My expertise is in helping driven Founders and Leaders become world-class CEOs. This Founder to CEO evolution is needed once the startup has found Product-Market fit (PMF) & is looking to scale. I use my 5D model to help the leader build their strategy, team & systems — so their startup ‘gets better, as it gets bigger’ — & they don’t burnout. More details below.
Over the last 15 years I have consulted & coached Founders, CEOs & Senior leaders of several startups across domains of Edtech, Education, Social enterprises & Technology. You can read their testimonies here.
If you want to speak with me on a potential consultation:
5D model of a CEO’s role
When I was CEO, the most common question I got: “What on earth does a CEO do?” After a decade of being a CEO & reading everything I could about it, I created my 5D model of a CEO’s role (see pic). My attempt was to create the most comprehensive yet simple & memorable articulation of a CEO’s role you will ever find. (When I shared it on Twitter & Linkedin, it got hundreds of saves/shares including by the founder of Reddit who shared it with a chef’s kiss).
Across these 5Ds — Direction, Diamonds, Delivery, Dollars & Decibels — there are 20 Areas that I support & consult CEOs on:
(I) DIRECTION → Define where the organization is going in an inspiring & memorable way
- Vision & Mission: Craft your big dream for the world and the role you want your org to play to make that dream a reality
- Strategy: Articulate who you are, your unique value & where you are going in the next few years in 1 line (Northstar) & 1 picture (flywheel). Figure out what you next product/service should be that will take the organisation to the next level
- Business Model: Create a sustainable & scalable model which streamlines your costs & gets you the money & resources you deserve for the incredible value you are creating
- Change Model: Describe how various parts of your theory of change coherently fit together to create your promised impact
(II) DIAMONDS → Recruit & Retain the best talent to pursue your Direction
- Org Design: Define which are the core teams (+ what’s the right size for each), who is on the leadership team (+ what should they own, who should they report to) and what should the Founder/CEO’s role be (where can you add unique value, what should your focus be, what should you delegate & how)
- Hiring: Build a world-class recruitment system that gets you the best possible talent without being a huge drain on time & resources
- Performance Evaluation: Create a system which clearly defines excellent performance, fairly evaluates people & gives them career paths they are excited about
- Surveys & Feedback: Design a system to regularly collect engagement & performance data so you always have a pulse on how people & teams are doing, are never caught by surprise & can address potential issues early
- Board: Create a world-class board, leverage board members strategically & run productive board meetings
(III) DELIVERY → Build a high performance culture that balances: Apt Support + High Ownership + Clear Accountability
- Goals & Planning: Create a Goal system that brings focus & alignment (within & across teams, from big picture to Individual level) and leverage Cycle Planning to deliver — quickly, with high quality, at scale — without burning everyone out
- Decision Making: Build a decision making system that leads to quick & high quality decisions that also have high team satisfaction
- CEO Calendar: Craft your calendar so you spend your ‘within org time’ in supporting your leaders (+ holding them accountable) & not in day to day fire-fighting
- CEO Dashboard: Create a dashboard that brings all key organisational metrics in 1 view so you can easily & regularly track how the org is doing & fix emerging problems before they become crises
(IV) DOLLARS → Deliver capital to pursue your direction & ensure there’s always cash in bank
- Fundraising Strategy: Define the ‘right’ funders for you, figure out how to attract them & show them your unique value
- Funder Engagement: Develop a simple system to keep funders updated and engaged in your organization so they stay invested and double down on their commitment
- Financial dashboard: Identify the key financial metrics for your organization & develop a dashboard & system to regularly review them
(V) DECIBELS → Communicate regularly to inspire & align all internal & external stakeholders
- Organisation Playbook: Build a fun & unique playbook that you can give to every employee to explain, inspire & align everything about your organisation
- Your Founder/CEO story: Learn how to tell your story powerfully so you can attract the people & resources you need (+ create variants for social media, elevator pitches, conferences)
- Your Organization pitch: Craft a pitch that shows the world your unique value and inspires people to take action (invest, buy, join)
- Lead Magnets: Create digital products that will build your brand, fill your funnel with relevant prospects & do automated outreach for you 24X7
Consulting Options
Across these 5Ds and 20 Areas, there are 2 Consulting Options I offer:
(A) DIRECTION
- Outcome → Using first-principles, create a ‘Direction’ that’s audacious, rigorous & inspiring
- For whom →
- A leader who is scaling their organisation & wants to make sure that all the Direction areas are aligned & coherent
- A leader whose organisation has attained some success & now they want to level-up by re-imagining their Direction
- Areas under Direction →
- Vision & Mission
- Strategy & Growth plan
- Business Model
- Change Model (Theory of Change)
- What you’ll get →
- I’ll deeply understand where you are as an organization, what’s worked so far, what’s not & where you want to go
- I’ll then diagnose the root causes for your challenges & share multiple solutions with their pros, cons & requirements
- Post that, I’ll support you in crafting a Direction that best fits your ambition & then help you articulate it to your team in a simple, memorable & inspiring way
- Project Details → Typically, 3-4 months, 8-12 calls
(B) DIAMONDS, DELIVERY DOLLARS, DECIBELS
- Outcome → Build world-class systems that accelerate your progress
- For whom → A leader who feels their organisation’s quality or speed or growth is getting limited because of their current systems
- Areas I offer support on →
- Diamonds (everything talent) → Org Design, Hiring, Performance Evaluation, Surveys & Feedback
- Delivery (everything performance) → Goals & Planning, Decision Making, CEO Calendar, CEO Dashboard
- Dollars (everything money) → Fundraising Strategy, Funder Engagement, Financial Dashboard
- Decibels (everything communication) → Org Playbook, Your Story, Organisational Pitch
- What you’ll get → For each area that you pick,
- I’ll review your existing systems, understand the challenges you are facing & help you identify gaps
- I’ll then share world-class exemplars & help you use them to create a new system relevant to your context
- Finally, as you roll all this out in your organization, I’ll help resolve any challenges & problems that emerge, to ensure a successful implementation
- Two Project options →
- (B1) Build world-class systems in any 2 Areas → Typically, 1-2 months, 4-6 calls
- (B2) Build world-class systems in any 5 Areas → Typically, 3-4 months, 8-12 calls
To know prices and more details, please reach out to me.
Testimonials
Nathan Pai Schmitt Co-Founder & Executive Director, HNC
My org has grown 3X every year for the past few years (currently ~$10M ARR). But we were struggling to manage this growth & I had reached my own "point of diminishing insight" around solving these scaling problems. That’s when we hired Gaurav as a consultant to help us with this. The question I put in front of him: "What do we need to do so our quality increases as we scale?". He 1st helped me figure out the principles needed for this. Then he worked with us in building org-wide systems to make this happen. The results have been transformative. We are now scaling much faster while increasing our quality & even the team stress is lower. After working with Gaurav, our organisation is proof that you can ‘get better as you get bigger’.
Girish Bhakoo Chief Investment Officer, TenCore Partners
I have known Gaurav for over a decade now. He has always been a deep learner and thinker. His learning lens is extremely broad—from lived experiences in challenged communities to reading from business, art, philosophy, psychology, history, etc. In addition, he has built exceptional teams throughout to help execute the vision. The teams he led always appeared to have that special energy and gleam that only comes through shared purpose, understanding, care, and ownership. Like others, I feel I learn and grow in his presence. And that’s before we start a conversation, which is always riveting and enlightening.
Harry Fletcher Wood Author & Head of School Surveys, Teacher Tapp
Gaurav applies his experience and wisdom to gently and humbly show how you can make your ideas better, your plans more robust, your organisation more effective. Across several years, Gaurav has helped me: (a) Write a better book (b) Design a better professional development programme (c) Create a better software product His help is invaluable: sign him up now.
Shaveta Sharma Kukreja CEO, Central Square Foundation
In my two decades of professional journey I have seen the difference good leaders can make. They shape organisations and their people for the now & for the future. I have known Gaurav for a long time & he stands out for his commitment to lead and not just manage, even more demanding for a young social entrepreneur. It has been inspiring to see his commitment, both in word & action, towards people and institution building from the earliest days of 321. Gaurav has approached his own leadership with a keen & curious mind, and always made the time to perfect it in practise!
Hiten Jethwa Director of Infrastructure & Leader Support, HNC
When Gaurav and I started working together, we were in the middle of building a very technically complex program. I was lost in the fog of balancing the urgency of day to day delivery while building an innovative & rapidly scaling program. The team was on the edge of burnout, overwhelmed and confused. Gaurav completely transformed this situation. He helped us quickly diagnose the root causes, prioritise them & then build solutions we could implement immediately. In a matter of weeks, we gained clarity, confidence & tools that we are confident will scale with our work. I was amazed at how it changed the team’s energy & motivation. Also it freed me to do more coaching & strategic thinking instead of being constantly stuck in fire-fighting. To say his consulting was a game-changer for us is an understatement!
Steven Farr Executive Director, Teach For All
Gaurav Singh is one of my favorite sources for learning about learning. . . and about leadership . . . and about management . . . and about strategic clarity. I’ve been a manager and senior leader at large national and international organizations and networks for over twenty years, and I still call on Gaurav to help me grow and develop. Not only does he keep up with the frontiers of management and leadership research he manages to apply them to his work. Even more remarkable (and rare) is his ability to make them accessible and actionable for others. The best management and leadership advice I can give is that if you have a chance to learn from and with Gaurav Singh, take it.
Tom Davies COO, LEEP
Gaurav is an outstanding leader. He is incredibly good at analysing situations, thinking strategically, creating powerful solutions, aligning people & ensuring implementation. As his manager, I admired the strong learning loops he built for himself which allowed him to get good very quickly. What’s been amazing is to see that he has managed to build teams that do the same. His teams learn from local & global contexts, are reflective, error correct rapidly & produce amazing results. I think a big reason for this is Gaurav’s ability to break down his own practice & teach it to his team. He has the rare combo of being a great leader & a great teacher.
Romana Shaikh Chief Program Officer, Kizazi
Gaurav is one of the first people I reach out to when I face a challenge as a leader. Many of my core leadership principles emerged from discussions with him. He showed me the importance of simplifying things for my team: simple so they knew where to focus, simple so they could leverage their strengths, simple so they knew where their responsibilities ended, simple so they could succeed. He helped me realise that my team’s success was my success & this helped me transition from task management to people management. I have seen him help several others to become better leaders & build great teams.
Pooja Warier Chief Revenue Officer, Apolitical & ex-CEO, Unlimited India
I have known Gaurav for a long time & been able to observe his leadership closely. I admire 3 things I have seen him do better than most leaders. Firstly he is able to navigate the difficult decisions & tricky situations that leadership involves through the lens of the big picture mission. This allows him to respond & not react to the multitude of difficult challenges every leader faces. Secondly he things deeply & critically about issues before forming an opinion. So he & his team have deep conviction in their decisions & are comfortable in going against the norm. Thirdly, he has always been at the cutting edge of thinking about management & work. For example, he moved 321 to a remote work setup even before Covid began, he started using modern goal setting methods like OKR before any other non profit in India & has been far ahead of most organisations in making learning a continuous process which scales with their team. He has certainly inspired me to apply these things in my own roles over the last decade, ranging from Senior Leader to CEO.
Joshua Prudowsky Partner, Praxis Institute & Faculty, University of Illinois at Chicago
I was a successful professional in the US before I moved to India to work with Gaurav. I learnt more from him in 2 years than I learnt in any other 2 year period of my life. After coming back I have started a successful company & a big reason is I just applied everything I learnt from Gaurav. Gaurav showed me a leadership style that I had seen quoted but never demonstrated. He showed me how to build teams that strived relentlessly for excellence, how to use data for decision making, how to align different teams to a common mission & clear goals & how to innovate when your back is to the wall. I also learnt from him the 2 things which are extremely hard for any leader: how to let people go quickly but respectfully & how to get teams to debate passionately but constructively. He is also one hell of a coach who will show you the best in you & then motivate you to deliver on your potential. I was lucky to work with & learn from him.
Saloni Gopani Founder & CEO, GoodStep
I was connected to Gaurav via the Level Up accelerator program. The most helpful aspect of our conversations was how easily he’d help me funnel down from strategy to tactical next steps. Gaurav is a realist and optimist at the same time, a super unique combination that’s very well-suited to any entrepreneur seeking motivation + honest advice. I especially loved how invested he was in making sure I was personally excited about the direction we were discussing for my startup. He struck a wonderful balance between giving objective and actionable business advice and igniting excitement and enthusiasm to go get those goals!
Pragati Sharma Co-founder & Director, i4consulting
Gaurav is a perfect motivator and guide: I had run a HR business successfully for 2 years and needed to scale. At the same time, we had been mulling over a product idea for over a year. As they say, daily urgencies take over in business and you lose sight of what is important for growth. There came Gaurav and showed me the forgotten path or shall I say the neglected goldmine of potential? He has the patience and positivity that is extremely rare to find for a mentor - He decluttered my mind and is today helping me build a product from scratch.Through the entire process, he has added more value than the program demanded and helped me structure the product, plan for its MVP and connect with the right people. Grateful that we connected.
Hemakshi Meghani Co-founder, Indian school of Democracy
Despite being a good public speaker, I had hit a road block as I prepared my pitch for a competitive international Fellowship. I felt my elevator pitch was not doing justice to our work & impact. I thank my stars that I spoke to Gaurav before my big interview. He helped me bring out my personal story & then weave it with that of the people we serve. He guided me on how to tailor my pitch for a diverse international audience, without diluting the work we did. I came into my chat with Gaurav feeling overwhelmed & uncertain. I left feeling energised, clear & confident. This showed in my pitch and we got this coveted fellowship. Later, when we were looking for a public speaking coach for our batch of aspiring public leaders, we brought Gaurav in. He was able to hold space for leaders from all over the country, with very diverse background and learning needs, & taught them how to tell their story in a way that is authentic & with a strong call to action. To this day they continue to use the learnings from this session with great success.
Karthik Ram CEO, Development Solutions
Leadership can be lonely. There is plenty of advice out there but it is rarely a) nuanced, b) contextualised and importantly c) practical. Gaurav is all of these. His insights are drawn from his own experience of being a visionary founder, and he is uniquely gifted at distilling learnings for wider applicability. Conversations with him have been particularly valuable in articulating, prioritising and navigating organisational challenges - strategic and operational. He is an excellent thought partner on strategy formulation and culture building. He has also helped push my thinking and challenge implicit biases.
Anjan Prakash Biomimicry Professional & Education Entrepreneur.
Gaurav is one of the most generous, joyful & natural guides a founder can have. When I spoke with him, I really felt my project was seen and heard patiently & respectfully. Many things I held intuitively he validated with his insights & wisdom. And many other things emerged which I had not thought/considered but which immensely helped me creating my business model & strategy. I can’t thank him enough for his generosity & guidance.
Mary Ellen Matsui Ex-CEO, ATMA
Gaurav is the best resource a leader can have. He does the thorough research you need in order to understand leadership principles and put them into practice. With a background in education his approach is always patient. Always focussed on sustainable growth for the individual, team and organization.
Azad Oommen CEO & Co-Founder, Global School Leaders
I have known Gaurav for over 10 years and seen his evolution as a leader. When we first met, he was a guy with a plan, and I was privileged to have a front row seat to see him lead the execution of his plan into a 75-person organization. What I appreciated the most about his journey was the commitment to understanding ideas, sourced from a lot of different fields, and seeing how they could be used in service of improving education for all children. Gaurav is deeply curious, a master synthesizer of ideas with the ability to convey complex thoughts simply, and one of the best teachers/trainers I have met
Bishakha Datta Executive Director, Point of View
Gaurav did a very insightful session on Monitoring & Evaluation with our team. 3 main things stood out: First of all, he showed how we could the work of researchers & academics, mix it with our practitioner’s lens & create something that has both theoretical depth & practical application. Second he showed us how to liberate M&E from a formulaic & right practice often done to us to being something that we can drive to pursue our intellectual curiosity & make our programs better. Third, I loved the details, examples, templates that he shared. Everything was very concrete, well thought out and immediately applicable. I think honestly, I feel like after this I’m really sold on ‘impact & measurement.’
Jaya George Ex-Head of Education, Christel House
I have known Gaurav for a long time & seen him in various roles: trainer, school leader, manager, CEO. From our 1st meeting. I was amazed at his intelligence, clarity of thought and his ability to mix an inspiring vision with a clear plan of action. When I became an advisory board member at 321, I was able to observe his leadership more closely. As a leader he led by example and everyone on his team had a voice in the decision making process. He saw to it that there was distributed leadership and that there was mutual respect and sharing among his team. Over the years I saw his team learning and growing and eventually taking on roles of responsibility within the organization. Most of his early team members are now in senior managerial positions and I would give due credit to Gaurav for training them, mentoring them and allowing them to grow. Gaurav is also a fantastic trainer & I learnt a lot from the trainings & meetings he conducted for the advisory board. His sessions were always impeccably planned & facilitated with every participant leaving with powerful learnings & a smile on their face.
Aditya Minocha Executive coach & Education Consultant, State Governments
For a decade Gaurav has been my go to advisor on topics of organizational strategy, leadership and team building. Gaurav’s gift is that for any problem you share with him he will first take you 50,000 feet above the problem to give you a bird’s eye view. Then he help you view the problem from multiple lenses. Finally he will take you 50 feet deep into the problem & share solutions that are wholesome, practical and systemic. He will give you solutions that address your immediate short term problem while helping you build long term systems that eliminate the problem completely. He has a deep understanding of human behaviour & team dynamics so he can design systems that actually work. If you are a CEO or leader struggling with an important problem or want to go to the next level of performance, I strong recommend reaching out to Gaurav.
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