Inner evolution. Outer Results. Organizational Impact.
COACHINGLeaders draw the map for what an organization can achieve. They shape the conditions for innovation, culture, and performance to thrive. The quality of leadership determines the scale of impact. Partner with Wind +Sail to develop leaders ready to navigate all waters.
What is coaching?
Leadership coaching is a structured, collaborative, and highly customized partnership between leader and coach to accelerate the leader’s development and create meaningful results for your organization.
RESULTS YOU CAN EXPECTOur coaching engagements are designed to create meaningful, measurable shifts for the leader and the organization. Leaders coached by Wind + Sail report significant gains in these common coaching areas:
Self-awareness and social-awareness
Setting vision and direction
Coaching for impact
Leading change
Executive presence
Influence and storytelling
Decision making
Emotional intelligence
Empowering teams
Peak performance
Work-life compatibility
Navigating M&A
Building trust
Inspiring and motivating teams
Teaming and collaboration
Strategic planning
Performance management
Work prioritization and delegation
CEOs, Investors, and Board Chairs call on W+S to level up their highest potential leaders. We coach Senior through C-Suite leaders across diverse industries, organizational sizes and roles.
IN THEIR WORDSI’ve worked with Wind + Sail across two PE-backed SaaS companies, Biscom and Medisolv, during periods of significant transformation, growth, and value creation.
The team brings a rare combination of pragmatism, psychology, grit, and wisdom to leadership development, organizational health, and executive team performance.
They deeply understand the realities of middle-market SaaS businesses — professionalizing teams, navigating change, and creating cultures where people challenge, debate, hold each other accountable, and still have fun doing hard things together. W+S has become a genuine trusted advisor to me on all things leadership, team, and people.
Dave Lucey, CEO Medisolv
COACHING JOURNEYA typical engagement spans the course of 6 months and includes assessments, manager alignment, ongoing fieldwork and a client dashboard to track progress
Set the course
Conduct & review assessments
360 assessment
Identify coaching engagement goals
Align goals with coaching sponsor
Zoom out
& refine
Gather progress feedback
Engage in fieldwork
& test new practices
Explore & experiment
Midpoint check-in to review and refine goals
Midpoint sponsor meeting to share progress
& solicit feedback
Set Sail
Review progress
& crystallize learnings
Set next steps for development beyond coaching
Reflect on journey
& celebrate successes
with coaching sponsor
The Impact of our coaches speaks for itself
Our coaches are exceptionally qualified. They hold high standards rooted in genuine care.
“Working with Wind and Sail has been an invaluable part of our executive development strategy, particularly for first-time CEOs navigating the complexity and demands of scaling a business. Their structured and highly practical approach provides C-suite executives with the right balance of strategic guidance, leadership coaching, and accountability during critical transition periods.
As a core component of our Peak CEO Development Program, their coaching framework has helped emerging CEOs strengthen decision-making, organizational leadership, and executive presence while successfully managing accelerated growth and change. What differentiates their team is their deep understanding of the unique pressures faced by leaders in private equity-backed environments.
We have also found tremendous value in how they partner not only with portfolio company executives, but also with private equity firm leaders during key transition and growth points. Their ability to align leadership development with business objectives creates meaningful impact across the organization and contributes directly to stronger executive performance and long-term value creation.
We view Wind and Sail as a trusted partner in developing high-performing leaders and organizations.”
Ann McCloskey, Managing Director, AKKR
Ready to work with a coach?
Want to learn more about working with a Wind + Sail coach? Contact us here to start the process of finding the right match.