About the Role

We're looking for a seasoned operator from the corporate travel world — someone who's built processes, managed teams, and thrives in the weeds of complex, high-stakes trip logistics. This is a builder role: you'll create the systems, SOPs, and escalation infrastructure that allows a team of 6–8 travel agents to deliver flawless experiences for ultra-high-net-worth clients at serious scale.

You'll be the operational backbone of our client services team, the final eye on quality, the architect of process, and the shield between the CEO and every request that doesn't need to reach her desk.

If you're energized by finding inefficiencies, fixing them before they happen again, and holding a team to an exceptionally high standard, this role was built for you.

What You'll Do

Team Management & Accountability

Directly manage 6-8 travel agents, overseeing daily workflows, scheduling, and performance against SLAs
Monitor a high-ticket request volume (100+ per week) across agents simultaneously managing multiple trips, events, and client requests
Audit team adherence to SOPs and provide consistent coaching to ensure 100% alignment with brand standards
Onboard and train new team members, building a repeatable ramp process
Forecast staffing needs based on trip volume and complexity to prevent burnout and coverage gaps
Deliver monthly reports on SOP adherence, QA results, team workload, and capacity planning

Process Architecture & The Playbook

Write, audit, and maintain the "Sienna Charles Way" — our SOPs for trip planning, vendor coordination, client communication, and escalation handling
Build and own a tiered escalation system that routes the right issues to the CEO while shielding her from requests that can and should be resolved at the team level
Conduct root cause analysis on service failures and escalations; document findings and update processes to prevent recurrence
Continuously analyze team feedback and client escalations to identify operational gaps and implement fixes fast

Quality Assurance & Compliance

Perform QA on all client-facing communications — itineraries, proposals, emails — ensuring they are error-free, logistically sound, and on-brand before they go out
Monitor the integrity of client profiles, vendor data, and trip details for accuracy at all times
Track and enforce SLA compliance across the full agent team

Trip Operations & Logistics

Monitor ALL active trips at all times - you are the eyes on the board
Oversee complex, layered itineraries with international partners across multiple time zones
Serve as the senior escalation point for in-trip issues, handling urgent situations with a structured, drama-free approach

Tech Stack & Automation

Serve as administrator for Monday.com, Kustomer, and Google Workspace
Build automations to eliminate manual data entry (booking confirmations, follow-up sequences, task routing)
Ensure all platforms communicate seamlessly to reduce double-work and human error
Note: We are developing a proprietary app later this year, so please highlight any relevant experience with product development, beta testing, or tech build-outs in your cover letter

Customer Success & Retention

Track membership timelines and execute proactive renewal workflows starting 60 days prior to expiration
Monitor at-risk client behavior and usage patterns to flag churn risk early and drive retention

What We're Looking For

5+ years in corporate or luxury travel, with at least 2 years in a team lead, operations manager, or senior agent role
Level 3 travel agent experience with a corporate or high-volume background — execution-first mindset required
Proven experience managing teams of 3+ and building operational infrastructure from scratch
Deep familiarity with complex touring programs and layered international logistics
Experience in process architecture, SOP development, automation, and QA
Proficiency with CRM platforms; Monday.com and Kustomer experience a strong plus
Background in customer success, experience in retention management a plus
Comfort working across time zones and with international vendor networks
Strong analytical instincts — you can read data, spot patterns, and act on them
Experience onboarding and training new team members
Salary range: $70-90k depending on experience

Who You Are

Detail-obsessed: You catch the typos, formatting glitches, and logic gaps others miss; and you build systems so they don't happen again
Calm under pressure: Urgent travel escalations don't rattle you; you triage, communicate, and resolve with structure
A builder: You're not here to maintain the status quo, you're here to create the playbook, then hold everyone to it
SOP-driven: You believe that great service is repeatable, and repeatability requires process

Sienna Charles

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