Remote Enterprise AI Training Sales Leader

Stride, Inc.; Santa Fe (NM); Remote; USD 90,000 - 110,000; Full time

Job summary

Stride, Inc. seeks an Enterprise Sales Manager to drive new-business growth across our learning and workforce development solutions.

This quota-carrying role focuses on acquiring enterprise customers, building pipeline, and guiding complex deals with senior decision-makers. You will partner with Marketing and Operations, manage CRM to forecast and report, and advance AI/technical training offerings in enterprise accounts.

Qualifications

• 5+ years of quota-carrying enterprise sales experience with a demonstrated track record of winning new business.
• Proven success in a complex sales environment with prospecting and pipeline generation.
• Experience selling SaaS, corporate training, workforce development, or related services into enterprise organizations.
• Strong prospecting, discovery, negotiation, and closing skills.
• Experience managing long sales cycles and multiple decision-makers within large organizations.
• CRM and Marketing Automation systems experience; HubSpot a bonus.
• Excellent communication, presentation, and executive engagement 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 new opportunities that support quarterly and annual revenue targets
• Engage senior business leaders to understand workforce development challenges and talent priorities
• Present tailored learning and workforce development solutions that align with customer goals
• Navigate complex enterprise buying processes involving multiple stakeholders and procurement teams
• Advance opportunities through qualification, discovery, proposal development, negotiation, and close
• Collaborate closely with Marketing and Operations to align outreach efforts and maximize growth opportunities
• Maintain accurate CRM records, pipeline reporting, forecasting, and sales activity metrics

Skills

Enterprise sales

Prospecting

Negotiation

Closing skills

Executive engagement

HubSpot / CRM

Tools

HubSpot

Job description

Stride, Inc. seeks an Enterprise Sales Manager to drive new-business growth across our learning and workforce development solutions.

This quota-carrying role focuses on acquiring enterprise customers, building pipeline, and guiding complex deals with senior decision-makers. You will partner with Marketing and Operations, manage CRM to forecast and report, and advance AI/technical training offerings in enterprise accounts.