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Roadshow Support Specialist (Part-Time, Weekends)

Remote · Kenya Full-time

True Classic is hiring a Part-Time Weekend Roadshow Support Specialist to lead weekend field execution and real-time support for our Costco roadshow program. In this role you will serve as the central point of contact for field teams, troubleshoot operational issues, and coordinate solutions to ensure seamless execution and maximize weekend sales performance. All of True Classic's roles are global and omni-channel, leading designated areas of accountability across all product categories, countries, and different sales & marketing channels. This means you will have the opportunity to impact our operations worldwide, ensuring a cohesive strategy that aligns with our overall business objectives and drives success across various markets and platforms Areas of Accountability Weekend Roadshow Support & Execution

  • Serve as the primary on-call support for weekend roadshows, ensuring rapid response to field team needs
  • Provide real-time troubleshooting across staffing, inventory, and merchandising execution

Field Communication & Coordination

  • Act as the central point of contact for field reps, regional managers, and Costco/warehouse partners
  • Maintain constant communication via Slack and other real-time tools to ensure alignment

Issue Resolution & Escalation Management

  • Quickly assess and resolve field issues that impact sales performance
  • Coordinate solutions for last-minute coverage gaps, including rep call-outs or absences

Performance Monitoring & Risk Mitigation

  • Monitor weekend performance and proactively flag risks to prevent lost sales opportunities
  • Support achievement of key metrics including sales targets, response times, and coverage

Cross Functional Collaboration

  • Field Sales Teams: Support reps in real-time to ensure strong execution and sales performance
  • Regional Managers: Partner to escalate issues, align on solutions, and maintain coverage
  • Retail Operations: Coordinate on inventory, merchandising standards, and operational execution
  • Customer Experience / Support: Ensure consistent communication standards and issue resolution
  • Planning & Inventory Teams: Flag inventory risks and support proactive solutions during peak periods

Qualifications

  • 2+ years of customer-facing or field support experience (retail, wholesale, or events preferred)
  • Proven ability to manage high-pressure situations and resolve escalations with urgency
  • Strong experience using Slack or similar real-time communication tools
  • Highly organized, responsive, and solutions-oriented
  • Availability to work weekends (Saturday–Sunday) and remain on-call during peak hours

Preferred Qualifications

  • Experience supporting Costco or roadshow environments
  • Background in retail field operations or event-based sales programs
  • Demonstrated success supporting revenue-driving initiatives
  • Familiarity with staffing coordination and last-minute coverage planning
  • Experience working in fast-paced, high-growth environments

Workplace Arrangement Remote This is a part-time role with required weekend coverage (Saturday–Sunday). The position is primarily remote but requires real-time support of field operations during peak selling hours, with an expectation of high responsiveness and availability.

Compensation

  • Salary Range: $20-$25/hour
  • PTO and sick time
  • $100/month Wellness Stipend
  • $1,000/year True Classic merchandise allowance

True Classic is proud to be an equal opportunity employer. We celebrate and support differences in race, religion, color, national origin, gender, sexual orientation, gender identity, age, veteran status, and abilities. If you need assistance or accommodation due to a disability, please contact Human Resources. About True Classic At True Classic, our purpose is simple: empower everyone to look good and feel good. Founded in 2019, we’re a fast-growing apparel brand obsessed with fit, quality, and impact. But we’re building more than great products—we’re building a high-performance team where smart, driven people do meaningful work, move fast, and see the direct results of what they create. Everything we do is guided by the True Classic Operating System (TCOS) —the principles that shape how we work, make decisions, and win together:

  • Move the Needle – Our #1 value and the ultimate filter for decision-making. We focus on delivering tangible, measurable results that drive real business impact.
  • Paint the Pic

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