Customer Success Manager - FrontlineIQ

Company Overview: FrontlineIQ, an UP.Labs company, is the AI sales coaching platform for in-person sales teams: on the floor, in the showroom, at the counter, or across the desk. We are transforming how frontline salespeople learn, practice, and perform through natural voice interactions, real-world role-plays, and AI-powered scrimmaging that builds confidence and sharpens instincts in the flow of work. Built for sales managers and their sales teams, FrontlineIQ delivers real-time coaching, automated goal setting, and actionable insights to help their teams grow revenue, boost engagement, and close more deals. While we started in retail, our platform is built for any in-person sales environment: branches, boutiques, dealerships, or showrooms, anywhere in the world. With growing customer traction and strong support from UP.Labs Venture Studio, we are scaling rapidly. We are looking for experienced, action-oriented people who can execute and drive results to join our team and help redefine how the world's best sales teams train and perform. Role Overview: As a Customer Success Manager, you will own onboarding, value realization, renewal, and expansion for your book of business. This individual will play a critical role in building and nurturing enterprise-level relationships with our customers, who are typically senior leaders in L&D, operations or sales managing large field sales organizations. You will be expected to multithread across the full organization, from the C-suite and VP level down to the frontline sales associates, building trust and alignment at every layer. Reports to the Head of Customer Success. Key metrics: Time to Value, Net Revenue Retention, CLTV and Customer Advocacy. Location: Remote, Canada Responsibilities: Onboarding and Value Realization Lead structured onboarding engagements typically 4 to 10 weeks depending on scope Align stakeholders on success criteria, milestones, and measurable outcomes Drive early wins and document ROI to build executive confidence Ensure clean handoff from Sales and clear documentation of goals and scope Adoption, Training, and Support Deliver live training for admins, managers, and end users Provide ongoing enablement and workflow optimization Act as primary support contact, resolving issues directly or coordinating with Product and Engineering Monitor usage data and proactively address adoption risks Relationship Management Build and maintain multithreaded relationships across the full customer organization, from executive sponsors and economic buyers down to frontline managers and sales associates Deliver compelling presentations independently to senior executive audiences, including groups of 10 or more VP and C-suite stakeholders Serve as strategic advisor on how FrontlineIQ supports business goals Bring structured customer feedback to Product and Leadership Retention and Growth Own renewal strategy, ROI storytelling, and contract coordination Identify and drive upsell and cross sell opportunities Develop risk mitigation plans when health signals decline Track and report on adoption, engagement, executive alignment, and ROI progress Required Experience: 5 or more years in a high touch Customer Success role within SaaS Experience managing enterprise accounts in the $200K to $300K+ ARR range, with demonstrated ability to navigate complex, multi-layered organizations Proven track record of multithreading relationships from frontline teams to the C-suite Comfortable presenting independently to senior executive groups without supervision Experience in an early stage startup, ideally Series A or earlier Demonstrated ownership of renewals and expansion Background in retail software or direct experience working in retail earlier in your career Understanding of coaching philosophy and how managers develop individual performers; able to bring both the art and the science to conversations about coaching program design Exceptional written and verbal English Professional fluency in Spanish and/or French is a plus What Sets You Apart: Relentlessly customer focused and outcome driven Comfortable operating in ambiguity and building process while executing Equally strong in strategy and hands on delivery Knows intuitively when to follow the CS playbook and when to adapt, proactively shaping the engagement cadence to serve the customer's actual needs rather than defaulting to a fixed schedule Data oriented and confident using analytics and AI tools Resourceful, biased to action, and highly accountable Strong emotional intelligence and executive presence Energized by helping sales teams improve performance Brings genuine warmth and energy to every customer interaction Experience building Customer Success processes from zero Nice to Have: Familiarity with HubSpot, Slack, Google Workspace, Monday.com Experience managing L1 and L2 support workflows Building Knowledge Hub resources Product marketing background Why FrontlineIQ: You will join at a pivotal stage, shape the foundation of Customer Success, and directly impact retention, growth, and product direction. Backed by experienced operators and venture funding, we have the traction and resources to win. Now we are building the team to scale.