Director of Business Development

Job summary

Drive new business and revenue growth across financial services, insurance, reinsurance, and related sectors in Bermuda and the English-speaking Caribbean while personally managing the full sales cycle. Coach a small sales team, develop account and territory strategies, manage vendor and partner relationships, and collaborate with leadership on forecasting, marketing, and sales strategy.

Job details

Director of Business Development- Financial Software Solutions | Full-Time | Remote 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 alsocoaching 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. Frank Squires - frank@squiresresources.com

What you’ll do

Drive new business and revenue growth across financial services, insurance, reinsurance, and related sectors in Bermuda and the English-speaking Caribbean while personally managing the full sales cycle. Coach a small sales team, develop account and territory strategies, manage vendor and partner relationships, and collaborate with leadership on forecasting, marketing, and sales strategy.

Requirements

Requires 10+ years of successful B2B software sales experience, a record of meeting or exceeding revenue targets, and experience leading or mentoring a small sales team. Candidates should be skilled in pricing and margin negotiations, software and services commercial arrangements, and vendor collaboration; financial services or insurance sales experience and Sage Intacct or Workiva experience are strong advantages.

Listed skills

• Full-Cycle Sales · Preferred
• Account Management · Preferred
• Business development · Preferred

Other relevant skills

Identified from the job description. Confirm important requirements above.

• B2B Software Sales
• Business Development
• Revenue Growth
• Sales Team Coaching
• Sales Team Mentoring
• Full-Cycle Sales
• Account Management
• Territory Strategy
• Pipeline Management
• Sales Forecasting
• Pricing Negotiation
• Margin Management
• Vendor Relationship Management
• Partner Relationship Management
• Marketing Strategy
• Financial Services Sales

Job areas

• Sales
• Management & Leadership
• Technology
• Finance & Accounting
• Marketing