Head of Customer Success

3 weeks ago


Chicago, United States Cargado Full time
About The Company

Cargado, the first invite-only load board for cross-border Mexico freight, launched in April 2024 by freight industry veterans Matt Silver and Rylan Hawkins. Cargado's product simplifies the cross-border freight experience and has helped drive the historic rise of nearshoring and growing demand for improved cross-border logistics. Over 70 logistics companies leverage Cargado to get loads booked faster with greater transparency and a trusted network of carriers. Cargado has raised nearly $10M since starting in October 2023 from investors such as Primary Venture Partners, Ironspring Ventures, Zenda Capital, Wischoff Ventures, and RyderVentures.

About the Role:

Cargado is seeking a dynamic and strategic Head of Customer Success to join our Go-To-Market team as a pivotal early hire. In this leadership role, you will be responsible for building and scaling our Customer Success (CS) function, defining foundational processes, and driving a customer-first culture that ensures long-term retention and growth.

What You’ll Do

  • Lead and Scale the Team: Build and manage a high-performing team of Customer Success Managers, with plans to expand throughout 2025 and beyond.
  • Establish Strategic Vision: Shape and execute the foundational processes, frameworks, and long-term vision for Cargado’s Customer Success function.
  • Drive Retention and Success: Own the retention goals for 2025, ensuring our customers achieve their desired outcomes with Cargado’s solutions.
  • Customer Advocacy: Oversee the end-to-end customer journey, including implementation, training, support, and ongoing engagement, ensuring a world-class customer experience.
  • Cross-Functional Partnership: Collaborate effectively with Sales, Product, and Engineering teams, acting as the "voice of the customer" to influence product development and organizational priorities.
  • Insights and Impact: Leverage customer data to drive actionable insights, measure success, and refine strategies for continuous improvement.

About You

  • Experience: 10+ years of experience in Customer Success, with a proven track record of building scalable processes and leading high-performing teams in a SaaS environment.
  • Customer-Centric Mindset: Deep passion for enabling customer success, demonstrated by a history of fostering strong customer relationships and driving retention and expansion.
  • Strategic Thinking: Ability to define and execute a vision for the CS function while balancing both immediate priorities and long-term goals.
  • Analytical Acumen: Strong analytical skills with the ability to interpret customer data and translate insights into actionable strategies.
  • Leadership: Skilled at coaching and developing individual contributors to achieve their full potential, creating a culture of excellence and accountability.
  • Collaborative: Exceptional communication and interpersonal skills, with the ability to build trust and alignment across diverse teams.


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