Remote Second Jobs in Romeo, MI (NOW HIRING)

At Wing, we give growing businesses access to the top tier of global remote talent supercharged by AI so they can scale without scaling headcount. From sales and support to operations and admin, Wing turns the recurring work that bogs teams down into reliable, AI-powered capacity that drives real output.

Trusted by 1000’s businesses and powered by a global talent pool and our proprietary Wing AI platform, we help startups, SMBs, and enterprises move faster and do more with less.

Our growth is fueled by hiring exceptional people, holding them to high standards, and giving them room to make an impact. If you’re hungry for growth and ready to get to work, you won’t find a better place to learn and accelerate your career.

What You’ll Do

• Prospect, educate, and qualify leads to create sales-ready opportunities and serve as the first point of contact for prospects evaluating Wing.
• Run high-volume, multi-channel outbound (calls, email, LinkedIn, events) and make strategic outbound touches daily to build pipeline and exceed meeting and SQL targets.
• Tailor outreach to each prospect’s goals and business model; master the Wing story and articulate our value in offloading repetitive work, scaling teams affordably, and increasing capacity and revenue.
• Partner with Account Executives to schedule calls, meetings, and demos, and ensure smooth handoffs that convert into opportunities and closed-won deals.
• Conduct discovery to qualify fit, pain, and timing; map stakeholders across Operations, Marketing, and Executive teams.
• Acquire key prospect data from the initial conversation, the web, and other sources; keep clean, accurate, up-to-date records in the CRM.
• Proactively stay current on the AI, staffing, and outsourcing landscape, and share market feedback with Sales, Marketing, and Product to sharpen messaging and cadences.
• Achieve or exceed monthly quotas of qualified appointments, scheduled demos, and pipeline generated.

What You’ll Bring

• 6 months–2 years of outbound sales experience (SDR, BDR, D2D, inside sales, or similar). (Adjust up to 1–3 years for a more senior bar.)
• Confidence on the phone and in writing you can articulate value whether it’s a 30-second cold call or a personalized email.
• A reliable home/remote work setup and the self-discipline to run a high-volume desk without an office around you.
• Comfort with high volume; you can run 50+ touches a day without sacrificing quality.
• CRM discipline: clean data, updated stages, notes your AEs can actually use.
• Strong work ethic, competitiveness with yourself, and an eagerness to learn you track your numbers, know your conversion rates, and treat every “no” as a signal about messaging, timing, or targeting.
• Nice to have: experience selling AI, SaaS, or staffing/BPO/outsourced services.

Benefits

• Salary 40k to 50k/year  + On-Target Earnings (~20k to uncapped)
• Health Insurance
• Flexible PTO plus holidays
• Fully remote work
• Company-wide virtual and/or in-person off-sites
• All core tools and software provided

Logistics

• Fully remote. Pacific Time/ Eastern Time
• 4-year degree preferred but not required.

Why You’ll Love Working Here

Wing is one of the best places to:

• Join the leaders in AI-powered remote work
• Unlock career-defining growth on a fast-scaling team
• Build alongside world-class talent, fully remote
• Make a real, measurable impact on the businesses we serve