Sales Development Representative

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

📋 Description

• Identify companies that are currently hiring for positions that Wing can support, including Executive Assistants, Administrative Assistants, Customer Support, Sales Support, Recruiting Support, Operations Support, and various other business support roles.

• Conduct research on target accounts to gain insights into their hiring needs, the reasons they may require assistance, and how Wing could be a suitable solution.

• Engage with potential customers through email, phone, LinkedIn, and other outbound communication channels.

• Execute targeted outbound campaigns focusing on hiring signals, job postings, company growth, and operational challenges.

• Conduct initial discovery discussions to comprehend the prospect's hiring requirements, challenges, urgency, and willingness to consider remote talent or AI-enhanced workforce solutions.

• Clearly articulate the services provided by Wing Assistant and their significance to secure follow-up meetings.

• Schedule qualified appointments for Account Executives with organizations that exhibit a clear need, relevant hiring activities, or a compelling use case for Wing.

• Collaborate closely with Account Executives to cultivate and sustain a healthy, well-qualified pipeline.

• Effectively transition opportunities, providing AEs with the necessary context to advance deals.

• Relay essential information from discovery calls, including the positions the company is hiring for, their current hiring process, challenges, timelines, budget indicators, and involved decision-makers.

• Maintain accurate and up-to-date activity logs, notes, and pipeline information in our CRM system.

• Relay insights gathered from prospects to the Sales, Marketing, and Product teams.

• Assist in refining messaging and outreach strategies based on what resonates with companies.

• Identify trends in hiring demand, objections, and sectors where Wing is gaining traction.

• Propose new outbound strategies based on job postings, hiring trends, and conversations with prospects.

⛳️ Requirements

• 1–4+ years of experience in sales, business development, appointment setting, cold calling, recruiting, staffing, or a similar outbound role.

• A genuine interest in B2B sales; additional points for experience in SaaS, AI, staffing, recruiting, outsourcing, or global workforce operations.

• Demonstrated experience in sales prospecting, cold calling, appointment setting, or high-volume outbound outreach.

• Excellent written and verbal communication skills; able to convey messages concisely and persuasively.

• Comfort in reaching out to companies that may not have previously considered remote assistants, virtual assistants, or offshore talent.

• Strong research capabilities and the aptitude to transform hiring signals into relevant outbound messaging.

• Exceptional organizational skills and the perseverance to continue despite challenges.

• A strong motivation driven by clear goals, activity metrics, and booked meeting targets.

• Ability to manage your own desk while effectively collaborating with team members.

• A sincere eagerness to quickly learn about the product, industry, and sales techniques.

🏝️ Benefits

• Compensation, Bonus, and Commission

• In addition to base salary, this position offers performance-based incentives linked to qualified meetings, sales outcomes, and weekly activity objectives.

• Appointment and Deal Bonuses

• Receive a bonus for every qualified meeting that attends.

• Earn an additional bonus when a qualified meeting converts into a closed customer.

• This structure rewards SDRs not only for booking activity but also for generating genuine opportunities that progress through the sales cycle.

• Weekly Competitions

• We conduct weekly competitions to foster a competitive spirit, motivation, and focus on the right activity metrics within the team.

• These incentives are tailored for SDRs who thrive on targets, enjoy competition, and seek direct rewards from their efforts.