Director of Customer Success

red-oak; United States; On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Equity units via EOP

Comprehensive health coverage: medical

401(k) with a 3% company contribution

20 days PTO annually, plus your生日 off

Enhanced family leave

Life insurance

Job summary

Red Oak is seeking a Director of Customer Success to own the CS motion across our combined customer base with MirrorWeb, spanning the Compliance Connectivity Platform and preservation products. This hands-on leadership role carries day-to-day accountability and a mandate to scale the function with clear standards and coaching rhythms.

You will hire, develop, and lead a growing CSM team, drive product adoption, manage risk, and partner with Sales, Product, and Revenue Operations to ensure

Qualifications

• Experience leading a Customer Success team through growth or scale.
• Own gross retention as a core metric.
• Design or evolve a CS operating model: segmentation, health scoring, engagement standards, and reporting.
• Hands-on people leadership: coaching and performance management of a CSM team.
• Collaborate 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.

Responsibilities

• Own the CS motion across Red Oak and MirrorWeb's combined customer base - spanning the Compliance Connectivity Platform and MirrorWeb's Preservation products.
• 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.

Skills

Team leadership

Gross retention

CS operating model design

Cross-functional collaboration

AI in CS workflow

Performance management

Tools

Gong

Salesforce

Nooks

Job description

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