How Pennock Plays to Win: A Peek Inside Our Strategy
In 2021, I wrote an article about how we were positioning Pennock to Play and Win in 2022. This approach came from a framework introduced to me by my executive coach at the time, Sharon Margules. It was a straightforward yet powerful way to structure Pennock’s vision, strategy, and execution—and it proved invaluable.
As a fully remote, service-based business, we don’t need pitch decks for investors. Instead, frameworks like this help us communicate our vision and strategy clearly to our team. Let me take you inside my thought process and how I applied this framework to shape Pennock’s direction.
What Is Strategy, Really?
At its core, strategy is about making deliberate choices—deciding what you will do and, just as importantly, what you won’t.
Even though Pennock has been around since 2020—a blink of an eye yet an eternity in startup years 😉—we still made some rookie mistakes in 2024. One key misstep was taking on brands before they had proven product-market fit or established other parts of their marketing funnel. Those hard lessons pushed us to refine our approach.
The WIN Strategy Framework
"Playing to Win" boils down to five key choices that cascade into a cohesive strategy.
1. What is your winning aspiration?
Define the purpose of your enterprise—your motivating aspiration. This is not just about company-level goals like revenue; it’s about product or service outcomes. For example, if your company’s goal is doubling customer count, your winning aspiration might focus on improving user experience to increase referrals.
2. Where will you play?
Choose your playing field. This includes your core target markets, customer segments, channels, products, and even geographic constraints. Keep it simple but clear.
3. How will you win?
Determine your competitive edge. What unique value will you bring to your chosen field? This requires a clear understanding of your competitors, your position in the market, and the specific actions you’ll take to win (and what you’ll avoid).
4. What capabilities must be in place?
Identify the skills, resources, and systems you need to execute your strategy effectively. Building capabilities often takes time and deliberate effort.
5. What management systems are required?
Define the tools and processes you’ll need to monitor progress, enable capabilities, and stay on track. Mature management systems are often the backbone of execution.
Pennock’s 2025 WIN Strategy
What is Pennock’s winning aspiration?
To take emerging brands to their next level of growth. We work with brands that have already proven their marketing playbook, achieving at least 30% year-over-year growth. We also ensure their business is financially sound, with no more than 60% of revenue attributed to ads.
Where will Pennock play?
DTC beauty and women’s sexual wellness brands with $1M–$10M ARR.
Physical service businesses (e.g., medspas) with similar ARR levels.
How will Pennock win?
By acting as a true strategic partner, monitoring client profitability daily and offering data-driven recommendations to sustain and accelerate growth.
What capabilities must be in place?
We’ve invested heavily in automation and workflows in 2024. As we move into 2025, we’ll continue testing and implementing new AI solutions to optimize operations and add value for clients.
What management systems are required?
Our tech stack includes Airtable, Lark, Slack, Claude, NotebookLM, and more. We’re always experimenting and evolving to stay ahead.
Ready to Play and Win?
The "Playing to Win" framework is a fast, effective way to align your business goals with actionable strategies. Download our Playing to WIN template to start crafting your own WIN strategy—complete with Pennock’s 2025 example to inspire you.
Happy strategizing,
Nikki