Director of Customer Experience

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

Job summary

Red Oak is seeking a senior leader to own the post-sale client journey across Implementation and Support. You will shape the organizational structure, scale a high-touch experience, and bridge two merging teams into one cohesive function.

You will guide leadership, set shared metrics, and drive faster time-to-value for Enterprise and digital accounts while preserving the high-quality experience that clients expect. This is a pivotal role at a defining moment for the company.

Qualifications

• 8+ years of post-sale experience across Implementation, Support, or Customer Experience.
• 5+ years leading teams in Implementation, Support, or Customer Experience.
• Strong SaaS mindset and service-excellence focus.
• Experience navigating organizational change, ideally post-merger or post-acquisition.

Responsibilities

• Own the end-to-end post-sale client experience across Implementation and Support, aligning strategy and standards.
• Manage Implementation and Support leadership, prioritizing resources and coaching across teams.
• Define and track shared metrics: timelines, time-to-value, response times, and client satisfaction.
• Build a single escalation path for cross-boundary issues with one accountable owner.
• Clarify scope of support versus customer success and re-align responsibilities accordingly.
• Leverage AI to scale service, including ticket triage, resolution, and onboarding automation.
• Tighten onboarding sequencing to shorten time-to-value for Enterprise accounts while supporting high-volume digital self-serve.
• Collaborate with Customer Success, Product, and Engineering to improve handoffs and address structural issues.

Skills

Post-sale experience

People leadership

SaaS expertise

Change management

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, alongside 1,550+ regulated firms. Our customers report $95-101T in combined AUM.

Why This Role Matters

Customer Experience is why Red Oak wins. Our NPS of 64 isn't a nice-to-have metric - it's the reason clients choose us and keep choosing us, and it's the foundation of our retention and satisfaction numbers. This role exists to protect that.

You'll bring Implementation and Support together as one unified Customer Experience function - one strategy, one bar for quality, one clear escalation path. And you're doing it at a pivotal moment: as we bring two customer bases that have each been served differently onto one model, you'll need to preserve the high-touch experience that earned that NPS score while moving fast to build the structure that lets it scale across a much bigger, more complex customer base. We serve everyone from SMB to large Enterprise, and each needs its own model - without the experience ever slipping.

Why now: the hard part of the merger - stabilizing two teams, two systems, two ways of working - is behind us. We're moving into BAU, which means we're ready to stop just integrating and start building again. You're not walking into a rescue mission; you're walking into a blank page with real resources and real momentum behind it. It's a genuinely exciting time to join.

High ownership. High ambiguity. High impact.

What Success Looks Like

Implementation and Support run as one function, not two - shared goals, one handoff, one accountable owner for anything that crosses the line.

Time-to-value drops, especially for Enterprise - tighter sequencing turns onboarding from a bottleneck into a differentiator.

SMB and Enterprise are served on models built for each - lighter-touch and self-serve at the low end, high-touch where it counts, without either feeling like an afterthought.

Support's scope is clear and escalations into Engineering fall, as customers self-serve more through the platform and knowledge base.

AI is doing real work, not window dressing - ticket triage, resolution, and onboarding scale through automation, and headcount stops being the default answer to growth.

NPS holds at 64+ as we scale - proof the merger strengthened the experience instead of diluting it.

Team leads are coached, growing, and running an org structure built for how the business actually works now.

The Role

You'll own the post-sale client journey end to end, across a book that spans self-serve digital accounts up through complex Enterprise implementations. You'll spend your early days figuring out how your teams should be structured to serve that range well, then build toward a model that keeps our service quality high without requiring it to be entirely hands-on.

• Own the end-to-end post-sale client experience across Implementation and Support, setting one strategy and one standard for both functions rather than letting them run as silos
• Manage Implementation and Support leadership, setting priorities, coaching, and resourcing both teams as you determine the right organizational structure
• Define and hold both functions accountable to shared metrics - implementation timelines and time-to-value, support response and resolution times, and client satisfaction
• Build a single, clear escalation path for issues that cross the Implementation/Support boundary, so complex client problems have one accountable owner
• Clarify the actual scope of support versus customer success - and re-align where necessary so each team is doing the work it's built for
• Use AI to scale service without losing quality - extending ticket triage and resolution automation, and building toward self-serve onboarding for our digital customer base
• Tighten onboarding sequencing to shorten time-to-value for Enterprise accounts, while scaling a lighter-touch model for the high-volume digital/self-serve base
• Partner with Customer Success on handoff quality from Implementation into steady-state, and with Product and Engineering on structural issues surfaced through Support
• Represent Customer Experience at the leadership level on retention risk and expansion readiness tied to onboarding and support quality

What You'Ll Bring

• 8+ years' experience in post-sale functions, including 5+ years leading Implementation, Support, or Customer Experience teams, with direct experience managing team leads or managers
• Strong SaaS background - you understand what it takes to scale a service organization without breaking the experience that got you there
• Experience navigating organizational change, ideally post-merger or post-acquisition - you know how to figure out where teams should sit and how to bring people along with the change
• A track record improving time-to-value and reducing escalat