Enterprise Sales Lead — AI Training & Workforce Growth

Stride, Inc.; Little Rock (AR); 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 training and workforce development solutions.

This role focuses on acquiring new enterprise customers, generating pipeline, and closing deals, with a proactive, quota-carrying mindset and a consultative, solution-oriented approach. You will identify opportunities, engage senior decision-makers, navigate complex sales cycles, and collaborate with Marketing and Operations to maximize growth while

Qualifications

• 5+ years in quota-carrying enterprise sales.
• Experience selling SaaS and enterprise solutions.
• Proven ability to manage long multi-stakeholder deals.
• Strong prospecting, discovery, negotiation, and closing skills.
• CRM and marketing automation experience; HubSpot bonus.

Responsibilities

• Build and manage a robust enterprise pipeline via outbound prospecting and referrals.
• Own the full sales cycle from initial outreach to contract execution.
• Generate opportunities to meet quarterly and annual targets.
• Engage senior leaders to understand workforce development needs.
• Present tailored learning solutions aligned with customer goals.
• Navigate complex buying processes with multiple stakeholders.
• Advance opportunities through qualification, discovery, proposal, negotiation, and close.
• Collaborate with Marketing and Operations to maximize growth.
• Maintain CRM, pipeline reporting, and forecasting.

Skills

Quota carrying sales

Enterprise sales

SaaS sales

Executive engagement

CRM systems

Tools

HubSpot

CRM software

Job description

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

This role focuses on acquiring new enterprise customers, generating pipeline, and closing deals, with a proactive, quota-carrying mindset and a consultative, solution-oriented approach. You will identify opportunities, engage senior decision-makers, navigate complex sales cycles, and collaborate with Marketing and Operations to maximize growth while