Enterprise Sales Leader – AI Training & Workforce Solutions

Stride, Inc.; Nashville (TN); Remote; USD 90,000 - 110,000; Full time

Job summary

Stride, Inc. seeks an Enterprise Sales Manager to drive new business growth for our learning and workforce development solutions. The role focuses on acquiring new enterprise customers, generating pipeline, and closing deals, with a consultative, solution-oriented approach.

You will engage senior decision-makers, navigate long sales cycles, and collaborate with marketing and operations to maximize growth. This is a remote, quota-bearing position with travel up to 15-20%.

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 where prospecting and pipeline generation are core responsibilities.
• Experience selling SaaS, corporate training, workforce development, learning solutions, technology solutions, 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.
• Self-motivated with the ability to work independently and consistently achieve performance targets.
• Highly resilient, competitive, and energized by the challenge of creating new opportunities and exceeding goals.

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

Quota carrying sales

Enterprise sales

Prospecting skills

CRM experience

Executive engagement

Independent work

Tools

HubSpot

Job description

Stride, Inc. seeks an Enterprise Sales Manager to drive new business growth for our learning and workforce development solutions. The role focuses on acquiring new enterprise customers, generating pipeline, and closing deals, with a consultative, solution-oriented approach.

You will engage senior decision-makers, navigate long sales cycles, and collaborate with marketing and operations to maximize growth. This is a remote, quota-bearing position with travel up to 15-20%.