Sales Jobs in Chicago

Freelance Sales Director Global Technology Staffing & Remote Workforce

Location: Chicago, Illinois, United States.

Experience: 8+ Years

People Prime is a global talent solutions company specializing in helping organizations build high-performing technology teams through Remote hiring, Staff augmentation, and Offshore delivery models.

Headquartered in India, People Prime connects companies worldwide with highly skilled technology professionals across emerging and advanced digital domains. We enable organizations to scale faster by providing access to a curated network of experienced engineers, AI specialists, data professionals, and technology consultants who can work remotely or as part of distributed global teams.

People Prime focuses on enabling companies to hire high-quality remote technology talent from India, one of the world’s largest and fastest-growing technology talent markets. Through our strong recruitment ecosystem and technical screening process, we provide organizations with access to professionals across a wide range of digital and enterprise technologies.

1. Artificial Intelligence & Machine Learning: Machine Learning Engineers: Generative AI Engineers: Prompt Engineers: Natural Language Processing (NLP) Specialists: Computer Vision Engineers: AI Model Training & Fine-Tuning Experts
2. Data Engineering & Analytics: Data Engineers, Data Architects: Data Scientists: Big Data Specialists, Data Platform Engineers: Analytics & BI Professionals
3. Cloud & DevOps: Cloud Architects (AWS, Azure, GCP): DevOps Engineers: Platform Engineers, Kubernetes Specialists: Infrastructure Automation Experts
4. Software Engineering: Full Stack Developers: Backend Engineers: Frontend Engineers: Mobile Application Developers: Microservices & API Developers
5. Enterprise Platforms: SAP Consultants: Salesforce Experts: ServiceNow Professionals: ERP & Digital Transformation Specialists

Key Responsibilities:

• Identify and acquire new clients seeking technology staffing or remote engineering teams

• Generate opportunities for contract staffing, staff augmentation, and distributed engineering teams

• Develop relationships with technology companies, startups, and enterprise clients

• Present People Prime’s global talent and offshore delivery capabilities

• Build and manage a strong pipeline of staffing opportunities

• Collaborate with delivery and recruitment teams in India to fulfill client requirements

• Negotiate client contracts, rate cards, and service agreements

• Track hiring trends in AI, data engineering, cloud, and software development

Required Qualifications:

• 8+ years’ experience in IT staffing business development or recruitment sales

• Proven track record of generating staffing opportunities and closing new clients

• Strong network within technology companies, startups, or enterprise organizations

• Experience selling staff augmentation or contract staffing services

• Excellent communication, negotiation, and relationship management skills

Preferred Experience:

• Experience selling offshore technology talent or remote engineering teams

• Exposure to hiring in AI, data engineering, cloud, or software development domains

• Understanding of distributed workforce and remote hiring models

Success Metrics:

Success in this role will be measured by:

• New client acquisitions

• Remote staffing requirements generated

• Revenue from staffing engagements

• Successful onboarding of consultants

• Client retention and satisfaction

Performance expectation:

Minimum 4 Contract placements per month

Compensation:

USD 1500 Payable on Every AI/ Technology Contractor Successful onboarding ( Minimum 5 Onboards Expected Every Month )

6% of gross margin for the first 6 months of each engagement

Why Join People Prime:

• Sell high-demand global technology talent solutions

• Work with a scalable offshore delivery model with great cost advantage to clients

• High earning potential with strong commission structure

• Exposure to fast-growing sectors such as AI, cloud, and data engineering

• Opportunity to build long-term partnerships with global technology companies.

With 10+ years of proven sales and expansion success, Elevation has consistently helped national brands increase revenue while developing the next generation of leaders.

Currently, we are hiring an Entry Level Sales Representative to join the team. This person will get hands-on training in our sales department and learn daily sales operations. Once proficient in sales, our Entry Level Sales Representatives start learning additional business systems and operations to build their leadership capabilities. 

Some of our most successful Sales Representatives come from various backgrounds and walks of life. We are an equal-opportunity employer actively seeking the kind of employee who works hard, has fun, and enjoys working with people. We do not work remotely so if you’re the kind of person who has been itching for that human connection, this is the place for you! You don’t need any experience in this role due to our training curriculum but you do need a great “go-get-em” attitude and work ethic. 

Initial Entry Level Sales Representative Responsibilities:

Our mission is to build a business for individuals who want to grow their careers and change their lives, while helping major corporations increase revenue through sales done with integrity.

• Engage with customers, in-person, and present sales solutions
• Manage given sales territory
• Generate sales among customer accounts
• Work with the team on sales goals and business development needs

Basic Qualifications for the Entry Level Sales Representative Role

• A Degree is preferred but not required
• Strong desire to self-develop, grow, and learn
• Good communication and interpersonal skills
• Confidence 
• Leadership
• Teamwork
• Systematic
• Reliable transportation (this position is based in Chicago and is not remote)

Work Perks:

With over a decade of success, national rankings, and consistent expansion, Elevation offers something rare: real opportunity paired with real support.

• Advancement Opportunities - we are growing with our clients and we are looking for someone to grow with us!
• Competitive compensation plan ranging from $5 depending on commissions
• Medical benefits
• Hands-on training & positioning techniques that will help you succeed anywhere!
• We are excited to provide growth and coaching for not only our clients but also our team!
• Positive light-hearted company culture!

If you’re motivated, coachable, competitive, and ready to bet on yourself,we want to meet you.

Whether you’re starting your career or looking for your next challenge, Elevation is a place where effort turns into opportunity.

The Aspen Group (TAG) is one of the largest and most trusted retail healthcare business support organizations in the U.S. and has supported over 20,000 healthcare professionals and team members with close to 1,500 health and wellness offices across 48 states in four distinct categories: dental care, urgent care, medical aesthetics, and animal health. Working in partnership with independent practice owners and clinicians, the team is united by a single purpose: to prove that healthcare can be better and smarter for everyone. TAG provides a comprehensive suite of centralized business support services that power the impact of five consumer-facing businesses: Aspen Dental, ClearChoice Dental Implant Centers, WellNow Urgent Care, Chapter Aesthetic Studio, and Lovet Pet Health Care. Each brand has access to a deep community of experts, tools and resources to grow their practices, and an unwavering commitment to delivering high-quality consumer healthcare experiences at scale.

ClearChoice Dental Implant Centers are a national network of dental implant centers founded in 2005 to provide innovative dental implant care to patients across the United States. ClearChoice has experienced strong growth over the years and today is a leader in the United States in providing dental implant treatments. Driven by a collective desire to improve the lives of prospective patients, ClearChoice helps people reclaim their health, smile and confidence. Beyond restoring teeth, this is about people getting their lives back. ClearChoice Management Services, LLC (CCMS) provides administrative practice management services to the ClearChoice network.

ClearChoice provides administrative practice management services to the ClearChoice network. When you join ClearChoice, you are joining a team of individuals with passion, conviction, and integrity whose mission is to be the Platform of Hope for those in need of our services.

As part of the Clinical Affairs team, you will take on a highly visible role that supports the clinical excellence and innovation of the entire organization. Your passion, creativity, and grit are supported by a robust team of experienced clinicians and strategists that are integral in writing the next chapter of our story.

About the Role:

In this newly created role, the Clinical & Development, Director will be focused on the scoping, development and implementation of new and existing programs, processes and systems, and other initiatives identified by Clinical Affairs and executive leadership teams. This role requires operating at a tactical, strategic, and operational level. The Clinical & Development Director will serve as an integrator connecting different work streams that would otherwise remain siloed. In partnership with Clinical Affairs leadership, this role is a key communicator linking the Clinical Affairs team and the broader organization. In this role, you will leverage your strategy and operations experience to ensure doctors, centers and field teams receive the support needed to successfully meet the demands of a highly dynamic industry. The Clinical & Development Director is part of a team that drives clinical excellence, value creation, growth, and optimization. Success in the role will require excellent listening, planning, assessment and communication skills, with an ability to identify gaps, recognize opportunities, and drive performance accountability.

Essential Responsibilities:

• Partner with Clinical Affairs, doctors, executive leadership, corporate strategy, field leaders and center managers to support the development of deployment approaches for key strategic clinical initiatives
• Identify gaps, constraints, and or roadblocks to adoption and integration of new initiatives; develop interventions at the center, region, division, and network level
• Mobilize internal resources (operations, strategy, field, sales, marketing, legal and compliance, IT) to overcome challenges, ensuring doctors, centers and field teams have support and training needed to fully adopt new treatments, systems, and processes
• Partner with field leadership to hold centers and field teams accountable to achieving adoption and implementation targets
• Liaise with doctors, field teams, operations teams, strategy, analytics, and finance; serve as a lynchpin among these teams to support prioritization of interventions and support
• Identify opportunities for improvement and optimization of key initiatives; recommend pilots, testing, and roadmaps to achieve optimization and performance enhancements of key strategic initiatives; Create compelling business cases for expansion of new programs and processes
• Identify, codify, and disseminate best practices
• Support administration of clinical programs

Key Competencies

• Planning and project management: Must have a keen attention to detail and be methodical in realistic planning and holding oneself and partners accountable to implementation plans.
• Team-Orientation: Must be able to work cross functionally across the organization and partner with key stakeholders for the right input in order to mobilize resources and effectively work towards solutions.
• Communication: Must be able to communicate effectively across all levels of the organization and to key stakeholders, including verbal, written, and presentation skills.
• Listening / observation: Must be able to observe behaviors and conduct gap analysis to identify opportunities for support.
• Resilience: Must remain engaged and effective in pursuit of objectives with or without immediate success, using both positive and negative outcomes as an incentive to move forward fulfilling personal and team goals.
• Creativity: Must be able to develop innovative solutions that meet the needs of our doctors and the business. He/she must be a strategic thinker, adaptable, and solution oriented.

Requirements/Qualifications:

• Bachelor’s Degree required; MBA preferred.
• 8+ years of progressive strategy and/or operations management experience in distributed multi-site services, preferably in premium healthcare, consumer/retail facing industries.
• Experience in clinical or doctor relationship management.
• Demonstrated success partnering in a matrixed environment to implement strategic initiatives within a distributed environment.
• Excellent professional written, verbal communication, and interpersonal skills. Strong presentation skills. Ability to communicate and interact with diverse constituencies and motivate teams.
• Strong analytical and business reporting skills.
• Hungry, humble, high emotional IQ, aspirational mindset.
• Mission/purpose-driven organization experience.
• The ability to conduct up to 25% domestic travel.

Additional Details:

• Base Pay Range if based in Chicago: $175,000 - $195,000, plus 25% annual bonus (Actual pay may vary based on experience, performance, and qualifications.)
• The position is based in Chicago, IL, with an expectation of 4 days per week in-office and 1 day remote. Candidates located outside the 35-mile radius of Chicago may still be considered on a case-by-case basis.
• A generous benefits package that includes paid time off, health, dental, vision, and 401(k) savings plan with match.
• If you are an applicant residing in California, please view our privacy policy here:

Primary Report: Executive Vice President

Job Summary

Riverside Investment & Development is seeking a full-time Vice President–level Asset Manager based in Chicago. This role will primarily focus on office buildings, with potential exposure to multifamily and mixed-use properties.

Key Responsibilities

The Asset Manager will support the Executive Vice President and select capital partners in all aspects of asset management, acquisitions, dispositions, financial decision-making, cash flow modeling, leasing strategy, investment analysis, negotiations, and legal documentation.

Responsibilities

• Develop and implement asset-level strategic plans
• Establish leasing objectives and guidelines; provide oversight of revenue management systems and strategies; manage the leasing process as needed for mixed-use assets and prepare recommendations for ownership
• Oversee property-level operating activities, including supervision of leasing agents and third-party property managers
• Direct the preparation of monthly reporting, quarterly valuations, and cash flow forecasts
• Review and evaluate prospective lease proposals
• Collaborate with and guide property managers in developing operating budgets, including capital and leasing plans
• Manage the internal process for obtaining Investment Committee approval for key decisions
• Participate in broader management team strategic initiatives at each property
• Manage recapitalization efforts and/or oversee the disposition process when assets are prepared for sale
• Oversee property-level financings and reporting with joint venture partners and lenders
• Lead weekly and monthly asset management meetings
• Monitor market trends and data, including investment sales, lease comparables, and occupancy levels
• Lead the preparation of quarterly asset management reports for ownership at the property level
• Review financial reports to monitor performance and ensure investment objectives are achieved
• Lead ownership and client presentations
• Manage loan requirements and covenants, including leasing conditions, future funding obligations, escrow reimbursements, and other lender requirements
• Review existing leases to analyze and determine renewal strategies or potential modifications
• Monitor, manage, and coordinate RIDC internal teams (construction management, leasing, and financial analysis)
• Perform special projects and additional responsibilities as assigned

Qualifications

• 8–12 years of commercial or investment real estate experience with asset management
• Strong office market experience required, with multifamily or retail knowledge considered a plus
• Excellent written and verbal communication skills
• Self-starter with strong analytical, quantitative, and problem-solving abilities
• Strong interpersonal skills with the ability to interact effectively with both internal and external stakeholders
• Demonstrated ability to lead, manage, and motivate junior staff, leasing teams, and analysts
• Ability to work effectively under pressure while managing multiple competing deadlines
• Experience with asset repositioning strategies

Skills

• Advanced proficiency in reviewing and analyzing financial models in Excel and Argus
• Strong organizational skills and attention to detail, with the ability to manage multiple projects simultaneously
• Experience negotiating leases and real estate legal documentation
• Strong sense of initiative, accountability, and entrepreneurial mindset
• Ability to work independently and collaboratively in a fast-paced environment
• In-depth knowledge of the Downtown Chicago office market; experience in other markets is a plus

Third Coast Roofing is an established solar energy company expanding into the residential and commercial roofing space. We’re building a dedicated roofing division from the ground up — and we’re looking for a driven sales leader to take ownership of that growth. This isn’t a corporate middle-management seat. This is a ground-floor opportunity with a clear path to equity and long-term ownership.

We’re hiring a Sales Manager to launch and scale our roofing division. You’ll come in as the lead salesperson, close deals using company-provided leads, and build out a full sales team as the division grows. You’ll have the resources of an established company behind you — including marketing support, lead generation, and operational infrastructure — with the upside of an entrepreneurial role.

After 12 to 24 months of proven performance, you’ll have the opportunity to earn an ownership stake in the roofing division. We want someone who thinks like an owner from day one — because that’s exactly where this is headed.

• Take ownership of the roofing sales pipeline from day one, working company-provided leads and door-to-door canvassing to close residential and commercial roofing projects
• Develop and execute a sales strategy to grow the roofing division’s revenue month over month
• Recruit, hire, train, and manage a sales team as volume increases
• Conduct in-home and on-site consultations, perform inspections, and present proposals to homeowners and property managers
• Build relationships with referral partners, insurance adjusters, and real estate professionals
• Track all activity, pipeline data, and KPIs using CRM tools
• Collaborate with operations, project management, and marketing to ensure a seamless customer experience
• Knock doors in targeted neighborhoods and storm-affected areas to generate additional pipeline
• Represent Third Coast Roofing with professionalism and integrity in the field and in the community
  

• 3+ years of sales experience in roofing, construction, home improvement, or a related field
• Proven ability to close deals and hit revenue targets
• Experience building or managing a sales team (or a strong desire and readiness to do so)
• Strong knowledge of residential and/or commercial roofing systems, materials, and installation processes
• Familiarity with insurance restoration and storm damage claims is a plus
• Excellent communication and presentation skills
• Comfortable with door-to-door sales and direct outreach in the field
• Self-starter mentality — you don’t wait to be told what to do
• Valid driver’s license and reliable transportation
  

• Competitive base salary plus uncapped commission on closed deals
• Company-generated leads plus door knocking opportunities — the company invests in lead generation so you’re not doing it all on your own
• Marketing and operational support from an established company
• CRM and technology tools to manage your pipeline
• Clear path to equity and ownership in the roofing division within 12 to 24 months
• The chance to build something from the ground up with real long-term upside
  

This role is built for someone who has been selling roofing (or a similar product) and is ready for the next step — not just another sales job, but a real stake in a growing business. If you’ve ever wanted to run your own roofing company but didn’t want to take on all the risk alone, this is your shot. You bring the sales ability and the hustle. We bring the brand, the leads, and the infrastructure.

Submit your resume and a brief note about why this opportunity fits where you’re headed. We’re not looking for a cover letter template — just tell us what drives you and what you’ve built so far.

The Trade Sales Manager is responsible for leading a team of professional sales consultants who are effective at building the Pella brand within the trade industry. Achieve group sales goals through coaching and developing team member skills in relational selling techniques throughout all active Pella product offerings. Model market expertise and business partner relationships with customers. Grow market share through continually reinforcing proactive development of new customer relationships. Coach and develop value selling and accuracy skills to deliver contribution margin goals and error control needed to ensure profitability. Develop team commitment to continually strive for 100% “Very Satisfied” customers.

The Trade Sales Manager’s (TSM) primary duty is developing an effective sales team. The TSM is required to spend over 50% of their time each workweek in the field with sales consultants observing and coaching effective sales skills.

What Pella has to offer:

• Unlimited mileage reimbursement
• Medical, dental, vision benefits
• 401k with company match
• 20 paid vacation days
• 9 paid holidays
• Sick and personal leave paid days
• Company paid short- and long-term disability insurance
• Company paid life insurance
• Employee assistance program
• Employee discount

This position offers a total target compensation range of $140,000 to $177,000 annually. This includes a base salary plus an uncapped target sales incentive bonus. Actual compensation within this range will depend on skills, experience, and performance.

Responsibilities/Accountabilities:

• Achieving team sales and customer satisfaction goals and objectives.
• Growing market share through sales consultant networking, lead and referral generation.
• Achieving team profitability goals through building value and strategic discounting with error-rate control.
• Assisting sales consultants with acquiring new customers and securing initial sales opportunities.
• Developing sales consultants’ ability to engage customers in consultative sales interactions, overcoming objections and reinforcing their techniques to closing the sale during all customer interactions.
• Recruiting, selecting, onboarding, and retaining high performing sales consultants with HR support.
• Partnering with sales consultants to represent Pella at company sponsored events, professional group’s invitations to discuss and/or present Pella products, trade association meetings and/or builder home shows.
• Developing sales consultants to maintain exceptional level of expertise of products/services relating to Pella’s customers and their ability to advise customers on manufacturer installation guidelines and field measure openings to ensure accuracy of product applications.
• Ensuring sales consultants’ quotes and orders accurately follow the Trade Selling Process.
• Driving customer retention and satisfaction by encouraging sales consultants to act as their customers’ central point of contact with Pella, and follow up with existing and potential clients as needed; i.e. send hand written thank-you cards to customers as a proactive measure of customer engagement.
• Encouraging independent decision making while striving for first-time resolution on all client problems/issues. Responding to escalated client concerns with sales consultant’s involvement.
• Evaluating performance and providing appropriate coaching and training as necessary.
• Leveraging customer database tools to develop sales consultants’ ability to manage all customer interactions.
• Fostering a cooperative team environment conducive to the sharing of best practices pertaining to sales challenges and competitive market information.
• Collaborating with Service/Operations teams to ensure successful after sales service requirements and installations.
• Interacting with Accounts Receivable department to address any potential billing/payment issues of customers.
• Assisting Sales GM with developing marketing tactics and events.
• Assisting in the development of annual budgets and monthly forecasts.
• Developing presentations to communicate progress to a variety of Pella audiences.
• Working variable, non-traditional hours making themselves available for sales consultants and customers during evenings and weekends.

Skills/Knowledge

• Coach sales consultants to:
• Meet and engage with prospective customers and demonstrate insight selling techniques
• Provide superb customer service and generate referrals through existing customers
• Develop partnerships with other business that serve the same customers
• Create a sense of trust and reliability with internal team and customers
• Skilled at relating to a variety of customers- balances poise and integrity with a service mentality
• Works collaboratively with Pella team members and customers
• Thrives on working in a fast-paced environment with a high sense of urgency and responsiveness to internal and external customer needs
• Demonstrates strong problem-solving skills and work ethic
• Demonstrates confidence balanced with humility
• Ability to persevere through sales challenges and setbacks
• Ability to motivate and persuade others in order to influence change and shift paradigms
• Seeks out internal experts and utilizes their knowledge
• Able to accurately read, interpret and take-off blueprints
• Exercises independent decision making; working well without close supervision but always keeping their manager informed
• Focused on details and follow through
• Proficiency with Microsoft Office and smart devices, and ability to learn internal software programs and applications

Qualifications

To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

Education and/or Experience

Bachelor’s degree (B. A.) from four year college or university; or three to five years related experience and/or training, or equivalent combination of education and experience. Individual’s motor vehicle record must also comply with company requirements. Must have the ability to manage multiple-tasks in an environment of constant interruptions and be able to prioritize responsibilities.

Language and Communication Skills

Ability to read and analyze documents related to contracts and work documents. Ability to write reports and business correspondence. Ability to verbally present information and respond to questions from customers, managers, and the general public.

Professional Skills

Must present a clean and neat physical appearance and strictly abide by company dress code serving as a role model for other employees, customer and visitors.

Reasoning Abilities

Ability to solve practical and arithmetic problems and deal with a variety of concrete variables in situations where only limited standardization exists.

Physical Demands

While performing the duties of this job, the employee is regularly required to drive an automobile, stand; walk; sit; use hands to finger, handle, or feel; reach with hands and arms; and talk or hear. The employee is occasionally required to climb or balance; stoop, kneel, crouch, or crawl. The employee must regularly lift and/or move up to 10 pounds and frequently lift and/or move up to 25 pounds, and occasionally lift and/or move up to 50 pounds using proper lifting techniques. Specific vision abilities required by this job include close vision, distance vision, color vision, and ability to adjust focus. The noise level in the work environment varies between low to moderate in administrative offices and to moderate on constructions sites.

Travel

The vast majority of travel will be local. Must be able to drive to showrooms, job sites and customer/contractor locations and required company functions at various locations.