Strategy And Operations Jobs in Calgary, AB (NOW HIRING)

The Vice President, Direct Venture Experience & Operations designs, builds and scales the member experience and operating capabilities required to launch and grow Wawanesa's Direct-to-Member (D2M) business. The role owns the model for a simple, intuitive, AI-first journey across quote, bind, onboarding, service, retention and future claims interactions. As a senior venture leader, the VP translates strategy into execution by establishing the service model, decision rights, routines and cross-functional ways of working for a high-growth digital insurance business. The VP will help to define what is delivered by enterprise functions, and how capabilities mature from test-and-learn through launch, scale and steady state, with focus on member experience, service operations, AI-assisted service, partner management, fraud, training, underwriting and claims integration, and lifecycle performance.  

• Lead the D2M Experience & Operations strategy and operating model for a simple, accessible, compliant and scalable experience across digital and assisted channels. 
• Establish capabilities, workflows, governance, service standards, routines, escalation paths and decision rights. 
• Build Experience & Operations as a core venture capability, clarifying D2M-owned versus enterprise-delivered capabilities from MLP to launch and scale. 
• Design the quote-to-bind-to-service model, including digital self-serve, AI-assisted service, licensed agent support, contact centre integration, escalation pathways and dual-licensed capabilities where applicable. 
• Partner across product, technology, data, marketing, underwriting, pricing, claims, legal, risk, compliance and shared services to embed requirements, controls and scalability. 
• Establish metrics for service levels, conversion, onboarding, resolution, quality, member effort, retention, NPS, complaints and risk indicators. 
• Use feedback, data, market learnings, automation, AI decision support, analytics and workflow tools to improve speed, quality and scalability. 
• Support fraud, risk, underwriting, claims and compliance interfaces, protecting member experience while maintaining controls. 
• Lead readiness for products, channels, pilots, campaigns and releases, ensuring processes, training, tools, controls, reporting and support models are in place. 
• Oversee vendor and partner management, commitments, capacity planning, issue resolution, reporting and governance. 
• Identify operational gaps, dependencies, risks and constraints; recommend trade-offs, sequencing, investment and resourcing. 
• Build a high-performing team and matrixed model; foster a member-first, test-and-learn culture balancing speed, discipline, readiness, resilience and growth. 
• Ground executive decisions in what can be delivered, scaled, measured and sustained in market. 
• Other duties as assigned.

• 15+ years of leadership experience in operations, customer/member experience, digital service, insurance operations, transformation or venture-scale business builds. 
• Senior leadership experience in insurance, financial services or another regulated environment where customer experience, controls, risk management and scalability are critical. 
• Experience designing, launching and scaling operating models, service models and customer/member experiences in ambiguous or fast-moving environments. 
• Understanding of direct-to-consumer or digital distribution models, including quote, bind, onboarding, servicing, retention, claims or issue-resolution journeys. 
• Experience integrating operations across product, technology, data, underwriting, pricing, claims, legal, risk, compliance, marketing and shared services. 
• Experience with AI-enabled, automation-enabled or digitally assisted operating models is a strong asset. 
• Ability to define service standards, metrics, controls and routines that balance member outcomes with business discipline. 
• Strong influence, relationship and judgment skills, including matrix leadership and balancing member experience, speed, scalability, cost, regulatory obligations and risk. 
• Experience building teams, clarifying accountabilities, developing leaders and scaling capabilities. 
• Knowledge of Canadian P&C insurance, contact centre, licensed agent, operational excellence, partner management, fraud or claims operations is an asset. 
• Post-secondary degree in a related field; MBA, CIP/FCIP, Lean/Six Sigma, Agile, Product, Operations or CX certifications are assets. 
• Bilingualism (English and French) is considered an asset. 

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