Sales Development Representative

Medium; San Jose (CA); On-site; USD 11,160 - 20,088; Full time

Benefits offered by this job

Performance-based bonuses

Weekly competitions

Growth opportunities

Job summary

Medium is looking for a Sales Development Representative in San Jose, California. In this role, you’ll be the first point of contact for potential customers, driving outreach to companies that need assistance with roles like Executive Assistants and Customer Support.

This position offers a competitive, energetic environment for someone eager to grow in their sales career. Your responsibilities will include sending outreach campaigns, booking qualified meetings for our Account Executives, and providing valuable feedback on hiring trends.

Qualifications

• 1–4 years of experience in sales or comparable outbound role.
• Interest in B2B sales, preferably in SaaS or AI.
• Proven track record in cold calling and appointment setting.

Responsibilities

• Identify and reach out to companies hiring for roles we support.
• Book qualified meetings for Account Executives.
• Conduct discovery conversations to understand prospects' needs.

Skills

Sales prospecting

Cold calling

Appointment setting

Listening skills

Written communication

Research skills

Tools

CRM tools

Job description

Wing Assistant is building the next generation of AI-enabled workforce solutions for growing businesses, and our growth depends on a steady flow of qualified sales opportunities. We're hiring a Sales Development Representative to be the tip of that spear: the first person prospective customers meet and the engine that keeps our pipeline full.

This is a high-energy, high-ownership seat for someone early in their sales career who wants to learn the craft fast and grow into bigger things. You'll identify companies that are actively hiring for roles Wing can support, reach out with a compelling alternative to traditional hiring, and book qualified meetings for our Account Executives.

It's a great fit for someone who's competitive, well-organized, motivated by clear targets, and genuinely curious about how AI, remote talent, and global workforce solutions are changing the way companies build teams.

What You'll Do

Generate and Qualify Pipeline

• Identify companies actively hiring for roles Wing can service, such as Executive Assistants, Admin Assistants, Customer Support, Sales Support, Recruiting Support, Operations Support, and other business support roles.
• Research target accounts to understand what they are hiring for, why they may need support, and where Wing could be a strong fit.
• Reach out to prospective customers across email, phone, LinkedIn, and other outbound channels.
• Run focused outbound campaigns around hiring signals, job postings, company growth, and operational pain points.
• Hold early discovery conversations to understand the prospect's hiring needs, pain points, urgency, and openness to remote talent or AI-enabled workforce solutions.
• Communicate what Wing Assistant does and why it matters clearly enough to earn the next meeting.
• Book qualified appointments for Account Executives with companies that have a clear need, relevant hiring activity, or a strong use case for Wing.

Partner with the Sales Team

• Work hand-in-hand with Account Executives to build and protect a healthy, well-qualified pipeline.
• Hand off opportunities cleanly, with the context AEs need to move deals forward.
• Share key details from discovery calls, including the role the company is hiring for, current hiring process, pain points, timing, budget signals, and decision-makers involved.
• Keep activity, notes, and pipeline data accurate and current in our CRM.

Bring the Market Back In

• Feed what you're hearing from prospects back to the Sales, Marketing, and Product teams.
• Help refine messaging and outreach based on what's actually landing with companies.
• Identify patterns in hiring demand, objections, and industries where Wing is resonating.
• Suggest new outbound angles based on job postings, hiring trends, and prospect conversations.

What We're Looking For

Core Requirements

• 1–4+ years in sales, business development, appointment setting, cold calling, recruiting, staffing, or a comparable outbound role.
• A real interest in B2B sales; bonus points if it's in SaaS, AI, staffing, recruiting, outsourcing, or global workforce operations.
• Proven background in sales prospecting, cold calling, appointment setting, or high-volume outbound outreach.
• Strong written and verbal communication; you can get to the point and make it compelling.
• Comfort reaching out to companies that may not have considered remote assistants, virtual assistants, or offshore talent before.
• Strong research skills and the ability to turn hiring signals into relevant outbound messaging.
• Strong organization and the resilience to keep going when a day doesn't go your way.
• The drive that comes from chasing clear goals, activity metrics, and booked meeting targets.
• The ability to run your own desk while still collaborating well across teams.
• A genuine eagerness to learn the product, the industry, and the sales craft quickly.

Nice to Have

• Exposure to staffing companies, recruiting firms, BPOs, outsourcing companies, virtual assistant companies, digital agent companies, or high-ticket professional services organizations.
• Familiarity with CRM and sales engagement tools such as HubSpot, Salesforce, Outreach, Salesloft, Apollo, Instantly, Clay, Close, or LinkedIn Sales Navigator.
• Familiarity with auto dialers, power dialers, cold calling workflows, and high-volume outbound systems.
• Experience prospecting into founders, executives, operations leaders, HR leaders, recruiting teams, customer support leaders, or sales leaders.
• Awareness of business support workflows such as executive assistance, admin support, sales support, customer support, recruiting coordination, inbox/calendar management, and back-office operations.

$1,000 - $1,800 a month

Compensation, Bonus, and Commission

In addition to base compensation, this role includes performance-based incentives tied to qualified meetings, sales outcomes, and weekly activity targets.

Appointment and Deal Bonuses

• Earn a bonus for every qualified meeting that shows up.
• Earn an additional bonus when a qualified meeting turns into a closed customer.

This means SDRs are rewarded not just for booking activity, but for creating real opportunities that move through the sales process.

Weekly Competitions

We also run weekly competitions to keep the team competitive, motivated, and focused on the right activity metrics.

These incentives are designed for SDRs who are driven by targets, enjoy competition, and want direct upside from their effort.