Director, Customer Success

TOTAL EXPERT; Minneapolis (MN); Hybrid; USD 180,000 - 200,000; Full time

Benefits offered by this job

Medical insurance

Dental insurance

Vision insurance

HSA

FSA

Life insurance

Disability insurance

Flexible PTO

Parental leave

401(k) with employer match

Job summary

Total Expert, the Customer Operating System for financial services, seeks a senior Customer Success leader to own retention, renewals, and commercial outcomes. This hybrid US role includes guiding a growing CS team and aligning with Sales and Product to drive multi-year renewals and customer value.

You will lead up to 10 CSMs, deploy AI-enabled CS workflows, and partner with various functions to scale retention and revenue. Base salary ranges around $180k–$200k with full benefits.

Qualifications

• 8+ years in Customer Success, account management, or retention in B2B SaaS with ownership of a retention or revenue number.
• 4+ years leading a Customer Success or account management team with renewal/retention quotas.
• 3+ years in mortgage, banking, fintech, or adjacent financial services.
• Proven track record of improving GRR and NRR and reducing churn and downsell.
• Experience operating a tiered coverage model and capacity planning.
• Hands-on experience with CS platforms (Planhat, Gainsight) and health scoring.
• Demonstrated ability to build renewal forecasts and governance cadences.

Responsibilities

• Own retention, renewal execution, and commercial outcomes for your portfolio.
• Set renewal cadences, forecasts, and escalation models; proactively manage renewals before expiration.
• Coach CSMs to operate as commercial owners alongside AEs and defend price for multi-year renewals.
• Deliver renewal forecasts with clear commit, upside, and at-risk categorization.
• Partner with Sales on renewal strategy, attrition mitigation, and multi-year positioning.
• Lead risk identification and renewal governance, using data-driven health scoring.

Skills

Customer Success

Account Management

Retention

Renewals

Leadership

Forecasting

Health Score

AI in CS

Tools

Planhat

Gainsight

Job description

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.

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

Compensation/Benefits

: The anticipated base salary range for this role is $180,000 - $200,000 annually. Final total compensation offered is dependent upon the selected individual's qualifications and experience. The role is also eligible for variable compensation based on achievement of quota targets. As an employee of the company, you will be eligible to participate in the Employee Stock Option Plan. Total Expert offers a competitive range of benefits including Medical, Dental, Vision, HSA (Health Savings Account), FSA (Flexible Spending Accounts), company paid Life Insurance, Short-Term Disability, Long-Term Disability, Flexible Time-Off (FTO), Paid Parental Leave, and 401(k) with employer match.

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.