Job Description

Here is your chance to join an organization that is evolving and poised to change the face of insurance  solutions. Currently, we have an exciting opportunity for a Temporary Full-Time IS Project Manager (approximately 24 months) to complement our IS Team.  

Reporting to the Manager of IS & Innovation, we are currently seeking a highly motivated, creative and  innovative thinker for a Temporary Full-Time IS Project Manager position. As a vital member of the  Information Systems (IS) Team, your key responsibility will be to plan, execute and deliver a corporate wide  project on time, within budget and in accordance to specifications.  

What Will You Be Doing? 

  • Act as a hands on project manager for a large scale Guidewire implementation project 
  • Champion the project through the entire lifecycle including the allocation of adequate resources, scheduling, documentation, budget, celebrating milestones and other factors necessary for success 
  • Conduct cost-benefit analyses, risk analyses, and ROI calculations to determine project feasibility
  • Responsible for regular written and verbal project reports to the Leadership Team as well as project communication meetings and presentations for team members and Leadership 
  • Negotiate with all teams to obtain required skill sets for project teams within the organization
  • Organize project teams into suitable workgroups and guide the teams throughout their efforts to produce deliverables according to specification 
  • Investigate problems to determine root cause and work with the vendor(s) to resolve 
  • Gather business requirements as needed for each project and turn business requirements into technical specifications
  • Ensure project remains within scope and within budget with regular reporting delivered to the Manager of IS and Innovation in this regard 
  • Develop an appropriate testing model in collaboration with Business Analysts and Project SME’s
  • Assure all team members understand their roles and accept their responsibilities 
  • Act as a role model, including coaching, mentoring, motivating and developing the team to ensure achievements of goals and objectives 
  • Change leadership – lead by example – manage change and take active leadership in timely decision making
  • Identify and resolve conflicts within project teams and associate work; create contingency plans to mitigate risk
  • Vendor Management: act as the company’s liaison with external IT vendors including but not limited to MCCG/ Cognition+, Hubio, Guidewire, Business Analysts, and Project managers 
  • Document issues and manage the issue resolution process with vendors and internal stakeholders
  • Keep abreast on the projects of external vendors recommending changes at the Company level for alignment
  • Negotiation with leadership teams to establish priorities 
  • Demonstrate excellent customer service 
  • Keep up to date with industry and market changes and developments 
  • Represent the company at industry functions and meetings as required 
  • Must be fully aware of, and comply with company confidentiality requirements at the highest level
  • Handle other duties as assigned by the Manager of IS and Innovation

 Who You Are: 

  • College Diploma or University degree in a related discipline Project Management Professional Certificate required
  • 10+ Years of Project management experience with demonstrated skills in planning and execution
  • Solid knowledge of Business Analysis Principles, best practices and industry tools 
  • Facilitation skills to guide and keep a group on track, recognize issues that need to dealt with and ensure everyone is heard. Guide the group through collaborative decision-making to achieve its goals. 
  • Ability to estimate resource requirements and staff to appropriate levels 
  • Advanced troubleshooting skills, with a high level of resourcefulness 
  • Highly effective negotiation, diplomatic, and conflict resolution skills 
  • Technical background sufficient to understand the technologies and technical issues involved, ability to anticipate and  identify critical technical instances and to make accurate technology decisions 
  • High level of attention to detail and accuracy is a must 
  • Good time management skills including the ability to multi-task, prioritize, work under pressure and meet deadlines
  • Able to work effectively and harmoniously in a team environment with both internal and external partners
  • Able to explain and discuss complex technical information so that non-technical individual(s) can understand it
  • Demonstrated communication and influencing skills along with analytical and problem-solving skills
  • Proven ability to negotiate resolution via influence 
  • Exceptional computer skills including Microsoft Excel, Office, Adobe Acrobat, required 
  • Ability to multi-task and take initiative to manage priorities effectively 
  • Flexible, positive and collaborative team member with ability to work with minimal supervision
  • Superior customer service skills through energy, enthusiasm and initiative 
  • Working knowledge of the Systems Development Life Cycle and Agile Programming methodologies
  • Understanding of programming languages used currently 
  • Excellent verbal and written communication skills 
  • Experience with successfully delivering change and transformation projects/programs for Guidewire Suite of Products  focusing on an end-to-end approach between Business and IT  
  • Excellent ability to gather and evaluate requirements as well as promoting and facilitating discussions to bridge gaps
  • Exceptional ability to build relationships, assess and resolve conflicts, and create buy-in during a long-term, multi-   stakeholder project timeline 
  • Able to manage and influence at all levels of the organization 
  • Understanding of the insurance industry because of significant time within the industry at various levels of  responsibility 
  • Leads with a customer-centric approach—able to understand how each decision and pathway will affect the end user  (both internally and externally)  
  • Experience with all aspects of the Guidewire platform, including claims, billing, policy administration
  • Experience managing and facilitating the implementation of all suites of the Guidewire platform is a considerable asset
  • Strong presentation skills, with the ability to simplify complex processes and issues to communicate to a wide range of  audiences 

This position will work primarily remotely from a home office with infrequent onsite interaction as  needed. As a remote worker, access to high speed internet and reliable connectivity is required. 

If you are a high performer who delivers more than what is expected, provides excellent service by  understanding customer needs, enthusiastically supports change, shares your expertise, takes  responsibility for your own development, who actively seeks new challenges and has a desire to learn and  grow, then we want to hear from you! 

We invite interested applicants to submit their resume to by October 27, 2020.  Applicants are thanked for their interest in this position, however, only applicants selected for an interview  will be contacted. Trillium is committed to providing accommodations and achieving a barrier free  workplace for individuals with disabilities. Should you require an accommodation in order to participate in  our recruitment process, we will support you by taking into account your individual needs. 

To learn more about Trillium Mutual visit us at our website 



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Education Required

College Secondary School Diploma

Minimum Experience Required

11 or more Years