Enterprise AI Training Solutions Sales Leader (Remote)

Stride, Inc.; Saint Paul (MN); Remote; USD 90,000 - 110,000; Full time

Job summary

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

You will build a robust pipeline, engage senior decision-makers, and own the full sales cycle from outreach to close in a home-based, highly autonomous role. You will need 5+ years in quota-carrying enterprise sales, a track record in complex enterprise deals, and strong CRM/HubSpot skills.

Qualifications

• 5+ years of quota‑carrying enterprise sales experience.
• Proven success in a complex sales environment with multiple stakeholders.
• Experience selling SaaS, corporate training, workforce development, or related services into enterprise organizations.
• CRM and Marketing Automation systems experience; HubSpot a bonus.
• Excellent communication, presentation, and executive engagement skills.
• Self‑motivated with the ability to work independently and meet targets.

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 with Marketing and Operations to align outreach efforts and maximize growth opportunities.
• Maintain accurate CRM records, pipeline reporting, forecasting, and sales activity metrics.

Skills

Quota carrying

Enterprise sales

SaaS sales

HubSpot

Executive engagement

Prospecting

Tools

HubSpot

Job description

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

You will build a robust pipeline, engage senior decision-makers, and own the full sales cycle from outreach to close in a home-based, highly autonomous role. You will need 5+ years in quota-carrying enterprise sales, a track record in complex enterprise deals, and strong CRM/HubSpot skills.