Executive coaching for the transitions that matter
The hardest shift isn’t in the business – it’s in you. I coach scaling founders and rising C-suite executives to evolve as fast as their reality.
Trusted by leaders and executives from:
Trusted by leaders and executives from:
Advisor. Coach. Mentor
Most coaching stay in one lane.
I step into the role you need in the moment.
As your Advisor
I bring pattern recognition from 20+ years building and scaling companies. When you’re facing critical decisions – pivot or persist, hire or fire, raise or bootstrap – I’ll share what I’ve seen work and what I’ve seen destroy companies. No guesswork, just proven playbooks.
As your Advisor
I bring pattern recognition from 20+ years building and scaling companies. When you’re facing critical decisions – pivot or persist, hire or fire, raise or bootstrap – I’ll share what I’ve seen work and what I’ve seen destroy companies. No guesswork, just proven playbooks.
As your Advisor
I bring pattern recognition from 20+ years building and scaling companies. When you’re facing critical decisions – pivot or persist, hire or fire, raise or bootstrap – I’ll share what I’ve seen work and what I’ve seen destroy companies. No guesswork, just proven playbooks.
As your Coach
I help you see what you can't see — the blind spots and mental models that got you here but won't get you there. We'll dig into why delegation feels like losing control, why conflict feels impossible, or why the wins feel empty. I'll hold up the mirror so you can clearly see how to evolve.
As your Coach
I help you see what you can't see — the blind spots and mental models that got you here but won't get you there. We'll dig into why delegation feels like losing control, why conflict feels impossible, or why the wins feel empty. I'll hold up the mirror so you can clearly see how to evolve.
As your Coach
I help you see what you can't see — the blind spots and mental models that got you here but won't get you there. We'll dig into why delegation feels like losing control, why conflict feels impossible, or why the wins feel empty. I'll hold up the mirror so you can clearly see how to evolve.
As your Mentor
I'm here as someone who's walked this path and remembers what it felt like. The impostor syndrome before board meetings. The loneliness of hard decisions. The weight of other people's livelihoods. When you're questioning if you're cut out for this, I'll remind you that discomfort means you're growing, not failing.
As your Mentor
I'm here as someone who's walked this path and remembers what it felt like. The impostor syndrome before board meetings. The loneliness of hard decisions. The weight of other people's livelihoods. When you're questioning if you're cut out for this, I'll remind you that discomfort means you're growing, not failing.
As your Mentor
I'm here as someone who's walked this path and remembers what it felt like. The impostor syndrome before board meetings. The loneliness of hard decisions. The weight of other people's livelihoods. When you're questioning if you're cut out for this, I'll remind you that discomfort means you're growing, not failing.
The inside-out methodology
Developing who you are and how you lead
Core Values + Goals
Align what drives you with where you're heading. When values match goals, motivation becomes effortless and sustainable.
Core Values + Goals
Align what drives you with where you're heading. When values match goals, motivation becomes effortless and sustainable.
Core Values + Goals
Align what drives you with where you're heading. When values match goals, motivation becomes effortless and sustainable.
Zone of Genius
Discover your unique abilities and highest-leverage contributions. Focus here, delegate there and watch everything accelerate.
Zone of Genius
Discover your unique abilities and highest-leverage contributions. Focus here, delegate there and watch everything accelerate.
Zone of Genius
Discover your unique abilities and highest-leverage contributions. Focus here, delegate there and watch everything accelerate.
Map of Reality
Uncover the mental models shaping your decisions. Upgrade limiting beliefs and expand what you believe is possible.
Map of Reality
Uncover the mental models shaping your decisions. Upgrade limiting beliefs and expand what you believe is possible.
Map of Reality
Uncover the mental models shaping your decisions. Upgrade limiting beliefs and expand what you believe is possible.
360 reviews
Get unfiltered feedback on your leadership impact. See how others experience you versus how you think you show up.
360 reviews
Get unfiltered feedback on your leadership impact. See how others experience you versus how you think you show up.
360 reviews
Get unfiltered feedback on your leadership impact. See how others experience you versus how you think you show up.
Game tape
Review recordings of your actual meetings. Spot patterns, blind spots, and opportunities for immediate improvement.
Game tape
Review recordings of your actual meetings. Spot patterns, blind spots, and opportunities for immediate improvement.
Game tape
Review recordings of your actual meetings. Spot patterns, blind spots, and opportunities for immediate improvement.
Scorecard
Track the metrics that matter — from leadership effectiveness to business KPIs. Measure progress, not just activity.
Scorecard
Track the metrics that matter — from leadership effectiveness to business KPIs. Measure progress, not just activity.
Scorecard
Track the metrics that matter — from leadership effectiveness to business KPIs. Measure progress, not just activity.
The coaching journey
From first conversation to lasting transformation
1
Discovery
Our first conversation determines fit — both ways. We'll discuss your challenges, what you've tried before, and whether my approach matches what you need. You should feel confident I can guide both the tactical and transformational work ahead.
1
Discovery
Our first conversation determines fit — both ways. We'll discuss your challenges, what you've tried before, and whether my approach matches what you need. You should feel confident I can guide both the tactical and transformational work ahead.
1
Discovery
Our first conversation determines fit — both ways. We'll discuss your challenges, what you've tried before, and whether my approach matches what you need. You should feel confident I can guide both the tactical and transformational work ahead.
2
Onboarding
We begin with intensive onboarding: defining success metrics, starting your 360 review, and establishing game tape review. This foundation ensures we hit the ground running with clear goals and baseline assessments.
2
Onboarding
We begin with intensive onboarding: defining success metrics, starting your 360 review, and establishing game tape analysis. This foundation ensures we hit the ground running with clear goals and baseline assessments.
2
Onboarding
We begin with intensive onboarding: defining success metrics, starting your 360 review, and establishing game tape review. This foundation ensures we hit the ground running with clear goals and baseline assessments.
3
Foundation
2x month coaching sessions drive the work forward. We tackle immediate challenges while connecting them to deeper patterns. Every session includes pre-work and detailed follow-up, maximizing our time together on transformation, not updates.
3
Foundation
2x month coaching sessions drive the work forward. We tackle immediate challenges while connecting them to deeper patterns. Every session includes pre-work and detailed follow-up, maximizing our time together on transformation, not updates.
3
Foundation
2x month coaching sessions drive the work forward. We tackle immediate challenges while connecting them to deeper patterns. Every session includes pre-work and detailed follow-up, maximizing our time together on transformation, not updates.
4
Calibration
Regular pulse checks track what matters: your leadership evolution, team dynamics, and business performance. We adjust our focus based on data, not assumptions.
4
Calibration
Regular pulse checks track what matters: your leadership evolution, team dynamics, and business performance. We adjust our focus based on data, not assumptions.
4
Calibration
Regular pulse checks track what matters: your leadership evolution, team dynamics, and business performance. We adjust our focus based on data, not assumptions.
5
Expansion
As you evolve, the work often expands — from individual coaching to co-founder alignment or team facilitation. Your growth creates ripple effects throughout the organization.
5
Expansion
As you evolve, the work often expands — from individual coaching to co-founder alignment or team facilitation. Your growth creates ripple effects throughout the organization.
5
Expansion
As you evolve, the work often expands — from individual coaching to co-founder alignment or team facilitation. Your growth creates ripple effects throughout the organization.
Leveraging therapy and AI
How psychology and technology deepen the coaching experience
Therapy
I'm not a licensed therapist, but I bring extensive training in psychospiritual modalities to our work. This means I can skillfully navigate past experiences and patterns when they arise—always in service of your future. The distinction matters: therapy often focuses on exploring and understanding, while coaching channels those insights into action and transformation. We go deep because surface fixes don't last, but we're always building forward, not just excavating backward.
AI
I integrate AI tools to accelerate pattern recognition, track your growth between sessions, and surface insights from our work together. But here's what it can't do: challenge your blind spots, navigate identity transitions, or hold space for the messy human work of leadership evolution. I use AI to enhance our work, not replace the fundamentally human process of transformation. Think of it as having the world's best research assistant supporting the deeply personal work only humans can do together.
What clients say
Real transformations from real leaders
Bootstrapped 8-figure business
Series B startup
Series A startup
Series A startup
Seed startup
Seed startup
PE-owned, 2400+ employees
Late stage startup, 400+ employees
Caleb Polley
CEO @ Cubby Beds
"Running an 8-figure bootstrapped company, I thought I had leadership figured out. But Dileepan revealed blind spots I didn't even know existed. He helped me transition from being the company's best problem-solver to its best problem-preventer. Through our work together, I learned to build systems that scale without me, delegate without losing quality, and make strategic decisions that compound over time. The result? We increased profit margins by 35% while I reclaimed 20 hours per week to focus on long-term vision instead of daily firefighting."
Bootstrapped 8-figure business
Series B startup
Series A startup
Series A startup
Seed startup
Seed startup
PE-owned, 2400+ employees
Late stage startup, 400+ employees
Caleb Polley
CEO @ Cubby Beds
Coming soon…
Bootstrapped 8-figure business
Series B startup
Series A startup
Series A startup
Seed startup
Seed startup
PE-owned, 2400+ employees
Late stage startup, 400+ employees
Caleb Polley
CEO @ Cubby Beds
"Running an 8-figure bootstrapped company, I thought I had leadership figured out. But Dileepan revealed blind spots I didn't even know existed. He helped me transition from being the company's best problem-solver to its best problem-preventer. Through our work together, I learned to build systems that scale without me, delegate without losing quality, and make strategic decisions that compound over time. The result? We increased profit margins by 35% while I reclaimed 20 hours per week to focus on long-term vision instead of daily firefighting."
Common questions
The practical details of working together
What happens between sessions?
While transformation happens in our calls, integration happens between them. I send prompts after each session to help you apply insights, and check in before the next one to surface what's emerging. Sharing your experiments and observations via email or text as they arise keeps momentum going.
What happens between sessions?
While transformation happens in our calls, integration happens between them. I send prompts after each session to help you apply insights, and check in before the next one to surface what's emerging. Sharing your experiments and observations via email or text as they arise keeps momentum going.
What happens between sessions?
While transformation happens in our calls, integration happens between them. I send prompts after each session to help you apply insights, and check in before the next one to surface what's emerging. Sharing your experiments and observations via email or text as they arise keeps momentum going.
How long are engagements?
Most clients work with me for 12-18 months, but note there is no contractual commitment. The average is just over a year — enough time for real transformation, not just surface changes.
How long are engagements?
Most clients work with me for 12-18 months, but note there is no contractual commitment. The average is just over a year — enough time for real transformation, not just surface changes.
How long are engagements?
Most clients work with me for 12-18 months, but note there is no contractual commitment. The average is just over a year — enough time for real transformation, not just surface changes.
What's the investment?
Monthly retainers range from $3,000-5,000 depending on company stage and scope. Growth stage leaders invest $3-4K/month while late stage and public company leaders are closer to $4-5K.
What's the investment?
Monthly retainers range from $3,000-5,000 depending on company stage and scope. Growth stage leaders invest $3-4K/month while late stage and public company leaders are closer to $4-5K.
What's the investment?
Monthly retainers range from $3,000-5,000 depending on company stage and scope. Growth stage leaders invest $3-4K/month while late stage and public company leaders are closer to $4-5K.
What kind of ROI can I expect?
While coaching can’t guarantee specific outcomes, my clients report 3-10x ROI through avoided mistakes, better decisions, and faster execution. Most see meaningful clarity within the first 30 days, with compound benefits over time.
What kind of ROI can I expect?
While coaching can’t guarantee specific outcomes, my clients report 3-10x ROI through avoided mistakes, better decisions, and faster execution. Most see meaningful clarity within the first 30 days, with compound benefits over time.
What kind of ROI can I expect?
While coaching can’t guarantee specific outcomes, my clients report 3-10x ROI through avoided mistakes, better decisions, and faster execution. Most see meaningful clarity within the first 30 days, with compound benefits over time.
Do you have capacity?
I maintain a limited practice of 12-15 or so clients to ensure powerful and present coaching containers. Spots open up on occasion but clients tend to stay for extended periods. Reach out to discuss current availability.
Do you have capacity?
I maintain a limited practice of 12-15 or so clients to ensure powerful and present coaching containers. Spots open up on occasion but clients tend to stay for extended periods. Reach out to discuss current availability.
Do you have capacity?
I maintain a limited practice of 12-15 or so clients to ensure powerful and present coaching containers. Spots open up on occasion but clients tend to stay for extended periods. Reach out to discuss current availability.
Do you work with my industry?
I've coached leaders across consumer and B2B, from software to hardware, marketplaces to SaaS. The leadership challenges at inflection points are remarkably similar across industries — it's about scaling yourself, not just understanding your market.
Do you work with my industry?
I've coached leaders across consumer and B2B, from software to hardware, marketplaces to SaaS. The leadership challenges at inflection points are remarkably similar across industries — it's about scaling yourself, not just understanding your market.
Do you work with my industry?
I've coached leaders across consumer and B2B, from software to hardware, marketplaces to SaaS. The leadership challenges at inflection points are remarkably similar across industries — it's about scaling yourself, not just understanding your market.
Ready to scale yourself?
Limited spots for leaders ready to evolve faster than companies
Underrated executive
Integrated leader
Ready to scale yourself?
Limited spots for leaders ready to evolve faster than companies
Underrated executive
Integrated leader
Ready to scale yourself?
Limited spots for leaders ready to evolve faster than companies
Underrated executive
Integrated leader