Senior Business Development Manager

Financial Software Solutions | Full-Time | Remote

Player-Coach Sales Leadership Role

Our client is an established technology provider serving Bermuda’s international and local financial services community. They are seeking a Senior Business Development Manager 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 guide and mentor 1-2 other sales professionals.

If you are a hands-on player-coach who thrives in a high-trust, entrepreneurial setting 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 coaching of a small team.

What You’ll Be Doing

- Drive new business opportunities and revenue growth within Bermuda’s financial services, FP&A;, insurance, reinsurance, and related sectors
- Coach and mentor 1-2 junior 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
- Build trusted relationships with senior decision-makers across finance, operations, technology, and executive leadership teams
- Conduct product demonstrations and solution presentations
- Lead regular pipeline review meetings and sales planning sessions




- Monitor sales performance and 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

- 10+ years of proven success in B2B software sales, ideally within financial technology, SaaS, ERP, FP&A;, consulting, or professional services
- Experience managing, mentoring, or informally leading a small business development or sales team
- Demonstrated ability to consistently achieve or exceed revenue targets
- Strong business development, relationship-building, and negotiation skills
- Excellent communication and presentation abilities
- 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 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

- Competitive base salary
- Attractive performance-based commission plan
- Total earnings potential of approximately USD $165,000+, including base salary and performance-based commission
- Additional growth opportunities as the business expands

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.

📌 Senior Business Development Manager (Ottawa)
🏢 Squires Resources
📍 Ottawa