Job Information
OSM Worldwide Sales Development Representative - Midwest in Chicago, Illinois
Launch Your Career in Sales with OSM:
Are you motivated, energetic, and ready to break into sales? OSM is looking for a Sales Development Representative (SDR) to help grow our customer base by introducing small and mid ‑ sized businesses to our package delivery solutions.
This is an entry ‑ level, hunter ‑ style sales role—perfect for someone who enjoys building relationships, thrives on outbound outreach, and wants hands ‑ on experience developing real sales skills in the field.
What You’ll Do:
As a SDR, you’ll focus on generating new business opportunities within an assigned geographic territory. We are looking for an SDR to be located within the Chicagoland area and will be assigned the mid-west territory.
Proactively reaching out to prospective customers through phone calls, emails, and in ‑ person visits.
Identifying and qualifying businesses that can benefit from OSM’s delivery solutions.
Following a structured sales process to open and close new customer accounts.
Meeting or exceeding activity goals and lead generation targets.
Researching prospects to identify decision ‑ makers and tailor outreach.
Managing prospect activity and interactions in Salesforce.
Overcoming common objections and clearly communicating our value proposition.
Partnering with sales leadership to refine messaging and territory strategies.
Handing off larger or more complex accounts to senior sales team members when appropriate.
What We’re Looking For
You don’t need decades of experience—we’re looking for drive, coachability, and hustle.
Required:
Bachelor's degree or equivalent experience.
Valid driver's license and ability to travel within territory.
Strong communication skills.
Preferred:
Previous sales, customer service, or outbound calling experience.
Familiarity with logistics, shipping, or supply chain.
Thrives in competitive environments with a track record of working toward measurable goals.
Motivated by metrics, coaching, and continuous improvement.
What We Offer:
Paid 6-week sales training program.
Comprehensive health benefits: medical, dental, and vision.
Employer-paid short-term disability and life insurance.
Immediate access to paid time off and holidays.
401(k) with 4–7% employer contribution and profit sharing.
Gym reimbursement.
Our Culture:
OSM is a dynamic, high-growth organization specializing in B2C eCommerce small parcel mail sortation. We’re a performance-driven organization that values initiative, collaboration, and integrity. Our team thrives on solving complex challenges, supporting one another, and celebrating wins — big and small. If you’re passionate about growth and making a measurable impact, you’ll fit right in.
Base salary of $48K with on-target earnings of $78K. This is a remote position with travel, as needed, locally to support customer growth.
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