VP, Direct Venture Experience & Operations

Wawanesa Insurance•Montreal, QC

1d•Hybrid

About The Position

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.

Requirements

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.

Nice To Haves

Experience with AI-enabled, automation-enabled or digitally assisted operating models is a strong asset.
Knowledge of Canadian P&C insurance, contact centre, licensed agent, operational excellence, partner management, fraud or claims operations is an asset.
MBA, CIP/FCIP, Lean/Six Sigma, Agile, Product, Operations or CX certifications are assets.

Responsibilities

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.