Sales Development Representative

Windward.ai is a global leader in maritime risk analytics, helping organizations make smarter, faster decisions by turning complex maritime data into clear, actionable insights. Our predictive insights support large, globally distributed teams in managing risk, protecting margins, and maintaining operational control across complex maritime supply chains and trade networks.

We are looking for a Sales Development Representative (SDR) to drive early-stage pipeline generation across large commercial enterprises worldwide. This role sits at the front of the enterprise revenue engine and is critical to building a qualified pipeline through strong discovery, precise value articulation, and confident live conversations with senior decision-makers.

This is an opportunity for an entrepreneurial, growth-minded professional with a passion for high-tech solutions to make a meaningful impact within complex, global enterprise environments.

What you’ll do

• Source and qualify opportunities across enterprise commercial maritime organizations
• Research large accounts, business units, and senior stakeholders to drive relevant, account-aware outreach
• Conduct outbound prospecting via email, phone, and LinkedIn
• Initiate and manage first conversations with prospects, focusing on enterprise-level pain discovery and qualification, primarily through calls
• Clearly communicate Windward’s value in the context of enterprise-scale operations, risk exposure, and decision complexity
• Confidently handle objections and guide conversations toward next steps
• Qualify opportunities before handing off to the sales team
• Use AI tools to prepare call talking points, research complex accounts, and continuously improve performance
• Maintain accurate CRM data and provide clear visibility into pipeline activity

Requirements

• Experience as an SDR in B2B SaaS contributing to enterprise pipeline generation
• Native-level English with strong written and verbal communication skills
• Additional languages are a plus
• Confidence speaking with senior enterprise stakeholders across different cultures and regions
• Experience working with large commercial, maritime, energy, trade, insurance, law firms or financial enterprises is a major plus
• Curiosity about risk, compliance, and operational decision-making in large, multi-layered organizations
• Leverage AI to improve research and outbound messaging

What success looks like

• High-quality enterprise meetings that convert into real pipeline
• Strong call performance and effective objection handling at senior levels
• Clear understanding of enterprise buyers, buying committees, and sales motions
• Strong alignment and trust with the sales team
• Consistently meet or exceed defined KPIs, including meetings booked, pipeline generated, and conversion rates