Remote Enterprise Sales Leader — AI Training Solutions

Stride, Inc.; Phoenix (AZ); Remote; USD 90,000 - 110,000; Full time

Job summary

Stride, Inc. is seeking an Enterprise Sales Manager to drive new business growth across our enterprise learning and workforce development solutions. This quota-carrying role focuses on acquiring new enterprise customers, generating pipeline, and closing deals, with travel up to 15–20%.

You will engage senior decision-makers, manage the full sales cycle, and collaborate with Marketing and Operations to maximize growth. A foundation in SaaS, training solutions, and enterprise sales is essential.

Qualifications

• 5+ years of quota-carrying enterprise sales experience.
• Proven success in complex sales with multiple stakeholders.
• Experience selling SaaS, corporate training, or enterprise learning solutions.
• Strong prospecting, discovery, negotiation, and closing skills.

Responsibilities

• Build and manage a robust pipeline of enterprise prospects through outbound prospecting, networking, referrals, and strategic outreach.
• Own the full sales cycle from initial outreach through contract execution.
• Generate 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 and procurement teams.
• Advance opportunities through qualification, discovery, proposals, negotiation, and close.
• Collaborate with Marketing and Operations to maximize growth opportunities.
• Maintain accurate CRM records, pipeline reporting, forecasting, and activity metrics.

Skills

Quota-carrying sales

Prospecting

Executive engagement

Tools

HubSpot

Job description

Stride, Inc. is seeking an Enterprise Sales Manager to drive new business growth across our enterprise learning and workforce development solutions. This quota-carrying role focuses on acquiring new enterprise customers, generating pipeline, and closing deals, with travel up to 15–20%.

You will engage senior decision-makers, manage the full sales cycle, and collaborate with Marketing and Operations to maximize growth. A foundation in SaaS, training solutions, and enterprise sales is essential.