Full-Time

Senior Support Services Implementation and Readiness Manager

Updated on 9/10/2026

Priceline

Priceline

1,001-5,000 employees

Online travel agency offering discount deals

Compensation Overview

CA$100k - CA$120k/yr

Toronto, ON, Canada + 1 more

More locations: New York, NY, USA

Hybrid

Two days on-site per week are required; remaining days may be remote or in the office.

Bachelor's

Category
Training (1)
Required Skills
Product Management
Quality Assurance (QA)
JIRA
Risk Management
Confluence
Google Workspace
Data Analysis

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Requirements
  • A bachelor's degree in business administration, learning and development, organizational development, operations management, project management, or a related field; equivalent relevant experience will be considered in lieu of education.
  • Seven or more years of progressively responsible experience in travel contact center operations, training, learning implementation, operational readiness, or a related discipline.
  • Five or more years of experience leading training implementations, train-the-trainer programs, trainer certification, or large-scale learning deployments.
  • Three or more years of leadership experience, including direct people leadership or formal responsibility for trainers, implementation teams, or complex workstreams.
  • Deep demonstrated knowledge of Flight servicing and training, including airline policies, fare rules, ticketing, exchanges, refunds, cancellations, schedule changes, irregular operations, and escalation practices.
  • Demonstrated travel-agent knowledge across Hotel and Rental Car products, servicing models, policies, workflows, and customer scenarios.
  • Demonstrated experience evaluating trainer readiness and establishing certification, remediation, and recertification requirements.
  • Experience translating complex business requirements into training, knowledge, Quality, technology, operational, and readiness plans.
  • Experience supporting multi-site, outsourced, BPO, or global contact center operations.
  • Experience managing implementations through planning, curriculum readiness, train-the-trainer, delivery, nesting, launch, stabilization, and transition.
  • Experience using learning and operational data to evaluate readiness, proficiency, and implementation performance.
  • Proficiency with Jira, Confluence, Smartsheet, Google Workspace, learning-management systems, and virtual-training platforms.
Responsibilities
  • Lead assigned Customer Care implementations from planning through readiness, launch, stabilization, transition, and closure.
  • Translate approved business, product, operational, and technology requirements into integrated implementation and training plans.
  • Define scope, milestones, deliverables, functional owners, dependencies, risks, decisions, and success measures.
  • Own implementation-specific organizational-readiness criteria and assessments.
  • Evaluate readiness across people, processes, training, knowledge, Quality, technology, communications, staffing, leadership support, and partner-site capability.
  • Ensure readiness gaps have clear owners, actions, target dates, mitigation plans, and escalation paths.
  • Prepare readiness summaries and go-live recommendations for Support Services and operational leadership.
  • Develop launch, support, escalation, contingency, and stabilization plans.
  • Maintain implementation records and reporting in accordance with established portfolio and Jira-governance standards.
  • Own the train-the-trainer strategy and execution for implementations across Flight, Hotel, and Rental Car.
  • Determine trainer prerequisites, preparation requirements, certification standards, and implementation-specific expectations.
  • Facilitate or oversee train-the-trainer sessions for internal and external contact center trainers.
  • Validate trainer subject-matter knowledge, system proficiency, facilitation capability, scenario application, and operational readiness.
  • Develop and maintain trainer assessments, observation practices, certification criteria, and supporting documentation.
  • Establish remediation and recertification requirements when trainers do not meet readiness standards.
  • Monitor trainer performance during initial delivery and provide targeted coaching, feedback, and reinforcement.
  • Document trainer-readiness results, certification decisions, identified risks, and required actions.
  • Ensure train-the-trainer practices support consistent delivery across sites, regions, and contact center partners.
  • Apply deep Flight knowledge to planning, curriculum validation, train-the-trainer, readiness assessment, and launch support.
  • Ensure Flight training addresses airline policies, fare rules, ticketing, exchanges, refunds, cancellations, schedule changes, irregular operations, and escalation procedures.
  • Evaluate whether trainers and learners can accurately apply complex Flight requirements to realistic customer scenarios.
  • Identify customer, financial, compliance, and operational risks associated with Flight knowledge, system, workflow, or readiness gaps.
  • Apply travel-agent knowledge across Hotel and Rental Car products, policies, workflows, servicing models, and customer scenarios.
  • Identify differences and dependencies among Flight, Hotel, and Rental Car that may affect curriculum, delivery, technology, Quality, or partner readiness.
  • Maintain current knowledge of travel operations, systems, product changes, and emerging capability requirements.
  • Partner with Instructional Design to ensure curricula, facilitator guides, learner materials, assessments, simulations, and job aids are ready for implementation.
  • Provide Flight, Hotel, Rental Car, and operational feedback regarding curriculum accuracy, usability, sequencing, and implementation risk.
  • Partner with Knowledge Management to ensure required procedures, policies, knowledge articles, and performance-support materials are approved and accessible.
  • Partner with Training Operations on trainer assignments, delivery capacity, learner schedules, classroom execution, nesting, and long-term ownership.
  • Partner with Quality on scorecard readiness, calibration, proficiency measures, early-tenure monitoring, and post-launch performance.
  • Partner with Product and Technology on requirements, system access, training environments, testing, defects, deployment timing, and operational support.
  • Partner with Learning Operations and Change Enablement on system assignments, Jira requirements, communications, stakeholder impacts, and adoption support.
  • Coordinate site-specific implementation plans while maintaining alignment with Priceline standards.
  • Serve as a primary implementation and training contact for external contact center partners.
  • Assess site readiness across trainer capability, learner prerequisites, classroom infrastructure, technology access, staffing, leadership support, and nesting.
  • Communicate requirements, milestones, risks, decisions, and readiness expectations clearly and consistently.
  • Facilitate partner feedback and ensure relevant operational considerations are incorporated into implementation plans.
  • Escalate readiness concerns that could affect training effectiveness, customer experience, compliance, or launch success.
  • Promote consistent training and certification practices while accounting for legitimate market, language, and operational differences.
  • Coordinate training-related launch, command-center, and hypercare activities when required.
  • Monitor trainer, learner, operational, Quality, technology, and customer indicators during launch and stabilization.
  • Track training completion, knowledge attainment, certification, graduation, proficiency, early-tenure Quality, productivity, and speed to competency.
  • Identify whether implementation gaps result from curriculum, trainer capability, facilitation, systems, knowledge, operational support, or learner proficiency.
  • Coordinate issue resolution and maintain visibility into severity, ownership, timing, and customer or business impact.
  • Determine when implementation and training stabilization criteria have been achieved.
  • Formally transition ongoing training ownership to the Senior Manager, Quality & Capability Development and Training Operations.
  • Ensure the receiving teams have the curriculum, documentation, trainer records, performance findings, outstanding actions, reporting, and support processes needed for ongoing execution.
  • Define implementation success measures with Quality, Training Operations, Operations, and other functional leaders.
  • Evaluate readiness, launch execution, trainer certification, learner proficiency, and stabilization outcomes.
  • Develop implementation dashboards, readiness summaries, risk reports, and leadership recommendations.
  • Conduct post-implementation reviews and document results, lessons learned, unresolved actions, and improvement opportunities.
  • Provide sustained performance findings to Quality and Training Operations for continued analysis and intervention.
  • Provide governance and process lessons to Learning Operations and Change Enablement for incorporation into future standards, workflows, and communications.
  • Improve train-the-trainer, certification, readiness, launch, and transition practices based on implementation outcomes.
  • Lead, coach, and develop assigned team members, trainers, implementation resources, and workstream leads.
  • Establish clear expectations and accountability for readiness and implementation deliverables.
  • Build productive relationships with internal leaders, external partners, trainers, subject-matter experts, and operational stakeholders.
  • Influence decisions across functional and organizational boundaries.
  • Communicate complex travel and implementation information clearly to operational, technical, partner, and executive audiences.
  • Create an environment of transparency, shared accountability, constructive challenge, and disciplined execution.
Desired Qualifications
  • Experience with airline reservation systems, Global Distribution Systems, Flight servicing platforms, or comparable travel technology is strongly preferred.

Priceline is an online travel marketplace that connects travelers with airlines, hotels, car rental companies, cruises, and vacation packages. It uses two business models: an agency model that earns commissions on bookings and a merchant model that buys travel services wholesale and resells them at a markup. It offers fixed-price listings and discount options such as Express Deals and Name Your Own Price, plus flexible options like free cancellations and pay-at-arrival, accessible via a mobile app. Under Booking Holdings, its goal is to help budget travelers access a wide range of options while giving consumers more negotiating power through transparent pricing and valuable deals.

Company Size

1,001-5,000

Company Stage

Series B

Total Funding

$77.4M

Headquarters

Norwalk, Connecticut

Founded

1998

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Simplify Jobs

Simplify's Take

What believers are saying

  • Q2 2026 Booking Holdings revenue hit $7.35 billion, with room nights up 5%.
  • Penny users saved nearly ten minutes per trip and converted better in testing.
  • Booking Holdings raised 2026 transformation savings to $650 million, funding Priceline investment.

What critics are saying

  • FTC staff threatened a 2026 lawsuit over disclosures, fees, support, and billing.
  • Anthropic, Google Cloud, and OpenAI commoditize Penny's AI edge within months.
  • Expedia, Booking.com, and direct supplier apps squeeze Priceline's margins and traffic.

What makes Priceline unique

  • June 3, 2026 Penny turned Priceline into an agentic booking workflow.
  • Priceline owns inventory, payments, and preferences across 100-plus countries inside one conversation.
  • Booking Holdings gives Priceline scale, supplier leverage, and capital behind product iteration.

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Benefits

Hybrid Work Options

Remote Work Options

Growth & Insights and Company News

Headcount

6 month growth

-1%

1 year growth

-2%

2 year growth

0%
PR Newswire
Jun 23rd, 2026
Americans cut alcohol, dining out to afford summer holidays despite rising costs

Priceline's 2026 State of Summer Travel Report reveals Americans are cutting back on nearly everything to fund summer holidays despite rising costs. The survey of 2,500 US adults found 79% plan to take at least one trip this summer, even though 44% say such a vacation feels out of reach. Eighty-four percent of Americans report paying more and getting less for travel, whilst 55% find it less affordable than last year. Over one-third have already cut everyday expenses to fund trips, with 83% of adults willing to give up alcohol before vacation. Parents and millennials face the most pressure, with 28% of millennials planning to spend $5,000 or more this summer. Sixty-nine percent regret past cost-cutting decisions, whilst half plan to use AI tools to find better deals.

PR Newswire
Jun 3rd, 2026
Priceline's Penny AI assistant goes fully agentic, booking trips in one conversation with Anthropic's Claude

Priceline has launched an enhanced version of Penny, its AI travel assistant, now powered by Anthropic's Claude. The agentic system allows travellers to move from trip planning to booking within a single conversation, handling complex requests like comparing flights across multiple destinations. The experience features an interactive map that updates during conversations, along with personalised recommendations called Penny's Pick and Penny's Take. Built on Priceline's proprietary AI stack, the system integrates Claude for conversational reasoning, whilst Google Cloud and OpenAI support search and voice capabilities. Penny connects to real-time inventory from thousands of partners across over 100 countries. Early testing shows travellers using Penny demonstrate higher conversion rates and save approximately ten minutes per trip compared to those calling customer support. The service now supports multiple languages.