Regional Sales Executive - Central US

Corestream; Chicago (IL); On-site; USD 120,000 - 190,000; Full time

Job summary

Corestream is seeking a consultative Sales Executive to build relationships, understand client needs, and grow enterprise partnerships. You will own the pipeline from outreach to close, with initiative and persistence and a relationship-focused selling approach.

The role requires traveling up to 40% and delivering compelling product demonstrations. The ideal candidate brings 3+ years of enterprise sales experience, a proven close record with high-value deals, and a data-driven, collaborative

Qualifications

• 3+ years of full-cycle enterprise sales experience.
• Independently create opportunities, develop leads, build a pipeline, and move prospects toward a decision.
• Proven track record of closing enterprise deals with high ACV.
• Comfort with SaaS platforms and learning new tools; experience with AI/automation in sales.
• Openness to feedback, coaching, and data-driven improvements.
• Strong verbal and written communication; ability to build trust with stakeholders.
• Willingness to travel ~40%.

Responsibilities

• Generate revenue by identifying and pursuing new business opportunities and closing enterprise accounts.
• Build and manage relationships with brokers and partners to expand opportunities.
• Lead product demonstrations (virtual and in-person) linking Corestream capabilities to HR and broker needs.
• Own the sales process from prospecting through close, with accurate CRM updates and KPI tracking.
• Collaborate with Marketing, Customer Success, and Product to tailor proposals and improve prospect experience.
• Aim to meet or exceed sales targets and share successful practices with the team.

Skills

Full-cycle sales

Enterprise sales

SaaS platforms

CRM expertise

Data-driven

Communication

Travel 40%

Tools

CRM

AI tools

Job description

Corestream is seeking a consultative Sales Executive to build relationships, understand prospective clients’ needs, and grow enterprise partnerships. We’re looking for someone who takes ownership of their pipeline, actively creates new opportunities, and follows through from initial outreach through close. Success in this role requires initiative and persistence, along with curiosity, collaboration, and a relationship-focused approach to sales. If this sounds like you, we’d love to hear from you.

Location: Corestream is headquartered in Tampa, FL, but the ideal candidate for this role will be based in the Central region of the US.

What You’ll Do

• Generate Revenue: Proactively identify and pursue new business opportunities, build a healthy pipeline, and close enterprise accounts through direct outreach, broker partnerships, referrals, and other creative prospecting strategies.
• Build Broker Partnerships: Cultivate and manage relationships with benefits brokers serving target accounts and collaborate on joint sales strategies and opportunities.
• Lead Product Demonstrations: Deliver engaging virtual and in-person demonstrations of the Corestream platform, connecting its capabilities to the needs of HR and broker stakeholders.
• Own the Sales Process: Take ownership of opportunities from prospecting through close while maintaining accurate and timely activity records, forecasts, pipeline updates, and KPI tracking in the CRM.
• Collaborate Across Teams: Partner with Marketing, Customer Success, and Product to tailor proposals, share market insights, and support a strong prospect experience.
• Achieve Sales Goals: Consistently meet or exceed sales targets while sharing effective practices and contributing to the success of the broader team.

What You’ll Bring

• Relevant Experience: 3+ years of full-cycle enterprise sales experience.
• Initiative and Follow-Through: A demonstrated ability to independently create opportunities, develop leads, build a pipeline, and move prospects toward a decision rather than waiting for opportunities to come to you.
• Enterprise Sales Success: A proven track record of closing enterprise deals with annual contract values of $100,000 or more.
• Technology Skills: Comfort demonstrating SaaS platforms and learning new tools and systems. Experience using AI, automation, or sales enablement tools to improve prospecting, streamline workflows, reduce manual work, and increase sales effectiveness.
• Learning and Accountability: Openness to feedback and coaching, willingness to adjust your approach, and consistent use of data and repeatable processes to improve results.
• Communication and Relationship Building: Clear verbal and written communication skills and the ability to build trust with a range of stakeholders.
• Travel: Ability to travel approximately 40%.

Cherries on Top

• Experience selling within voluntary benefits, employee benefits, insurance, HR technology, or SaaS.
• Experience navigating complex enterprise sales cycles with multiple stakeholders and decision-makers.
• A track record of building new territories or pipelines from the ground up.
• Familiarity with broker-led or channel-influenced sales models.

Corestream is a fast-growing, cutting-edge financial and benefits technology company. We are an industry leader in the delivery of Voluntary Benefits; our proprietary software is the engine for large, Fortune-500 companies to easily and cost-effectively offer unlimited Voluntary Benefits to its employees through payroll deduction.

We have a driven, flexible, and fun team and offer competitive compensation and benefit packages. Although we are over ten years old, we still have a “start-up” culture and when we are in the office we have a casual dress code, free snacks and beverages, and Wednesday lunches are on the house.

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.