Enterprise Sales Trainer – Customer Success at Upwork

Company Overview Upwork is the world’s work marketplace. We serve everyone from one-person startups to large, multinational corporations with a full range of services that enable companies to find, hire, and work with the best talent to get work done. Upwork is a remote-first company, embracing a culture that values flexibility, autonomy, and collaboration across distributed teams. We empower our employees to work from anywhere in the USA, fostering a diverse and inclusive environment where everyone can thrive. Position Summary Upwork is seeking a highly motivated and experienced Enterprise Sales Trainer - Customer Success to join our dynamic team. This is a fully REMOTE position, where you will play a pivotal role in onboarding, training, and continuously developing our Customer Success team. You will be responsible for designing, delivering, and evaluating engaging training programs that equip our Customer Success Managers (CSMs) with the knowledge, skills, and confidence to effectively drive customer adoption, retention, and growth on the Upwork platform. This role requires a strong understanding of customer success methodologies, enterprise sales processes, adult learning principles, and remote collaboration best practices. Key Responsibilities Conduct comprehensive needs assessments to identify knowledge and skill gaps within the Customer Success team. Design, develop, and deliver engaging and effective training programs, including virtual instructor-led training (VILT), e-learning modules, on-demand resources, and blended learning solutions. Create training materials, such as presentations, job aids, simulations, and assessments, that are tailored to the specific needs of the Customer Success team. Facilitate virtual training sessions using various online platforms and tools, ensuring a highly interactive and engaging learning experience. Collaborate with subject matter experts (SMEs) to ensure the accuracy and relevance of training content. Evaluate the effectiveness of training programs through various methods, such as surveys, quizzes, and performance data analysis. Continuously improve training programs based on feedback and performance data. Stay up-to-date on the latest trends in customer success, enterprise sales, and adult learning. Manage the Customer Success training calendar and ensure that training programs are delivered on time and within budget. Act as a resource and mentor for Customer Success Managers, providing ongoing support and guidance. Contribute to the development of a strong Customer Success culture within Upwork. Required Qualifications 5+ years of experience in customer success, sales training, or a related field, preferably in the technology industry. Proven ability to design, develop, and deliver engaging and effective training programs. Strong understanding of customer success methodologies, enterprise sales processes, and adult learning principles. Excellent communication, presentation, and facilitation skills. Proficiency in using virtual training platforms and tools, such as Zoom, Microsoft Teams, and learning management systems (LMS). Ability to work independently and as part of a remote team. Excellent time management and organizational skills. Must be able to work remotely from anywhere in the USA. Ability to work within Pacific Time Zone (PST/PDT) business hours. Technical Requirements To ensure a seamless remote working experience, you will need the following: Dedicated home office space that is quiet and free from distractions. High-speed internet connection with a minimum upload and download speed of 25 Mbps. Reliable computer equipment, including a laptop or desktop computer, webcam, and headset. Proficiency in using collaboration tools, such as Slack, Google Workspace, and Salesforce. Desired Skills Experience with instructional design software, such as Articulate Storyline or Adobe Captivate. Certification in customer success or sales training. Experience working in a fast-paced, high-growth environment. Familiarity with the Upwork platform. Compensation & Benefits The annual salary range for this REMOTE position is $110,000 - $140,000, depending on experience and location within the USA. Upwork offers a comprehensive benefits package, including: Medical, dental, and vision insurance. Paid time off and holidays. 401(k) with company match. Employee stock purchase plan. Home office stipend to help you set up your remote workspace. Flexible working hours. Opportunities for professional development and growth. Virtual team building activities to foster connection and collaboration. Occasional travel may be required for team meetups (approximately 1-2 times per year). How to Apply If you are a passionate and experienced sales trainer with a proven track record of success in a remote environment, we encourage you to apply. Please submit your resume and cover letter. Our virtual onboarding process ensures a smooth transition into our remote-first culture at Upwork. We look forward to hearing from you!