’s goals and evolving needs.
  • Help determine capital investment parameters, priorities and risks for enterprise-wide IT initiatives to maximize the return on investment and advise and provide support on new and legacy technology transitions.


  • Develop an IT vision, strategy, and a roadmap, and lead the IT team and its business partners in effective execution.
  • Ensure, on an ongoing basis, that current and planned technical architecture, investments and solutions are aligned with company business objectives.
  • Prepare and monitor IT operational budgets that meet prevailing objectives and constraints.
  • Develop and execute an analytics program that will allow company business leaders to make data-based decisions.
  • Build strong relationships with business groups and their leaders across the enterprise, and develop a detailed understanding of their issues, challenges and opportunities.
  • Implement the most appropriate and effective IT organizational design to support and engage with the business.
  • Ensure transparency and collaboration between the IT organization and its business partners.

Team Development

  • Hire, develop, evaluate, reward, and retain a highly-qualified team of IT professionals.
    Foster a culture of innovation, transparency and accountability where performance is recognized and rewarded.
  • Promote a “business-first” mentality at all levels of the IT organization.
  • Ensure that the organization has strong systems analysis and project management skills, and the ability to execute business-critical projects.
  • Develop and maintain a plan that provides for succession and continuity in the most critical IT management positions.

IT Operations

  • Lead the planning for and implementation of transformational new core business systems that ensure that LAWPRO’s IT infrastructure is capable of handling the increasing complexity of its current business, the requirements of an online world and new opportunities, all while maintaining full business functionality.
  • Direct the design, planning, implementation, and maintenance of the computing infrastructure that supports the company’s operations and business applications.
  • Establish metrics for managing IT effectiveness and for measuring the impact of IT on the business.
  • Establish appropriate service levels and the processes to ensure that KPIs are met.
  • Maintain oversight of all IT projects, ensuring that commitments are properly planned, staffed, monitored, delivered and reported.
  • Support efforts to ensure compliance with regulatory and audit requirements.
  • Establish a comprehensive enterprise information security program to ensure the integrity, confidentiality and availability of relevant data.
  • Support and update enterprise-wide disaster recovery and business continuity planning.
  • Establish and enforce IT policies, processes, portfolio management, development standards and methodologies.
  • Monitor the industry for developments in IT operations; evaluate and implement relevant new tools and service management frameworks.
  • Review, recommend, and oversee all vendors and managed service agreements for computing, telecommunications, IT services, and equipment.


Leadership and Communications

  • Can create a clear strategic vision for information technology that supports business objectives and can execute on that vision.
  • Able to work collaboratively with diverse leaders, communicate an IT vision and strategy across all levels of the organization, and build consensus around key initiatives and projects.
  • Possesses exceptional interpersonal and communication skills, both oral and written; able to articulate ideas to both technical and non-technical audiences.
  • Demonstrated ability to recruit, hire and motivate a high performing IT team that values transparency and accountability.
  • Possesses exceptional business acumen, analytical and problem-solving abilities.
  • Excellent negotiating skills with internal customers and external service providers.
  • Comfortable with ambiguity; can handle the unexpected with flexibility and resilience.
  • A team player who favors collaborative approaches when working with internal and external partners.
  • Proven ability to build trust with others through a commitment to the highest ethical and professional standards.
  • A high energy executive; tenacious and passionate about reaching the goal, while keeping ego in check.


  • Demonstrated experience driving digital transformation and business growth through innovation and the implementation of technology.
  • Possesses solid knowledge in emerging technologies, and the ability to apply these in the service of the company’s key business goals.
  • Experience leading complex, major change initiatives; demonstrated skills in change management.
  • Experience building an enterprise level data analytics capability.
  • An entrepreneurial mindset; able and interested to pursue new business opportunities.
  • Customer-service oriented.
  • Builder of strong technology vendor partnerships, and able to manage multiple vendor relationships to ensure the best performance and financial return.
  • Demonstrated experience with SaaS, cloud-based, and outsourced solutions through third party providers.

IT Operations

  • Knowledge of a range of vendor technology solutions; able to select and integrate the most appropriate technologies to support the business.
  • Demonstrated ability to design and implement comprehensive approaches to cyber security and risk management.
  • Experience designing and managing an effective IT governance framework across the spectrum of IT service delivery.
  • Outstanding organizational skills, and the ability to manage multiple priorities in a fast paced, high pressure environment.
  • A strong background in operational and capital finances, and IT budget development.
  • Understands ITIL and other service management frameworks, and how to scale and implement them.


  • Demonstrated ability to successfully lead technological change/transition projects, ideally involving legacy systems.
  • 15+ years of career experience in technology, including a minimum of 5 years in a leadership position.
  • Insurance industry experience, preferably in an IT leadership role.
  • Experience leading an agile development organization.
  • Experience managing outsourcing partnerships.
  • An advanced degree in a related field, such as computer science, engineering and/or business (MBA) is preferred.


Should you have any questions regarding this exciting and challenging opportunity, please contact:

Tim Hewat, Partner
E-mail: [email protected]
Tel#: 416.640.4323

Apply via the Amrop Knightsbridge website.

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