Remote Enterprise Sales Leader: AI & Workforce Training

Stride, Inc.; Carson City (NV); Remote; USD 90,000 - 110,000; Full time

Job summary

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

This home-based role targets new enterprise customers, builds a robust pipeline, and closes deals while navigating complex buying processes. You will engage senior decision-makers, tailor learning solutions, and collaborate with marketing and operations to maximize growth.

Qualifications

• 5+ years of quota‑carrying enterprise sales experience.
• Proven success in complex sales environments with long cycles.
• Experience selling SaaS, training, or enterprise learning solutions into enterprises.
• Strong prospecting, discovery, negotiation, and closing skills.
• Experience engaging senior decision-makers and managing multiple stakeholders.

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 opportunities that support quarterly and annual revenue targets.
• Engage senior leaders to understand workforce development challenges and goals.
• Present tailored learning solutions aligned with customer objectives.
• Navigate complex enterprise buying processes with multiple stakeholders.

Skills

Quota-carrying sales

Complex sales cycles

Executive engagement

SaaS enterprise solutions

Prospecting

Tools

HubSpot CRM

Job description

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

This home-based role targets new enterprise customers, builds a robust pipeline, and closes deals while navigating complex buying processes. You will engage senior decision-makers, tailor learning solutions, and collaborate with marketing and operations to maximize growth.