Remote Enterprise Sales Leader - AI Workforce Training

Stride, Inc.; Jefferson City (MO); Remote; USD 90,000 - 110,000; Full time

Job summary

Stride, Inc. is seeking an Enterprise Sales Manager to drive new business growth for our learning and workforce development solutions.

This home‑based role targets enterprise customers, with travel of 15–20% to engage senior decision‑makers and close deals. The role requires 5+ years of quota‑carrying enterprise sales, proven capability to navigate long cycles, and a consultative, solution‑oriented approach.

Qualifications

• 5+ years of quota‑carrying enterprise sales experience with a track record of winning new business.
• Experience selling SaaS, corporate training, workforce development, or related services into enterprise organizations.
• CRM and Marketing Automation systems experience; HubSpot is a bonus.

Responsibilities

• Build and manage a robust pipeline of enterprise prospects through outbound prospecting and strategic outreach.
• Own the full sales cycle from initial outreach through contract execution.
• Generate new opportunities that support quarterly and annual revenue targets.
• Engage senior leaders to understand workforce development challenges and goals.
• Present tailored learning solutions aligned with customer objectives.
• Navigate complex buying processes with multiple stakeholders.

Skills

Quota carrying sales

Enterprise sales

SaaS sales

CRM & marketing automation

Tools

HubSpot

Job description

Stride, Inc. is seeking an Enterprise Sales Manager to drive new business growth for our learning and workforce development solutions.

This home‑based role targets enterprise customers, with travel of 15–20% to engage senior decision‑makers and close deals. The role requires 5+ years of quota‑carrying enterprise sales, proven capability to navigate long cycles, and a consultative, solution‑oriented approach.