Sales Leader Jobs in Chicago, IL
Sales Leader jobs in Chicago are in strong demand, concentrated in the Loop, River North, and Fulton Market across financial services, technology, and healthcare. Employers actively hiring include KI, Telus, and Bonobos. Scan the live roles below and apply to whichever ones fit.
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TELUS Health is empowering every person to live their healthiest life. Guided by our vision, we are leveraging the power of our leading edge technology and focusing on the uniqueness of each individual to create the future of health. As a global-leading health and well-being provider – encompassing physical, mental and financial health – TELUS Health is improving health outcomes for consumers, patients, healthcare professionals, employers and employees.
Retirement and Benefits Solutions (RBS) improves the financial health and well-being for individuals and strengthens organizational resilience for employers through sustainable and flexible retirement and benefits solutions. Our comprehensive benefits administration support, powered by cutting-edge technology, enables clients to tailor and manage employee benefits programs seamlessly, covering health and welfare, and defined benefits pension plans to suit their specific requirements.With a reach extending to 11.9 million plan participants, we simplify the complexities of benefits management, offering streamlined solutions that enhance our clients’ operational efficiency and elevate the benefits experience. Our services encompass the administration of benefits and retirement programs on an outsourced or co-sourced basis for defined benefits, defined contribution, and health and welfare plans in the US and Canada.
WHAT YOU’LL DO
Leadership
Lead US sales team to achieve Health & Welfare and Defined Benefit market targets.
Accountable for team success against annual sales targets set with management
Provide strong leadership and coaching to team members, facilitate career development, and nurture a high performance team
Set personal and team sales quotas based on objectives and identify target market segments.
Lead strategies, projects or programs to success, invoking deep understanding of industry specific solutions to create unique business value
Recruit, select, and onboard staff, adjusting plans to meet targets if necessary.
Forge strong relations with the national sales organization and other business units
Sales
Develop and execute a US sales plan and strategy via TELUS Premier Sales Organization process
Engage in business development, client pursuits, RFPs, and finalist presentations.
Project and forecast new business revenue annually and quarterly.
Conduct regular team meetings to review performance and ensure adherence to Premier Sales Organization processes, leading in alignment with company culture and values.
Track and report sales team metrics, collaborating with marketing and channel development for lead generation.
Industry
Interact with search consultants to maintain Top Tier provider status and secure RFPs.
Monitor competition and industry trends to maintain market understanding.
Network with potential clients, search consultants, and participate in industry events.
Own and manage relationships with strategic external partners
Participate in regional and cross-LOB strategies and initiatives as needed.
WHAT YOU BRING
Leadership
5+ years' experience leading high performance sales teams
Demonstrated leadership skills with extensive experience in building and developing high performance teams within large complex organizations
Ability to create the environment for success and promote behaviors to deliver superior performance against targets
Collaborative and effective communicator across teams
Sales
10+ years' successful sales experience in B2B
Detailed understanding of the sales process and a proven track record of achieving sustainable, predictable and profitable business results
Proven experience presenting to C-suite customer stakeholders, and internal C-suite
You have a deep passion for customers, people, sales process and success
Forge strong relations with the national sales organization and other business units
Strong use of sales tools and selling methodology to support a differentiated sales experience for customers
Industry
Deep knowledge of USA market along with developed relationships, with specific expertise in the US benefits administration market
Deep understanding of the Health and Welfare and Defined Benefits/Pension landscape within the US market
Strong grasp of competitive positioning and market dynamics in the US benefits administration and retirement solutions industry
Familiarity with the third-party consultant and TPE (Third-Party Employer) ecosystem as a primary distribution channel
Salary Range: $160,000 - $215,000
Sales Incentive Plan Range: $106,000 - $144,000
Actual total compensation will be determined based on factors such as knowledge, skills, performance and experience. We encourage all qualified candidates to apply, even if the posted salary range doesn't match your expectations. We're open to discussing competitive compensation packages tailored to your experience level and expertise.
A bit about us
We’re a people-focused, customer-first, purpose-driven team who works together every day to innovate and do good. We improve lives through our technology solutions and foster a culture of innovation that empowers team members to solve complex problems and create remarkable human outcomes in a digital world.
TELUS Health is an Equal Opportunity Employer that aims to foster an inclusive culture that embraces diversity. It is our policy to hire without regard to race, color, creed, religion, national origin, citizenship status, sex, marital status, age, disability, sexual orientation or veteran status.We offer accommodation for applicants with disabilities, as required, during the recruitment process.
By applying to this role, you understand and agree that your information will be shared with the TELUS Group of Companies’ Talent Acquisition team(s) and/or any leader(s) who will be part of the selection process.
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Who's Hiring



Top Industries Hiring
- Technology & Software
Sales Leader Jobs in Chicago: Frequently Asked Questions
How do I get a sales leader job in Chicago?
Target Chicago's strongest hiring corridors: fintech and insurtech firms in the Loop, SaaS and cloud companies in River North and Fulton Market, and health systems on the Near North Side. Candidates with enterprise B2B experience and a demonstrated ability to build Chicago-area pipeline stand out. Attending local revenue leadership meetups and connecting with hiring managers at Chicago-headquartered firms accelerates the search considerably.
Which companies hire sales leaders in Chicago?
Companies currently hiring sales leaders in Chicago include KI, Telus, and Bonobos, per current listings on Migrate Mate as of November 2026. Chicago's mix of Fortune 500 headquarters, fast-scaling mid-market tech firms, and large regional insurers means demand comes from a wide range of employer types across the city.
Are there remote sales leader jobs in Chicago?
Yes, though remote availability depends heavily on the role, since sales leaders managing local teams or territory-based accounts typically require an on-site or hybrid presence. About 0% of sales leader openings tied to Chicago are remote or hybrid as of November 2026, with remote arrangements most common in SaaS and enterprise software companies headquartered downtown.
How can I get a sales leader job in Chicago with little or no experience?
The most realistic entry path in Chicago is stepping into a senior individual contributor role first, typically an account executive or senior sales representative position at a mid-market tech or insurance firm, then transitioning into a team lead title within 12 to 18 months. Chicago's dense SaaS corridor in River North and Fulton Market regularly promotes strong closers into their first leadership role from within.
Which industries hire the most sales leaders in Chicago?
Chicago sales leader roles concentrate in Technology & Software, based on current listings on Migrate Mate as of November 2026. Chicago's position as a national hub for financial services, enterprise software, and healthcare administration keeps consistent demand for sales leadership talent across all three sectors throughout the year.
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