Our client is an established technology provider 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. 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, we would welcome a confidential conversation.

This role is best suited to someone who can operate independently, build trusted relationships with senior financial services decision-makers, and balance personal revenue production with day-to-day management of a small team.

What You’ll Be Doing

• Drive new business opportunities and revenue growth within Bermuda and 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.
• Coordinate product demonstrations and solution presentations.
• Monitor sales performance and regularly review pipeline activity against established targets.
• Collaborate with leadership on sales strategy, forecasting, and market opportunities.
• Develop and manage marketing strategies that support lead generation, market positioning and revenue growth.
• Serve as a role model by maintaining a strong personal sales performance.

What We’re Looking For

• 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.
• Small, agile, entrepreneurial culture.
• 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. Apply in confidence for immediate consideration.

Last update: September 1, 2026