About ToptalToptal is a global network of top talent in business, design, and technology that enables companies to scale their teams, on-demand. and team members based around the globe, Toptal is the world’s largest fully remote workforce. We take the best elements of virtual teams and combine them with a support structure that encourages innovation, social interaction, and fun. We see no borders, move at a fast pace, and are never afraid to break the mold.

As Manager, Enterprise Sales Development you will have the chance to lead and scale a world-class sales development team for one of the world’s most disruptive companies. You will be responsible for managing end-to-end sales development operations targeted towards acquiring new enterprise clients. You will lead the success of a high-energy team of Sales Development Representatives (SDRs).

You will be collaborating with marketing and lead-generation teams to plan and execute SDR goals, strategy, and tactics to grow the Toptal brand. This is a remote position. Resumes and communication must be submitted in English.

Hire, onboard, train, and manage a team of Sales Development Representatives. Motivate SDRs to exceed goals through coaching and incentives, and develop and maintain key performance metrics and dashboards that focus on maximizing performance. Drive AI innovation by identifying automation opportunities, rolling out agent-powered workflows for prospect research and personalized outreach, and coaching the team on adapting these in their daily practices.

Work with Enterprise Sales and Client Partner teams to optimize lead and pipeline creation.



Prospect, educate, qualify, and develop sales-ready leads and opportunities from lead-generation activities and outbound cold-calling into targeted accounts. Interact with prospects via phone and email to explain Toptal’s vision, identify opportunities, and generate interest.

Disseminate opportunities to appropriate sales reps, educate reps as necessary about the opportunity, and recommend follow-up action items. Coach and mentor team members, provide feedback, conduct performance reviews, and implement performance improvement plans if needed. Learn our sales method and selling process.

Be an active member of the SDR and Enterprise Sales Executive Leadership team, contributing to excellence. Scale the impact of the SDR function as you optimize the sales development process and build out your team. Bachelor’s degree is required.

Minimum of 6 years of experience as a Sales Development Representative or in an outbound sales role is a must.

Experience with Salesloft, Salesforce, LinkedIn Sales Navigator, and modern lead-generation tools is a must. Hands-on experience designing, building, and deploying AI agents to support outbound sales motions (e.automated prospect research, personalized outreach messages, sequences, or lead qualification) to improve SDR productivity or pipeline health. Be a creative, process-oriented person who is skilled at building relationships and composing effective communications.

Have a talent for writing compelling emails and subject lines for prospecting, directed to a technical and/or senior audience.

📌 Head of Sales Development (Remote) (Winnipeg)
🏢 Toptal
📍 Winnipeg