Content Specialist Team Lead

Company Overview

Milestone Technologies is a global IT managed services firm that partners with organizations to scale their technology, infrastructure and services to drive specific business outcomes such as digital transformation, innovation, and operational agility. Milestone is focused on building an employee-first, performance-based culture and for over 25 years, we have a demonstrated history of supporting category-defining enterprise clients that are growing ahead of the market. The company specializes in providing solutions across Application Services and Consulting, Digital Product Engineering, Digital Workplace Services, Private Cloud Services, AI/Automation, and ServiceNow. Milestone culture is built to provide a collaborative, inclusive environment that supports employees and empowers them to reach their full potential.

Our seasoned professionals deliver services based on Milestone’s best practices and service delivery framework. By leveraging our vast knowledge base to execute initiatives, we deliver both short-term and long-term value to our clients and apply continuous service improvement to deliver transformational benefits to IT. With Intelligent Automation, Milestone helps businesses further accelerate their IT transformation. The result is a sharper focus on business objectives and a dramatic improvement in employee productivity. Through our key technology partnerships and our people-first approach, Milestone continues to deliver industry-leading innovation to our clients. With more than 3,000 employees serving over 200 companies worldwide, we are following our mission of revolutionizing the way IT is deployed.

Job Overview

Position Summary

The Content Specialist Team Lead is responsible for leading the organization's technical writing function while driving the execution, governance, and continuous improvement of enterprise knowledge management initiatives. This role combines technical writing expertise, stakeholder management, project leadership, and direct team leadership to ensure documentation is accurate, standardized, and aligned with operational and business objectives.

The Lead serves as the primary point of contact for documentation governance, manages the Technical Writing team, and partners with client stakeholders, engineering, IT Service Management (ITSM), operations, and service delivery leadership to drive documentation initiatives from intake through retirement.

This is a hands‑on leadership role focused on leading the Technical Writing function, enabling consultative engagement, and ensuring successful execution of strategic knowledge‑management initiatives.

Key Responsibilities

Team Leadership & Capacity Management

Serve as the Team Lead for the Technical Writing function, providing day‑to‑day leadership, coaching, prioritization, and workload management while maintaining sufficient capacity to support the team.

Team Leadership

• Lead, mentor, and develop Technical Writers through coaching, performance feedback, and professional development.
• Coordinate work assignments, priorities, and resource allocation across documentation initiatives.
• Balance workload and capacity to ensure timely delivery of documentation commitments.
• Foster a culture of collaboration, accountability, and continuous improvement.
• Identify training opportunities and coordinate skill development across the team.

Capacity & Delivery Management

• Maintain visibility into team capacity, project commitments, and documentation backlog.
• Prioritize competing requests based on business impact and stakeholder needs.
• Remove delivery blockers and proactively manage execution risks.
• Monitor team performance, quality, and productivity metrics.
• Provide regular status reporting to leadership.

Consultative Documentation Leadership

Lead the organization's transition from traditional documentation support to a proactive, consultative knowledge‑management model.

Responsibilities include:

• Coordinate and oversee the Technical Writer upskilling roadmap, including stakeholder engagement, project management, knowledge management, and consulting skills.
• Protect Technical Writer capacity to enable proactive discovery sessions, documentation planning, taxonomy improvements, and stakeholder engagement.
• Drive documentation strategy rather than reacting to documentation requests.
• Promote documentation best practices and governance across the organization.

Stakeholder Management & Governance

Serve as the primary liaison between client stakeholders, ITSM content owners, technical teams, operations, and leadership.

Responsibilities include:

• Build and maintain trusted relationships with