Client Success Manager (Canada) at DianaHR (W24) $40 - $55 CAD / hourly An AI-Powered HR Person CA / Remote (CA) Full-time US citizenship/visa not required 3+ years About DianaHR DianaHR is looking to disrupt the HR space by providing AI-enhanced support to the 1.4 million small and medium businesses within the U.S. that are struggling with their HR and people operations needs. Our goal is to provide these business owners with the expertise to setup and run their payroll, remain in compliance with state governments, maintain HR documentation, and onboard/offboard employees. About the role Client Success Manager This is a remote, contract role based in Canada and open only to Canadian residents. DianaHR is reshaping how small and medium-sized businesses manage their HR and people operations. We provide AI-enhanced support to help businesses set up payroll, stay compliant, manage onboarding, and handle employee documentation. Our team combines smart technology with human judgment to give business owners peace of mind. We’re a small, early-stage startup — which means the work is fast-paced, dynamic, and constantly evolving. We work hard, move quickly, and value people who can bring structure to ambiguity, stay steady under pressure, and thrive in the unstructured opportunity that comes with building something new. We’re looking for a Client Success Manager to join our growing team. This is a high-impact, client-facing role focused on driving excellent service delivery, managing HR-related workflows, and supporting operational excellence across multiple client accounts. What You’ll Do As a Client Success Manager, you’ll be the primary account manager and trusted partner for a portfolio of clients — building lasting relationships while ensuring smooth, compliant people operations. You will: Own client relationships Act as the day-to-day point of contact for multiple client accounts. Build trust through proactive communication, clear updates, and high-quality delivery. Anticipate client needs and provide confident, solution-oriented support. Drive HR-related operations for your client portfolio Oversee and execute workflows for: Payroll registration and setup Offer letters, onboarding, and employment documentation Basic benefits enrollment support State and local compliance filings Coordinate with third-party vendors (e.g., Gusto, ADP, brokers) to ensure timely and accurate completion of deliverables. Support & adhere to DianaHR operations Track client deliverables, deadlines, and compliance requirements to keep all accounts running smoothly. Identify potential risks or delays early and take ownership of driving solutions. Partner with Product and Engineering teams to improve DianaHR’s tools and automation. Work with the team to create and maintain proper documentation of all HR processes for clients. Mentor and lead within the team Serve as a pod leader, training and mentoring junior operators. Help shape our operational strategy while staying hands-on with client execution. Who You Are You don’t need to be an HR expert — but you do need to be an exceptional operator who can manage multiple client accounts with confidence and clarity. About you: 2-4 years of experience in client operations, customer success, strategy, or startup ops roles. Proven ability to manage multiple workflows and ensure deadlines are met without sacrificing accuracy and attention to detail Communicates clearly, professionally, and proactively with external clients. Learn quickly — especially when navigating new tools, regulations, or workflows. Highly organized and detail-oriented. Accuracy and follow through are your strengths. Thrives in fast-paced, evolving environments: adaptable, resourceful, and solution-oriented Motivated individual contributor who brings structure to ambiguity and enjoys building systems from the ground up Comfortable working with tools like Google Workspace, Notion, Slack, Zendesk, or similar. Bonus points if you have: Experience managing or mentoring others. Familiarity with HR platforms such as Gusto, ADP, Rippling, or similar Experience working with or alongside HR, payroll, or legal teams. Salary range is dependent on geographic location, prior experience, seniority, and demonstrated role related ability during the interview process. Why Join DianaHR? Meaningful work: We help small businesses thrive by taking complex HR work off their plates. Growth opportunity: You’ll wear many hats and help build systems from the ground up. Tight-knit team: We’re collaborative, high-performing, and focused on learning and impact. Culture of ownership: We value initiative, detail-orientation, and a willingness to roll up your sleeves.