Candidates with experience in SaaS or compliance/regulated environments and a track record of owning gross retention will find this leadership role in a fast-growing organization with high visibility and impact.
Derived from job-description analysis by Serendipath's career intelligence engine.
Original posting from Red Oak via Ashby
ABOUT RED OAK
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 MATTERS
Red 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 LIKE
- Gross 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.
THE ROLE
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
WHAT YOU'LL BRING
- 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
BENEFITS
- 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
HOW WE WORK
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 STRUCTURE
Location: Austin HQ
Source: Red Oak careers (Ashby)