Director, Customer Success

Total Expert is the Customer Operating System for financial services. Our purpose-built platform combines a system of context with a system of action that enables humans and AI Assistants to engage in the moments that matter and earn customers for life. Since 2016 Total Expert has enabled more than seven trillion dollars of funded loan volume. The Director of Customer Success leads the CSM organization at Total Expert and owns the execution of our retention operating model. Reporting to the Chief Lending Officer and managing a team of up to 10 Customer Success Managers, this leader is accountable for Gross Revenue Retention and Net Revenue Retention, for reducing controllable churn and downsell, and for ensuring our customers consistently realize measurable, defensible value from the Total Expert platform. This is a quota-bearing role. You and every CSM on your team carry annual NRR and attrition targets, and your CSMs are commercial owners alongside their Account Executives, responsible for renewal, health, and expansion on their assigned accounts, including multi-year renewal positioning. Just as important, this role is a maturity mandate. Total Expert has defined its Customer Success operating model, tiered coverage model, proactive risk identification, renewal governance, and an AI-enabled path to drive efficiency throughout Customer Success. We are looking for a leader who understands our customers deeply, has operationalized a model like this before, and can take our CS function from defined to consistently executed and measurably predictable. You should expect to spend as much time building the machine as running it. This position is remote for candidates residing outside of Minneapolis, MN. For candidates based in the Minneapolis, MN area, the position follows a hybrid schedule with three on-site days per week in our St. Louis Park, MN office. What you'll be doing Own retention, renewal execution, and commercial outcomes Own overall customer retention, renewal execution, and downsell mitigation for your portfolio, delivering against annual GRR, NRR, and gross attrition targets Establish and enforce consistent renewal cadences, forecasting processes, and escalation models — and ensure every renewal is proactively managed well in advance of contract expiration Coach CSMs to operate as true commercial owners alongside their AEs: build the value case, defend price, position multi-year renewals, and negotiate to durable outcomes Deliver a renewal forecast with clear commit, upside, and at-risk categorization that holds up under executive and customer scrutiny Partner with Sales on renewal strategy, attrition mitigation, upsell opportunities, multi-year positioning, and commercial alignment Serve as the escalation point for high-risk and strategic customer situations, engaging customer executives directly Run proactive risk identification and renewal governance Operate our risk model so that attrition risk is flagged multiple quarters ahead of renewal not discovered during the renewal process Leverage data-driven health scoring across adoption, usage, engagement, and sentiment, and continuously improve the weighting and predictive accuracy of the model Diagnose risk by driver, and match the mitigation play to the driver rather than applying a generic save motion, ultimately turning these into playbooks that enable all CSMs Build joint CSM and AE mitigation plans with named executive sponsors, and hold the team to documented success plans Run the weekly and monthly at-risk pipeline and renewal governance cadences, keeping Sales, Finance, and Product aligned on exposure and actions Use ROI and success metric data to quantify realized value per customer and convert it into the renewal business case Operate and mature the tiered coverage model Execute and refine our tiered coverage model, high touch for Tier 1–2, medium touch for Tier 3, and a digital-first low-touch motion for Tier 4, so the right resources sit on the right customers Own segmentation, book balancing, and capacity planning across the team, and build the data-backed case for headcount and coverage changes Codify and automate success playbooks, including Product Adoption Acceleration, Customer Intelligence Activation, and Executive Alignment Set and enforce forecast hygiene, health scoring discipline, and QBR/EBR tracking standards in Planhat, partnering with CS Operations on centralized CSP administration Ensure a consistent QBR and EBR cadence with structured success planning across the portfolio Lead, coach, and develop the team Lead, coach, and develop a team of up to 10 CSMs as a hands-on player-coach, in the accounts, on the calls, and in the room for the hard conversations Recruit, hire, and onboard CSMs against a structured 60-day ramp plan that reaches full book ownership on a predictable timeline Run a consistent coaching cadence of 1:1s, call and QBR/EBR shadowing, and written development plans reviewed quarterly Manage to the variable comp plan, making NRR and multi-year renewal targets clear, visible, and coachable at the individual level Set clear performance expectations, address underperformance early and directly, and build career paths that develop your own successor Drive AI-enabled and Digital Customer Success Partner with CS Operations to evolve toward Digital Customer Success, automated campaigns executed on behalf of the CSM, auto-generated account briefs and QBR decks, and coverage that scales without added headcount Deploy predictive health scoring and AI-prescribed save plays, and hold the team accountable for acting on the signal Apply conversation intelligence, call summaries, action items, and sentiment analysis, to surface competitive and churn language early Drive CSM productivity through AI-assisted workflows and building AI-agents that can autonomously assist daily CSM activities, automating forecast hygiene and note