Director, Strategic Business Development & Enterprise Sales

Objectway; Toronto; On-site; CAD 180,000 - 200,000; Full time

Job summary

Objectway is seeking a senior Director, Strategic Business Development & Enterprise Sales to lead enterprise growth in Canada. You will engage C-suite executives and coordinate with our global teams to deliver tailored wealth management solutions that drive measurable business outcomes.

You will own the Canadian enterprise strategy, build a robust pipeline, and partner with large financial institutions to extend Objectway’s market presence across enterprise wealth management.

Qualifications

• 10–15+ years in enterprise business development or related consulting in financial services.
• Established network of senior executive relationships within Canadian banks, wealth managers and large institutions.
• Proven ability to originate, develop and close complex enterprise opportunities.

Responsibilities

• Own and execute Canada’s enterprise growth strategy with pipeline and revenue accountability.
• Originate and close complex enterprise opportunities with Tier 1 banks and wealth managers.
• Lead full sales cycles from discovery to contract execution with cross-functional teams.
• Develop strategic accounts and territory plans to maximize long‑term revenue.
• Collaborate with global experts to translate client needs into commercial solutions.
• Represent Objectway at executive meetings, industry forums and strategic events.

Skills

Executive network

Enterprise sales

Consultative selling

Canada banking knowledge

Tier 1 banks

Commercial acumen

Needs-based discovery

Stakeholder management

Wealth management domain

Sales pipeline management

Job description

Who We Are:

Objectway is a global fintech and technology services provider with over 30 years of experience supporting the wealth, banking and asset management industries.

Serving more than 250 financial institutions across 15+ countries, Objectway provides end-to-end technology solutions and services that help financial institutions modernize their operations, improve efficiency, and deliver exceptional client experiences.

In January 2024, Nest Wealth joined the Objectway Group, strengthening our Canadian presence and expanding our ability to deliver comprehensive wealth management solutions across the entire value chain.

As we continue to grow our presence in Canada, we are looking for a senior business development professional who can help establish Objectway as a trusted strategic partner to Canada’s leading banks, wealth managers and financial institutions.

The Opportunity:

We are seeking a well-connected and entrepreneurial Director, Strategic Business Development & Enterprise Sales to lead our enterprise growth efforts in Canada.

This is a unique opportunity for someone who combines deep knowledge of the Canadian financial services and wealth management industry with an established network of executive relationships and a proven ability to originate and close complex enterprise opportunities.

Unlike traditional product-led sales roles, this position requires a consultative, solution-oriented approach. Our clients are large, sophisticated financial institutions with complex business challenges. We are looking for someone who can understand those challenges, identify opportunities for transformation, and position Objectway’s integrated technology and services capabilities to deliver meaningful business outcomes.

Lead our enterprise efforts in Canada using significant autonomy while leveraging the expertise and resources of our global team.

The ideal candidate is comfortable engaging C-suite executives in strategic conversations, and personally driving opportunities from initial discovery through to signed commercial agreements.

What You’ll Do

1. Enterprise Business Development & Sales

• Own and execute the Canadian enterprise business development strategy, with accountability for pipeline development, new client acquisition and revenue growth.

• Identify, originate and close complex enterprise opportunities with Tier 1 banks, wealth management firms, asset managers and other large financial institutions.

• Lead the full enterprise sales cycle, including prospecting, discovery, solution development, proposals, commercial negotiations and contract execution.

• Develop strategic account and territory plans that prioritize high-value opportunities and long-term revenue potential.

• Build and maintain a qualified sales pipeline, ensuring disciplined opportunity management, forecasting and reporting.

• Manage complex sales cycles by engaging and aligning stakeholders across business, technical, operational, procurement, and executive teams.

1. Consultative & Solution-Based Selling

• Engage prospective clients to understand their business strategies, operational challenges, technology environments, and transformation priorities.

• Lead discovery conversations that uncover underlying business needs rather than focusing on individual product features.

• Position Objectway as a strategic technology and services partner, leveraging our end-to-end wealth management capabilities to develop tailored client solutions.

• Collaborate with our global subject‑matter experts to translate client requirements into commercially viable solutions.

• Develop compelling business cases and value propositions that demonstrate measurable outcomes, including operational efficiency, scalability, cost optimization, and business growth.

• Build credibility as a trusted advisor capable of connecting complex business challenges with practical, long‑term solutions.

1. Executive Relationships & Strategic Partnerships

• Leverage an established network of senior executives and decision‑makers across Canadian banking, wealth management, asset management and financial services.

• Build and maintain trusted relationships with CEOs, COOs, CIOs, CTOs, Heads of Wealth Management and other senior business and technology leaders.

• Open doors to strategic conversations and identify opportunities that may not emerge through traditional sales channels.

• Develop relationships with consulting firms, technology partners and other industry stakeholders to expand Objectway’s market presence.

• Represent Objectway at executive meetings, industry forums, conferences and strategic networking events.

• Establish long‑term partnerships that support client retention, account expansion, and sustainable commercial growth.

1. Canadian Market Development & Commercial Strategy

• Serve as Objectway’s primary business development representative in Canada, taking ownership of local enterprise activities and market development.

• Develop a strong understanding of the competitive landscape, emerging industry trends, and evolving client needs.

• Identify opportunities for Objectway to expand its presence within Canada’s enterprise wealth management and financial services ecosystem.

• Partner with Canadian and global leadership to align market opportunities with Objectway’s broader enterprise strategy.

• Provide market intelligence, insights and recommendations to inform product positioning, service development, and strategic investment.

• Balance strategic relationship development with the hands‑on execution required to generate and close business.

1. Global Collaboration & Client Engagement

• Act as the bridge between Canadian clients and Objectway’s global technology, product and delivery teams.

• Coordinate internal resources to support client discovery, solution development, proposals, and commercial negotiations.

• Ensure proposed solutions are aligned with Objectway’s capabilities, delivery commitments, and commercial objectives.

• Facilitate effective handoffs to Implementation, Delivery and Customer Success teams while maintaining strategic client relationships.

• Work collaboratively across a global, matrixed organization to deliver a consistent and high‑quality client experience.

What You’ll Bring

Required Experience & Qualifications

• An established and active network of senior executive relationships within Canadian banks, wealth management firms and large financial institutions.

• Significant experience in enterprise business development, consultative solution selling, strategic account management or financial services technology consulting, ideally 10–15+ years.

• Deep knowledge of the Canadian banking, wealth management and asset management industries, including business models, operating challenges and technology transformation priorities.

• Demonstrated success originating, presenting, developing, negotiating and closing complex, high‑value enterprise opportunities.

• Experience selling integrated technology solutions, professional services, consulting engagements or technology‑enabled business transformation.

• Proven ability to lead needs‑based discovery, develop tailored commercial solutions and articulate measurable business value.

• Experience navigating complex enterprise buying processes and building consensus across multiple stakeholders.

• Strong commercial acumen, negotiation skills and experience managing enterprise sales pipelines and revenue forecasts.

• Ability to operate independently, build a market from the ground up and balance strategic thinking with hands‑on execution.

It would be GREAT if you had:

• Established relationships with consulting firms, system integrators and strategic partners serving Canadian financial institutions.

• Experience working with or selling to Tier 1 Canadian banks and major wealth management institutions.

• Background in financial services consulting, wealth technology, digital transformation or enterprise technology services.

• Understanding of wealth management platforms, investment operations, portfolio management, financial planning and related technology ecosystems.

• Experience working within a global fintech, professional services or enterprise technology organization.

What Success Looks Like

Success in this role will be measured through a combination of commercial results, strategic relationships, and market development.

Enterprise Revenue Growth

• Originate and close new enterprise business opportunities.

• Achieve agreed revenue and new client acquisition targets.

• Progress qualified opportunities through complex enterprise sales cycles.

Strategic Relationships & Market Penetration

• Establish meaningful relationships with senior decision‑makers across priority Canadian financial institutions.

• Generate qualified opportunities through executive relationships, referrals, and strategic partnerships.

• Increase Objectway’s visibility and credibility within the Canadian wealth management market.

Pipeline Development & Commercial Execution

• Build and maintain a healthy, qualified enterprise sales pipeline.

• Develop and execute strategic account plans for priority institutions.

• Demonstrate disciplined opportunity management, forecasting and deal progression.

Consultative Selling & Client Value

• Identify complex client challenges and translate them into commercially viable solutions.

• Develop compelling business cases that connect Objectway’s capabilities to measurable client outcomes.

• Establish long‑term client relationships that support continued growth and expansion.

$180,000 - $200,000 a year, base salary + performance-based variable compensation

What you can expect in the interview process:

30 min “get to know you” interview withthetalent team

60 min “meet the hiring manager” interview

60 min “leadership interview” with decision makers

Accommodation Statement:

Objectway is an equal opportunity employer committed to inclusive, barrier‑free selection processes and work environments. We will accommodate any applicant under the Accessibility for Ontarians with Disabilities Act (AODA) and the Ontario Human Rights Code. If you require accommodation during any part of the hiring process, please let us know so that we can work with you to meet your needs.

Equality Policy:

We are an equal opportunities employer, and we welcome applications from all suitably skilled or qualified applicants, regardless of their race, sex, disability, religion/beliefs, sexual orientation or age.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.