Senior Manager, Customer Enablement

Toptal, LLC

Job Overview

Location

Canada

Job Type

Full-time

Full Job Description

📋 Description

• Lead the design, execution, and continuous improvement of scalable customer enablement programs that empower sales teams across Enterprise, SMB, and Services to sell confidently and effectively.
• Partner with executive leadership to translate business priorities into strategic enablement initiatives aligned with company objectives and sales goals.
• Own end-to-end enablement programs including planning, development, delivery, and measurement of outcomes using clear success metrics and data-driven insights.
• Design and deliver engaging learning experiences through instructor-led training, self-paced modules, live webinars, workshops, and reinforcement sessions using Toptal’s LMS and other tools.
• Develop and maintain comprehensive enablement resources including playbooks, learning paths, reference materials, and knowledge repositories to support seller adoption and performance.
• Define and track key performance indicators such as adoption rates, certification completion, behavior change, and business impact to evaluate program effectiveness.
• Collect and analyze qualitative and quantitative feedback from learners and stakeholders to refine programs and prioritize future investments.
• Build and maintain trusted relationships with Sales Leadership and cross-functional teams to understand business needs and align enablement solutions with evolving go-to-market strategies.
• Influence priorities and drive alignment across stakeholders using the enablement calendar and clear communication of program goals and timelines.
• Communicate program impact and recommendations to executives with tailored messaging appropriate for senior leaders, managers, and front-line sellers.
• Develop and implement change management strategies to drive long-term adoption of new products, messaging, tools, and sales motions beyond initial training.
• Create reinforcement plans that include coaching resources, manager enablement, targeted communications, and ongoing support to sustain behavioral change.
• Ensure all enablement materials remain organized, accessible, up-to-date, and aligned with current product offerings and sales processes.
• Support onboarding programs and knowledge management systems to ensure new hires and existing sellers have timely access to critical information.
• Manage incoming enablement requests while balancing strategic priorities and operational efficiency.
• Continuously evaluate and improve the seller experience by identifying gaps through performance data, stakeholder feedback, and sales insights.
• Collaborate with the existing enablement team to co-create release strategies, communications, and improvement initiatives.
• Independently own and lead enablement programs by the sixth month, driving internal change and increasing team effectiveness.
• Become a trusted business partner to Customer Leadership and stakeholders across Toptal by the first year, transforming how enablement supports client-facing teams.
• Operate in a fully remote, global environment requiring exceptional written and verbal communication across diverse geographies, time zones, and personality types.
• Thrive in a fast-paced, rapidly growing organization with multiple competing priorities, tight deadlines, and a high degree of autonomy.
• Contribute as a world-class individual contributor—this role requires hands-on execution, not just delegation.
• Bring a fun, collaborative, and proactive attitude to a team that values problem-solving, cohesion, and a sense of humor.

🎯 Requirements

• Bachelor’s degree required
• 5-7+ years of experience in Enablement, Operations, Strategy, or similar role
• Proven experience building training programs and supporting sales organizations
• Experience with learning management systems (LMS) and sales tools
• Strong project management and stakeholder management skills
• Excellent written and verbal communication skills in English

🏖️ Benefits

• Fully remote work environment with global team members
• Opportunity to work with a high-performing, fast-paced, and innovative company
• Collaborative culture that encourages innovation, social interaction, and fun
• Autonomy to lead strategic initiatives and drive measurable business impact
• Exposure to executive leadership and cross-functional teams across the organization
• No visa sponsorship offered

Skills & Technologies

Senior

Remote

Degree Required

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Toptal, LLC

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About Toptal, LLC

Toptal operates a global marketplace that screens and connects businesses with freelance software engineers, designers, finance experts, product managers, and project managers. Founded in 2010, the company uses a rigorous vetting process—accepting fewer than 3% of applicants—to supply on-demand talent for short-term contracts or long-term engagements. Clients range from startups to Fortune 500 enterprises seeking scalable teams without traditional hiring overhead. Toptal handles talent matching, contracts, and payments, enabling remote collaboration across time zones. The fully distributed organization itself has no central headquarters and relies on the same freelance model internally.

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