Wind + Sail Leadership Partners

What Wind + Sail Leadership Partners does

Wind + Sail Leadership Partners is a privately-held, boutique leadership development firm founded in 2018 and headquartered in Chicago, with an additional presence in Washington DC. The firm is co-founded by Katrina Calihan (formerly of Bain & Company) and Amanda Mills Cutright (formerly VP of Executive Learning at Teach For America), and operates with a bench of roughly thirteen senior executive coaches drawn from operating roles at organizations including Intel, Google, Bain & Company, Frito-Lay, Bank of America, Capital One, Lockheed Martin, and Stanley Black & Decker. Its core methodology combines 1:1 executive coaching with proprietary cohort-based and team programs built around established assessment frameworks, notably The Leadership Circle 360 and a proprietary Compass Diagnostic.

The firm packages its services as an organizational scaffold designed to develop leaders from frontline through executive levels while creating shared language, skills, values, and direction across an organization. Product lines include Coaching (1:1 engagements, typically six months), Helm (executive team offsites with Compass Diagnostic assessment), Propel (signature cohort-based program with six full days across two offsites plus 1:1 coaching), Passage (3-4 day immersive senior-leader retreats), Mainsail (six-session program for frontline managers), and Speaking + Special Events. Pricing is quote-based and not publicly disclosed; engagements are custom-designed, typically multi-year, and sold via direct enterprise field sales.

The firm's go-to-market is heavily weighted toward private equity sponsors and their portfolio companies, with anchor relationships including American Industrial Partners (20+ portfolio companies, 100+ leaders engaged), ParkerGale (nearly a decade, hundreds of leaders graduated), Thoma Bravo's Continuous, Pamlico's Profisee, and AKKR's Arcline Aerospace & Defense. Additional customers span healthcare technology (Medisolv), industrial (Attindas Hygiene Partners), security/technology (Biscom), consumer services (Somersault/The Little Gym), and software (Veryon). The firm reports a 91% average NPS, 100% coaching client satisfaction, a 51% reported increase in leadership at full potential, and a 39% increase in evolved, mindful, skillful leadership among program participants. The company is bootstrapped, founder-owned, with no disclosed institutional funding, and operates without any AI/ML technology layer — its value proposition is entirely human-delivered.

Name

Wind + Sail Leadership Partners

Legal name

Wind + Sail Leadership Partners

Website

https://windandsail.co

Company type

Private

Founded year

2018

Operating status

Operating

Headcount range

11–50 employees

Short description

Wind + Sail Leadership Partners is a privately-held, Chicago-based boutique founded in 2018 that delivers cohort-based leadership development, executive coaching, and team offsites primarily to private equity sponsors and their portfolio companies, using a structured program portfolio spanning frontline through executive levels.

Ownership category

akta.pro rank

Headquarters

HQ city

Chicago

HQ country

United States

HQ region

North America

Offices2 records

Markets served

GTM type

B2B

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales

Revenue model

1. 1:1 Executive Coaching: Individual leadership coaching engagements for senior through C-suite leaders, typically spanning 6 months with assessments, ongoing fieldwork, and progress tracking.
2. Propel Cohort-Based Program: Signature cohort-based leadership development program including 6 full days of training across 2 three-day offsites plus 1:1 leadership coaching based on Leadership Circle 360 assessment data.
3. Passage Leadership Experience: Immersive 3-4 day leadership retreat experience in peaceful retreat environments, offered in small cohorts of 12 or fewer participants.
4. Mainsail Program: Cohort-based program of six interactive sessions for frontline managers and emerging leaders, delivered virtually or in person.
5. Helm Executive Team Engagement: Executive team offsites and team coaching engagements with Compass Diagnostic assessment across 6 core dimensions.
6. Speaking and Special Events: Keynote speaking, master facilitation, and custom-designed event engagements for organizations.

Pricing tiers

Go-to-market motion2 records

Distribution channels1 record

Marketing channels4 records

Core offering

Wind + Sail Leadership Partners is a boutique leadership development firm that delivers 1:1 executive coaching, cohort-based leadership training programs (Propel, Mainsail), executive team offsites and team coaching (Helm), immersive leadership retreats (Passage), and keynote speaking engagements. Programs are designed as an organizational scaffold from frontline through executive levels, leveraging research-backed methodologies including The Leadership Circle 360 and Compass Diagnostic assessments to develop evolved, mindful, skillful leaders.

Product overview

Wind + Sail Leadership Partners is a boutique leadership development firm offering a portfolio of interconnected coaching and training programs. The core offerings include Coaching (1:1 executive coaching), Helm (executive team retreats), Propel (cohort-based leadership development), Passage (immersive leadership retreats), and Mainsail (frontline manager development), plus Speaking + Special Events. Programs are designed as an organizational scaffold that develops leaders from frontline through executive levels while creating shared language, skills, values, and direction across organizations.

Differentiator

Problem solved

Functional benefit

Brands

• Propel: A cohort-based leadership development program with 6 full days of training across 2 three-day offsites plus 1:1 coaching based on Leadership Circle 360 assessment.
• Passage
• Helm
• Mainsail

Products and services

• Coaching One-on-one leadership coaching partnership designed to accelerate leader development and create measurable results for organizations, typically spanning 6 months with assessments, manager alignment, ongoing fieldwork, and progress tracking for senior through C-suite leaders.
• Helm Executive team offsites and team coaching retreats that help leadership teams deepen trust, sharpen strategy, create action plans, and build leadership disciplines. Engagements begin with the Compass Diagnostic assessment across 6 core dimensions.
• Propel Signature cohort-based leadership development program consisting of 6 full days of training across 2 three-day offsites, combined with 1:1 leadership coaching based on The Leadership Circle 360 assessment data.
• Passage An immersive 3-4 day leadership retreat experience for senior leaders and executives, designed to examine inner operating systems, beliefs, mindsets, and patterns that shape leadership effectiveness. Offered in small cohorts of 12 or fewer in peaceful retreat environments.
• Mainsail Cohort-based program of six interactive sessions for frontline managers and emerging leaders, delivered virtually or in person, focusing on research-backed content and practical skill practice.
• Speaking + Special Events Keynote speakers and master facilitators who partner with organizations to deliver memorable events including workshops on feedback, coaching skills, change management, team empowerment, and culture building.

Quantifiable outcome

• 91% Average Net Promoter Score across engagements
• +6 more outcomes

Named customers10 records

Segments7 records

Ideal customer profiles4 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Scale indicators9 records

Recent moves6 records

Expansion highlights6 records

Broad incumbents

• Egon Zehnder: Global executive search and leadership advisory firm with a strong leadership coaching and team effectiveness practice. Comparable buyer set (CEOs, boards, large enterprises) and overlap with Wind + Sail's executive team / Helm engagements.
• Center for Creative Leadership (CCL): Globally recognized leadership development research-and-practice firm offering executive coaching, assessments, and cohort programs. Overlaps with Wind + Sail's research-backed coaching and Propel-style cohort methodology, with deeper academic provenance but less PE specialization.
• Spencer Stuart: Global executive search and leadership advisory firm offering CEO succession, board advisory, and leadership development services. Overlaps with Wind + Sail's executive coaching and PE portfolio company work, particularly first-time CEO development.
• DDI (Development Dimensions International): Large leadership development firm specializing in frontline-to-executive programs and assessments. Direct overlap with Wind + Sail's Mainsail-frontline-to-Helm-executive scaffold, though DDI operates at materially greater scale with more productized offerings.
• FranklinCovey: Large, publicly-traded leadership and organizational performance firm offering cohort-based programs and content (e.g., 7 Habits, Leading at the Speed of Trust). Directly comparable to Wind + Sail's cohort-based leadership development motion but at materially greater scale and breadth across industries.
• Korn Ferry: Global organizational consulting firm with a substantial leadership development and executive coaching practice. Competes for the same enterprise and PE portfolio company buyers as Wind + Sail, though operating at much larger scale across talent, consulting, and executive search.

Direct peers

• ghSMART: Talent management consultancy focused on CEO coaching, executive assessment, and board advisory — with particular strength serving PE-backed companies. Closely comparable to Wind + Sail's PE-portfolio CEO coaching motion and AKKR Peak CEO Development-style work.
• RHR International: Boutique executive development and leadership assessment firm serving senior leaders and teams. Highly comparable to Wind + Sail's 1:1 executive coaching and team-coaching (Helm-style) offerings, with a similar premium-buyer mix including private equity and large enterprises.
• Marshall Goldsmith Group: Executive coaching firm built around Marshall Goldsmith's stakeholder-centered coaching methodology and 1:1 engagements with senior leaders. Closely comparable to Wind + Sail's premium 1:1 executive coaching motion targeting C-suite and PE-backed CEOs.
• The Leadership Circle: Leadership assessment and development firm that publishes the Leadership Circle 360 — the same instrument Wind + Sail uses in Propel. Highly comparable methodology and shared buyer base, with deeper assessment-IP specialization.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat4 records

Key risks6 records

Key highlights6 records

Customer concentration

• LinkedInlinkedin.com/company/wind-sail-leadership-partners

Revenue estimate

Valuation estimate

Number of profiles

Profiles16 records

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Wind + Sail Leadership Partners