Customer Service Trainer

Proper is a quickly growing startup that values your skills, voice, and happiness.  

We’re a team of developers, designers, engineers, accountants, CPAs, project managers, and creatives worldwide. But we’re also surfers, hikers, Sichuan-eaters, photographers, artists, world travelers, meme lovers, and life-havers.  Together, we provide the most technologically advanced property accounting services in the world. We’re proud to be creating something new that improves people’s lives while working together in a culture of collaboration, respect, communication, joy, and personal growth.Read more about what we do at Proper.ai

We’re seeking a Customer Service Trainer to join our team.

Proper is seeking a Customer Service Trainer who will not only facilitate training but will also monitor performance, iterate on methodologies, and ensure that the team consistently delivers a world-class customer experience. We’re looking for someone with a collaborative, positive, proactive attitude, and strong communication skills, who are excited to be working in a fast-paced environment that’s continuously evolving.  If that sounds like you and you’re excited by the idea of joining a world-class team that’s passionate about growing together, we look forward to hearing from you! Proper is a San Francisco-based tech startup. This full-time position would be based in LATAM.

• The Customer Service Trainer will be responsible for training and coaching customer-facing roles within the Accounting Team, primarily accountants transitioning into customer-facing responsibilities. This role will also work closely with the Operations Excellence Team to define, document, and implement Standard Operating Procedures (SOPs) and best practices for customer service.

• Training Development & Facilitation
• Design, develop, and facilitate customer service training programs tailored to accountants transitioning into customer-facing roles.
• Implement best-in-class training methodologies, including experiential learning, role-playing, and case studies.
• Conduct in-person and virtual training sessions in English (Bilingual Spanish/English required).
• SOPs & Best Practices Development
• Collaborate with the Operations Excellence Team to define and document customer service SOPs and best practices.
• Develop guidelines for handling difficult customer interactions, de-escalation techniques, and proactive engagement.
• Coaching & Continuous DevelopmentMonitor customer-facing team performance to identify skill gaps and training opportunities.
• Provide one-on-one coaching to team members struggling with assertiveness, confidence, or customer empathy.
• Conduct regular training refreshers to reinforce key customer service principles.
• Performance Measurement & Feedback
• Develop and track key performance indicators (KPIs) for customer service training effectiveness.
• Conduct post-training assessments to measure knowledge retention and application.
• Partner with leadership to implement feedback loops for continuous improvement.
• Cultural & Soft Skills Development
• Help accountants develop soft skills such as active listening, empathy, assertiveness, and relationship-building.
• Instill a mindset of customer-centric service to enhance overall client satisfaction.

• Hard/technical skills
• Customer service training development and facilitation.
• Experience training technical professionals (e.g., accountants, engineers, or analysts) in soft skills.
• Knowledge of customer service excellence frameworks (e.g., Ritz-Carlton Gold Standards, Disney Institute methodologies).
• Experience in developing and implementing SOPs for customer service teams.
• Strong knowledge of de-escalation techniques and customer engagement strategies.
• Fluent proficiency in English.
• Experience working in startup or BPO environments.
• Soft skills (e.g.: leadership, organizational skills, etc.)
• Effective communication and coaching skills.
• Ability to simplify complex customer interactions into structured training.
• Strong problem-solving and adaptability in high-growth environments.
• Confidence in working across multiple teams and departments.
• Data-driven decision-making for training effectiveness.

• Background in hospitality or luxury service training.
• Experience with Learning Management Systems (LMS) to track training progress.
• Exposure to coaching frameworks (e.g., GROW Model) for ongoing development.

• Business Administration, Communications, Education, Hospitality Management, or a related field.

• 5+ years of experience in training
• Prior experience training technical professionals to become customer-facing representatives is highly preferred.