Sales Director Jobs in Chicago, IL
Sales Director jobs in Chicago are concentrated in the Loop, River North, and Fulton Market, with strong demand from technology, financial services, healthcare, and B2B services firms. Employers hiring right now include Epsilon, EY, and JPMorganChase. Scan the live roles below and apply to whichever ones fit.
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- Own accountability for the total commercial volume required to fully load the repair network, measured by cars inducted, shop days sold, and capacity utilization by shop and region.
- Develop and execute the commercial strategy for AITX’s railcar repair business in alignment with the growth and profitability objectives of the Repair business and the enterprise.
- Establish annual and long-term repair commercial objectives, including volume commitments by shop and region, revenue and margin targets, customer growth priorities, market development opportunities, and strategic account plans.
- Identify opportunities to expand AITX’s repair business through new customers, additional service offerings, geographic opportunities, and increased share of existing customer spend.
- Develop and maintain strong relationships with key customer decision-makers and senior stakeholders, serving as a strategic commercial partner and trusted resource.
- Lead commercial strategy for significant customer opportunities, RFPs, proposals, contract discussions, and other major pursuits.
- Share joint accountability with Repair Operations leadership for network loading and capacity fill, including redirecting demand toward underutilized shops, closing gaps between booked volume and available capacity, and aligning the commercial mix with operational capability and profitability expectations.
- Develop a strong understanding of customer fleet strategies, repair requirements, business objectives, and emerging needs to identify opportunities for AITX to provide differentiated solutions.
- Monitor railcar repair market conditions, customer trends, competitive activity, regulatory developments, and other factors that may influence demand or commercial strategy.
- Develop market and competitive intelligence to inform business development priorities, pricing decisions, customer strategies, and investment opportunities.
- Establish and maintain a disciplined sales pipeline and forecasting process, providing visibility into opportunities, expected revenue, customer activity, and potential risks.
- Evaluate sales performance and market results against established objectives and recommend adjustments to commercial strategy as needed.
- Collaborate with Repair Operations, Account Management, Finance, and Marketing to develop coordinated customer strategies and ensure effective execution of commercial commitments.
- Partner with the lease fleet Sales team to capture repair and maintenance volume from AITX’s owned and managed fleet, coordinating program work, compliance and requalification cycles, and lease return and turnaround activity to support network loading.
- Develop compelling customer presentations, proposals, value propositions, and commercial solutions that clearly differentiate AITX’s repair capabilities.
- Own pricing strategy and lead commercial negotiations, with accountability for margin performance across the repair portfolio and for balancing rate against volume and shop utilization.
- Identify strategic customer or market issues and work cross-functionally to develop solutions that strengthen customer relationships and support long-term growth.
- Represent AITX at relevant industry events, customer meetings, conferences, and other forums to strengthen market presence and develop new business opportunities.
- Where direct reports are assigned, lead, develop, and hold accountable the repair commercial team, including hiring, goal setting, territory and account coverage, performance management, and succession planning; where they are not, drive coverage and activity through influence across Repair account management, field sales, and shop-level commercial resources.
- Promote commercial discipline, accountability, collaboration, and continuous improvement across the repair sales process.
- Provide regular reporting and analysis regarding sales performance, pipeline activity, market conditions, customer trends, competitive developments, and progress against strategic objectives.
- Perform other duties as assigned.
- Bachelor’s degree in Business, Marketing, Engineering, Transportation, or a related field preferred; equivalent combination of education and relevant industry experience will be considered.
- 10+ years of progressive commercial, sales, or business development experience within the railcar, tank car, rail transportation, or repair services industry; prior experience leading a commercial or sales team preferred.
- Demonstrated experience developing and executing sales or commercial strategies that deliver measurable revenue and profitable growth.
- Experience leading and developing a commercial or sales team — including goal setting, quota or target assignment, performance management, and talent development — preferred; demonstrated ability to lead and drive accountability through influence required.
- Strong knowledge of the railcar repair market, including customer requirements, competitive dynamics, repair services, and industry trends.
- Demonstrated ability to build and maintain relationships with senior-level customer stakeholders and influence complex commercial decisions.
- Experience leading significant customer pursuits, proposals, RFPs, negotiations, and commercial agreements.
- Demonstrated accountability for volume, throughput, or capacity utilization in an operations-intensive services business — not revenue alone.
- Strong business and financial acumen with the ability to evaluate opportunities based on revenue potential, profitability, operational feasibility, and strategic value.
- Ability to translate market intelligence, customer needs, and business data into actionable commercial strategies.
- Demonstrated ability to work effectively across Sales, Operations, Finance, Account Management, and other functional areas.
- Excellent communication, negotiation, presentation, and executive-level relationship management skills.
- Strong analytical skills with experience using sales forecasting, pipeline management, market analysis, and performance metrics to support decision-making.
- Ability to think strategically while maintaining accountability for execution and measurable business results.
This is a general description of the Duties, Responsibilities and Qualifications required for this position. Physical, mental, sensory, or environmental demands may be referenced to communicate the way this position traditionally is performed. Whenever necessary to provide individuals with disabilities an equal employment opportunity, AITX will consider reasonable accommodations that might involve varying job requirements and/or changing the way this job is performed, provided that such accommodations do not pose an undue hardship.
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Who's Hiring



Top Industries Hiring
- Technology & Software15
- Consulting & Professional Services11
- Banking & Financial Services6
- Investment & Asset Management6
- Fintech4
Sales Director Jobs in Chicago: Frequently Asked Questions
How do I get a sales director job in Chicago?
Focus your search on Chicago's strongest hiring pockets: enterprise software and SaaS firms in the Loop and Fulton Market, financial services companies in the West Loop, and healthcare and med-tech employers anchored along the Magnificent Mile and in the suburbs. Candidates who combine a proven quota-carrying background with familiarity in one of those verticals move fastest. Networking through local industry associations and Chicago-area alumni groups also opens doors that cold applications rarely do.
Which companies hire sales directors in Chicago?
Employers hiring sales directors in Chicago right now include Epsilon, EY, and JPMorganChase, based on current listings on Migrate Mate as of September 2026. Chicago's mix of global headquarters, regional offices of Fortune 500 firms, and a dense mid-market SaaS scene means the hiring base is broad, covering both enterprise accounts and high-growth startups.
Are there remote sales director jobs in Chicago?
Yes, though sales director roles tied to territory management or in-person client relationships are less commonly fully remote. About 62% of sales director openings tied to Chicago are remote or hybrid as of September 2026, reflecting employer flexibility on strategic and inside-sales leadership positions. Roles focused on national accounts or SaaS renewals tend to offer the most remote flexibility among Chicago-based postings.
How can I get a sales director job in Chicago with little or no experience?
The most realistic entry path in Chicago is moving up from a senior account executive or regional sales manager role at one of the city's mid-market SaaS, fintech, or distribution companies, where director-track promotions happen on defined timelines. Employers in Chicago's manufacturing and logistics sectors also promote from within more consistently than tech firms do. Building a track of closed enterprise deals, even at a lower title, and earning visibility through a Chicago-area sales leadership peer group accelerates the transition considerably.
Which industries hire the most sales directors in Chicago?
The sectors hiring the most sales directors in Chicago are Technology & Software, Consulting & Professional Services, and Banking & Financial Services, based on current listings on Migrate Mate as of September 2026. Chicago's role as a headquarters city for financial services, a growing SaaS hub in Fulton Market, and a major logistics and distribution center means those sectors consistently generate the highest volume of director-level sales openings locally.
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