Regional Sales Executive - Western US

Corestream; Chicago (IL); On-site; USD 90,000 - 130,000; Full time

Job summary

Corestream is seeking a results-driven Sales Executive to build relationships, drive enterprise opportunities, and own the end-to-end sales cycle. Based in the Western US region, you will engage HR leaders and benefits brokers, deliver tailored product demonstrations, and advance opportunities from outreach to close.

You will collaborate with Marketing, Customer Success, and Product to tailor proposals and optimize the prospect experience, while tracking KPIs in the CRM and pushing for quarterly

Qualifications

• 3+ years of full-cycle enterprise sales experience.
• Ability to build a healthy pipeline and close enterprise accounts.
• Willingness to travel ~40% and manage complex stakeholder engagements.

Responsibilities

• Generate revenue through direct outreach, broker partnerships, and referrals.
• Own the sales process from prospecting to close with accurate CRM updates.
• Lead product demonstrations to HR and broker stakeholders.
• Collaborate with Marketing, Customer Success, and Product.
• Meet or exceed sales targets and contribute to team success.

Skills

Full-cycle enterprise sales

Pipeline management

CRM & forecasting

Communication skills

Relationship building

Prospecting & lead generation

Learning and accountability

Travel readiness

Tools

CRM systems

AI/sales enablement tools

SaaS platforms

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 Western 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.