Director of Talent Development & Performance

Director of Talent Development & Performance

Reports to: Senior Leadership
Location: Chicago, IL

About Skybox Capital

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.

The Opportunity

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.

What You'll Do

Performance Management & Evaluation

• 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

Manager Development & Coaching

• 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

Talent Development & Career Pathing

• 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

Culture & Team Building

• 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

Organizational Effectiveness

• 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

Who You Are

Required:

• 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

Ideal:

• 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

Personal Attributes:

• Deeply curious about what makes people and teams perform at their best
• Direct communicator who delivers honest feedback with care and respect
• Systems thinker who can design scalable processes without losing the human touch
• Empathetic listener who builds psychological safety and trust
• Results-oriented professional who measures impact and continuously improves
• Adaptable and comfortable with ambiguity in a growing organization
• High emotional intelligence and ability to navigate complex interpersonal dynamics
• Passionate about developing others and seeing them succeed

Why Join Skybox

Define the Role: Build this function from the ground up and shape how we develop talent and drive performance.

Direct Impact: Work closely with leadership and see your work directly influence how the organization performs.

Exceptional Talent: Develop smart, driven professionals across finance, investments, operations, and technology.

Global Scope: Support teams across the U.S., Israel, Canada, and Asia — building cohesion across cultures.

Modern Approach: Use data, technology, and evidence-based practices to build a best-in-class talent development function.

Entrepreneurial Environment: Operate with autonomy in a fast-paced firm that values innovation and continuous improvement.