Account Executive

The Strategic Account Executive is responsible for driving high-value revenue growth by acquiring new enterprise clients and expanding relationships within existing strategic accounts. This role focuses on identifying complex opportunities, engaging senior executives, and delivering tailored solutions that address workforce, compliance, and operational challenges. The Strategic AE owns the full sales cycle for large, multi-stakeholder deals and serves as a trusted advisor to enterprise customers. Due to the strategic nature of this position, candidates for the position should expect around 50% travel. Candidates will also need to reside in the greater Chicago, Denver, or Orlando areas.

Key Responsibilities

New Business Acquisition

• Target, engage, and secure new enterprise-level customers across priority verticals.
• Lead executive-level discovery to uncover business objectives, operational gaps, compliance pressures, and workforce development needs.
• Build ROI-driven proposals and solution recommendations that align with strategic customer outcomes.
• Own the end-to-end deal process including prospecting, qualification, solution design, pricing, negotiation, and closing.

Expansion & Growth in Existing Accounts

• Develop and execute strategic account plans to expand product adoption, increase revenue penetration, and strengthen customer relationships.
• Identify upsell and cross-sell opportunities across industries, geographies, and product lines.
• Partner with customer success and implementation teams to ensure delivery of customer outcomes that support expansion opportunities.
• Maintain strong relationships with senior decision-makers and influence multi-year investment strategies.

Account & Territory Management

• Manage a pipeline of complex, high-value opportunities with disciplined forecasting and CRM accuracy.
• Lead contract negotiations for strategic accounts.
• Collaborate closely with marketing, product, and revenue operations to ensure alignment of customer needs and strategic initiatives.

Market & Customer Insights

• Stay informed on industry trends, regulatory shifts, and competitive dynamics impacting enterprise clients.
• Gather and communicate customer insights to drive product improvements and strategic decision-making.
• Represent the company at key industry events, conferences, and executive briefings.

Qualifications

• 5–10+ years of enterprise or strategic account sales experience with a consistent track record of exceeding quota.
• Proven success managing complex sales cycles and selling into multi-location, multi-stakeholder organizations.
• Experience in workforce development, training, compliance, SaaS, or enterprise solutions strongly preferred.
• Strong executive presence and ability to lead C-suite level conversations.
• Expertise in developing business cases, ROI models, and negotiating large, multi-year agreements.
• Proficient with CRM platforms (e.g., Salesforce) and managing pipelines in a structured, data-driven manner.