Playing to Win™ Masterclass
A One Year Intensive Journey to Transform your Business from Strategy, Culture, Mindset to Execution: Master the Playing to Win™ framework that unlocked S$224M+ Growth Revenue for 30+ SMEs!
Why 96% of Singapore SMEs Struggle to Scale Beyond $10M Annual Revenue...
No Alignment of Objectives, Planning & Decisions
There's a big disconnect between Goals, Objectives and what is actually Executed on the ground.
It feels like everyone is working in silos, and teams are not working as one unit to achieve the company goals.
It feels like everyone is working in silos, and teams are not working as one unit to achieve the company goals.
People Do The Same Things, Expecting Different Results
There is no direction and employees end up demotivated.
The leadership team does not know where to prioritise or what else to do to develop a next-stage growth engine.
The leadership team does not know where to prioritise or what else to do to develop a next-stage growth engine.
Firefighting Daily - Everyone is Stuck IN the Business
Everyone seems to be working on what's urgent, not what's important.
The company is constantly in firefighting mode and growth initiatives are often stuck.
The company is constantly in firefighting mode and growth initiatives are often stuck.
In Short, Most SMEs are Stuck because they Play to Participate, or Play NOT To Lose!
These are the symptoms of a business that lack a Winning Strategy:
Weak Company Culture
Your team lacks ownership and struggles with effective communication, and are disconnected from the company's purpose.
Poor Customer Satisfaction
Your business sells to everyone. The majority of your clients do not purchase from you again.
Shrinking Margins
Your business model does not produce the margins necessary to create Wins for your clients, your business and your employees.
Direction Keeps Changing
Without hard data, it is difficult to measure progress and identify areas for improvement. You make business decisions based on gut feel.
So, What Does It Mean to Play to Win™?
Strategy is simply choosing the most Optimum Path to Win... and nothing less.
It is not a set of lofty goals, or a collection of tactics. It is a comprehensive plan that aligns decisions, people, resources and actions to create a sustainable competitive advantage.
The Playing to Win™ Strategy is a series of 5 coordinated and integrated choices, that align your entire organisation towards the same goals.
It is not a set of lofty goals, or a collection of tactics. It is a comprehensive plan that aligns decisions, people, resources and actions to create a sustainable competitive advantage.
The Playing to Win™ Strategy is a series of 5 coordinated and integrated choices, that align your entire organisation towards the same goals.
The Playing to Win™ Masterclass Combines Strategy with Execution
This is a proven, 12-month intensive program that will re:Design your SME to become a Growing & Scalable Enterprise (GSE).
Each cohort will consist of 15-20 business leaders who will be guided through the Playing to Win™ Strategy to Execution Framework, in full.
We will meet once every 2 weeks (24 sessions total) for a full day engagement of thinking, feeling, reflecting, sharing, communicating, designing and planning.
Each cohort will consist of 15-20 business leaders who will be guided through the Playing to Win™ Strategy to Execution Framework, in full.
We will meet once every 2 weeks (24 sessions total) for a full day engagement of thinking, feeling, reflecting, sharing, communicating, designing and planning.
The Playing to Win™ Curriculum
Format
24 Sessions over 12 Months (Once per Fortnight)
Duration
8 Hours per Day
Cohort Size
15 - 20 Participants
Materials
Lifetime Access to Slides, Digital Boards & Recordings
#1
Strategic Foundation
Lay the groundwork by defining your company’s Purpose, Vision, Mission, Values, and Brand Promise. This clarity drives alignment and decision-making across all levels of the business for the 5 Strategic Choices of Winning Aspirations, Where to Play, How to Win, Core Capabilities & Management Systems.
#2
Growth Culture Design
Build a culture with a strong foundation of Core Values that supports Agility, Ownership, and Learning, so your team can execute with energy and resilience. We’ll tie things together with Performance & Consequence Management to align culture with strategy and performance.
#3
Effective Communication
Learn to communicate strategy clearly across departments to avoid misalignment, confusion and silos. This module introduces tested and proven frameworks like S.M.A.R.T., Definition of Done, Asking Clarifying Questions (1H5W), Root Cause Analysis using 5 Whys, RACI Matrix and Responsibility & Accountability.
#4
Identify your Winning Aspirations
Define what exactly Winning looks like for you in the next 12-24 months using measurable strategic outcomes. This becomes your North Star for prioritisation and growth so that you can say “No” to everything else.
#5
Management Frameworks
Explore structured frameworks such as RACI, OKRs, 1-on-1 Accountability Check-Ins, Daily Huddles, Eisenhower Matrix, Monthly Management Performance Progress, Quarterly Strategic Business Review and 1% Daily Improvement mindset to bring discipline to execution and continuous improvements to processes and systems.
#6
Where to Play?
Decide which customer segments, geographies, and channels to focus on for the greatest growth and strategic fit. Develop your Ideal Customer Profile (ICP), messaging and Value Proposition. You’ll learn to make focused choices instead of spreading efforts too thin.
#7
How to Win?
Craft a “Differentiated” Value Proposition and competitive strategy to succeed in your chosen Where to Play segments. We’ll analyse case studies and use guided tools to identify clear advantages.
#8
Agile Execution
Adopt agile methods like Scrum, Sprint Planning & Planning with P.A.P.E.R. to speed up data-driven decision-making, reduce time wastage & rework, and boost team accountability, teamwork and performance. You’ll leave with templates you can immediately apply to drive short-term WINs within 30 – 45 days of implementation.
#9
Core Capabilities
Identify and develop the unique capabilities your business needs to deliver its Strategy and Outcomes effectively. This module helps you invest in strengths that are hard to replicate and deeply tied to your Where to Play & How to Win Value Proposition.
#10
Management Systems
Finally, install the structure, systems, rhythms and processes that keep strategy and execution connected – like strategic reviews, management reporting and dashboards. These systems ensure you’re not just planning, but achieving business Outcomes consistently that you can see improving every fortnight.
Be Warned:
This is NOT your typical 'rah-rah' and 'trainer talk, you sit and listen' program.
The Scaling-Up! Playing to Win™ Masterclass is a practical Capabilities Development program customised for SME Leaders to ask clarifying questions, seek to understand, and then think, plan, design and implement advanced tools, agile frameworks and strategies to drive alignment, execution and results, facilitated by our Principal Facilitator, Moonshi Mohsenruddin.
The Scaling-Up! Playing to Win™ Masterclass is a practical Capabilities Development program customised for SME Leaders to ask clarifying questions, seek to understand, and then think, plan, design and implement advanced tools, agile frameworks and strategies to drive alignment, execution and results, facilitated by our Principal Facilitator, Moonshi Mohsenruddin.
Who Should Attend?
This program is ideal for you, if you:
• Are an SME Leader - Founders, Directors, General Managers, CXOs
• Have been in business for 7 years or more
• Employ 25 - 200 employees
• Revenue between SGD $2M - $15M
• Are able to deliver your products/services reasonably well
• Can allocate 8 hours per week on Strategic & Growth planning and management activities
• Are an SME Leader - Founders, Directors, General Managers, CXOs
• Have been in business for 7 years or more
• Employ 25 - 200 employees
• Revenue between SGD $2M - $15M
• Are able to deliver your products/services reasonably well
• Can allocate 8 hours per week on Strategic & Growth planning and management activities
Financial Grant Support
For qualified SMEs, get up to 70% grant for your managers to attend the Scaling-Up! Plan to Win™ Masterclass Series.
Qualifying criteria:
✅ $5M to $100M revenue
✅ 25 to 1,000 employees
✅ Business entity registered and operating in Singapore
✅ The company/business entity has at least 30% local equity held directly or indirectly by Singaporean(s) and/or Singapore PR(s), determined by ultimate individual ownership.
✅ The company/business entity is financially ready to start and complete the project. Grant is only claimable after project ends.
Qualifying criteria:
✅ $5M to $100M revenue
✅ 25 to 1,000 employees
✅ Business entity registered and operating in Singapore
✅ The company/business entity has at least 30% local equity held directly or indirectly by Singaporean(s) and/or Singapore PR(s), determined by ultimate individual ownership.
✅ The company/business entity is financially ready to start and complete the project. Grant is only claimable after project ends.
"We finally have clarity on our direction and strategy after developing it using the Playing to Win™ framework.
We are very clear what we are going to do, where we want to go and which kind of company we want to be."
"I'm very thankful because with Moonshi's engagement we can go deeper and communicate more with other leaders... so that all our initiatives can be smoother."
Steven Shi
CEO
Evernet
Hear Direct from Our Clients!
"I really want to thank Moonshi! Without him, we can't think out of the box. He actually opens up the sky for us, we have the power to do even more with his help."
Maha
Specialty Chemicals & Industrial Solutions
"Developing our purpose, vision and mission was a fantastic experience, because I've been working with my co-founders for a long time, but I never knew them as good as I do now."
Magloft
SaaS
"Moonshi has taught us a lot of things - the thinking, processes, frameworks. Everybody is putting in a lot more effort, and they're all working closer together now. I'm really very grateful he's putting in a lot of effort, as if it's his own business."
White Restaurant
F&B
"We finally have clarity on our direction and strategy after developing it using the Playing to Win™ framework. We are very clear what we are going to do, where we want to go and which kind of company we want to be."
Evernet
IT Services
"In 50 years of business, this is the first time we published our financials and set clear KPIs for the entire company. It was amazing, the morale is very good. All of them are very motivated to turn this around, in fact they did better than expected."
Woodlands Transport
Private Transportation
"I think being together with my colleagues to solve problems has been the most valuable. Because communication is one of our biggest problems, and in these two days we understood how to communicate better - that is very useful for us."
White Restaurant
F&B
Apply for the Playing to Win™ Masterclass:
