Head of Sales - AI-Powered Maritime Compliance SaaS

About the Role

Kaiko Systems is seeking a Head of Sales to join our fast-growing team in the maritime compliance SaaS sector. As a Head of Sales, you will play a crucial role in driving new business acquisition and sales execution for our AI-powered vessel inspection and compliance tools. This position is fully remote, allowing you to work from anywhere while leading a team of account executives and sales development representatives (SDRs). You will report directly to the COO and be responsible for managing the entire sales pipeline.

What You'll Do

• Own the full new business pipeline from qualified opportunity to signed contract.
• Execute a structured sales process based on MEDDPICC qualification, ensuring no passenger deals and no wishful forecasting.
• Lead, coach, and develop a team of account executives and SDRs, listening to calls, resolving issues quickly, and maintaining high standards.
• Deliver accurate weekly forecasts to the COO, ensuring you know where every deal stands and why.
• Position and sell our complete platform, understanding all six modules and coaching your team to do the same.

Requirements

• 5+ years in B2B SaaS sales, with at least 2 years managing a team.
• Strong MEDDPICC or equivalent qualification discipline; this is non-negotiable.
• Proven track record of hitting and exceeding ARR targets in a mid-market or enterprise environment.
• Direct and honest communication style.
• Comfortable selling a technical product into a conservative, relationship-driven industry.
• Experience in the maritime or industrial sector is a bonus, but not required.

What We Offer

• Competitive base salary plus uncapped commission tied to new ARR closed.
• Equity options available.
• Flexible remote work environment.
• Opportunity to lead and develop a high-performing sales team.
• Engaging and dynamic work culture focused on innovation and growth.