Job Description
Job Title: Field Sales Representative
Pay Rate: $63.86/hr on W2
Location: Remote Chicago, IL Field-Based
Contract Length: 6 Months
Potential: Contract extension or conversion to FTE based on performance, attendance, and business needs
Work Schedule: Monday Thursday Field Work | Friday Administrative/Desk Work
Local Travel: Primarily within approximately 100 miles of the assigned market
Job Summary
Pay Rate: $63.86/hr on W2
Location: Remote Chicago, IL Field-Based
Contract Length: 6 Months
Potential: Contract extension or conversion to FTE based on performance, attendance, and business needs
Work Schedule: Monday Thursday Field Work | Friday Administrative/Desk Work
Local Travel: Primarily within approximately 100 miles of the assigned market
Job Summary
- Block is seeking a Field Sales Representative City Launch & Merchant Success to drive merchant adoption, education, engagement, and long-term success for the Neighborhoods program across launch markets.
- This is a field-based position where you will spend the majority of your time meeting merchants face-to-face. You will visit restaurants and local businesses, build relationships with business owners and staff, support program launches, conduct merchant training, and participate in community events.
- You will serve as the face of Neighborhoods in the Chicago market and act as a key connection between local merchants and Block's Product, Operations, and Go-to-Market teams.
- Build trusted, long-term relationships with local merchants and business owners.
- Spend the majority of your time in the field visiting restaurants and other local businesses.
- Support merchants throughout the launch process, from pre-launch preparation through activation and post-launch follow-up.
- Provide hands-on support and live transaction walkthroughs for owners, managers, and frontline employees.
- Conduct merchant onboarding, training sessions, workshops, and educational events.
- Organize and support community events, office hours, and other merchant engagement activities.
- Monitor merchant adoption, engagement, and retention and proactively address challenges.
- Gather merchant feedback and identify operational issues or opportunities for improvement.
- Partner with Product, Operations, and Go-to-Market teams to support successful city launches and market expansion.
- Work closely with Account Managers, where applicable, to provide an exceptional merchant experience.
- Troubleshoot issues, remove obstacles, and take ownership of merchant concerns.
- Develop repeatable training materials, playbooks, and community engagement strategies that can be used in future markets.
- Serve as the voice of the merchant by bringing valuable field insights back to internal teams.
- 5 7+ years of experience in merchant success, hospitality, field operations, community management, training, account management, retail, restaurant operations, sales, or another customer-facing environment.
- Strong interpersonal and relationship-building skills.
- Comfortable meeting new people and establishing authentic relationships quickly.
- Comfortable walking into local businesses and engaging directly with owners, managers, and staff.
- Experience conducting customer training, workshops, presentations, or educational sessions.
- Strong communication, organization, and follow-through skills.
- Ability to work independently and take initiative in a fast-paced environment.
- Strong problem-solving skills and the ability to remove obstacles quickly.
- Ability to balance strategic thinking with hands-on execution.
- Comfortable spending the majority of the workweek in the field.
- Willingness and ability to travel locally, generally within approximately 100 miles of the assigned market.
- Passion for supporting local and independent businesses.
- Ability to build relationships and represent the company professionally in the local business community.
- Associate's or Bachelor's degree preferred, and/or
- 5+ years of relevant professional experience.
- #TMCA
Numbers & Facts
| Location | Chicago, IL (Remote) |
| Industry | Staffing/Employment Agencies |
| Salary | $63.86 Per Hour |
| Company Size | 1,000 to 1,499 employees |
| Year Founded | 1968 |
| Website | https://www.tailoredmanagement.com/ |
About Company
CONNECTING TOP TALENT WITH TOP-TIER OPPORTUNITIES
Tailored Management is a global staffing firm that specializes in partnering with large organizations that run their contingent labor program in a VMS/MSP environment. We have the unique capacity to support programs across all scopes and geographic locations from a single headquarters, successfully elevating program performance across the board and minimizing costs, miscommunication and delivery times. But what do we really do? We bring together the best talent with the greatest opportunities.
Skills
- Communication Skillsunmatched
- Community Supportunmatched
- Customer Relationsunmatched
- Customer Trainingunmatched
- Field Salesunmatched
- Follow Throughunmatched
- Identify Issuesunmatched
- Interpersonal Skillsunmatched
- Onboardingunmatched
- Operations Managementunmatched
- Problem Solving Skillsunmatched
- Restaurantunmatched
- Retail Operationsunmatched
- Salesunmatched
- Sales Managementunmatched
- Training/Teachingunmatched
- Willing to Travelunmatched
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