Director, Operational Training

Core Spaces•Chicago, IL

1d•$165,000 - $185,000•Hybrid

About The Position

The Director of Operational Training is responsible for setting the vision, strategy, and operating rhythm for training at Core Spaces. Reporting to the Vice President of Research & Operations Training, this role oversees the full training function across Student Housing and Build-to-Rent (BTR), ensuring learning is timely, practical, scalable, and directly tied to business performance. This leader builds and leads a high-performing training organization—balancing strategy with execution—while ensuring the right people, programs, and platforms are in place to support community teams, managers, and leaders at critical moments. The Director of Operational Training establishes clear ownership across the team, drives cross-functional alignment, and ensures Core’s learning investment produces measurable results. Helps set training organization design, capacity planning, and resourcing decisions.

Requirements

Bachelor’s degree in Education, Business, Organizational Development, or a related field
8–10+ years of progressive experience in Learning & Development, training, enablement, or operational training
3+ years leading teams and people managers
Experience building scalable training programs in a multi-site, operations-driven environment
Demonstrated experience using learning technologies and data to drive measurable outcomes

Nice To Haves

Student housing, multifamily, hospitality, or BTR environments
Leading change and large-scale program rollouts
Curriculum strategy and role-based pathway development
Creating strong governance across content, platforms, and stakeholder expectations
Executive communication—making training impact clear, concise, and tied to business performance

Responsibilities

Set and execute Core’s enterprise training strategy aligned to operational excellence, financial performance, and Core’s culture (UX Starts with U).
Own the annual and quarterly training roadmap and prioritization process, aligning training delivery to business cycles such as onboarding, leasing readiness, budgeting, turn, move-in, and policy changes.
Lead, coach, and develop a multi-disciplinary training team, including people managers and individual contributors; establish clear role ownership, standards, and accountability.
Establish governance and quality standards for learning content across channels (self-paced, ILT, job aids, playbooks), ensuring consistency, version control, and a single source of truth.
Establish and maintain visibility mechanisms (curriculum tracker, program one-pagers, launch calendars, governance notes) and run the recurring cross-functional cadence that keeps stakeholders aligned.
Shape curriculum strategy across core operating functions (sales/leasing, resident experience, financials, turn/move-in, leadership) and ensure programs progress from onboarding to proficiency to leadership readiness.
Own executive oversight of high-impact training programs and platforms (e.g., Trailblazer Training, L&D SharePoint/resource hub, Turn/Move-In readiness programming, and major content launches), ensuring clear owners, timelines, and delivery.
Own the training intake process (e.g., HappyFox), including triage, stakeholder consultation, prioritization, and defined decision rights/SLAs/escalation paths (standard vs urgent) to protect the roadmap.
Partner with subject matter experts (Operations, Sales/Leasing, Accounting, Business Systems, Asset Management, Development) to translate business needs into scalable learning solutions, and ensure training is deployed ahead of operational moments—never after the fact.
Ensure continuous improvement through learner feedback, manager input, field performance insights, and post-program evaluations; stop/refresh low-impact training and scale what works.
Own the learning technology ecosystem strategy and adoption, ensuring platforms and tools are used effectively, integrated where possible, and continuously improved.
Define and track KPIs for training effectiveness, adoption, and business impact; review results with leadership and drive improvements based on data.
Serve as the executive-facing voice of Training—providing clear reporting, and recommendations to improve performance, consistency, and team capability.
Manage vendor relationships and performance (LMS, content tools, external content providers)
Create the training budget (tools, vendors, content production, including ROI rationale, contract strategy and forecasting.
Define and maintain Core’s curriculum architecture across Student Housing and BTR, including role-based learning pathways, sequencing, and proficiency expectations.
Own governance of core curriculum (onboarding pathways, required courses, and recurring readiness programming tied to the operating calendar).
Oversee seasonal programming to ensure teams are ready ahead of critical operating moments tied to the operating calendar.
Ensure leadership and soft-skill development is built as a progression (new manager → experienced manager → promotion-ready).
Maintain an annual refresh cadence to retire outdated content, close training gaps, and align content to policy and systems changes.
Ensure policies, SOPs, and training remain aligned (partnering with Policy Owners/Legal/Compliance); coordinate training updates to launch in sync with policy and system changes, and maintain a policy-training refresh cadence.
Adoption & compliance: completion rates by role/region, reduction in past-due courses, and timely completion tied to onboarding milestones.
Program effectiveness: learner satisfaction, pre/post checks where applicable, application/confidence measures, and manager skills assessment trends.
Operational readiness: improved readiness ahead of turn/move-in and leasing cycles (measured by readiness checks, reduced repeat errors, fewer escalations tied to training gaps).
Business impact correlation (in partnership with Operations): improvements in execution and reduction of repeat operational misses where training is the lever.
Efficiency & throughput: intake responsiveness, time-to-launch for priority programs, content freshness/retirement cadence, and reduction in duplicative/rogue content.
Stakeholder trust: on-time delivery against the training roadmap and positive feedback from Operations and cross-functional leaders.
Oversee compliance training governance (e.g. Fair Housing, Sexual Harassment, Cybersecurity) across jurisdictions: cadence, assignment rules, completion tracking, in partnership with HR/Legal & Compliance departments.
Perform all other duties and tasks as assigned by management
Must be able to complete all physical requirements of this role with or without a reasonable accommodation

Benefits

A culture that provides you with a sense of belonging
Hybrid or remote work options may vary by role to support work-life balance
Competitive pay that values your contributions
Incentives designed to reward your achievements
Paid flexible PTO to disconnect or celebrate life milestones
Paid 14+ holidays, including your birthday, to disconnect and celebrate
Paid Parental Leave that begins after 90 days
Paid volunteer time off to give back to your community
Monthly workshop weeks; fewer meetings & more collaboration
Robust health plan options that begin within at least 30 days of your employment
Monthly phone reimbursement
Wellness allowance and perks, including a yearly subscription to a meditation app
An environment that provides you a voice to share your perspectives
Employee Assistance Program (EAP) for access to confidential support services
Company retirement options including 401(k) + matching & Roth account option