Senior Support Specialist, Customer Satisfaction

About the role

Senior Support Specialist, Customer Satisfaction & Incident (CSI)

The Opportunity

As a Senior Support Specialist based in Chicago or Dallas, you will own our most complex, sensitive and high-risk escalations from first contact to final resolution. This includes frontline and executive escalations, regulatory matters, partner and supplier complaints, and technical or pricing issues. You would also be a direct point of contact for our partners when a situation calls for it, and you will work closely with our Partner Success, Commercial and other teams based in multiple locations across the world.

This role calls for sound judgment, strong ownership and calm, decisive communication in high-stakes situations. You will often work in grey areas where standard processes need careful, case-by-case handling, and you will make well-reasoned decisions that balance customer satisfaction with financial, legal and reputational risk.

What you'll do

• Own high-risk cases end to end, from intake to final resolution, including escalations from frontline teams, senior leadership, partners and third parties such as government bodies or attorneys. Cases can run for days or weeks and need persistence and clear accountability.
• Speak with customers/partners by phone, video or in person when needed, to resolve escalations, explain outcomes and protect the relationship.
• Work closely with Partner Success, Commercial and other teams in multiple locations, joining regular calls to align partner issues, risks and follow-ups.
• De-escalate and negotiate with highly emotional, frustrated or sensitive customers who have already been through standard support, reaching resolutions that protect the customer relationship, our partners and the business.
• Investigate complex situations by gathering and reconciling information from many, often conflicting, sources, and keep thorough, accurate and timely records of every action and decision.
• Make sound, defensible decisions within your authority, and escalate promptly when financial, legal, regulatory, privacy, safety or reputational thresholds are reached.
• Turn complex cases into short, factual updates for senior leaders and, where needed, regulators, focused on impact, resolution and preventing recurrence.
• Partner with teams such as Legal, Fraud, Finance, Public Relations, Product, Technology and Supply, clearly explaining what you need and why it matters, and influencing action without direct authority.
• Identify major errors, fraud indicators or suspicious customer or property behavior, and act to reduce risk to customers, partners and the company.
• Respond quickly to critical incidents and urgent escalations, coordinating stakeholders and keeping communication clear under pressure.
• Prioritize a complex caseload by business risk, financial impact and deadlines rather than arrival order, and adjust quickly as new information comes in.
• Analyze case trends and run root-cause analysis to find systemic gaps, take part in post-incident reviews, and propose preventive improvements.
• Turn new or unusual case resolutions into clear, reusable guidance for the wider team, and flag procedures that need updating.
• Give respectful, constructive feedback to frontline teams to improve case handling and prevent repeat errors, and ensure smooth handover of cases.

What you'll need to succeed

• At least 4-5 years of relevant experience in customer escalations, complaints resolution, incident management or partner-facing support.
• Excellent written and spoken English, with the ability to explain complex situations clearly and confidently to anyone, from upset customers to partners and senior executives.
• Confidence speaking directly with business partners and senior stakeholders, with excellent phone and email manner.
• Strong listening, negotiation and de-escalation skills, and emotional resilience to stay objective and professional under pressure.
• Sound judgment in ambiguous situations, with a critical-thinking, investigative approach and close attention to detail.
• A data-driven approach: comfort using data and case trends to spot systemic issues and support recommendations.
• A strong understanding of compliance, data privacy and risk, and a commitment to keeping actions and communications within legal and regulatory requirements.
• A high degree of integrity, impartiality and confidentiality when handling sensitive cases.
• The ability to manage your own caseload independently and to work well in a diverse, cross-functional team.
• Based in, or within commuting distance of, Chicago, IL (USA) or Dallas, TX (USA).

Nice to have

• Spanish language skills.
• Experience leading or coordinating major incidents across multiple stakeholders with limited information, and knowledge of incident management processes.
• SQL or similar data skills to analyze trends in customer issues and support data-driven decisions.
• Experience in travel, hospitality or online marketplaces.

Working hours and location

• Core working hours follow US Central Time including weekdays and weekends. On-call or extended hours may be needed on an ad hoc basis to meet business needs.
• Hybrid working with office 3 days a week.
• Location:
• Chicago, Illinois, USA
• Dallas, Texas USA

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Note on general employment requirements

Candidates should be authorized to accept employment in the US from any employer and must be able to work a hybrid work schedule with 2-3 days per week in the stated physical office (unless otherwise indicated).