Director of Business Development

Our client is an established technology provider (ERP, FP&A, financial and regulatory reporting,) serving Bermuda's international and local financial services community. They are seeking a Director of Business Development to remotely drive revenue growth across enterprise and local accounts, while also coaching a small sales team in a hands-on player-coach capacity.

This is an ideal opportunity for a proven software sales professional who enjoys opening new accounts, deepening client relationships, and taking on meaningful leadership responsibility without stepping away from the sales process. Ideally based in the Eastern or Atlantic time zone, you will continue to carry a personal sales mandate while helping manage and mentor 1-2 other sales professionals. If you are a hands-on, player-coach who thrives in a high-trust, entrepreneurial environment and wants to help grow a specialized financial software business.

What You'll Be Doing

• Drive new business opportunities and revenue growth primarily within Bermuda but including the English-speaking Caribbean's financial services, insurance, reinsurance, and related sectors.
• Coach and mentor 1-2 sales professionals through regular deal review, pipeline discipline, and practical business development guidance.
• Develop and execute account and territory growth strategies.
• Manage the full sales cycle from prospecting through contract negotiation and close.
• Manage target margins and profitability requirements.
• Manage vendor and partner relationships.
• Build trusted relationships with senior decision-makers across finance, operations, technology, and executive leadership teams.
• Monitor sales performance and regularly review pipeline activity against established targets.
• Collaborate with leadership on sales strategy, forecasting, and market opportunities.
• Serve as a role model by maintaining a strong personal sales performance.

What We're Looking For

• Approximately 10+ years of proven success in B2B software sales, ideally within financial technology, SaaS, ERP, FP&A, consulting, or professional services. Demonstrated ability to consistently achieve or exceed revenue targets. Experience selling Sage Intacct and/or Workiva would be a significant advantage.
• Experience managing, mentoring, or leading a small business development or sales team.
• Experience with pricing negotiation ensuring target margins and profitability requirements.
• Experience managing the commercial implications of software licensing, professional services, managed services and third-party solutions.
• Experience maintaining strong relationships & working collaboratively with vendor account teams, leveraging vendor programs and staying current on vendor products, pricing, incentives, certifications and go-to-market strategies.
• Self-motivated and comfortable working remotely from Canada, with the flexibility for occasional visits to Bermuda.
• Experience selling into insurance, financial services, or reinsurance organizations would be considered a strong asset.

Why This Opportunity?

• Fully remote position based in Canada, ideally in the Eastern or Atlantic time zones.
• Opportunity to work with a highly respected niche software provider.
• Direct impact on company growth and strategy.
• Leadership responsibility while continuing to own and close meaningful sales opportunities.
• Significant autonomy and flexibility.
• Opportunity to grow into broader leadership responsibilities as the business expands.

Compensation

Total earnings potential of approximately CAD $200,000 (paid in USD) including base salary and performance-based commission.

This is a unique opportunity to combine personal sales success with leadership impact, while helping shape the growth of a specialized software business serving one of the world's premier financial services markets.