Next generation, evidence-based leadership coach matching.
Built for unconventional founders and family businesses adapting fast.
Limited 2026 cohort.
"After leading large teams in high-pressure environments at the BBC, I retrained as a coach and psychotherapist to understand what truly drives performance. Now I work at both levels-practical leadership and the patterns beneath it."
Sarah
|Executive Coach & Psychotherapist
How Our Coaching Works
Coaching is the process of uncovering layers to remove what holds you back from goals both business and personal.
Together, you embark on a journey and build competencies to achieve your goals sustainably and live with more freedom.
How Our Coaches & Ecosystem of Specialists Work Together
All packages include access and sessions with hand picked specialists who provide tactical and execution support in areas where founders and growing businesses need it.
Get Started
1. Orientation Call
Book in a 20min call with us to see if Sideways is a good fit for you and your business.
2. Start Your Journey
Review coaches who will resonate, using the world's most advanced personality framework and explore specialists to level up.
3. Enter Sideways
Hold your first coaching session on us. Choose a package and unlock access to the best minds and skills and global events and retreats.
Specialist Ecosystem
Our Specialists
Specialists and experts at your fingertips for all areas of growth whenever you need it. Both Integrative and holistic.
Exit & Legacy Planning
Jen · Founder Strategist & Fractional CMO
STARTS AT 2 CREDITS
AI Reality Check
Danish · Unbiased AI Review and Integrations
STARTS AT 2 CREDITS
International Finance & Tax
Tom · Founder Finance
STARTS AT 2 CREDITS
The Declutter Diagnostic
Nina · Clarity & Streamlining
STARTS AT 2 CREDITS
Digital Experience Audit
Cath · UX & Product Design
STARTS AT 2 CREDITS
Spatial Entrepreneurship
TBA · Spatial & Location Strategy
STARTS AT 2 CREDITS
Sustainability Audit
TBA · Sustainability & Impact
STARTS AT 2 CREDITS
Mindful Leadership Audit
Samantha · Mindful Leadership
STARTS AT 2 CREDITS
Team & Organisation Diagnostic
Lynn · Founder & Organisation Design
STARTS AT 2 CREDITS
Stuck to Scaled
Jen · Founder Strategist & Fractional CMO
STARTS AT 2 CREDITS
Core Capital
Keren · Body & Performance Specialist
STARTS AT 2 CREDITS
Hormonal Performance Diagnostic
Mariel · Hormonal & Performance Specialist
STARTS AT 2 CREDITS
Lead With Your Cycle
Mariel · Leading in a Female Body
STARTS AT 2 CREDITS
The Founder Parent
Mariel · Parenthood & Leadership
STARTS AT 2 CREDITS
Burnout Diagnostic
Glynis · Burnout & Prosilience
STARTS AT 2 CREDITS
ADHD Leadership Diagnostic
Rosie · ADHD & Neurodiversity
STARTS AT 2 CREDITS
Voice Under Pressure
Ilhem · Voice & Presence
STARTS AT 2 CREDITS
Founder Psychotherapy
Sarah · Transactional Analysis Psychotherapist
STARTS AT 3 CREDITS
Psychosexual Therapy
Sarah · Psychosexual & Relational Specialist
STARTS AT 2 CREDITS
Where most founders start
Your Biology Has a Blueprint.
The leaders we work with think they have a stress problem. Most of them have a biology problem. Our specialist brings 35 years of clinical experience and the world's most advanced biological science to read the body the way a founder reads a business - root causes, not surface symptoms. No guessing.
Two credits from your allowance. Most coaches book this in your first month.
Packages
Choose the depth of support that matches your journey. Larger packages unlock more specialist credits and deeper benefits.
Quest
3 months
- 4 coaching sessions across 3 months
- 6 specialist credits
- Lumina behavioural report
- Retreat and event access (2027)
- Book coaching sessions 4 weeks in advance
Voyage
9 months
- 8 coaching sessions across 9 months, front-loaded
- 12 specialist credits
- Lumina behavioural report
- Priority retreat and event access (2027)
- Book coaching sessions 8 weeks in advance
Odyssey
12 months
- 12 coaching sessions across 12 months
- 20 specialist credits
- A session with your co-founder or partner
- Book coaching sessions 12 weeks in advance
- 25% retreat discount
- Access to new global markets and introductions
Voyage
9 months
- 8 coaching sessions across 9 months, front-loaded
- 12 specialist credits
- Lumina behavioural report
- Priority retreat and event access (2027)
- Book coaching sessions 8 weeks in advance
Quest
3 months
- 4 coaching sessions across 3 months
- 6 specialist credits
- Lumina behavioural report
- Retreat and event access (2027)
- Book coaching sessions 4 weeks in advance
Odyssey
12 months
- 12 coaching sessions across 12 months
- 20 specialist credits
- A session with your co-founder or partner
- Book coaching sessions 12 weeks in advance
- 25% retreat discount
- Access to new global markets and introductions
We're Experts In Navigating
Founder Bottleneck
The business still runs through you. Control habits, decision strain, difficulty building autonomy in others.
Scaling Without Structural Readiness
Revenue growing faster than systems. Lifestyle business evolving into structured SME — not yet sale-ready.
Leadership & Culture Misalignment
Different visions, generational gaps, communication fractures. Scaling the team without losing the spark and intentional rhythm.
Innovation & Future Pressure
AI, tech disruption, market shifts. Knowing you must adapt — unsure how fast, where, and with what structure.
Strategic Fog During Growth
Momentum without clarity. Too many opportunities, shifting markets, uncertain priorities. The bigger picture keeps slipping away.
Energy, Identity & Resilience Strain
Burnout cycles. Isolation at the top. Passion erosion. Succession or exit questions emerging. This is what we help you reclaim.
Where most founders start
AI Without the Hype
Our independent AI specialist cuts through the noise to show you what AI can genuinely do for your business - no tools to sell, no agenda. With a decade of experience inside the platforms vendors are now pitching you, their independence is the point. Already have someone leading your AI initiatives? Our specialist can audit your current strategy, pressure-test your roadmap, and identify high-impact optimisations you may be missing.
Two credits from your allowance. Most coaches book this in your first month.
Matched To YourFrequency
UNDERLYING
Your natural state
EVERYDAY
Daily professional life
OVEREXTENDED
Under stress
Hover over each persona to explore your frequency spectrum
Hear From Our People
Real conversations with the coaches and specialists who make Sideways what it is.
Meet a Coach
Samie
Coach
Meet Keren
Keren
Specialist
Retreats, Events & Community
Access global retreats and events. Human connection is the new oil of the world. As everything becomes increasingly digital, genuine relationships become invaluable.
Global Retreats
In-person gatherings in inspiring locations. Deep work, real connection, transformational experiences.
Founder Community
A curated network of like-minded leaders. Share challenges, celebrate wins, grow together.
Peer Growth
Learn from others who've walked similar paths. Unconventional founders supporting unconventional founders.
Future Retreat Locations and Events
Retreat priority access is included with the Voyage and Odyssey packages and available as a separate experience.
Exceptional Coaches
We intentionally work with a highly curated group of coaches for a higher impact.
Global cohort of high impact coaches
A carefully assembled network of 17 coaches, spanning 11 countries from diverse cultures & disciplines. United by one standard: measurable impact.
Deep experience with founders & family business challenges
Our coaches bring in-depth, lived experience navigating the unique pressures of founders, C-Suite and family centric buinesses.
Curated for quality, not volume
We onboard a limited number of clients per year as we're not a marketplace. Every coach passes a rigorous selection process so you only ever work with the best.
Start with a 7-min coach pairing assessment.
No commitment, no pressure. The first step toward growth.