Head Of Sales Jobs in Chicago, IL
Head Of Sales jobs in Chicago are in strong demand, concentrated in the Loop, River North, and Fulton Market across fintech, SaaS, healthcare technology, and B2B services. Employers hiring right now include SentiLink, Northern Trust, and Google. Scan the live roles below and apply to whichever ones fit.
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The Head of Sales is responsible for driving revenue growth by developing and executing strategic sales initiatives, managing customer relationships, and expanding client portfolio. Reporting to the President, this role leads the sales process from prospecting through contract execution while collaborating with operations to ensure successful service delivery and long-term customer satisfaction. The Head of Sales is accountable for achieving sales targets, identifying new business opportunities, and representing the company's values and commitment to exceptional service
Essential Job Responsibilities:
Develop and execute strategic sales plans to achieve revenue and growth objectives.
Recruit, train, and oversee sales personnel, currently one direct report with growth to up to four as the team reaches full staffing.
Identify, prospect, and secure new commercial real estate and facility management clients through networking, referrals, cold outreach, and industry events.
Build and maintain strong relationships with prospective and existing customers to identify opportunities for additional services and long-term partnerships.
Manage the full sales cycle, including lead generation, needs assessments, proposal development, presentations, contract negotiations, and closing.
Collaborate with operations and leadership to develop customized service solutions that meet customer needs while supporting company profitability.
Collaborate with the operations team on pricing, proposals, and contracts while ensuring compliance with company policies and approval processes.
Maintain an active sales pipeline and provide regular forecasts, activity reports, and market updates to leadership.
Monitor industry trends, competitor activity, and market conditions to identify growth opportunities and maintain a competitive advantage.
Partner with operations during customer onboarding to ensure a smooth transition from sales to service delivery.
Represent the company at networking events, industry associations, trade shows, and customer meetings.
Maintain accurate customer information, sales activities, and opportunity tracking within the company's CRM system.
Foster a high level of customer satisfaction by responding promptly to customer needs and helping resolve concerns throughout the sales process.
Collaborate with marketing and leadership to support business development initiatives and brand awareness.
Perform other duties as assigned to support business growth and organizational objectives.
Requirements:
Bachelor's degree in Business, Marketing, Sales, or a related field, or equivalent combination of education and experience.
5+ years of successful B2B sales experience, preferably in commercial real estate services, facility management, building maintenance, or a related industry.
Demonstrated ability to consistently meet or exceed sales goals and revenue targets.
Strong consultative selling, negotiation, and relationship-building skills.
Experience managing complex sales cycles involving multiple stakeholders.
Excellent verbal, written, and presentation communication skills.
Strong organizational, time management, and problem-solving abilities.
Proficiency with CRM software and Microsoft Office 365 applications.
Ability to analyze sales data, develop forecasts, and identify business opportunities.
Self-motivated with the ability to work independently while collaborating effectively across departments.
Valid driver's license and ability to travel as needed to customer locations, networking events, and company meetings.
Preferred Qualifications:
Experience selling commercial building maintenance, engineering, janitorial, or facility management services.
Existing relationships within the commercial real estate, property management, or facility management industry.
Experience responding to RFPs and developing service proposals.
Knowledge of contract negotiation and commercial service agreements.
Experience using CRM platforms such as Salesforce, HubSpot, or similar sales management systems.
The Head of Sales is responsible for driving revenue growth by developing and executing strategic sales initiatives, managing customer relationships, and expanding client portfolio. Reporting to the President, this role leads the sales process from prospecting through contract execution while collaborating with operations to ensure successful service delivery and long-term customer satisfaction. The Head of Sales is accountable for achieving sales targets, identifying new business opportunities, and representing the company's values and commitment to exceptional service
Essential Job Responsibilities:
Develop and execute strategic sales plans to achieve revenue and growth objectives.
Recruit, train, and oversee sales personnel, currently one direct report with growth to up to four as the team reaches full staffing.
Identify, prospect, and secure new commercial real estate and facility management clients through networking, referrals, cold outreach, and industry events.
Build and maintain strong relationships with prospective and existing customers to identify opportunities for additional services and long-term partnerships.
Manage the full sales cycle, including lead generation, needs assessments, proposal development, presentations, contract negotiations, and closing.
Collaborate with operations and leadership to develop customized service solutions that meet customer needs while supporting company profitability.
Collaborate with the operations team on pricing, proposals, and contracts while ensuring compliance with company policies and approval processes.
Maintain an active sales pipeline and provide regular forecasts, activity reports, and market updates to leadership.
Monitor industry trends, competitor activity, and market conditions to identify growth opportunities and maintain a competitive advantage.
Partner with operations during customer onboarding to ensure a smooth transition from sales to service delivery.
Represent the company at networking events, industry associations, trade shows, and customer meetings.
Maintain accurate customer information, sales activities, and opportunity tracking within the company's CRM system.
Foster a high level of customer satisfaction by responding promptly to customer needs and helping resolve concerns throughout the sales process.
Collaborate with marketing and leadership to support business development initiatives and brand awareness.
Perform other duties as assigned to support business growth and organizational objectives.
Requirements:
Bachelor's degree in Business, Marketing, Sales, or a related field, or equivalent combination of education and experience.
5+ years of successful B2B sales experience, preferably in commercial real estate services, facility management, building maintenance, or a related industry.
Demonstrated ability to consistently meet or exceed sales goals and revenue targets.
Strong consultative selling, negotiation, and relationship-building skills.
Experience managing complex sales cycles involving multiple stakeholders.
Excellent verbal, written, and presentation communication skills.
Strong organizational, time management, and problem-solving abilities.
Proficiency with CRM software and Microsoft Office 365 applications.
Ability to analyze sales data, develop forecasts, and identify business opportunities.
Self-motivated with the ability to work independently while collaborating effectively across departments.
Valid driver's license and ability to travel as needed to customer locations, networking events, and company meetings.
Preferred Qualifications:
Experience selling commercial building maintenance, engineering, janitorial, or facility management services.
Existing relationships within the commercial real estate, property management, or facility management industry.
Experience responding to RFPs and developing service proposals.
Knowledge of contract negotiation and commercial service agreements.
Experience using CRM platforms such as Salesforce, HubSpot, or similar sales management systems.
See All 81 Head Of Sales Jobs in Chicago
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Find Head Of Sales JobsHead Of Sales Job Market in Chicago
Who's Hiring
Top Industries Hiring
- Technology & Software10
- Investment & Asset Management3
- Medical Devices1
- Banking & Financial Services1
- Healthcare & Medical Services1
Head Of Sales Jobs in Chicago: Frequently Asked Questions
How do I get a head of sales job in Chicago?
Focus your search on Chicago's Loop, Fulton Market, and River North corridors, where fintech, enterprise SaaS, and B2B services firms concentrate their commercial leadership hiring. Candidates with a demonstrable record of building and scaling sales teams in complex or consultative environments stand out locally. Networking through Chicago-area revenue leadership groups and targeting mid-market tech companies based in the West Loop gives you a concrete edge over applicants searching nationally.
Which companies hire head of saless in Chicago?
Companies currently hiring head of saless in Chicago include SentiLink, Northern Trust, and Google, per current listings on Migrate Mate as of October 2026. Chicago's hiring base is broad, pulling from established enterprise software firms, high-growth fintech startups, and large healthcare services organizations all anchored in the city.
Are there remote head of sales jobs in Chicago?
Yes, though head of sales roles tend to be less remote-friendly than individual contributor positions because they require in-person team leadership and client relationship management. About 81% of head of sales openings tied to Chicago are remote or hybrid as of October 2026, with remote options most common at SaaS and technology companies. Strategic and analytical parts of the role, such as pipeline forecasting and territory planning, are most adaptable to remote work locally.
How can I get a head of sales job in Chicago with little or no experience?
The most realistic entry path is moving up through a senior account executive or sales manager role at a Chicago-based mid-market SaaS or fintech company, where promotion to head of sales is common as teams scale. Companies in Fulton Market and River North often grow internal talent rather than hire externally for this level. Building fluency with Chicago-specific verticals like financial technology or healthcare IT, and demonstrating you can recruit and develop reps, closes the gap quickly.
Which industries hire the most head of saless in Chicago?
The sectors hiring the most head of saless in Chicago are Technology & Software, Investment & Asset Management, and Medical Devices, based on current listings on Migrate Mate as of October 2026. Chicago's position as a national hub for financial services, enterprise technology, and healthcare administration means commercial leadership roles in these fields are consistently active across the city.
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