Remote Enterprise Sales Manager, AI & Workforce Training

Stride, Inc.; Oregon; Hybrid; USD 90,000 - 110,000; Full time

Benefits offered by this job

Remote work

Travel 15-20%

Job summary

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

This home-based role focuses on acquiring new enterprise customers, building a robust pipeline, and closing deals across the full sales cycle. You will engage senior decision-makers, navigate complex buying processes, and collaborate with Marketing and Operations to maximize growth.

Qualifications

• 5+ years of quota-carrying enterprise sales experience
• Proven success in a complex sales environment with pipeline generation
• Experience selling SaaS, corporate training, or enterprise learning solutions
• Strong prospecting, discovery, negotiation, and closing skills
• Experience managing long sales cycles with multiple decision-makers
• CRM/Marketing Automation experience (HubSpot a bonus)
• Excellent communication, presentation, and executive engagement skills
• Self-motivated with ability to work independently and hit targets
• Resilient and competitive with a drive to exceed goals
• Foundational understanding of AI, software, data science, and agile concepts

Responsibilities

• Build and manage a robust pipeline of enterprise prospects via outbound prospecting, networking, referrals, and outreach
• Own the full sales cycle from initial outreach to contract execution
• Generate new opportunities to support quarterly and annual revenue targets
• Engage senior leaders to understand workforce development challenges and talent priorities
• Present tailored learning and workforce development solutions aligned with customer goals
• Navigate complex enterprise buying involving multiple stakeholders and procurement
• Advance opportunities through qualification, discovery, proposal, negotiation, and close
• Collaborate with Marketing and Operations to align outreach and maximize growth
• Maintain accurate CRM records, pipeline reporting, forecasting, and activity metrics

Skills

Quota-carrying sales

Enterprise sales

SaaS sales

Executive engagement

CRM/MARKETING automation

Tools

HubSpot

Job description

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

This home-based role focuses on acquiring new enterprise customers, building a robust pipeline, and closing deals across the full sales cycle. You will engage senior decision-makers, navigate complex buying processes, and collaborate with Marketing and Operations to maximize growth.