Enterprise SaaS Sales Leader — AI Training Solutions

Stride, Inc.; Columbia (SC); Remote; USD 90,000 - 110,000; Full time

Job summary

Stride, Inc. is seeking an Enterprise Sales Manager to drive new business growth across our enterprise training and workforce development solutions. This home-based role concentrates on acquiring new enterprise customers, generating pipeline, and closing deals, with 15-20% travel.

The candidate will engage senior decision-makers, navigate complex sales cycles, and partner with Marketing and Operations to maximize growth. A proven track record in SaaS or training solutions is essential.

Qualifications

• 5+ years of quota-carrying enterprise sales.
• Proven success in complex sales and pipeline generation.
• Experience selling SaaS, training, workforce development, or enterprise learning solutions.
• Strong prospecting, discovery, negotiation, and closing skills.
• Experience managing long sales cycles and multiple decision-makers.
• CRM and marketing automation experience; HubSpot a bonus.
• Excellent communication, presentation, and executive engagement skills.
• Self-motivated with the ability to work independently and meet targets.
• Understanding of AI, software, data science, and agile concepts.

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

SaaS sales

Prospecting & pipeline

Executive engagement

CRM & marketing automation

Tools

HubSpot

Job description

Stride, Inc. is seeking an Enterprise Sales Manager to drive new business growth across our enterprise training and workforce development solutions. This home-based role concentrates on acquiring new enterprise customers, generating pipeline, and closing deals, with 15-20% travel.

The candidate will engage senior decision-makers, navigate complex sales cycles, and partner with Marketing and Operations to maximize growth. A proven track record in SaaS or training solutions is essential.