With over 20 years of professional experience, Dave has built on a reputation of collaboration, diverse technical and business skills and mentorship.  From working with some of the largest financial institutions in Canada to deploy hardware and software to developing innovative solutions for the local garage and rural economic development officers Dave has the skillset to rapidly understand your business, your goals and develop and execute a technology strategy to support you!

David Cripps, PMP

Professional Experience

Deployment Program Director (contract)     

Intact Financial Corporation Toronto Ontario

  • Key accomplishments: Develop team of national distribution directors within Operation Performance department into primary change management team for deployment of commercial system, process redevelopment and organizational change projects
  • Provide project leadership, project manager development and mentorship to directors, analysts and project managers.
  • Develop communication, governance, strategy, and training to support change management and program management activities for deployment, broker and ancillary projects.

Key Projects:

Contact CL 2.0 Deployment: Facilitate collaboration with various business units, operations and planning, IT to plan testing, quality, defect prioritization and execution of all deployment activities related to new policy administration and quoting system.

Commercial Process Deployment:  Evaluate existing commercial lines workflows.  Enhance and test process in alignment with current and future strategies.  Execute implementation of process in parallel to deployment of relevant system components.  Collect metrics and report to senior executive.  Prioritize and re-plan according to progress on a divisional/national basis.

Broker Commercial Deployment:  Meet with external stakeholders and complete needs (and wants) analysis for quote system.  Create roadmaps for broker deployment, as well as MVP deliverables and change management requirements.

KPI Project:  In collaboration with Atlantic divisional lead facilitate visioning sessions and develop national requirements for reporting and key performance indicators.  Develop models and requirements with business.  Deliver requirements to partners in IT and other departments.  Assist with prioritization of items and transitioning to national delivery teams.

Training:  Plan, facilitate and execute training for 300 users on deployed commercial lines policy admin system nationally.  Pivot training plan to remote delivery (given Covid19 issues).  Train a team of trainers and provide support to trainers over 6 week window.  Manage technical and users issues as they manifested and arrange platinum support and follow-up to deliver a platinum user experience.

Senior Project Manager (contract)     

Great West Life Toronto Ontario

  • Key accomplishments: Setup Confluence and Jira tools to host portfolio and project assets for Individual Health Service business unit.  Includes project sites, Kanban boards, project assets etc.
  • Provide project leadership, project manager development and mentorship to junior project managers/team leads and scrum masters.
  • Develop communication, governance, strategy, and training to support change management activities for IHS staff.

Key Projects:

IHS Integration:  Create tools and assets for project management lifecycle for acquired organization.  Develop governance for both operations and project delivery.  Provide training and change management activities for IT staff in areas such as: KANBAN, Confluence, SDLC, PMLC, and GWL internal systems.

Confidential Move Project:  Develop and execute plan to relocate 30 staff from one office to existing head office. Project included infrastructure and application relocation, call centre outsourcing, development of PCI API, business readiness and internal and external communications.  Total Project budget $400,000.  Business Units impacted: 8 Project Team: 30 (both IT and Business resources)

Product Harmonization Project:  Plan and execute project to facilitate product updates and consolidation on custom policy admin system.  Also create methodology including IT staff training to support project and operations work.  Total Project budget $320,000 Business Units impacted: 5 Project Team: 15 (Product, Marketing & IT)

Service Manager/Analyst (contract)     

Butterworths Autopro, Ingersoll Ontario

  • Key accomplishments: Working with vendor; configure and deploy email communication module in existing ERP system for customer bookings, follow-up and feedback.
  • Develop and execute social media strategy for auto repair facility, identify metrics to track communications with customers.  Utilize and incorporate national NAPA advertising campaign assets into local ad campaigns.
  • Work in service manager role to understand business processes, identify owner priorities and assist with developing strategies in technology, workforce management and marketing.
  • Create various templates and processes to support service manager role. 
  • Identify technology options to enhance or support business operations (identify annual savings in reduction of redundant various software subscriptions and IT activities)
  • Identify and produce scheduled content for multiple social media channels.


All Celebrations, Ingersoll Ontario

  • Key accomplishments: Identify and implement cloud based small business IT solutions for Finance, HR, and CRM/ERP.
  • Facilitate company start-up including inventory acquisition, develop process and procedures, identify vendors both to support ongoing operations and expansion.
  • Provide training and on boarding for part time seasonal employees in relation to both operations and health & safety.
  • Develop marketing and social media strategy to support startup enterprise, including website.
  • Draft business plan to support various funding opportunities.

Key Projects:

GoodShuffle Implementation:  Assess multiple ERP and CRM solutions for small enterprise.  Work with vendor to provide training and implementation process.

Website & Social Media Marketing Strategy:  Source vendors and develop website for client marketing presence as well as training on content updates.  Develop social media strategy and facilitate regular posting of content and social media marketing campaigns.

Senior Project Manager  (contract)   

Economical Insurance, Waterloo Ontario

  • Key accomplishments: Complete integrated conversion work breakdown structure with IT Development Director, Functional Business Leader and Operational Impacted Team Leaders.
  • Provide project leadership, project manager development and mentorship to junior project managers/team leads and scrum masters.
  • Develop governance, project assets (IE Confluence site) and contribute to overall program development and communication.

Key Projects:

PAS Conversion Project:  Work with senior business and IT leaders to craft integrated strategy and plan to execute 12 sprint conversion project from legacy policy admin system to Guidewire. 

National Processing Centre, Sales & Distribution Readiness Projects: Develop program and project governance and direct planning and integration of change management and readiness activities.

Post Go Live Project: Completed strategy and plan to execute phased post go live activities to minimize operational and broker impact of Guidewire implementation.  Included business/IT support integration, risk identification and mitigation planning, transition planning and “war room” planning.                  

Total Program budget $25,000,000+.  Resources assigned:  90+.  Business Units impacted: multiple.

Senior Project Manager – Distribution & Marketing Portfolio                      Sun Life Financial, Waterloo Ontario

  • Key accomplishment: Led team, completed business case and initiated pilot for cross functional collaboration tools to improve efficiency of PM, BSA and development practice areas.  Projected ROI 200K per year.
  • Work with senior business and IT leaders to plan and develop 10 year Individual IT strategy.
  • Provide project leadership, project manager development and mentorship to junior project managers.

Key Projects:

Individual IT Strategy:  Work with senior business and IT leaders to craft both medium and long term IT strategy for Individual Wealth, Marketing & Distribution and Insurance products. 

Distribution & Marketing Wholesale Presentation and Content Repository: Led strategic sourcing initiative to identify vendor to provide web and tablet based solution for content distribution by third party advisors.  Total Project budget $800,000.  Business units impacted: 4

Web App Replacement Project: Led IT initiative to plan and assess internally developed web application for online policy sales, including UX/and UI design and Salesforce.com integration.                   

Total Program budget $12,000,000.  IT resources assigned:  40+.  Business Units impacted: multiple.

Portfolio Manager, Individual Application Services (contract)                    Sun Life Financial, Waterloo Ontario

  • Key Accomplishments: mentored junior PMs who were promoted to more senior roles, identified savings of 10% in Distribution Compensation Portfolio through project amalgamation. Succeeded in exceeding projects for ROI on Direct mailing automation campaign project (2 years earlier then outlined in business case)
  • Provide project leadership, project manager development and mentorship to junior project managers.
  • Contribute feedback to development and implementation of Lean (Agile) software development lifecycle.
  • Member of pilot/steering committee evaluating various tools.
  • Identified savings of roughly 25% through amalgamation of portfolio projects.

Key Projects:

Advisor Compensation Program:  Manage IT and business resources located onshore and off shore: (mainframe development, middle tier/ETL development, web development, operations and records management).  Project integrated mainframe and existing advisor facing web components, leveraging ETL and multiple technology teams.  Work included 5 core streams each following SDLC.  Duration: 14 months Total Program budget $1,200,000.  IT Project Team: 30 – 35 resources.  Business Units impacted: 5.

Distribution Compensation Portfolio: Work with business partners to prioritize and evaluate business maintenance projects.  Direct 5 project managers on 9 initiatives.  Identified savings of roughly 80K through grouping of like work packages into single project initiatives.  Oversee operational projects including tax slips, and external audit data preparations.  Total Portfolio budget $800,000.  IT resources assigned:  15 – 40.  Business Units impacted: 1.

Client Solution Direct Mailing Automation and Campaigns:  Execute multiple product mailing campaigns while automating reinsurance, client exposure and product pricing components.  Leveraged Agile techniques including: sprints, backlogs and regular stand up meetings.  Campaigns and components we delivered to business units incrementally to incorporate feedback in following implementations.  Lessons learned from the project contributed to development of formalized Lean(Agile) lifecycle adopted by various PMOs.  Total project budget $1,000,000.  IT resources assigned: 20.  Business Units impacted: multiple

Project Manager, Individual Distribution & Marketing                                      Great West Life Co (London Life)

  • Key Accomplishments: Identified 100K savings and collaborated in achieving savings with NBT program development.
  • Contributed to Sharepoint project site pilots and development of corporate Agile software development lifecycle.

Key Projects:

Online Advisor Tool/Client Sites: Assumed leadership of two core projects for wealth management program.  Developed trusted stakeholder relationships allowing alignment and execution of project with marketing, actuarial, product, IS and multiple vendor requirements.  Adopted Agile techniques to provide ongoing and regular feedback to both program and key stakeholders.  Developed process for implementation of AODA standards.  Leveraged on and offshore project resources.   Duration: 8 months Program budget: $8,000,000 Projects managed: $1,500,000 and $2,100,000.  IT resources 23 Vendors 2. 

Advisor Portal Refresh: Initiated, planned and executed multisite mainframe to portal enhancement and conversion project.  Worked with both on-shore and off-shore resources.  Identified and implemented cost savings of 15%.  Incorporated Agile techniques within existing SDLC, contributing foundation for Agile Development Life Cycle Project.  IT resources 15.  Budget: $750,000

Project Manager, Technical Infrastructure                                                            The Economical Insurance Group

  • Key Accomplishments:  Played key leadership role in developing standards for IT infrastructure program and project delivery, and implemented new processes and version of CA Clarity PPM for  50% of budget project costs.
  • Liaise with senior leadership (director and VP level), key stakeholders and end user committees on business case, process and standards development for Clarity (CA Clarity PPM) portfolio management tool, Enterprise Sharepoint roll-out, and data leakage protections and data classification projects.
  • Participate in weekly CAB meetings, discussing progress and priority of various change initiatives and organizational implementations.

Key Projects:

CA Clarity Upgrade:  Responsible for both managing upgrade project and change/process enhancements.  Worked with various stakeholders to develop and incorporate process improvement and update to existing resourcing, project management and portfolio management strategies leveraged through the Clarity tool.  Procured vendor arrangements for 50% cost reduction in overall project.  Developed work packages, end user and management training for both internal resources and contractors located in the US.  Project initiated September 2011, Implemented February 2012.  Project team:  12 internal resources + vendor.  Budget $100,000.  Over 300 stakeholders involved. 

Sharepoint Program:  Evaluate vendors for both cloud based Sharepoint solutions and internal solutions.  Develop 24 month schedule and plan for companywide roll-out, including infrastructure and software procurement.  Worked with all business units on planning tailored deployment as well as developing change management strategies.  Project team: 20 (business and IT). Budget $500,000.   Companywide interactions.  Initiated December 2011.

Data Leakage Prevention Tactical Project:  In support of the demutualization process, assumed responsibility for planning, execution, monitoring and controlling of this tactical project.  Worked with internal security resources to develop data identification and technical resources to implement tools to accommodate DLP.  Spearheaded significant enterprise change management to raise awareness, related to upcoming DLP requirements.

Implementation required close monitoring of change requests, and an iterative planning approach.  Project Team: 12.  Project executed from August – December 2011.

Development Manager/Project Manager                                                                The Guarantee Company of North America/Cowan Insurance Group

  • Key accomplishments:  Led creation of PMO, Created one of the first online quote/bind e-signature insurance product applications available on the market
  • Led change management activities for multiple significant enterprise projects (Marketing/Distribution, Website, Intranet, Project Management Office)
  • Managed development portfolio for all specialty products business lines.
  • Responsible for all aspects of recruitment of non mainframe programming and systems integration staff.
  • Developed both project and portfolio management standards, Agile software development lifecycle methodology and associated templates and processes. 

Key Projects:

Online Electronic Quote and Policy System:  Responsible for all aspects of project including business case development, Agile sprints, broker communication plan and elicitation.  Developed backlog, detailed project schedule, budget, warranty and training plans, and measures for project ROI and success factors.  Project created quote and bind system for brokers, leveraging integration from legacy policy system for Not for Profit Shield product.    Project duration 8 months.  Project team: 15. Budget $75,000K.  Positive ROI in year 2 of operation

Implementation of Web services for Personal Lines:   Completed build vs buy assessment with customer (VP of Personal Lines) opted to staff project internally.  Project provided for extraction and conversion of mainframe data to desktop application.  Obtained budget savings of over 200%.   Expanded implementation to Quebec region.

Integration of Webwriter Inspection System with AS400:  Provided project planning, and execution of first significant two-way mainframe data integration with web based operations system.  Required cross functional project team including external vendor support.  Project was completed on time and under budget, provided foundation for further “black boxing“ of core policy system.

Oracle Product Upgrade Project:  Managed all aspects (including technical design and hardware procurement) of Oracle 9i – 10g database, operating system and middleware upgrade. 

IT Administrator                                                                                                                Stevenson & Hunt Insurance Brokers

  • Manage all day to day information technology operations for 150 seat multi site brokerage.
  • Initiated monthly change and opportunity identification meetings with all department heads.
  • Co-ordinate external vendor activities.
  • Manage 400K IT budget.
  • IT planning aligned with strategic objectives.

Key Projects:

Disaster Recovery Implementation:  Designed technical specification for robust disaster recovery environment.
Broker Management System Upgrade:  Lead upgrade with vendor.

Compuquote Upgrade:  Performed upgrade based on vendors project methodology.

Setup of New Vaughn Office:  Scoped and executed technical aspects of office setup, provided multiple risk and issue mitigation efforts, ensured office moved as per schedule

Database & Systems Administrator                                                                            The Guarantee Company of North America

  • Systems administration: Oracle, Solaris, Suse Linux, Redhat Linux, Novell.
  • Ongoing production of ad-hoc reporting for marketing

Key Projects:

Surety System legacy replacement:  Involved in all aspects of project from business case design, project initiating, scoping, and budgeting both as a project coordinator and technical lead.  Responsible for ensuring the delivery of specific work packages under the guidance of an Oracle project manager.  Surety System data conversion:  Responsible for scoping, mapping and executing data conversion and migration from six regional systems into one central database.

Solaris to Linux migration:  Coordinated migration of database and application system software to Intel solution, responsible for planning, risk assessment and executing.


Kanban & Scrum Fundamentals, Construx                                                                               

Confluence & Jira, Deloitte                                                                                                       

Advanced Sharepoint, Microsoft                                                                                              

Covey Foundations, Franklin Covey                                                                                        

Agile Foundations, Project Management Institute                                                                   

PMP, PMI (South Western Ontario Chapter member)                                                              

Masters Certificate in Project Management, York University                                                  

Athabasca University (Economics, Composition,  Marketing, Law,  Human Resources)                               

ITIL Foundations V3, Destech                                                                                                 

Oracle OCP courses, Oracle Education                                                                           

Business Information Systems Diploma, Fanshawe College