Training & Readiness Manager
Microsoft
San José Province, San José, Costa Rica
If you love the pursuit of excellence and are inspired by the challenges that come through driving innovation that impact how the world lives, works and plays, then we invite you to learn more about Microsoft Operations and the value we deliver across Microsoft and our customers. We offer unique opportunities to work on interesting global projects in an environment that appreciates diversity, focuses on talent development, and recognizes and rewards great work. We make doing business with Microsoft easy.
Field & Scale Operations, within Microsoft Business Operations, provides operations support for Microsoft Services Customers and Sellers to accelerate seller productivity across the Services business. We are accountable for designing and executing deal management services across the customer lifecycle. We deliver process efficiency, timeliness, quality and compliance while providing an exceptional customer experience. We are looking for team members to join our team to focus on delivering exceptional experience with deep expertise in contracting, order management, billing, and customer relationship management.
The Training & Readiness Manager plays a key role in building and sustaining readiness for an operational Services organization. This role shapes and delivers learning, enablement, and readiness strategies that accelerate time-to-productivity, support operating model adoption, and enable consistent, high-quality execution aligned with business priorities. The role partners closely with broad business stakeholders, translating strategy and change into clear learning paths, readiness plans, and measurable capability improvements—ensuring teams are prepared to execute effectively as the business evolves. The ideal candidate is an innovative learning strategist, passionate about enabling growth, accelerating change, and maximizing the potential of Microsoft’s most valuable asset, its people. They will champion the integration of customer feedback, empathy, and proactive problem-solving into training materials and processes, ensuring every learning intervention aligns with the needs and expectations of internal and external customers. By prioritizing the customer perspective, this role enables the team to deliver exceptional service, build lasting relationships, and continuously improve customer experience.
Microsoft’s mission is to empower every person and every organisation on the planet to achieve more. As employees, we come together with a growth mindset, innovate to empower others, and collaborate to realise our shared goals. Each day we build on our values of respect, integrity, and accountability to create a culture of inclusion where everyone can thrive at work and beyond.
Responsibilities
Training Program Management & Orchestration
Partner with process owners and service leaders to identify capability gaps and define training priorities that align to business outcomes and customer experience.
Orchestrate across stakeholders (Field, Operations, Process, Quality, Tools, and Change) to remove readiness blockers and maintain momentum for learning launches.
Apply disciplined needs analysis and learning design reviews to validate that content is accurate, appropriately scoped, and aligned with role expectations and standards.
Support teams through complex or ambiguous operational changes by translating intent into clear learning paths, job aids, and readiness plans.
Enforce consistent execution of training governance, deployment playbooks, and engagement models.
Drive effective stakeholder partnerships: demonstrated impact and influence skills, including cross-boundary collaboration and the ability to build solid relationships with individuals at all levels.
Learning Design, Delivery & Readiness
Design and deliver onboarding and role-based learning ensuring accuracy, completeness, and alignment to business rules and policies.
Manage readiness planning for process, policy, and tooling changes including communications, enablement assets, and stakeholder alignment.
Ensure learning content and guidance are consistently represented and discoverable across Microsoft systems and channels (e.g., SharePoint/Teams, knowledge bases, or internal tooling).
Proactively identify and resolve issues impacting learning effectiveness (content gaps, adoption barriers, or unclear process steps) in partnership with subject matter experts.
Learning Quality, Risk Management & Measurement
Identify learning risks, readiness gaps, or knowledge‑base hygiene issues early and drive resolution through appropriate channels.
Anticipate downstream impacts of tooling, policy, or process changes on frontline execution and take early corrective action through targeted readiness and communications.
Ensure training content adheres to required business rules, approval requirements, and compliance policies, and that completion and certification expectations are clearly defined.
Continuous Improvement & AI‑Enabled Learning
Demonstrate a growth mindset by identifying recurring learner pain points, enablement inefficiencies, or quality issues and contributing actionable insights to continuous improvement initiatives.
Leverage data and stakeholder feedback to improve learning effectiveness, readiness quality, and time‑to‑productivity.
Adopt and support AI‑assisted learning content creation and delivery workflows to reduce manual effort, improve accuracy, and increase training velocity.
Reinforce alignment to the operating model standards by embedding readiness checkpoints, role clarity, and measurable proficiency expectations.
Qualifications
Minimum / Required Qualifications:
- Bachelor's Degree in Business, Operations, Finance or related field AND 4+ years work experience in program management, process management, or process improvement OR equivalent experience.
- This role requires proficiency in written, reading, and conversational English as all business operations as well as customer communications are conducted in English.
Preferred Qualifications
Proven track record of designing and executing successful learning initiatives at scale
Demonstrated project management, organizational, and analytical abilities
Ability to manage multiple projects simultaneously in a fast-paced, dynamic environment
Experience supporting deal execution, pre-sales, renewals management, sales operations, or delivery in a large, matrixed organization.
Familiarity with Professional Services, enterprise services constructs, or complex commercial deal models.
Experience in a customer service environment in a large, matrixed multinational company.
Experience coordinating cross‑functional stakeholders across Sales, Finance, Legal, and Delivery.
Demonstrated ability to operate effectively in ambiguous or evolving environments and apply sound judgement.
Exposure to continuous improvement methodologies (e.g., Lean, Kaizen, Six Sigma) or data‑driven process improvement.
Passion for technology, AI skilling, innovation, and leading change.
- On‑site presence expected at least three days per week, in alignment with team and business need
This position will be open for a minimum of 5 days, with applications accepted on an ongoing basis until the position is filled.
Microsoft is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, citizenship, color, family or medical care leave, gender identity or expression, genetic information, immigration status, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran or military status, race, ethnicity, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable local laws, regulations and ordinances. If you need assistance with religious accommodations and/or a reasonable accommodation due to a disability during the application process, read more about requesting accommodations.