Sales Development Representative

This is a fully remote position, open to applicants in Massachusetts.

📋 Description

• Identify, educate, and qualify leads to generate sales-ready opportunities, serving as the initial point of contact for prospects considering Wing.

• Execute high-volume, multi-channel outbound strategies (calls, emails, LinkedIn, events) while making strategic daily outreach to build a robust pipeline and surpass meeting and SQL targets.

• Customize outreach according to each prospect’s objectives and business model; become proficient in the Wing narrative and convey our value in alleviating repetitive tasks, scaling teams cost-effectively, and enhancing capacity and revenue.

• Collaborate with Account Executives to arrange calls, meetings, and demos, ensuring seamless transitions that result in opportunities and successful deals.

• Conduct discovery sessions to assess fit, pain points, and timing; identify stakeholders within Operations, Marketing, and Executive teams.

• Gather essential prospect information from initial conversations, online research, and other sources; maintain clean, accurate, and up-to-date records in the CRM system.

• Stay informed about the AI, staffing, and outsourcing landscape, providing market insights to Sales, Marketing, and Product teams to enhance messaging and outreach strategies.

• Meet or surpass monthly targets for qualified appointments, scheduled demos, and generated pipeline.

⛳️ Requirements

• 6 months to 2 years of outbound sales experience (SDR, BDR, D2D, inside sales, or related roles). *(Adjustable to 1–3 years for a higher seniority level.)*

• Confidence in phone and written communication, able to articulate value effectively, whether in a 30-second cold call or a tailored email.

• A dependable home/remote work setup and the self-discipline necessary to manage a high-volume desk without an office environment.

• Comfortable with high volume; capable of executing 50+ touches daily without compromising quality.

• CRM proficiency: maintain clean data, updated stages, and notes that are useful for your AEs.

• Strong work ethic, self-competitiveness, and a desire to learn; you track your metrics, understand your conversion rates, and view every “no” as feedback on messaging, timing, or targeting.

• Nice to have: experience in selling AI, SaaS, or staffing/BPO/outsourced services.

🏝️ Benefits

• Fully remote work

• Career-defining growth

• Collaborate with world-class talent

• Create a real, measurable impact

• Access to a top tier of global remote talent