Director, Customer Success

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 capture so CSMs spend more time in customer conversations
• Partner with Product and Enablement on Pendo-driven in-app education and awareness campaigns that lift adoption at scale

Partner across the business

• Partner closely with the Director of Technical Account Management, CS Operations, and the Strategic Account Director to deliver one coherent customer experience across the CS organization
• Function as an elevated voice of the customer, translating field signal into prioritized, evidence-backed input to Product and Engineering
• Partner with Professional Services on implementation quality and time-to-value, and with Support on escalation paths and root-cause follow-through
• Provide regular metrics and KPIs to the Chief Lending Officer on operating model execution, retention forecasting, team performance, and portfolio risk trends

What we're looking for

• 8+ years in Customer Success, account management, or retention in B2B SaaS, including direct ownership of a retention or revenue number
• 4+ years leading a Customer Success or account management team, including teams carrying individual NRR, renewal, or retention quotas
• 3+ years in mortgage, banking, credit union, fintech, or adjacent financial services, at a lender or financial institution, or selling and delivering into one
• Proven track record of improving GRR and NRR and reducing controllable churn and downsell, with a credible account of the mechanisms that drove it
• Experience operating a tiered or segmented coverage model, not a single flat book, including the capacity planning and playbook design behind it
• Hands-on experience leveraging and maturing a Customer Success Platform (Planhat, Gainsight, or similar), including health score design and forecast governance
• Demonstrated ability to build a renewal forecast that holds, and to run a disciplined at-risk pipeline and renewal governance cadence
• Commercial fluency: co-owning renewals with Sales, building ROI and value-realization business cases, defending price, and positioning multi-year agreements
• Working knowledge of the mortgage lifecycle, from lead generation and application through closing, servicing, and borrower retention, and how loan officers, marketing teams, and production leaders operate
• Hands-on leader with a player-coach mentality and genuine comfort in customer conversations at the executive level
• Strong executive presence, presentation skills, and analytical mindset
• Ability to travel up to 25%

Preferred

• Experience implementing Pendo or a similar product experience platform to drive end-user awareness, education, and adoption
• Experience building a digital or low-touch CS motion for a long-tail segment, and scaling coverage through automation rather than headcount
• Practical experience deploying AI into a CS workflow, predictive scoring, prescribed plays, conversation intelligence, or automated account briefing
• Prior experience at a mortgage-focused or financial-institution-focused SaaS or fintech vendor
• Hands-on time inside a lending operation, loan officer, branch or production manager, or marketing leader at a lender
• Familiarity with Lender ecosystems, including LOS and POS platforms and the surrounding lender tech stack
• Comfort operating with a regulated buyer, including RESPA, TCPA, and UDAAP awareness and familiarity with financial institution security, compliance, and procurement review cycles
• BI and analytics fluency (Domo, Looker, Tableau, or similar) sufficient to interrogate a health score model rather than just consume a dashboard