I’m a serial entrepreneur turned executive coach.

I transform underrated executives into integrated leaders.

Who I Coach

Building a company isn’t for the faint of heart. And for every success story, there are many more about burning out, losing relationships and not having much to show for it at the end. So why do we do it? Ask any founder why they chose to be an entrepreneur and you’ll get one answer. Money. Ask again and you’ll get another. Status. Dig even deeper and they’ll reply in no uncertain terms: to prove them wrong.

Most founders I work with are driven to prove that they can do the impossible. Because somewhere in their past, someone didn’t believe you could do it. You were underrated. This is a powerful driver out the gate but it can’t sustain you. It may even break you. My work is to help you integrate more of who you are into how you lead so that you can play the long game in order to manifest your unique vision in the world.

Most of my clients are early to growth stage founders where I help them scale themselves so they can scale their company. Sometimes I coach senior executives tasked with scaling their business unit. And every now and then I work with executives in transition from one career to the next or those looking to find deeper meaning and purpose in their vocation.

As a former revenue leader and founder turned coach, I leverage my expertise when needed. I’ve bootstrapped a startup to profitability and north of $1B GMV and scaled several startups from seed to Series C, and later acquisition, as well as helped raise over $100M in venture capital. I’ve also led business divisions at Twitter and eBay focused on expanding core product offerings to new markets to increase top line growth.

  • "I needed help in almost every aspect of running a company. How to manage the board, how to build a team and most importantly, how to manage my own emotions. What I appreciate about Dileepan is that I could go to him for everything in the business and help me up level from founder to CEO.”

    CEO @ Series B startup

  • “Dileepan is not only insightful and precise in his professional guidance, but the compassion and kindness he brings to every interaction truly sets him apart. It's exceedingly rare to find a coach who can so seamlessly blend deep personal insights with business and strategy expertise.”

    Co-founder CTO @ Series A startup

  • “Dileepan has been a much needed counterbalance to the loneliness of the startup journey and an inspirational source of wisdom to me as a startup executive. I couldn’t be happier about the ‘battle rhythm’ of our sessions fielding questions about both the fire of the day and addressing long-term foundational work.”

    Growth Lead @ Series A startup

  • "Dileepan’s coaching was invaluable to me in choosing to build a startup, and to do so as a solo founder. And his ability to combine this with the inner game of entrepreneurship helped me find joy in the startup journey. I’m also braver and have the courage that I didn't know I had.”

    Founder @ Seed startup

  • “What stands out is Dileepan’s ability to take charge of session agendas and goals, a refreshing shift from previous coaches who relegated this responsibility to me. He excels in exposing the ‘unknown unknowns’ which is what working with an exceptional coach is all about.”

    Senior Product Lead @ Adobe

“If you are struggling with the demands of being the boss, the first thing to realize is you are not alone. It is a super hard job. The second thing is to get some help. From someone who has done it before and knows what to do.”

— The CEO Mentor and Coach, Fred Wilson @ Union Square Ventures

My Approach

My approach combines strategic and tactical advice with inquiry and integrated coaching. Most leaders come to coaching to help solve pressing challenges in their business. I work with leaders to help them work on their business, not in their business. Working in your business leads to burnout. Working on it leads to scale.

If you can’t scale yourself, you can’t scale your company.

As we start to work through different issues, we’ll start to uncover recurring behaviors, patterns and beliefs that show up in your work, and in your life overall. Building a company not only provides you with the unique opportunity to manifest your vision in the world and achieve outer success, but also the chance to reflect how and where you need to grow as an integrated leader.

My coaching helps achieve results through transforming yourself into who you uniquely are as a leader. Too often, the ideas we have about what leadership–or success–looks like aren't our own.

My job is to help you become the leader only you can be.

This can be deep, and transformative work. But it requires accountability and commitment. And this is how coaching is not talk therapy. My style is challenging and direct as well as empathetic and forgiving. Breakthroughs ask us to dance with our edge.

How It Works

Initial Consultation

An initial consultation will help us determine client and coach fit which is critical. You need to not only feel confident in my ability to coach your outer game, you also need to feel safe and secure enough to trust that I can help your inner one. If we’re not the right fit, I can refer you to other coaches who may be.

Discovery Session

If we do decide to partner, we would kick off our engagement with a discovery session. In addition to committing to agreements including confidentiality, we’d explore your short and long-term goals and how this connects to where you are in the arc of your work and life journey. We’d also discuss what has or hasn’t worked for you based on any prior experience with advisors, coaches or therapists.

Coaching Sessions

The focus of our work together is the ongoing coaching session that happens at least twice a month. While you may come to most sessions with a specific topic or set of items to discuss, my job is to help you connect this to the outer game of achieving your goals and the inner game of transforming limiting patterns and beliefs.

Using the outer game to inform the inner game over time allows us to integrate more of who you uniquely are as a leader into your work and life. Otherwise, we’re scratching the surface every week without digging deeper. My coaching is not “How was your week?” therapy.

Feedback + Iteration

Feedback is the lifeblood of any coaching engagement. In addition to informal feedback during sessions, I use formal approaches including short surveys in between sessions to ensure that I’m serving you at the highest level. This is especially important in the first month or two in coaching so we can iterate.

Offerings

One-on-One Coaching

At least two one hour sessions each month with additional support between sessions via email, text or phone when needed.

Co-Founder Coaching

A set number of sessions for co-founders needing a strong foundation to start a company or co-founders scaling one who need to tackle a specific business challenge.

Team Coaching

A set number of sessions for executive teams needing a strong foundation to enter a new market, launch a new product or tackle a specific team dynamic.

Assessments

Outer game assessments (360 reviews) and inner game exercises (Core Values, Energy and Time Audit, Zone of Genius) to uncover your unique ability and purpose.

Operating Systems

Implement an OS relevant to who you are and how you work as a Founder as well as the stage and type company you are building.

Off-sites + Retreats

Quarterly or biannual executive team offsite and company retreat facilitation focused on both the business and people aspects of building and scaling a company.

  • Results are tied to both short and long-term goals but I find that most clients start to see outer and inner game shifts in the first month or two of working together. What we’re working towards is either incremental shifts that compound over time or transformative ones that can happen in one session.

  • Coaching engagements average about 9 to 12 months with some clients continuing on past one year as they continue to scale their company. My only ask is an energetic commitment for at least three months when we start which I find is the minimum amount of time to set the foundation for a transformative partnership.

  • One-on-one coaching is priced as a monthly retainer and not a per session fee. The retainer includes the ongoing coaching sessions (at least two per month) and any additional live or asynchronous support between sessions as needed.

    My monthly retainer is $2,500 per month. And I have a sliding scale for leaders that cannot afford this rate when we start working together. We can discuss more during the initial consultation and I’m always willing to refer if there isn’t a fit.

Contact me.

hello@dileepansiva.com