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CloudTrucks

Head of Customer Success

Sorry, this job was removed at 06:13 p.m. (PST) on Monday, Sep 29, 2025
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In-Office
San Francisco, CA
160K-200K Annually
In-Office
San Francisco, CA
160K-200K Annually

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The trucking industry is the backbone of the global economy. More than 70% of what we consume in the U.S. is moved by trucks. Those trucks are powered by over 3.5 million drivers per year and  create over $700B in annual revenue. Trucking is a massive industry but it is a traditional industry and like many traditional industries, it is ripe for innovation.

CloudTrucks is building the operating system for trucking and is the first platform specifically designed to empower truck drivers. Our all-in-one, “business in a box” solution optimizes and automates operations and accelerates cash-flow for drivers, so they can focus on building their business.

CloudTrucks is looking for a seasoned and experienced Customer Success leader to propel the Customer Success organization to the next level. The Head of Customer Success will work closely with CloudTrucks’ management team to shape the company’s commercial strategy. They will lead the execution of this strategy, drive revenue, and build an organization that is capable of operating at scale. This is a fantastic opportunity with a company that has a huge (and growing) market, strong product-market fit due to an early lead, and a strong founding team. As an integral member of the organization, you will play a key role in CloudTrucks’ success.

What you’ll do:
  • Lead the entire customer success org

  • Drive product alignment across customer prioritization and needs

  • Analyze customer usage data and key performance indicators (KPIs) to assess customer growth opportunities

  • Program manages the execution of strategic initiatives in partnership with cross-functional partners (Product, Sales, Marketing, Ops, Data Analytics, etc.)

  • Identifying opportunities to improve efficiency, productivity, and cost-effectiveness through process optimization and streamlining operations

  • Collaborating with other executives and departments to ensure alignment and synergy across functions, fostering cross-functional communication and collaboration

  • Nurture and mentor the team, establishing clear goals and fostering a spirit of collaboration and innovation

Qualifications:
  • 5+ years of experience leading and scaling Customer Success teams

  • Ability to translate customer needs into product and service improvements

  • You have succeeded in high-growth teams (whether in tech, operations, strategy, consulting, banking, or a related experience), and you've led teams to achieve audacious goals

  • Proven track record working directly with executives across multiple business lines.

  • Bias towards action, with the ability to quickly consider what long-term decisions must be made today and what can start as an MVP

  • A proven track record of concurrently managing multiple complex projects to completion within tight deadlines

  • You love thinking about problems from a fundamentals approach; you translate strategic vision into measurable success metrics and applicable plans

  • You back your decisions up with data, and you're comfortable pulling SQL or modeling in Excel (can maintain complex spreadsheets)

  • You're equally comfortable operating at 10,000 feet and 1 foot. You don't hesitate to get in the weeds and operate at the lowest level of detail, but you're just as comfortable thinking long-term and inspiring a team. No job is beneath you.

Nice to haves:
  • Experience in marketplaces and startups

  • Freight Industry background

  • Scaled CS teams growing from $50-100M+

  • Have succeeded in high-growth teams (whether in tech, operations, strategy, consulting, CS, or a related experience), and led teams to achieve audacious goals

A bit about our culture:

We value high autonomy, ownership, and delivering results - in short - whatever it takes to set our customers up for success. We encourage each other to push the envelope, execute quickly, and be resilient to failure. We also work occasional late nights or weekends to deliver an above-and-beyond customer experience, while respecting and celebrating each other's personal background, values and commitments. In return, we are well compensated, take pride in seeing outsized impact to our product, and have memorable experiences learning and growing alongside a truly exceptional set of peers.

About CloudTrucks

CloudTrucks is a virtual trucking carrier in the multi-billion dollar trucking space. Core to this industry are over 3.5M truck drivers. They move more than 70% of all goods transported around the U.S., yet operate in a highly fragmented industry with huge opportunities for products, services and automation. We strive to deliver solutions that help truck drivers operate with much greater efficiency, increase their revenue, and offload business complexity. We are looking for uniquely exceptional people to join us on our journey as we massively scale into an industry-defining business.

We provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

*This role requires 4 days in office in San Francisco. Our work from home day is Friday.

About CloudTrucks

CloudTrucks is a virtual trucking carrier in the multi-billion dollar trucking space. Core to this industry are over 3.5M truck drivers. They move more than 70% of all goods transported around the U.S., yet operate in a highly fragmented industry with huge opportunities for products, services and automation. We strive to deliver solutions that help truck drivers operate with much greater efficiency, increase their revenue, and offload business complexity. We are looking for uniquely exceptional people to join us on our journey as we massively scale into an industry-defining business.

We provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws.

HQ

CloudTrucks San Francisco, California, USA Office

San Francisco, California, United States, 94103

What you need to know about the San Francisco Tech Scene

San Francisco and the surrounding Bay Area attracts more startup funding than any other region in the world. Home to Stanford University and UC Berkeley, leading VC firms and several of the world’s most valuable companies, the Bay Area is the place to go for anyone looking to make it big in the tech industry. That said, San Francisco has a lot to offer beyond technology thanks to a thriving art and music scene, excellent food and a short drive to several of the country’s most beautiful recreational areas.

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