Enterprise Sales Representative Jobs in Illinois
Enterprise Sales Representative jobs in Illinois are concentrated in Chicago, Naperville, and Schaumburg, where major technology, healthcare, and financial services companies anchor steady hiring demand. Firms like Salesforce, Oracle, and CDW maintain significant Illinois presences and consistently seek enterprise sales professionals with expertise in SaaS platforms, cloud infrastructure, and managed services. The market draws candidates at every level, from account executives moving into enterprise territory to senior reps managing Fortune 500 relationships. See the openings below and apply to the ones that match your experience.
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Showing 5 of 6+ Enterprise Sales Representative jobs
ABOUT US
HirexHire (pronounced hire by hire) is a Chicago-based recruiting and talent consultancy that integrates with companies short-term to provide long-term talent solutions. We take a seat in our client’s everyday operations to understand their people's goals, gaps, and challenges. We then develop and implement the processes and technologies to execute a sustainable and scalable talent plan.
We partner with companies expecting or experiencing high growth who need to hire at scale or fill a critical role rapidly. Our clients are not looking for quick-fix placements but are thoughtfully building a hiring strategy to scale their businesses.
OUR CLIENT
Location: Remote
Industry: Healthcare Technology (SaaS)
Company Size: 50+
What They Do: Our client is a cloud-based software platform and patient engagement technology that automates the collection of patient reported outcomes. It also offers procedure-specific education modules to help prepare patients for treatments and proactively monitors their recovery.
Contact HirexHire for more client information
THE ROLE
The Enterprise Business Development Representative (BDR) will drive net-new pipeline by prospecting into and engaging senior stakeholders at large, complex healthcare organizations. This role will own the top of the funnel for the enterprise segment, including researching target accounts, crafting personalized outreach, and booking qualified meetings for Account Executives. The BDR will navigate multi-stakeholder buying committees and the longer sales cycles typical of enterprise deals to identify and develop new business opportunities.
WHAT YOU WILL DO
Conduct outbound prospecting (email, phone, LinkedIn, and other channels) into enterprise-level target accounts.
Leverage AI tools to research accounts, map buying committees within target accounts, and to personalize outreach at scale — while ensuring messaging still feels human and relevant.
Personalize outreach based on account-specific context, trigger events, and relevant use cases.
Comfortable using AI-powered sales tools (e.g., for prospecting research, email/message drafting, or call summarization) to work faster and smarter, not just to increase volume.
Qualify inbound and outbound leads against our ICP (ideal customer profile) and BANT/MEDDIC-style criteria.
Maintain accurate, up-to-date records in the CRM (activity, notes, next steps).
Partner closely with Account Executives and Marketing on account-based campaigns and target account lists.
Continuously test and refine outreach messaging, sequences, and cadences.
Consistently hit or exceed monthly/quarterly pipeline generation targets.
WHAT YOU WILL NEED
Prior experience as a BDR/SDR in B2B SaaS, with a track record of outbound prospecting into enterprise accounts.
Experience researching and engaging multiple stakeholders within a single target account (not just single-threaded outreach).
Comfort with a longer, more consultative sales cycle versus SMB/mid-market prospecting.
Strong written and verbal communication skills — able to craft compelling personalized outreach at scale.
Familiarity with sales engagement tools (Sales Navigator, Outreach, Salesloft,) and CRM platforms (Salesforce, HubSpot, etc.).
Resilient, coachable, and metrics-driven — comfortable with high-volume outreach and a fair amount of rejection.
Strong organizational skills to manage a large territory of accounts and contacts.
Experience in US B2B SaaS healthcare technology, familiarity with ABM tools (e.g., 6sense, CommonRoom, ZoomInfo), and knowledge of structured sales methodologies (e.g., MEDDIC, Challenger, Command of the Message) are a plus.
WHAT OUR CLIENT OFFERS YOU
Our client was selected as one of the top 50 "Best Small Companies to Work For in Chicago" and they pride themselves on their team culture and shared passion for working together to solve meaningful problems in health care to improve patient lives. Check out a few of their benefits below:
Great Benefits - top-notch health, dental and vision insurance. Additional perks available including 401K.
They are Mission Driven - our client's team is motivated to solve complex problems, drive medicine forward, and ultimately improve patient outcomes.
True Idea Meritocracy - great ideas win out. They encourage all team members to challenge the status quo because their mission demands this.
Flexible Time Off - they trust you to take the time you need when you feel it is appropriate, given your workload and responsibilities. No need to track it or save up.
World-Class Team - they’re at the top of our industry because of our employees. They’re the best investment they can make, and they never forget that.
Fast Growing - they are building the largest platform for healthcare providers, industry partners, researchers, and others to collaborate on the mission to improve patient outcomes.
ABOUT US
HirexHire (pronounced hire by hire) is a Chicago-based recruiting and talent consultancy that integrates with companies short-term to provide long-term talent solutions. We take a seat in our client’s everyday operations to understand their people's goals, gaps, and challenges. We then develop and implement the processes and technologies to execute a sustainable and scalable talent plan.
We partner with companies expecting or experiencing high growth who need to hire at scale or fill a critical role rapidly. Our clients are not looking for quick-fix placements but are thoughtfully building a hiring strategy to scale their businesses.
OUR CLIENT
Location: Remote
Industry: Healthcare Technology (SaaS)
Company Size: 50+
What They Do: Our client is a cloud-based software platform and patient engagement technology that automates the collection of patient reported outcomes. It also offers procedure-specific education modules to help prepare patients for treatments and proactively monitors their recovery.
Contact HirexHire for more client information
THE ROLE
The Enterprise Business Development Representative (BDR) will drive net-new pipeline by prospecting into and engaging senior stakeholders at large, complex healthcare organizations. This role will own the top of the funnel for the enterprise segment, including researching target accounts, crafting personalized outreach, and booking qualified meetings for Account Executives. The BDR will navigate multi-stakeholder buying committees and the longer sales cycles typical of enterprise deals to identify and develop new business opportunities.
WHAT YOU WILL DO
Conduct outbound prospecting (email, phone, LinkedIn, and other channels) into enterprise-level target accounts.
Leverage AI tools to research accounts, map buying committees within target accounts, and to personalize outreach at scale — while ensuring messaging still feels human and relevant.
Personalize outreach based on account-specific context, trigger events, and relevant use cases.
Comfortable using AI-powered sales tools (e.g., for prospecting research, email/message drafting, or call summarization) to work faster and smarter, not just to increase volume.
Qualify inbound and outbound leads against our ICP (ideal customer profile) and BANT/MEDDIC-style criteria.
Maintain accurate, up-to-date records in the CRM (activity, notes, next steps).
Partner closely with Account Executives and Marketing on account-based campaigns and target account lists.
Continuously test and refine outreach messaging, sequences, and cadences.
Consistently hit or exceed monthly/quarterly pipeline generation targets.
WHAT YOU WILL NEED
Prior experience as a BDR/SDR in B2B SaaS, with a track record of outbound prospecting into enterprise accounts.
Experience researching and engaging multiple stakeholders within a single target account (not just single-threaded outreach).
Comfort with a longer, more consultative sales cycle versus SMB/mid-market prospecting.
Strong written and verbal communication skills — able to craft compelling personalized outreach at scale.
Familiarity with sales engagement tools (Sales Navigator, Outreach, Salesloft,) and CRM platforms (Salesforce, HubSpot, etc.).
Resilient, coachable, and metrics-driven — comfortable with high-volume outreach and a fair amount of rejection.
Strong organizational skills to manage a large territory of accounts and contacts.
Experience in US B2B SaaS healthcare technology, familiarity with ABM tools (e.g., 6sense, CommonRoom, ZoomInfo), and knowledge of structured sales methodologies (e.g., MEDDIC, Challenger, Command of the Message) are a plus.
WHAT OUR CLIENT OFFERS YOU
Our client was selected as one of the top 50 "Best Small Companies to Work For in Chicago" and they pride themselves on their team culture and shared passion for working together to solve meaningful problems in health care to improve patient lives. Check out a few of their benefits below:
Great Benefits - top-notch health, dental and vision insurance. Additional perks available including 401K.
They are Mission Driven - our client's team is motivated to solve complex problems, drive medicine forward, and ultimately improve patient outcomes.
True Idea Meritocracy - great ideas win out. They encourage all team members to challenge the status quo because their mission demands this.
Flexible Time Off - they trust you to take the time you need when you feel it is appropriate, given your workload and responsibilities. No need to track it or save up.
World-Class Team - they’re at the top of our industry because of our employees. They’re the best investment they can make, and they never forget that.
Fast Growing - they are building the largest platform for healthcare providers, industry partners, researchers, and others to collaborate on the mission to improve patient outcomes.
See All 6 Enterprise Sales Representative Jobs in Illinois
Find roles in Illinois that match your experience and apply in just a few clicks.
Find JobsEnterprise Sales Representative Jobs by City in Illinois
Where Illinois roles are concentrated, by current openings.
Enterprise Sales Representative Job Market in Illinois
A snapshot from current Illinois openings, updated as new roles post.
Who's Hiring
Top Industries Hiring
- Accounting & Auditing
- Technology & Software
- Marketing & Advertising
What Illinois Employers Look For
The qualifications that appear most often in enterprise sales representative jobs across Illinois.
- Bachelor's degree in business, marketing, or a related field required by most Illinois employers
- Three or more years of B2B or enterprise sales experience selling complex solutions
- Demonstrated ability to manage full sales cycles and close six-figure annual contracts
- Proficiency with CRM platforms such as Salesforce, widely used across Illinois technology firms
- Strong understanding of consultative selling methodologies including MEDDIC or Challenger
- Willingness to travel within Illinois and the broader Midwest region for client meetings
Enterprise Sales Representative Jobs in Illinois: Frequently Asked Questions
How do you become a enterprise sales representative in Illinois?
Enterprise sales representative roles in Illinois do not require a state-issued license or registration. Most employers expect a bachelor's degree in business, communications, or a technical field, combined with prior B2B sales experience. Candidates who have sold complex software, cloud services, or managed IT solutions to mid-market or enterprise accounts are consistently preferred by Illinois-based hiring teams. Earning a recognized sales certification such as Salesforce Administrator or a solution-selling credential strengthens a candidate's profile considerably.
How much do enterprise sales representatives make in Illinois?
Enterprise sales representatives in Illinois earn a median of about $73,510 a year, based on May 2025 Bureau of Labor Statistics wage data, ranging from around $44,130 for the lowest 10% to over $134,030 for the top 10%. Pay rises with experience, specialty, and employer.
Which companies hire enterprise sales representatives in Illinois?
Employers hiring enterprise sales representatives in Illinois right now include Google, Groupon, and SyndiGO, based on current listings on Migrate Mate as of November 2026. Illinois's deep concentration of technology, healthcare IT, and financial services headquarters means hiring tends to be consistent throughout the year rather than seasonal.
Which Illinois cities have the most enterprise sales representative jobs?
Chicago and Schaumburg have the most enterprise sales representative openings in Illinois. Chicago leads because it serves as the regional headquarters for numerous technology vendors, financial institutions, and healthcare companies, while Naperville and Schaumburg attract openings tied to the large corporate campuses and technology parks that have grown along the Interstate 88 corridor west of the city.
Are there remote enterprise sales representative jobs in Illinois?
Yes, and more than most fields. About 60% of enterprise sales representative openings tied to Illinois are remote or hybrid as of November 2026, reflecting the role's natural fit for distributed work. The prospecting, discovery, and demonstration stages of enterprise sales translate well to video and phone, though roles requiring on-site executive presentations or territory travel in the Midwest typically come with hybrid expectations.
How can I get hired as a enterprise sales representative in Illinois with little or no experience?
The most realistic entry path is moving from a sales development representative or inside sales role into an enterprise account executive position. Large Illinois-based technology employers and staffing firms in Chicago regularly hire SDRs with no prior enterprise experience and promote from within after consistent quota attainment. A Salesforce certification or HubSpot credential signals readiness. Candidates from adjacent roles such as account management, customer success, or channel sales at Illinois technology or healthcare IT companies frequently make the lateral transition into enterprise sales without starting over.
Where can I find and apply to enterprise sales representative jobs in Illinois?
You can find and apply to enterprise sales representative jobs in Illinois on Migrate Mate, which lists current Illinois openings updated regularly. Search for roles that match your industry background, territory preference, or solution specialty, then apply directly to the ones that fit your experience level and target employer type.
See All 6 Enterprise Sales Representative Jobs in Illinois
Find roles in Illinois that match your experience and apply in just a few clicks.
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