Director of Customer Experience

Red Oak; Austin (TX); Hybrid; USD 140,000 - 190,000; Full time

Benefits offered by this job

Equity units via EOP (Employee Owned)

Comprehensive health coverage

401(k) with company contribution

PTO and birthday off

Enhanced family leave

Life insurance

Job summary

Red Oak, a leading compliance software provider for financial services, seeks a senior leader to unify Implementation and Support. You will shape the post-sale journey across SMB to Enterprise, building scalable structures and leveraging AI to maintain high-quality service as we grow.

You will define shared metrics, coach leaders, and partner with Product and Engineering to resolve cross-functional issues. A strong SaaS background and change-management experience are essential.

Qualifications

• 10+ years in customer-facing roles within SaaS, with 5+ years leading Implementation, Support, or CX teams.
• Proven track record reducing time-to-value and escalations through process improvements.
• Ability to structure blended teams for SMB to Enterprise accounts and use AI to scale operations.

Responsibilities

• Own end-to-end post-sale client journey across Implementation and Support.
• Define and drive shared metrics for timelines, time-to-value, response times, and CSAT.
• Build clear escalation paths and align where needed with Product and Engineering.

Skills

Leadership

SaaS

Post-sale Experience

AI in Support

Education

Bachelor's degree

Tools

Salesforce

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 escalations through process

• Hands-on experience deploying AI and automation in support or onboarding - you've architected ticket triage, resolution, or self-serve systems yourself. This is a builder mandate, not an adopter one.

• Clear, direct communication - you can set a shared standard across two teams that haven't operated under one leader before

• A bias toward figuring things out - this role starts with more open questions than answers, and you'll be expected to build the structure

• Nice to have: experience serving Enterprise accounts alongside a high-volume digital/self-serve motion

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 you to build structure where none exists yet. You'll get real autonomy and real ownership from day one, and we expect you to use AI as a first resort in how you build and scale your team's work.

Work Structure

Reports to: Chief Operating Officer

Location: Austin HQ - hybrid, in office Tuesday, Wednesday and Thursday

Red Oak is an equal opportunity employer. We welcome applicants of all backgrounds and do not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, veteran status, or any other legally protected characteristic.