Senior Customer Success Manager

We are seeking a Senior Customer Success Manager to drive adoption, retention, and expansion across our customer base. This role combines strategic account ownership with operational execution, leveraging data, workflows, and AI-driven insights to deliver measurable customer outcomes. You will work with customers whose teams are often busy and not highly technical, guiding them to fully integrate Jobba’s platform into their business processes. You will also play a key role in operationalizing Customer Success through our Customer Success Platform (CSP), Planhat, ensuring consistent, scalable delivery across onboarding, adoption, and ongoing success management. As a Senior Customer Success Manager , you will manage complex and high-value accounts while contributing to the development of scalable CS processes, playbooks, and AI-driven workflows that improve Net Revenue Retention (NRR) and customer experience. Responsibilities Lead the successful transition from sale to client, executing structured onboarding workflows aligned to standardized implementation frameworks. Drive customer outcomes through defined success plans, milestones, and measurable adoption KPIs. Leverage Planhat (CSP) to: Manage customer health scoring, lifecycle stages, and risk signals Execute automated workflows (onboarding, adoption, risk mitigation, expansion) Maintain accurate customer data as a system of record Build trusted advisor relationships by understanding customer business models and aligning Jobba solutions to operational and financial outcomes. Proactively monitor usage, engagement, and sentiment data to identify churn risks and expansion opportunities early. Conduct data-driven Executive Business Reviews (EBRs) focused on value realization and ROI. Partner with Product and Support to close the feedback loop on feature requests, issues, and roadmap alignment. Support and influence expansion and upsell opportunities based on adoption patterns and customer maturity. Contribute to customer segmentation strategies (high-touch vs. scaled/AI-led engagement models). Develop and deliver training programs leveraging modern content delivery (LMS, video, knowledge base). Drive improvements in customer-facing processes, including onboarding standardization and adoption frameworks. Coach and mentor junior team members and contribute to a scalable CS operating model. Specific duties and responsibilities may be requested based on company need without changing the general nature and scope of the job or level of responsibility. Required Skills 5–7 years of experience in Customer Success, Consulting, or SaaS implementation. Proven ability to drive adoption, retention, and expansion (NRR-focused) in a B2B SaaS environment. Experience working with a Customer Success Platform (CSP) such as Planhat (preferred), Gainsight, Totango, or similar. Strong data orientation with the ability to translate usage data, health scores, and customer signals into actionable insights. Ability to operate in both high-touch (strategic accounts) and scaled (process-driven / automated) CS models. Strong business acumen with the ability to connect product usage to customer ROI and operational outcomes. Excellent communication skills, including executive-level storytelling and consultative engagement. Technical aptitude to navigate tools such as Planhat, Zendesk, Jira, BI tools, and CRM systems. Preferred Skills Experience implementing or operating within a Planhat-driven CS environment, including workflows, health scoring, and automation. Familiarity with AI-enabled Customer Success practices (predictive risk identification, automated playbooks, next‑best actions). Experience building or contributing to CS playbooks, success plans, and standardized onboarding frameworks. Knowledge of customer portals, LMS platforms, and scalable training delivery models. Construction, field service, or job management software experience. Background in process transformation or operational scaling within a CS organization. Experience working in environments transitioning from reactive to proactive/predictive Customer Success models. Experience operating in a Customer Success organization transitioning to a predictive, AI-enabled, and CSP-driven model is strongly preferred. Why Jobba Jobba Trade Technologies is built on cross‑team collaboration created through customer and team interactions. Our Rosemont location has easy access to the Blue line and freeways. In addition to having ample office space to provide a comfortable working environment, we offer an onsite gym, free parking, cafés, and knowledgeable team members you can learn from & grow with. While we are primarily onsite (4/1), we each have priorities outside of work and are flexible to support our team. Company Benefits Jobba offers attractive and generous employee benefits. A comprehensive list can be found on our website: About Jobba Trade Technologies Jobba Trade Technologies is a cloud‑based SaaS that helps roofing companies communicate between the field team and office teams to provide effective job management with an engaging customer experience. These client management solutions create important outcomes— increased profits and better client retention and referrals. At Jobba, we focus on continuous improvement—of our product, of our company, and of ourselves. We don’t expect our employees to be perfect. We know you’ll be excited to be learning and growing all while positively impacting our clients and our business. Jobba Trade Technologies offers a comprehensive benefits package including health, dental, vision, life, 401K and 401K matching. We are an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. For this role, we are unable to sponsor or take over sponsorship for work visas. #J-18808-Ljbffr Jobba Trade Technologies