Remote Enterprise Sales Lead - AI Training Solutions

Stride, Inc.; Juneau (AK); Remote; USD 90,000 - 110,000; Full time

Benefits offered by this job

Commission

OTE up to $240k

Job summary

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

This home-based role requires building a robust enterprise pipeline, managing the full sales cycle, and engaging senior decision-makers to close new business across the United States. You will target large organizations, navigate complex buying processes, and collaborate with Marketing and Operations to maximize growth.

Qualifications

• 5+ years of quota-carrying enterprise sales experience.
• Experience selling SaaS and enterprise training to large organizations.
• Strong prospecting, discovery, negotiation, and closing skills.
• Experience managing long sales cycles with multiple decision-makers.
• CRM and Marketing Automation experience; HubSpot bonus.

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

Complex sales

SaaS sales

Prospecting

Discovery

Negotiation

Closing

Multi-stakeholder

CRM experience

Executive engagement

Self-motivation

AI basics

Tools

HubSpot CRM

Job description

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

This home-based role requires building a robust enterprise pipeline, managing the full sales cycle, and engaging senior decision-makers to close new business across the United States. You will target large organizations, navigate complex buying processes, and collaborate with Marketing and Operations to maximize growth.