Red Oak builds compliance software for financial services firms.
Our vision: We become the compliance layer every Financial Services firm runs on.
Today, we serve 19 of the top 20 global asset managers, including BlackRock, Vanguard, PIMCO, and Morgan Stanley. Our customers report $95–101T in combined AUM.
Why This Role MattersRed Oak and MirrorWeb are integrating two organizations during a period of significant growth, and Customer Success is scaling with it — a team of three CSMs growing to five, serving nearly 1,600 customers on a combined platform. This role owns that motion end to end: how success is measured, how risk is caught before it becomes churn, and how a growing team operates with consistency and accountability. The Director of Customer Success will define the future of the function — operating model, team structure, and customer motions.
High ownership. High visibility. High impact.
What Success Looks LikeGross retention. Drive GRR consistently above target, with customer risk identified and addressed well ahead of renewal.
Team standard. CSMs operate with clear ownership, standardized engagement models, and coaching rhythms that scale as the team grows.
Product adoption. Customers actively adopt the products they own, with value documented through success plans and outcome tracking.
Operating model. A data-driven CS function with clear health indicators, segmentation, and AI-powered workflows built to scale.
You'll own the Customer Success motion across Red Oak and MirrorWeb's combined customer base — spanning the Compliance Connectivity Platform (Ad Review, Registration Management, 4U Connect, 4U Engage, digital communications surveillance) and MirrorWeb's Preservation products. This is a hands-on leadership seat with direct accountability for day-to-day CS execution and team performance.
Build and operationalize a proactive CS motion with clear standards for engagement, success planning, risk management, and customer outcomes
Hire, develop, and lead a growing CSM team — setting expectations, coaching rhythms, performance management, and accountability
Drive adoption across the combined product suite so customers understand, use, and realize measurable value from what they own
Identify whitespace and expansion opportunities within the CS book of business and partner with Account Management on handoff
Own decision-making for CS operating model, team structure, segmentation, and engagement standards
Build a scalable, data-driven CS operating model with clear health indicators, segmentation, and reporting
Define and drive how AI is adopted across Customer Success — use AI tools like Gong, Salesforce, and Nooks to surface risk signals, automate account prep and follow-up, and prioritize where CSMs spend their time
Partner cross-functionally with Product, Support, Implementation, and Revenue Operations to ensure customers onboard, adopt, and renew predictably
Experience leading a Customer Success team through a period of active growth or scale, ideally in a SaaS or compliance/regulated environment
A track record of owning gross retention as a core, accountable metric
Experience designing or evolving a CS operating model: segmentation, health scoring, engagement standards, and reporting
Hands-on people leadership — hiring, coaching, and performance management of a CSM team
Comfort operating cross-functionally with Sales, Account Management, Product, and Revenue Operations
AI fluency in your CS workflow: using tools like Gong, Salesforce, and Nooks to surface risk, automate account prep, and drive team productivity. This is table stakes here
Clear, direct communication style — comfortable setting expectations and holding a team accountable
A bias toward proactively building and defining the function as the organization scales
Equity units via EOP (Employee Ownership Plan): share in what we're building
Comprehensive health coverage: medical, dental, and vision
401(k) with a 3% company contribution
20 days PTO annually, plus your birthday off and paid sick leave
Enhanced family leave
Life insurance
We move fast and expect ownership at every level. You'll have direct access to Product, Sales, and Revenue Operations leadership, and the latitude to build the CS function the way it should work.
Work StructureLocation: Austin HQ
Skills Required
- Experience leading a Customer Success team through active growth or scale, ideally in a SaaS or compliance/regulated environment
- Track record of owning gross retention as a core accountable metric
- Experience designing or evolving a Customer Success operating model, including segmentation, health scoring, engagement standards, and reporting
- Hands-on people leadership, including hiring, coaching, and performance management of a Customer Success Manager team
- Ability to operate cross-functionally with Sales, Account Management, Product, and Revenue Operations
- AI fluency in Customer Success workflows, including tools such as Gong, Salesforce, and Nooks
- Clear, direct communication style with the ability to set expectations and hold a team accountable
- Bias toward proactively building and defining the Customer Success function as the organization scales
What We Do
Red Oak’s Compliance Connectivity Platform unifies content creation, review, distribution, and supervision into a single, compliance-grade system built specifically for financial services. Powered by transparent, auditable AI, Red Oak streamlines marketing review workflows, reduces friction between compliance and marketing teams, and enables faster, compliant growth. Once approved, content flows seamlessly through 4U for compliant distribution, engagement, and analytics—giving firms end-to-end visibility and control. Built by compliance experts and delivered with white-glove implementation and support, Red Oak helps firms stay audit-ready while moving faster with confidence. Red Oak also offers modular solutions to further automate compliance operations, including attestations, forms review, gifts and non-cash compensation, regulatory inquiries, AML and fraud case management, and RFP review.
