Vice-President - National SalesHalpenny Insurance Brokers with Windley Ely Integration FocusCompanies: Halpenny Group (P&C Insurance Broker & Group Benefits) & Windley Ely (Claims Management)Location: Ottawa or Toronto (primary) | Travel up to 25% across national officesReports To: Chief Executive Officer / Executive LeadershipEmployment Type: Full-Time, PermanentCompensation: Base Salary ($175,000 – $225,000) + Performance IncentiveAbout Halpenny Group & Windley ElyHalpenny Insurance Brokers is one of Ontario’s leading independent commercial P&C and group benefits brokers, with offices in Ottawa and Toronto. Windley Ely is a national claims management company headquartered in London, ON, with branches in Calgary, Vancouver, Montreal, and Ottawa. Under shared ownership, these two firms represent a powerful combination of brokerage, benefits, and claims expertise — with significant untapped revenue potential across a combined client base of approximately 205 professionals nationwide.Position SummaryThe Vice-President - National Sales is the senior revenue leader for Halpenny Group and Windley Ely, responsible for driving organic growth through sales strategy, producer performance, and cross-firm collaboration. This leader is both a strategist and an active closer — equally comfortable setting national direction and sitting across from a CFO to close a complex, multi-line deal. The role exists to turn the Halpenny + Windley Ely combination into a cross-selling engine: breaking silos between P&C, group benefits, and claims/risk consulting, monetizing the existing client base across both firms, and building repeatable systems for multi-line client penetration.Key ResponsibilitiesBuild the Cross-Sell Engine (Primary Focus)Identify and prioritize cross-sell opportunities: Halpenny clients → Windley Ely claims/disability/WCB services; Windley Ely clients → Halpenny P&C and group benefitsDesign cross-sell playbooks by segment: mid-market, large accounts, and industry verticalsImplement referral protocols, joint account planning processes, and shared pipeline reporting across both firmsBuild robust alignment with commercial lines, group benefits, and claims/risk practices to leverage the full combined value propositionLead National Sales StrategyOwn revenue growth across new business, cross-sell,



and key account expansionSet, monitor, and deliver on annual sales targets for new business, retention, and cross-sell activity by region and product lineUtilize sales analytics, pipeline metrics, and dashboards to track progress, identify opportunities, and implement course correctionsContribute to business planning, budgeting, and sales reviews in partnership with leadershipLead & Develop Producers and Business Development TeamsProvide direct leadership of Account Executives (producers) and Business Development/hunter rolesSupport producer efforts throughout the full sales cycle — developing, qualifying, strategizing, and winning new business opportunitiesJoin producers at early-stage prospect meetings, participate in sales negotiations, and attend client presentations as neededDevelop creative solutions on new business opportunities; articulate Halpenny andWindley Ely differentiators to turn prospects into clientsAttract, develop, and retain top sales talent to meet future growth needs across both Ottawa and Toronto marketsFoster a culture of accountability and recognition that rewards excellence, collaboration, and continuous improvementShift producer mindset from “my book” to firm-wide client valueInstitutionalize Cross-Firm CollaborationBreak down cultural barriers and compensation misalignment between Halpenny and Windley Ely teamsIntroduce joint sales calls, shared incentive structures, and cross-training programs across both firmsLead the change management required to make cross-sell a standard operating practice, not an afterthoughtDrive Client & Market EngagementBuild and maintain strong relationships with key clients, carrier partners, and community leadersRepresent the Halpenny + Windley Ely brand externally through leadership in industry associations and client eventsChampion a consultative,



risk-advisory sales approach across all producer teamsPersonally engage in top-tier, multi-line opportunities at the CFO, CHRO, and Risk Manager levelCreate Visibility & AccountabilityImplement cross-sell pipeline tracking, share-of-wallet reporting, and producer performance dashboardsEstablish KPIs tied to cross-sell outcomes — not just gross written premiumKey Success Metrics% of clients with 2+ product/service lines across both firmsCross-sell revenue growth year-over-yearRevenue per client (share of wallet trend)Producer cross-sell activity rates and new business conversionRetention and expansion of top accountsQualificationsRequired Qualifications10–15+ years in insurance brokerage, group benefits consulting, or risk advisoryMinimum 5 years in a senior sales leadership role with direct producer management responsibilityProven success supporting the full sales cycle — qualifying, strategizing, and closing complex multi-line opportunitiesDemonstrated ability to attract, develop, and retain top producer talentProven success in post-merger, multi-division, or integrated service environmentsDeep knowledge of at least one: commercial P&C, group benefits, or claims/disability managementStrong understanding of commercial insurance products, carrier markets, and competitive dynamicsEntrepreneurial mindset with the ability to balance strategy, execution, and operational disciplineBachelor’s degree in Business, Finance, or a related field (advanced degree an asset)Credentials (Preferred)P&C: CIP, CAIB, or FCIPBenefits: CEBS or GBAFunctional bilingualism in French and English an assetWhat We OfferCompetitive base salary ($175,000 – $225,000) with performance-based incentiveComprehensive group benefits plan including health, dental, wellness savings account, and Group RRSPA genuinely unique mandate — building a cross-sell revenue engine across two established Canadian firmsDirect access to ownership with the authority and resources to execute your visionProfessional development support including designation sponsorship (CIP, FCIP, CAIB, CHRL)Hybrid work flexibility across Ottawa and Toronto officesHalpenny Group and Windley Ely are committed to equity, diversity, and inclusion. Accommodations are available on request throughout the selection process.#J-18808-Ljbffr

📌 Vice-President - National Sales - C$175,000 - C$225,000 A Year (Winnipeg)
🏢 Halpenny Group & Windley Ely
📍 Winnipeg