Contract Jobs in Chicago, IL

5,894 open positions · Updated daily

Looking for Contract jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Contract position in the Chicago, IL area.

Field Sales Representative – Hiring Immediately

Company: Lee Company

Location: Oak Lawn, IL

Posted Nov 20, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling sales reps to focus on selling. The company offers competitive compensation including draw against commission, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Sales reps are expected to prospect, qualify, and close new sales, manage territories, inspect properties for damage, and build relationships with homeowners. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and CRM experience.

Outside Sales Rep Now Hiring

Company: Lee Company

Location: Oak Lawn, IL

Posted Nov 20, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling sales reps to focus on selling. The company offers competitive compensation including draw against commission, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Sales reps are expected to prospect, qualify, and close new sales, manage territories, inspect properties for damage, and build relationships with homeowners. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and CRM experience.

Direct Hire Consultant (HC)

Company: Addison Group

Location: Chicago, IL

Posted Nov 20, 2024

Addison Group, a rapidly growing private staffing firm, is seeking a Direct Hire Recruiter. The role involves prospecting candidates and clients, researching business deals, scheduling interviews and meetings, developing relationships, negotiating deals, and representing the company professionally. The ideal candidate should have a four-year degree, strong communication skills, ability to thrive in a fast-paced environment, and a competitive spirit. Benefits include customizable healthcare, 401(k) with matching, flexible PTO, weekly pay with uncapped commissions, and more. Addison Group values a fun learning environment and offers comprehensive training and development programs.

Outside Sales Reps Hiring Immediately

Company: Lee Company

Location: Crestwood, IL

Posted Nov 20, 2024

AmeriPro Roofing is hiring Outside Sales Representatives in the South and Southwest Chicagoland areas. They provide fully staffed departments for every stage of the job process, giving representatives more time to focus on sales. The company offers competitive compensation, benefits, and opportunities for growth and advancement.

Outside Sales Reps Hiring Immediately

Company: Lee Company

Location: Joliet, IL

Posted Nov 20, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling representatives to focus on sales. The company offers competitive compensation including draw advancement, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Responsibilities include prospecting, qualifying, and closing sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and CRM experience.

Roofing Sales Hiring Now Training Provided

Company: Lee Company

Location: Aurora, IL

Posted Nov 20, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. The company stands out due to its fully staffed departments, allowing reps more time for sales. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Outside Sales Rep Now Hiring

Company: Lee Company

Location: Joliet, IL

Posted Nov 20, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling representatives to focus on sales. The company offers competitive compensation including draw advancement, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Responsibilities include prospecting, qualifying, and closing sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and CRM experience.

Outside Sales Rep Now Hiring

Company: Lee Company

Location: Romeoville, IL

Posted Nov 20, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling sales reps to focus on selling. The company offers competitive compensation including draw against commission, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Sales reps are expected to prospect, qualify, and close new sales, manage territories, inspect properties for damage, and build relationships with homeowners. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and CRM experience.

Outside Sales Rep Now Hiring

Company: Lee Company

Location: Orland Park, IL

Posted Nov 20, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling sales reps to focus on selling. The company offers competitive compensation including draw against commission, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Sales reps are expected to prospect, qualify, and close new sales, manage territories, inspect properties for damage, and build relationships with homeowners. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and CRM experience.

Field Sales Representative - $60k - $200k Compensation

Company: Lee Company

Location: Downers Grove, IL

Posted Nov 20, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. The company stands out due to its fully staffed departments, allowing sales reps more time for tasks. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with a 4% employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing new sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Outside Sales Representative

Company: Lee Company

Location: Aurora, IL

Posted Nov 20, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in West Chicagoland. These representatives will educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. The company stands out due to its fully staffed departments, allowing reps more time for sales. Compensation includes a draw against commission, commission on approved sales, a vehicle allowance, quarterly bonuses, full insurance benefits, a 401K with employer match, and a training & development program. Responsibilities involve prospecting, qualifying, and closing sales, managing territories, inspecting properties for damage, and building customer relationships. Qualifications include 2+ years of full-cycle sales experience, a reliable vehicle, excellent communication skills, and CRM experience.

Field Sales Representative - Hiring Now

Company: Lee Company

Location: Tinley Park, IL

Posted Nov 20, 2024

AmeriPro Roofing, a leading residential roofing contractor, is hiring Outside Sales Representatives in South and Southwest Chicagoland areas. These representatives educate homeowners about storm damage entitlements for roofing, siding, and gutter projects. AmeriPro Roofing stands out due to its fully staffed departments, enabling sales reps to focus on selling. The company offers competitive compensation including draw against commission, commission on approved sales, vehicle allowance, quarterly bonuses, full insurance benefits, and a 401K with employer match. Sales reps are expected to prospect, qualify, and close new sales, manage territories, inspect properties for damage, and build relationships with homeowners. Qualifications include 2+ years of sales experience, reliable vehicle, strong communication skills, and a valid driver's license.

Frequently Asked Questions

What are the typical hourly or weekly rates for contract tech roles at different seniority levels?
Entry‑level contractors earn $30–$50 per hour, mid‑level $50–$80, senior‑level $80–$120, specialist roles such as AI/ML or security typically $100–$150, and lead or architect positions can exceed $150 per hour. Regional cost of living and the specific technology stack also influence these ranges.
What skills and certifications are most sought after for contract tech positions?
High‑demand skills include cloud platform expertise (AWS Certified Solutions Architect, Azure Solutions Architect, GCP Professional Cloud Architect), Kubernetes & Helm, Terraform, CI/CD tools like Jenkins or GitLab CI, security certifications such as CISSP or CompTIA Security+, data engineering tools (Snowflake, BigQuery), programming languages (Python, Go, TypeScript), and Agile or Scrum facilitation. Demonstrated project experience on similar stacks is often required.
Can contract tech roles be performed remotely, and what is the typical remote work policy?
Approximately 80–90% of contract tech positions are fully remote, with clients providing VPN access and collaboration tools. Some contracts may require occasional on‑site visits for client meetings or data‑center access, but most clients emphasize a remote‑first workflow and enforce compliance with local data‑residency laws.
How can contractors advance their careers while staying in contract work?
Contractors can build a strong portfolio, specialize in high‑paying stacks, pursue advanced certifications, and secure retainer or multi‑project contracts. Continuous learning keeps rates high, and many contractors transition into permanent roles with the same clients or move into consulting, contract management, or specialized advisory positions.
What current industry trends are influencing the demand for contract tech talent?
Digital transformation, cloud migration, AI/ML adoption, cybersecurity needs, remote‑first culture, microservices architecture, edge computing, and the rise of platform‑as‑a‑service (PaaS) are driving companies to hire contractors for rapid experimentation, scaling, and expertise that is too scarce for full‑time positions.

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