Customer Success manager and leader (US or Canada)

We are seeking an experienced proactive manager and leader for our Customer Success team to help shape the next version of Customer Success at Tiller, integrating AI tools, building proactive customer education, and growing deeper product collaboration. The ideal candidate brings a deep understanding of customer success in a B2C SaaS environment, a passion for personal finance, and the ability to manage, evolve, and optimize both support processes and our broader customer success strategy in a fast-changing landscape. Success Ensure new and existing customers successfully onboard with Tiller’s services and make meaningful steps towards financial clarity. Deliver effective, efficient support that customers rave about. Proactively facilitate trial-to-paid conversion, strengthen retention, and continuously improve the customer journey. Key Responsibilities • Customer Onboarding & Education: • Design, iterate, and optimize educational resources (help center content, Intercom campaigns, videos, webinars, and AI) to help customers onboard and retain, all rooted in a Jobs To Be Done framework. • Ensure Customer Success is actively present in the Tiller Community forums, answering questions, sharing resources, and fostering engagement. • Team Management: • Recruit, coach, and retain a high-performing Customer Success team that reflects Tiller’s mission and values as the front line with customers. • Oversee day-to-day operations, ensuring timely, effective resolution of customer inquiries and issues. • Develop and refine support processes to leverage AI, improve efficiency, and boost customer satisfaction. • Ensure escalated customer issues are resolved effectively through coordination with the CS team, product, and engineering. • Metrics & Reporting • Success is measured by faster onboarding, higher adoption, stronger retention, and advocacy. • Report on key metrics related to customer success and the efficacy of onboarding and educational experiments and processes. • Customer Engagement • Proactively engage with and interview customers to understand their needs and share learnings with product, marketing, and engineering teams. • Identify opportunities for upselling and cross-selling additional features that align with customers’ goals. • Team Collaboration: • Share customer success insights that provide context to the rest of the Tiller team so they can do their jobs most effectively. • Provide structured customer insights with the product team to directly influence features and roadmap. Qualifications • Proven experience in a Customer Success Manager role, preferably within a B2C SaaS environment to drive engagement, retention, and customer growth. • Comfortable experimenting with AI-assisted workflows and evolving processes. • Experience managing and developing a Customer Success team, with a strong understanding of support processes and best practices. • Strong understanding of personal finance, budgeting, and using spreadsheets for financial management. • Excellent communication and interpersonal skills, with the ability to build rapport and trust across diverse customer groups. • Analytical mindset with the ability to interpret data and translate insights into actionable strategies. • Hands-on experience with Intercom, including automating workflows and managing messaging campaigns • Self-motivated, highly organized, and able to work effectively in a remote environment. • Flexible and creative thinker with experience building and executing engagement strategies from customer journey maps. Why Tiller? • Mission-Driven: Be part of a team that is passionate about helping people take control of their financial lives. Hear about Tiller in our team's own words: • Growth Opportunities: We support our team members’ career development and offer opportunities for growth within the company. • Collaborative Environment: Work with a talented and supportive team that values innovation, creativity, and continuous improvement. • Remote-First Culture: Work anywhere with the flexibility to balance work and life. How to Apply If you’re excited about helping people achieve their financial goals and have the skills to drive customer success, we’d love to hear from you! US and Canada applicants only please. Please apply by filling out an application here. Apply tot his job