Lead enterprise sales development remotely at Toptal, combining outbound sales leadership with AI-powered prospect research and personalized outreach.

As Manager, Enterprise Sales Development, you will scale a Sales Development Representative team focused on acquiring enterprise clients. You will manage sales development operations, collaborate with marketing, lead-generation, Enterprise Sales, and Client Partner teams, and grow the Toptal brand. The role requires coaching, metrics management, and modern sales technology expertise.

Key Responsibilities

Hire, onboard, train, and manage Sales Development Representatives

Develop dashboards, metrics, coaching, and performance incentives

Deploy AI workflows for research and personalized outreach





Optimize lead and pipeline creation with Enterprise Sales

Coach prospecting, qualification, prospect handoffs, and follow-up

Requirements

Bachelor’s degree required

Six years’ outbound sales or Sales Development Representative experience

Two years’ leadership experience

Salesloft, Salesforce, LinkedIn Sales Navigator, and lead-generation tools

Hands-on experience building and deploying AI agents for outbound sales

Bring enterprise pipeline leadership, AI sales innovation, and SDR coaching expertise to Toptal’s fully remote workforce.

📌 Enterprise Sales Development Manager (Winnipeg)
🏢 Toptal
📍 Winnipeg