Senior Python Backend Engineer Mission Critical

About UsWe are a 26-year established Destination Management Company (DMC) operating under theAmstar DMC brand, the official destination services and tour operator brand ofHyatt Corporation.We support major North American travel brands including:Apple VacationsAmerican Express VacationsCheapCaribbeanExpediaHyattAnd more than 12 additional travel brandsOur platform supports daily operational workflows for:Transfer bookings (airport ↔ hotel)Tours and excursionsVacation-related servicesAutomated dispatch and resource allocationSupplier coordinationOperational handlingFinancials (invoicing, payments, credit card payments etc)The system automatically assigns drivers, vehicles, and partner companies required for service delivery.This is a real-time operational system used daily in production.Current System (Legacy Overview)We operate a 24-year-old Perl-based monolithic application.Codebase~250,000 lines total~100K core Perl code63K template toolkit43K configuration system17K Perl scripts25K web frameworkSingle monolithic architectureSingle MySQL database178 tables10 background jobsORM used since inception (limited direct SQL usage)IntegrationsGoogle DriveGmailFlightStatsWhatsAppStripe (payments)Additional workflows:Email parsers reading Excel attachmentsCSV generation & ingestion via Google DriveGoogle Forms integrationsBlocking page flows in current UIInfrastructureHosted on DigitalOcean VPSUbuntu 22.10 (scheduled for upgrade)Dev / Stage / Production environmentsPython services are DockerizedPerl system is not containerizedPartial CI/CD automation (Python only)Infrastructure managed by current Senior DeveloperAutomated database backups + monthly restore testingNo replication currentlyDowntime tolerance: up to 8 hours (business continuity procedures exist)Migration Status & GoalWe are executing a phased migration from Perl to Python.~20% already migratedTarget: >80% migrated within 12 monthsEnd goal: full replacement of legacy Perl systemCurrent modernization streams:Migrate email & WhatsApp handling to AI-driven solutionRebuild core order management functionality in Python (FastAPI)Develop new UI for drivers and hostessesGradually decouple monolith into modular servicesThis is a controlled, staged production migration.Team Structure1 senior developer (20 years on system)1 QANo dedicated DevOpsRequirements defined by business + management + senior devProduction incidents handled by senior devVery stable production system (minimal incidents in last 12 months)This role will significantly strengthen and eventually take ownership of the modernization effort.Required Technical Skills (Must Have)Strong Python experienceProven production experience with FastAPIStrong MySQL knowledge (schema, indexing, query optimization)Comfortable in Linux (Ubuntu) CLIExperience with pytestGitHub + GitHub Actions CI/CDExperience deploying behind Nginx or ApacheDocker experienceProfessional use of VS Code or similarUnderstanding of API design and system decouplingSecondary (Nice to Have)Ability to read Perl codeExperience modernizing monolithic systemsExperience with Google APIsExperience with Stripe or payment systemsBasic React experience (for internal admin tools)React is not a primary frontend role requirement.Work EnvironmentFully remoteDaily scrum (max 30 minutes)Structured weekly planningFlexible working hours24/7 operational business contextThis is not a constant on-call role, but production responsibility is real.Emergency incidents are rare but must be handled professionally.We value:TransparencyOwnershipIntegrityClear documentationStructured decision-makingWhat You Will OwnBuild production-ready FastAPI servicesDefine migration architectureImprove CI/CD maturityStrengthen infrastructure reliabilityDesign rollback-safe deploymentsDocument architectural decisionsGradually replace the legacy monolithThis is a high-autonomy, high-responsibility role.

About UsWe are a 26-year established Destination Management Company (DMC) operating under theAmstar DMC brand, the official destination services and tour operator brand ofHyatt Corporation.We support major North American travel brands including:Apple VacationsAmerican Express VacationsCheapCaribbeanExpediaHyattAnd more than 12 additional travel brandsOur platform supports daily operational workflows for:Transfer bookings (airport ↔ hotel)Tours and excursionsVacation-related servicesAutomated dispatch and resource allocationSupplier coordinationOperational handlingFinancials (invoicing, payments, credit card payments etc)The system automatically assigns drivers, vehicles, and partner companies required for service delivery.This is a real-time operational system used daily in production.Current System (Legacy Overview)We operate a 24-year-old Perl-based monolithic application.Codebase~250,000 lines total~100K core Perl code63K template toolkit43K configuration system17K Perl scripts25K web frameworkSingle monolithic architectureSingle MySQL database178 tables10 background jobsORM used