Director of Talent Development & Performance

Skybox Capital•Chicago, IL

About The Position

Skybox Capital is a dynamic family office and private equity firm investing across the capital structure, with a focus on middle-market private equity and incubating innovative businesses. Our diverse portfolio spans operating companies, private equity funds, credit, and real assets across multiple countries including the U.S., Israel, Canada, and Asia. We operate lean, leverage AI and modern tools across functions, and empower our team to move quickly and think strategically. As we scale, we're committed to building a high-performing organization where top talent thrives, managers develop as leaders, and every team member has a clear path for growth. We're seeking a Director of Talent Development & Performance to elevate our people and culture. This isn't a traditional HR role focused on benefits administration or compliance — it's a strategic position dedicated to unlocking the potential of our team and building a high-performance culture. You'll partner with leadership and managers across the organization to create rigorous performance evaluation systems, develop our managers into effective coaches and leaders, design career development pathways, and foster collaboration across our global team. Your success will be measured by how well our people grow, how effectively our managers lead, and how cohesively our teams work together. This role is ideal for someone who is passionate about talent development, understands what drives high performance, and wants to build the systems and culture that help exceptional people do their best work.

Requirements

7+ years of experience in talent development, organizational development, people operations, or related roles
Proven track record designing and implementing performance management systems
Experience coaching managers and developing leadership capabilities
Strong understanding of adult learning principles and talent development best practices
Excellent interpersonal skills with the ability to build trust across all levels of an organization
Demonstrated ability to have difficult conversations with empathy and directness
Strategic thinker who can also execute tactically
Experience working in fast-paced, entrepreneurial, or high-growth environments

Nice To Haves

Background in professional services, private equity, venture capital, family offices, or financial services
Experience managing talent across multiple geographies and cultures
Familiarity with AI tools and modern HR technology platforms
Background in organizational psychology, industrial-organizational psychology, or related field
Experience facilitating workshops, offsites, and team development sessions
Knowledge of competency frameworks and career architecture design

Responsibilities

Design and implement a comprehensive performance evaluation system that drives accountability and growth
Establish clear frameworks for goal-setting, feedback, and performance reviews
Train managers on how to conduct effective performance conversations
Oversee the performance review cycle and ensure consistency across the organization
Develop metrics and dashboards to track team and individual performance
Create calibration processes to ensure fair and consistent evaluations
Build systems to identify high performers, address underperformance, and recognize achievement
Coach managers to become more effective leaders, mentors, and talent developers
Provide 1-on-1 coaching to help managers navigate difficult conversations and team challenges
Design and deliver manager training programs on topics like feedback, delegation, coaching, and team building
Help managers identify development opportunities for their team members
Create resources and playbooks that help managers lead more effectively
Partner with managers to create succession plans and build bench strength
Conduct career development conversations with employees across all levels
Help team members identify their strengths, growth areas, and career aspirations
Create clear career frameworks and progression pathways for different roles
Design development plans that align individual goals with organizational needs
Identify skill gaps and create learning opportunities to address them
Build mentorship programs and cross-functional learning initiatives
Support high-potential employees with targeted development experiences
Foster collaboration and strong working relationships across teams and geographies
Design and facilitate team-building activities and offsites that strengthen connections
Create forums for knowledge sharing and cross-functional collaboration
Build rituals and practices that reinforce our values and culture
Address team dynamics and interpersonal challenges proactively
Develop initiatives that make Skybox a place where top talent wants to stay and grow
Gather employee feedback and translate insights into actionable improvements
Identify opportunities to improve how teams work together and execute
Partner with leadership to optimize organizational structure and workflows
Design onboarding experiences that set new hires up for success
Create systems for internal mobility and role transitions
Support leadership in talent planning and organizational design decisions
Use data and feedback to continuously improve people practices