About Sienna Charles

Sienna Charles is a boutique luxury travel and lifestyle company serving ultra-high-net-worth

individuals. Our clients expect flawless execution, discretion, and white-glove service at every

touchpoint. Everything we do reflects that standard.

About the Role

We're looking for a Head of Client Operations & Experience to own the day-to-day operational excellence of our business. This is a hands-on role that combines quality management, process design, client success, and systems administration. You'll be the operational backbone that enables our Travel Team to focus on delivering exceptional client experiences.

Why this role matters: Our team's success depends on seamless operations, documented

processes, efficient systems, and proactive client management. You'll directly impact client

satisfaction, team productivity, and our ability to scale — all while upholding the standard of

quality our clients expect.

Key Responsibilities

Quality Assurance & Compliance (30%)

● QA client-facing communications (emails, confirmations, itineraries) before they go out

● Manage client issue audits — investigate escalations, document root causes, and implement corrective actions

● Create quality checkpoints across the trip lifecycle (pre-trip, during-trip, post-trip)

● Monitor SOP adherence and provide coaching when standards aren't met

● Track data accuracy across trip requests, vendor information, and client preferences

● Develop and maintain quality standards and client satisfaction metrics

Measures of Success: Client communications are consistently polished and error-free · every

escalation has a documented root cause and resolution · the team follows SOPs reliably · client

satisfaction remains high

Process Management & Documentation (25%)

● Write, edit, and maintain SOPs for all trip-related processes (planning, vendor coordination, escalation handling, etc.)

● Create and update macros, checklists, and templates across our tools

● Document lessons learned from escalations and complex scenarios

● Implement process improvements based on team feedback, client feedback, and operational gaps

● Audit process adherence and coach team members when SOPs aren't being followed

● Maintain version control so documentation stays current and accessible

Measures of Success: Every core process is documented and easy to find · the team adopts

new SOPs quickly and consistently · processes improve month over month · there is never

ambiguity about "how we do things"

Systems & Automation (20%)

● Administer core systems: Kustomer, Dialpad, HubSpot, Monday.com

● Build automations for repetitive work; booking confirmations, follow-ups, escalation routing, etc.

● Design workflows that reduce manual data entry and human error

● Configure templates and macros for common tasks (welcome emails, proposals, QC

checklists)

● Manage integrations across tools to ensure smooth data flow

● Evaluate and recommend new features or capabilities as processes scale

Measures of Success: Manual and repetitive work decreases meaningfully over time ·

common workflows are automated · systems run reliably without disruption · the team spends

less time on admin and more time on clients

Client Success & Renewals (10%)

● Monitor trip progress and proactively communicate with clients throughout their journey

● Track renewal timelines, build renewal workflows, and ensure seamless continuation of service

● Maintain up-to-date client profiles, preferences, and history

● Track usage across membership types and flag at-risk clients

● Manage post-trip follow-ups — thank-you notes, feedback surveys, and renewal outreach

● Report on retention trends and identify what's working

Measures of Success: Renewals are proactive, not reactive — clients hear from us well before

expiration · at-risk clients are identified early · client records are accurate and current · retention

stays strong

Onboarding & Training (10%)

● Manage client onboarding: welcome communications, profile setup, preference gathering

● Train new Travel Team members on processes, tools, and Sienna Charles standards

● Maintain training materials — documentation, checklists, video walkthroughs

● Track training completion and ensure competency before granting independence

● Configure system access, permissions, and settings for new hires

Measures of Success: New clients feel welcomed and organized from day one · new team members ramp quickly and confidently · training materials are current and comprehensive · system setup for new hires is seamless

Capacity Planning & Reporting (10%)

● Monitor team workload, identify staffing gaps, and forecast capacity needs

● Track request volume, complexity, and turnaround time

● Generate monthly operational reports with metrics, trends, and recommendations

● Deliver dashboard reporting to leadership: SOP adherence, escalations, QA results, client health

● Translate data into actionable insights for improving operations

Measures of Success: Leadership has clear, timely visibility into operational health · capacity issues are flagged before they become problems · reporting drives real decisions · the team's workload is balanced and sustainable

Who You Are

Ideal Background

Strong Fit — You've Done This Before

● 4+ years in operations, client experience, or quality management within luxury travel,

hospitality, or high-touch lifestyle brands

● Direct experience administering platforms like Kustomer, HubSpot, Monday.com, or Dialpad

● Track record of designing and enforcing SOPs in a client-facing environment

● Background working with high-net-worth or ultra-high-net-worth clientele

Great Fit — Transferable Experience

● 3+ years in operations or client experience within premium SaaS, concierge services, private aviation, luxury retail, or wealth management

● Experience administering CRMs, helpdesks, or workflow tools — even if not the exact platforms listed above

● Strong documentation and process design skills developed in a quality-sensitive

environment

● Familiarity with the expectations and discretion required when serving affluent clients

Emerging Fit — High Potential

● 2+ years in a detail-intensive operations or client success role in any industry

● Demonstrated ability to learn and configure new tools quickly (CRMs, project management platforms, telephony systems)

● Exceptional writing and documentation skills with a natural eye for quality

● Genuine interest in luxury, travel, or hospitality — and the operational rigor behind it

What Sets You Apart Regardless of Background

● Eye for quality and luxury — You instinctively know what "polished" looks like and won't let anything substandard reach a client

● Documentation-first mindset — You believe if it's not written down, it doesn't exist. You create clarity where there is none

● Technical acumen — You're comfortable configuring workflows, building automations, and managing admin settings across multiple platforms. You don't need to be an engineer, but you're well beyond "just a user"

● Attention to detail — You catch typos, inconsistencies, and process gaps that others miss. In UHNW client work, this is non-negotiable

● Proactive and self-directed — You identify what needs to be done and execute without being asked

● Composed under pressure — You manage escalations and urgent issues without drama

● Collaborative — You work effectively across the Travel Team, Chief of Staff, and leadership

● Curious — You ask "why?" and continuously look for ways to improve

First 90 Days

Days 1–30: Learn

● Deep dive into all current processes and understand the status quo

● Meet every team member and understand their pain points

● Identify 3–5 quick wins (automations, template improvements, SOP gaps)

● Stand up a basic QA process for client communications

● Establish a weekly operations meeting cadence

Days 31–60: Build

● Implement 2–3 quick wins (process improvements, new automations)

● Document all critical SOPs in a centralized location

● Build a client success tracking dashboard

● Train the team on new processes and tools

● Establish monthly reporting cadence to leadership

Days 61–90: Deliver

● All critical processes documented and being followed

● 2–3 major automations live and reducing manual work

● Client success and renewal system in place

● QA process embedded with zero quality surprises

● Reporting processes running smoothly and data-driven

● Show measurable impact across quality, efficiency, and client satisfaction

Growth Path

● 6 months: If excelling, explore expanded scope — additional functions like client support or operations team coordination

● 12 months: Potential to manage a larger team as the company scales

● 18+ months: Path toward Director of Client Experience Operations or Head ofOperations

Compensation & Benefits

● Base salary: $135,000/year

● Health insurance: Medical, dental, and vision

● 401(k): With employer match (if eligible)

● Professional development: Quarterly stipend

● Performance bonus: Discretionary, based on operational impact

Sienna Charles

Vacatures

Head of Client Operations