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Senior Technical and Onboarding Specialist

Remote / Online - Candidates ideally in
Chicago, Cook County, Illinois, 60601, USA
Listing for: mewssystems
Full Time, Remote/Work from Home position Listed on 2026-11-15
Job specializations:
Salary/Wage Range or Industry Benchmark: 105500 - 136500 USD Yearly USD 105500.00 136500.00 YEAR

Job Description & How to Apply Below

Position: Senior Technical Application and Onboarding Specialist
Role overview

A senior specialist position within a hospitality technology platform, focused on owning one product area end-to-end from a dedicated specialist hub. The role combines deep technical implementation work, third-tier escalation ownership, and operational stewardship of onboarding health and documentation. It sits at the intersection of customer success, onboarding, product, and engineering, shaping how complex configurations, API work, and integrations are resolved, documented, and fed back into the product.

Responsibilities
  • Lead complex implementations for the assigned product area, including non-standard configuration, integrations, APIs, and bespoke technical requirements, serving as the main escalation point when a go-live is blocked.
  • Act as third-tier support to onboarding managers and customer success on configuration, troubleshooting, and edge cases, and advise account leads on what is technically feasible for prospective customers.
  • Own performance metrics such as CSAT, time to resolution, repeat question rate, and deflection rate, intervening early when SLAs, timelines, or overall onboarding health are at risk.
  • Maintain and continuously improve the knowledge base for the product area, using AI to rethink how content is authored, kept current, and verified, and codifying approaches the wider specialist hub can reuse.
  • Partner with product and engineering on technical escalations, recurring onboarding issues, and product feedback, contributing to testing cycles, hackathons, and strategic initiatives.
  • Translate patterns from real customer implementations into durable improvements in process, tooling, and product behaviour.
Requirements
  • Three or more years in technical applications, implementation, onboarding, or technical support within a SaaS environment, with a track record of supporting complex implementations and managing multiple priorities independently.
  • Hands-on troubleshooting across software configuration, integrations, and APIs, with the ability to translate a customer's technical requirements into the right implementation approach.
  • An analytical, metrics-led mindset for spotting risk early and acting on it, combined with the project management skills to keep several implementations moving in parallel.
  • Experience designing or improving processes rather than only following them, plus clear communication with both technical and non-technical audiences.
  • Practical use of AI to redesign how work gets done, with the judgement to validate outputs against real product behaviour before they reach customers or colleagues.
Nice to have
  • Working knowledge of Salesforce, Jira, and Confluence.
  • Background in hospitality technology or with property management, payments, or distribution systems.
  • A bachelor's degree in a relevant field, or equivalent practical experience.
Benefits and work setup
  • Remote-first working model with flexibility to work abroad for short periods each year.
  • Relocation options available after one year of tenure.
  • Hybrid working flexibility and a home office setup budget, plus a monthly work-from-home allowance.
  • Access to AI tokens to support workflow automation and productivity experiments.
  • Location-dependent benefits that may include healthcare, retirement plans, and team events, discussed during the interview process.
  • US base salary range of $105,500 to $136,500 USD, with final compensation determined by experience and market conditions.

Position Requirements

10+ Years work experience
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