Talent Harbor · 5 days ago
Outside Sales Representative - Chicago, IL
Greater Chicago Area
Full-time
Onsite
Entry, Mid Level
$65K/yr - $200K/yr
2+ years expTalent Harbor is expanding in the Chicago market and is seeking an Outside Sales Representative to build a territory from the ground up. The role involves proactive prospecting, managing the full sales cycle, and building long-term client relationships with SMB owners.
Hiring Manager
Javier Andres Mendez Barrero
Responsibilities
Proactively prospect SMBs through cold calling, in-person visits, and local networking
Run consultative discovery meetings with founders and decision-makers
Own the full sales cycle from first contact to signed agreement (3–4 week cycle)
Generate referrals and build long-term client relationships
Represent the company at trade associations and local business events
Maintain accurate pipeline and forecasting in HubSpot
Partner internally to deliver high-quality remote talent solutions
Qualification
Required
2+ years of B2B sales experience (outside / territory sales strongly preferred)
Documented history of hitting or exceeding quota
Experience building a book of business from scratch
High activity level (cold calls, visits, follow-ups, networking)
Strong consultative and closing skills
Excellent communication and executive presence
Preferred
HubSpot or similar CRM
SMB-focused selling background
Experience in construction, home services, logistics, or professional services
Benefits
Monthly health insurance stipend
401(k) with company match
Client entertainment budget + mileage reimbursement
Company
Talent Harbor
Talent optimization and leadership placement for businesses powered by EOS®. Hiring the Right Person. For the Right Seat. Guaranteed.
11-50 employees
Funding
Current Stage
Early StageCompany data provided by crunchbase