Head of Customer Success & Support

Ripple•Chicago, IL

11h•Hybrid

About The Position

Ripple Treasury is a high-growth, $100M ARR SaaS business delivering mission-critical solutions for the Office of the CFO. Our adaptable, native digital platform serves the world’s most demanding finance organisations — enabling CFOs, Controllers, and Treasury teams to operate with greater speed, accuracy, and confidence; the “Clarity to Act”. Our customers are large and enterprise-scale organisations, and we serve them through a fundamentally high-touch, relationship-driven model. We operate globally with significant presence across North America (US & Canada), Europe (London, Dublin, and Geneva), and Asia-Pacific (Singapore and Sydney). We are on a clear trajectory toward category leadership and are investing decisively in our customer experience and go-to-market capabilities to get there. As Head of Customer Success, you will own the full post-implementation customer experience — from go live through to deep adoption and long-term advocacy — for a global, enterprise customer base where relationships are complex, stakes are high, and expectations are demanding. This is a seat on the Leadership Team and a pivotal role in driving how we retain, grow, and scale with our customers. Your primary commercial mandate is the protection and growth of recurring revenue through disciplined retention management, pricing stewardship, and a deep commitment to driving product adoption. Where customers are getting maximum value from the platform, expansion naturally follows — and you will build the adoption engine that makes this a repeatable, measurable reality. You will lead Customer Success, Support, and Customer Education, building the systems, talent, and AI-powered tooling required to deliver measurable, repeatable value at scale. You will be the voice of the customer in the leadership team, a trusted commercial partner to Sales, and the leader who sets the standard for what great customer experience looks like in enterprise FinTech. Central to this role is the ownership of Ripple Treasury’s Customer Reference Programme. In enterprise software sales, references are not a courtesy — they are a commercial weapon. A well-prepared, enthusiastic reference from a peer CFO can accelerate a deal and eliminate competitive risk; a poor or unprepared one can destroy months of sales effort. Building a deep, diverse, and actively managed panel of reference customers is therefore a strategic priority for the business, and this role owns it end to end. The programme begins at implementation — identifying and nurturing potential advocates from the moment a customer goes live — and evolves throughout the customer lifetime into formal references, case studies, executive peer relationships, and public advocacy. Done well, the reference programme becomes one of Ripple Treasury’s most powerful go-to-market assets.

Requirements

10+ years of progressive experience in customer-facing leadership roles within B2B enterprise SaaS, with at least 3–5 years at the top table with clear ownership of post-sale revenue and retention.
Demonstrated track record of achieving and defending strong GRR metrics at scale — ideally in a $50M–$200M ARR SaaS business — with experience navigating complex enterprise renewal negotiations.
Proven experience building and scaling product adoption programmes that create a measurable link between feature engagement and commercial outcomes.
Deep experience partnering with Sales on customer-led growth motions — turning CS insight into pipeline and customer advocacy into revenue.
Hands-on experience deploying AI and automation tools within a CS or Support organisation — including customer health platforms, AI-assisted workflows, and self-serve/deflection tools.
Experience serving customers in the Office of the CFO, financial technology, ERP, FP&A, treasury, or GRC verticals is highly desirable — the ability to converse credibly with CFOs and finance leaders is essential.
Proven ability to manage high-touch relationships with enterprise or Fortune 500 customers, including executive sponsorship at C-Suite level across multiple geographies.
Track record of building globally distributed teams that operate cohesively across time zones, cultures, and regulatory environments.
Customer obsessed — you hold a deeply held belief that customer outcomes and business outcomes are inseparable, and you bring this perspective to every internal decision.
Commercially grounded — you understand that retention, pricing, and adoption are interconnected levers, and you manage them with precision and strategic intent.
AI-forward — you are genuinely enthusiastic about the potential of AI to change how customer organisations operate, and you have the credibility and hands-on experience to lead this transformation.
Data-driven — you operate from insight, not instinct alone; you are comfortable with health scoring models, cohort analysis, adoption funnels, and leading vs lagging indicators.
Executive presence — you are credible, compelling, and confident in front of enterprise customer executives.
Builder’s mindset — you are energised by the opportunity to create structure, process, and capability in a business that is still scaling, and you know the difference between building for now and building for scale.
Collaborative and Sales-aligned — you see CS and Sales as one commercial team with different roles, and you invest in making the partnership between them a genuine competitive advantage.

Nice To Haves

Experience in financial technology, ERP, FP&A, treasury, or GRC SaaS solutions.
Previous exposure to private equity or venture-backed high-growth environments.
Familiarity with market leading CS and CRM platforms.
Working knowledge of AI tools relevant to CS operations: LLM-based summarisation, predictive health scoring, AI-assisted communication, and in-product guidance platforms.
Multilingual capability or deep experience leading teams across English, Spanish, French, and German-speaking markets.

Responsibilities

Own gross revenue retention (GRR) as the primary commercial accountability of the role — building the operational rigour, early-warning systems, and executive relationship depth to protect and grow the recurring revenue base.
Lead the annual and in-cycle renewal process for enterprise accounts, ensuring renewals are managed proactively, professionally, and with a clear commercial strategy that reflects the value delivered.
Act as a key voice in pricing decisions — partnering with Finance, Product, and Sales leadership to ensure price positioning is grounded in demonstrated customer value, market context, and long-term retention dynamics.
Develop and manage a tiered account coverage model that matches resource intensity to account risk, strategic importance, and growth potential across the global portfolio.
Maintain a real-time view of customer health, renewal risk, and commercial exposure across all regions, and report this clearly and confidently to the leadership.
Define and own the adoption framework for the business — including feature activation milestones, user engagement benchmarks, and outcome-based success metrics aligned to CFO priorities.
Build structured Customer Success programmes — health check cadences, QBRs, and executive business reviews — that create a continuous conversation around value delivery and adoption progress.
Partner with Product to ensure the platform is intuitive, well-documented, and supported by in-app guidance, self-serve resources, and AI-assisted help that reduces friction and accelerates time-to-value.
Develop a Customer Education capability — including digital learning pathways, and power-user programmes — that embeds deep product knowledge within customer organisations.
Use adoption data to generate account-level intelligence that Sales can act on: identifying expansion-ready customers, surfacing whitespace opportunities, and flagging where new use cases are gaining traction.
Work closely with Sales and Marketing on the customer-led growth motion — ensuring CS insight feeds pipeline generation, case studies, and customer referral programmes.
Oversee the global Customer Support organisation, ensuring consistent, high-quality service delivery across all geographies and time zones (US, Canada, UK, Ireland, Switzerland, Singapore, and Australia).
Set and hold the team accountable to SLA commitments and customer satisfaction benchmarks — including CSAT, NPS, and time-to-resolution — that reflect the high standards our enterprise customers expect.
Drive a shift toward intelligent, AI-augmented support — deploying deflection tools, predictive issue detection, and AI-assisted case resolution that reduce effort for customers and free the team to focus on complex, high-value interactions.
Ensure Support is positioned as a proactive function, not just a reactive one — flagging adoption gaps, product friction, and at-risk signals to CS and Product in real time.
Define and own the AI and technology roadmap for the Customer organisation — selecting, deploying, and continuously improving the tools that underpin CS, Support, and Education workflows.
Champion the use of AI-driven customer health scoring that synthesizes product usage data, support ticket patterns, engagement signals, and sentiment to provide a predictive, real-time view of each account.
Deploy AI-assisted tooling for CSMs and Support teams — including intelligent playbook recommendations, automated at-risk alerts, AI-drafted customer communications, and summarisation of account history — to increase capacity and consistency.
Use AI to scale the Quality Business Review process: automating data preparation, surfacing the most relevant insights per account, and enabling CSMs to spend more time on strategic conversation and less on slide preparation.
Leverage AI-powered self-serve and in-product guidance to accelerate adoption journeys — reducing dependency on human-led intervention for common tasks and feature discovery.
Build a culture of experimentation within the team — regularly testing new AI tools, measuring their impact on key metrics, and scaling what works across the global CS organisation.
Partner with the Chief Technology Officer and Chief Product Officer to ensure the AI tooling strategy for the Customer team is aligned with the broader platform and data architecture.
Build and own a structured Customer Reference Programme that begins at implementation — identifying and nurturing potential reference customers from go-live, before they are ever needed by Sales, so that relationships are warm, stories are authentic, and references are given willingly rather than reluctantly.
Partner with the implementation and onboarding teams to embed reference-readiness into the customer journey from day one — setting expectations with new customers early, capturing initial success stories at go-live, and progressively building the relationship depth required for credible, high-quality references as the account matures.
Maintain a live, actively managed reference panel — segmented by industry, geography, use case, and customer size — that gives Sales the right reference for the right prospect at the right moment in every deal cycle. A generic reference is rarely as powerful as a matched one.
Protect reference customers with the same rigour as pipeline — monitoring their health, acting quickly when sentiment shifts, managing reference fatigue by rotating requests thoughtfully, and ensuring that every reference commitment is properly briefed, prepared, and followed up with appropriate recognition.
Work closely with Sales leadership to understand the deals where references are material to close — and escalate rapidly when a reference risk is identified. A single poor or unprepared reference in a competitive enterprise deal can be decisive; this function must be treated as a commercial priority, not an administrative one.
Expand advocacy beyond individual reference calls — building a programme that includes executive peer networks, customer advisory boards, co-authored thought leadership, conference speaking opportunities, and case studies that give willing customers meaningful ways to advocate publicly for Ripple Treasury in the CFO community.
Track reference programme health as a formal metric — including the size and quality of the active reference panel, reference request fulfilment rates, and the contribution of references and advocacy to Sales win rates — and report this to leadership alongside the core retention and adoption scorecard.
Serve as the definitive internal champion for the customer, synthesising feedback, usage trends, and renewal signals into actionable insight for Product, Engineering, Marketing, and leadership.
Establish robust VoC programmes — including NPS, QBRs, advisory councils, and win/loss analysis — that create a closed feedback loop from the frontline to the product roadmap and commercial strategy.
Partner closely with the Head of Sales to align on the commercial handoff from post-sale to Sales, ensuring expansion opportunities identified through adoption data are translated into qualified pipeline.
Represent the customer perspective in all leadership discussions.
Build, lead, and inspire a globally distributed customer-facing organisation across Customer Success and Support, with a culture that is accountable, data-driven, and genuinely customer-obsessed.
Develop a high-performance environment with clear career paths, coaching frameworks, and recognition programmes that attract and retain top talent across the US, Canada, UK, Ireland, Switzerland, Singapore, and Australia.
Drive AI literacy and adoption within the team — ensuring every CSM and Support professional is equipped and expected to use AI tools as a core part of their daily workflow, not an optional add-on.
Build the operational infrastructure — playbooks, KPI frameworks, health scoring, CS platforms, and reporting cadences — that makes the team scalable without losing the quality and personalisation that enterprise customers expect.

Benefits

Competitive salary, bonuses, and equity
Competitive benefits that cover physical and mental healthcare, retirement, family forming, and family support
Employee giving match
Mobile phone stipend
R&R days so you can rest and recharge
Generous wellness reimbursement and weekly onsite & virtual programming
Generous vacation policy - work with your manager to take time off when you need it
Industry-leading parental leave policies.
Family planning benefits.
Catered lunches, fully-stocked kitchens with premium snacks/beverages, and plenty of fun events