[Hiring] Sales Development Representative @Windward Software Systems Inc.

Role Description

We are looking for an Intermediate Sales Development Representative (SDR) to help drive new customer growth for our business management software solutions. This role focuses on identifying, engaging, and qualifying prospective customers, while working closely with Marketing and Business Development to support the full sales cycle.

We are looking for someone who is skilled at engaging in quality sales and prospecting conversations, modern prospecting techniques, and thoughtful qualification, supported by the effective use of technology and AI enabled tools.

Qualifications

• 2–3 years of experience in a B2B SDR, BDR, or similar sales development role
• Experience working with SMB or mid‑market prospects and customers
• Strong communication, discovery, and qualification skills
• Comfort using AI‑enabled sales tools to support research, outreach, and follow‑up
• Experience using a CRM system (HubSpot, Salesforce, or similar)

Requirements

• Identify and engage prospective customers within defined industries and ideal customer profiles, including prospecting list development and hygiene
• Execute targeted outbound outreach using phone, email, LinkedIn, and modern sales tools
• Leverage AI‑assisted tools to research accounts, personalize messaging, and prioritize outreach
• Respond within established service levels to inbound inquiries and marketing‑generated leads
• Conduct discovery conversations to understand prospect needs, challenges, and existing systems
• Identify decision‑makers, buying processes, and timelines
• Use AI‑supported insights (e.g., call summaries, account research, messaging optimization) to improve discovery quality
• Qualify or disqualify opportunities based on fit, readiness, and long‑term value alignment
• Schedule qualified discovery or demo meetings with a Senior Business Developer
• Provide thorough and accurate handoff notes, including business context, pain points, and stakeholders
• Collaborate with sales and marketing leadership to continuously refine targeting, messaging, and qualification standards
• Maintain accurate CRM records for all activities, conversations, and lead status
• Use AI‑enabled CRM features responsibly to improve efficiency, data quality, and follow‑through
• Follow defined sales development and qualification processes

Benefits

• Consistently generating high‑quality, sales‑ready opportunities
• Strong alignment with the sales and marketing teams on opportunity quality
• Professional, consultative conversations with prospective customers
• Effective and ethical use of AI to enhance productivity and buyer experience
• Accurate CRM records and reliable follow‑through