Regional Sales Executive - Western US

Summary

Corestream is a financial and benefits technology company focused on delivering voluntary benefits through its proprietary software platform. The Regional Sales Executive will build enterprise partnerships, generate new business, manage broker relationships, lead product demonstrations, own the full sales process, and achieve sales targets in the Western U.S. region.

Responsibilities

• 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
• Cultivate and manage relationships with benefits brokers serving target accounts and collaborate on joint sales strategies and opportunities
• Deliver engaging virtual and in-person demonstrations of the Corestream platform, connecting its capabilities to the needs of HR and broker stakeholders
• Take ownership of opportunities from prospecting through close while maintaining accurate and timely activity records, forecasts, pipeline updates, and KPI tracking in the CRM
• Partner with Marketing, Customer Success, and Product to tailor proposals, share market insights, and support a strong prospect experience
• Consistently meet or exceed sales targets while sharing effective practices and contributing to the success of the broader team

Skills

• 3+ years of full-cycle enterprise sales experience
• 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
• A proven track record of closing enterprise deals with annual contract values of $100,000 or more
• 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
• Openness to feedback and coaching, willingness to adjust your approach, and consistent use of data and repeatable processes to improve results
• Clear verbal and written communication skills and the ability to build trust with a range of stakeholders
• Ability to travel approximately 40%
• 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

Qualifications

Must Haves

• 3+ years of full-cycle enterprise sales experience
• 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
• A proven track record of closing enterprise deals with annual contract values of $100,000 or more
• 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
• Openness to feedback and coaching, willingness to adjust your approach, and consistent use of data and repeatable processes to improve results
• Clear verbal and written communication skills and the ability to build trust with a range of stakeholders
• Ability to travel approximately 40%

Nice to Haves

• 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

Benefits

• Remote work
• Casual dress code when in the office
• Free snacks and beverages
• Wednesday lunches are on the house