Strategic Enterprise Account Executive

Tapcheck•Plano, TX

7d•Hybrid

About The Position

We are looking for a strategic and highly driven Strategic Enterprise Account Executive to join our sales team. This role will focus on building relationships with employers of 15,000+ employees and driving growth through a rigorous, process-oriented approach. As a Strategic Enterprise AE, you will leverage your network, build playbooks, and partner across multiple levels of an organization. This is a multidimensional role that requires working with sales, marketing, and product teams to create alignment and expand Tapcheck’s reach. You’ll operate several layers above the day-to-day sale, navigating executive conversations, engaging multiple stakeholders, and using every lever available to unlock opportunity. This role offers both a remote and hybrid option. Employees located within 30 miles of Plano TX, are required to be in-office Tuesday through Thursday each week. Those residing beyond this radius may be considered for a fully remote arrangement, depending on experience and business needs.

Requirements

7+ years of enterprise sales experience with a proven record of selling into employers of 15,000+ employees.
A history of building and executing complex, multithreaded deals with multiple stakeholders and long sales cycles.
Experience creating and leveraging sales playbooks to drive repeatability and scale.
Strong executive presence with the ability to engage C-level leaders and influence at multiple organizational levels.
Demonstrated ability to bring rigor, process, and structure to enterprise sales.
Proven success collaborating across Marketing, Product, and Customer Success to align strategy and execution.
Self-starter with the ability to navigate ambiguity, leverage networks, and identify the right levers to move deals forward.
Bachelor’s degree or equivalent experience

Responsibilities

Develop and execute a strategic enterprise sales plan to drive penetration within Fortune 1000 and other large employers (15,000+ employees).
Act as a trusted advisor, tailoring solutions to client needs rather than selling “out of the box.”
Partner with Marketing and Product Management to refine messaging, tailor solutions, and influence roadmap priorities.
Create and refine repeatable playbooks to scale the enterprise sales motion.
Build and maintain a robust pipeline through outbound prospecting, industry networking, and executive engagement.
Lead multithreaded sales cycles, engaging decision-makers across HR, Finance, Benefits, and C-Suite levels.
Deliver compelling presentations and executive-level business cases to highlight the impact of Tapcheck’s solution.
Leverage financial and analytical insights to build persuasive business cases for partner organizations.
Navigate complex corporate structures and stakeholder dynamics to demonstrate value across the enterprise.
Drive rigor and process throughout the sales cycle, ensuring accuracy in forecasting and CRM hygiene.
Collaborate with internal teams to ensure seamless onboarding and long-term client success.