Senior Business Development Insurance Jobs in Toronto, ON

                                                                                    Job Description: 

Role Overview

CORA Loyalty is seeking a highly experienced Senior Business Development Director to lead new-business development across North America, with primary responsibility for building qualified pipeline, converting enterprise opportunities, and helping establish a repeatable go-to-market motion across the United States and Canada.

This is a senior commercial leadership role for someone who can open executive relationships, shape opportunity strategy, lead complex enterprise pursuit cycles, and win high-value business in a disciplined way. The post is not a junior hunting role and it is not a channel co-ordination role dressed up with a bigger title. It is a true enterprise business development leadership brief with meaningful new-logo accountability.

The successful candidate will be comfortable developing business in complex organisations, navigating large buying groups, working through formal procurement and legal processes, and bringing together product, delivery, client services, finance, and leadership teams around a coherent commercial strategy.

Key Responsibilities

• Own and develop a defined portfolio of target prospects across the United States and Canada, with clear accountability for pipeline creation, opportunity progression, proposal quality, and new-logo conversion.
• Act as the senior commercial lead for named prospects, building trusted relationships with executive stakeholders across marketing, loyalty, digital, customer engagement, operations, finance, procurement, and partner teams.
• Develop and lead robust opportunity plans covering client priorities, stakeholder mapping, competitive positioning, commercial strategy, pilot structure, proposal approach, negotiation path, and close plan.
• Drive disciplined new-business performance across the region, with clear accountability for qualified pipeline, forecast accuracy, commercial progression, and closed-won outcomes.
• Lead discovery sessions, executive meetings, solution discussions, proposal reviews, and commercial negotiations with prospects, ensuring CORA Loyalty is positioned as a strategic partner rather than a feature-led vendor.
• Lead with the right entry play for the right opportunity, whether enterprise loyalty modernisation, rewards marketplace expansion, B2B and channel incentives, or a managed-services-led wedge.
• Partner closely with product, delivery, client services, analytics, support, finance, and leadership teams to ensure opportunities are shaped credibly, solutions are commercially sound, and commitments are aligned with operational reality.
• Identify and convert selected cross-border or partner-supported opportunities, including those introduced through strategic relationships, alliances, and reseller routes, without losing focus on the core North American direct-business development mandate.
• Dedicate roughly 20% of role focus to market-building activity, including selective partner support, strategic introductions, channel relationships, and the development of repeatable North American business development assets and commercial discipline.
• Help shape how CORA Loyalty approaches the North American market, including target-account selection, qualification discipline, proposal standards, forecast rigour, and business development process maturity.
• Support commercial negotiations, proposal development, pricing discussions, contract strategy, and close planning in conjunction with leadership and relevant functional teams.
• Maintain strong CRM discipline, ensuring every live opportunity is clearly documented with owner, stage, next step, commercial value, and expected timing.
• Work closely with Client Services and implementation teams to ensure a clean and credible handoff from close into mobilisation, without blurring accountability for post-live account leadership.
• Represent market feedback internally, helping refine proposition, packaging, proof points, and go-to-market priorities based on what is landing with enterprise buyers in the region.

What Success Looks Like

• North America has a credible and well-managed new-business pipeline, with strong opportunity visibility, sound qualification discipline, and realistic forecasting.
• CORA Loyalty has stronger executive access and broader stakeholder coverage across target prospects in the United States and Canada.
• Opportunities are shaped with commercial rigour, competitive realism, and clear close plans rather than hopeful activity without structure.
• New-logo wins are secured in a disciplined way, with strong internal alignment and a clean transition into delivery and client services.
• Partner and introduction-led activity contributes sensible additional access and optionality, without distracting from the direct North American business development mandate.
• The North American business development motion becomes more structured, commercially sharper, and more scalable over time.

Required Experience and Capabilities

• 10 to 15+ years of experience in enterprise business development, commercial leadership, consulting, or related growth roles within loyalty, SaaS, MarTech, rewards, payments, commerce, incentives, or adjacent technology-enabled services.
• Significant experience winning large, complex, multi-stakeholder enterprise deals, ideally across both the United States and Canada or in one market with meaningful exposure to the other.
• Strong track record of originating, progressing, and closing new-business opportunities involving long enterprise buying cycles, formal procurement processes, and senior executive stakeholders.
• Experience engaging credibly with C-suite and executive-level decision-makers, with the judgement and presence to lead commercially important conversations.
• Demonstrated ability to lead opportunity strategy while co-ordinating product, delivery, finance, legal, support, and leadership teams in a matrixed environment.
• Experience working with complex commercial structures, including MSAs, SOWs, pilots, pricing discussions, procurement processes, security review, and contract negotiations.
• Exposure to partner, reseller, channel, or alliance-led growth models, with the judgement to know when those routes accelerate growth and when they merely create noise.
• High commercial acumen, strong written and verbal communication, and the executive presence to operate effectively in a demanding North American market.
• Ability to operate with autonomy, structure ambiguity, and maintain clear priorities across a broad territory and a relatively lean organisation.
• Strong command of CRM, pipeline discipline, forecasting, and pipeline reporting.
• Willingness and ability to travel across the United States and Canada as required.

Preferred Experience

• Experience in loyalty, rewards, engagement, channel incentives, or customer marketing.
• Experience developing business in financial services, retail, travel, hospitality, telecoms, or other complex consumer-facing sectors.
• Experience in a platform-plus-services environment, where client value depends on both technology and ongoing strategic support.
• Experience in a North America-based role, ideally with direct exposure to both US and Canadian buyers.
• French language capability would be an advantage, but is not essential.

Personal Attributes

• Commercially sharp, but not reckless.
• Strategic in outlook, but willing to get into the detail.
• Calm under pressure, with sound judgement in difficult commercial situations.
• Credible with executives, delivery teams, and client leaders alike.
• Naturally collaborative, but comfortable taking ownership and making decisions.
• Ambitious enough to build, not merely execute against an existing playbook.

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                                                                                    Business Unit: Carlson Marketing Solutions - Canada                                                                                    Scheduled Weekly Hours:37.5                                                                                    Number of Openings Available: 1                                                                                    Worker Type: Regular More About Jonas Software:

Jonas Software is a leading provider of enterprise management software solutions, serving a wide range of vertical markets including hospitality, healthcare, construction, education, personal care, fitness, leisure, moving and legal services, to name a few. Within these markets, Jonas is comprised of over 65 distinct brands, each a respected leader in its domain.

Jonas' vision is to be the branded global leader across these verticals and to be recognized by customers and industry stakeholders as the trusted provider of "Software for Life." We are committed to technology, product innovation, quality, and exceptional customer service.

Jonas Software supports over 60,000 customers in more than 30 countries. We employ over 6,000 skilled professionals, including industry experts and technology specialists. Across our broader network, we support a global workforce of more than 30,000 employees.

Headquartered in Canada, Jonas Software has a global footprint with offices around the world. We're a 100% owned subsidiary of Constellation Software Inc., based in Toronto, publicly listed on the TSX (CSU.TO), and a member of the S&P/TSX 60 Index.