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How to build a winning holiday strategy

How to build a winning holiday strategy

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How to build a winning holiday strategy

Holiday success isn’t built on one great promotion or one viral social post. It’s built through months of planning, realistic forecasting, thoughtful innovation and strong execution across every part of the business. The brands that consistently win the holiday season are those that treat it as an integrated strategy, aligning product, inventory, operations, merchandising, marketing and prioritizing retailer collaboration around a shared goal. We sat down with Tony Davis, CEO and founder of Bakeful to get his playbook for optimizing around holiday.

“Whether you’re preparing for your first holiday launch or refining an existing strategy, the most successful founders approach the season as a coordinated business plan, not simply a promotional calendar,” says Tony.

The first piece of advice Tony would offer founders is to start earlier than you think. One of the biggest misconceptions among emerging brands is that holiday planning begins in the fall. In reality, many major retailers begin reviewing holiday assortments as early as January or February. That means founders should start preparing well before buyer meetings by identifying seasonal opportunities, exploring new product concepts, evaluating manufacturing timelines and understanding operational requirements.

Early planning gives brands time to develop seasonal products and packaging, validate manufacturing capabilities, build accurate inventory forecasts, align marketing and merchandising plans and collaborate with retail buyers before key assortment decisions are made. The earlier these conversations happen, the more flexibility brands have to create programs that work for both them and their retail partners.

Another important reminder when thinking about holiday is to create seasonal products that feel true to your brand. “Holiday products should create excitement, but they should also feel like a natural extension of your brand,” offers Tony.

The strongest seasonal launches build on products customers already know and love rather than introducing something completely unfamiliar. A limited‑edition holiday flavor, festive packaging or gift‑ready bundle can create urgency while reinforcing your brand identity.

Some helpful questions to ask yourself when creating your holiday offerings are:

  • Does this feel authentic to our brand?
  • Will our existing customer recognize it immediately?
  • Does it encourage first‑time shoppers to discover our core assortment?

Holiday innovation should invite new consumers into your brand, not distract from it.

Holiday inventory requires a different mindset than year‑round planning. Unlike everyday products, many seasonal retail programs receive one firm purchase order with little or no opportunity for replenishment. If inventory sells out early, there may not be another order. If it doesn’t sell through, brands may face markdowns that impact profitability.

Founders should work closely with both retailers and manufacturing partners to answer critical questions early:

  • What production lead times are required?
  • What are the minimum order quantities?
  • Can manufacturing support holiday‑specific packaging or bundles?
  • How much inventory can the business realistically support?

Strong forecasting balances ambition with discipline. While every founder hopes for a sell‑out, planning conservatively helps protect cash flow and minimizes costly markdowns after the season ends.

During the holidays, shoppers are navigating crowded aisles filled with competing products. Packaging often becomes the deciding factor. Seasonal colors, festive design elements and clear messaging help products stand out while communicating their value in just a few seconds.

“Great holiday packaging doesn’t require reinventing your brand. Instead, it should amplify what’s already working while adding enough seasonal energy to capture attention,” explains Tony. “Think of packaging as your silent salesperson, especially when consumers are making quick purchasing decisions.”

Holiday marketing isn’t about changing your brand’s voice. It’s about adapting your message to meet shoppers where they are. Consumers are buying for celebrations, entertaining, gifting and creating traditions. Marketing should reflect those moments while remaining consistent with the brand’s overall identity.

A coordinated holiday strategy may include:

  • Social media content showcasing seasonal uses.
  • Influencer partnerships that demonstrate gifting ideas.
  • Email campaigns highlighting limited‑time products.
  • SMS reminders around key shopping moments.
  • Retail‑focused messaging that directs customers to store locations.

The strongest campaigns create multiple touchpoints throughout the shopping journey instead of relying on a single promotional push.

Retail success is built on partnership. Founders who come to buyer meetings with thoughtful ideas and a willingness to collaborate often build stronger long‑term relationships. Rather than presenting finished plans, use early conversations to gather insights.

Ask questions like:

  • What seasonal trends are emerging?
  • Which flavors, colors or themes are gaining momentum?
  • What price points resonate with shoppers?
  • Are there merchandising opportunities beyond the shelf?

Retail buyers have deep category knowledge. Their perspective can help brands refine ideas before significant investments are made. “Strong partnerships are built through dialogue, not assumptions,” Tony says.

“Receiving a purchase order isn’t the finish line,” Tony reminds us. “Execution at the store level matters just as much as securing placement.”

Founders should monitor product availability throughout the season by conducting store visits, working with merchandising partners and ensuring products are displayed where shoppers expect to find them. Even the strongest product can’t generate sales if it never makes it from the stockroom to the shelf.

If you’re preparing for your first holiday season in retail, focus on three fundamentals:

  • Deliver an exceptional product. Holiday excitement may drive trial, but quality creates repeat customers.
  • Invest in standout packaging. Seasonal design helps products capture attention in crowded retail environments.
  • Work closely with your retail partners. Collaborate on pricing, pack sizes, merchandising and operational planning early to avoid surprises later.

The biggest holiday advantage is preparation with your offerings, marketing and inventory. When every piece works together, the holidays become more than a sales event. They become an opportunity to introduce new shoppers to your brand, deepen customer loyalty and build momentum that lasts well beyond the season.

Looking for more tips and tools? Sign up here for our monthly newsletter for more access and insights to resources and stories to help accelerate your business.

About the author

Tony Davis, Founder and CEO. Tony is a multi‑time CEO of venture‑backed, high‑growth CPG food and technology companies, with experience across global brands and more than $650M in capital transactions, including $145M raised for his most recent company. He is known for accelerating growth, building brands and leadership teams, scaling emerging businesses and identifying market opportunities that lead to successful liquidity events. Prior to starting Bakeful, Tony was the CEO of N!CK’S, making and selling a full line of better‑for‑you ice creams and protein snack bars.

Post topic(s): Business advice

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