The Founder’s Playbook to Navigating and Winning Black Friday & Cyber Monday

 

Black Friday and Cyber Monday (BFCM) aren’t just shopping holidays — they’re high-stakes opportunities that can make or break your Q4. Founders who win during BFCM don’t rely on luck. They move with precision, backed by plans for ads, inventory, and retention that leave little to chance.

Whether you’re gearing up for your first BFCM or looking to sharpen your approach, this playbook gives you the founder’s lens on how to navigate the chaos — and win.

1. Start Earlier Than You Think

Successful founders begin planning BFCM in September (or earlier). Why?

• Ad costs spike during the holiday window

• Inventory lead times increase

• Shoppers are researching long before they buy

Set key milestones ahead of time:

• Creative finalized by October

• Ad audiences warmed up in early November

• Retargeting and email flows locked in well before Thanksgiving

2. Dial In Your Paid Ad Strategy

Ad budgets can evaporate fast during BFCM if you’re not strategic. Founders winning the ad game do three things:

➤ Warm up your audiences early

Start running engagement campaigns 3–4 weeks ahead to build retargeting pools.

➤ Segment like a pro

Don’t treat all buyers the same. Segment by:

• High-intent users

• Past purchasers

• Cart abandoners

• First-time visitors

➤ Use tiered offers

Test different discount levels for different customer segments (e.g. 20% off for returning customers, 30% for new).

3. Inventory: Know What You Can Actually Sell

One of the most expensive mistakes you can make during BFCM is overpromising and underdelivering.

What founders do differently:

• Audit inventory now: What can you realistically push?

• Forecast demand: Look at historical sales and upcoming trends

• Double down on your winners: Promote products that are already moving well — don’t force new or untested SKUs into the spotlight

Pro tip: Add urgency to your marketing by clearly showing “limited quantity” or “fast-moving” items — but only if it’s real.

4. Retention is the New Conversion

Acquiring a new customer is great. Keeping them? That’s profitable.

Winning founders plan retention during BFCM before the sales start:

• Add post-purchase email flows (e.g. welcome, referral, cross-sell)

• Offer loyalty perks or sneak peeks into future drops

• Create reactivation campaigns for December and January

Think beyond the one-time deal — how does BFCM become a gateway to your brand’s long-term ecosystem?

5. Your Ops Need to Be Just as Sharp as Your Ads

Behind every smooth BFCM campaign is a well-oiled back end. Plan for:

• Customer support volume spikes

• Shipping delays

• Return and refund requests

If your site crashes or support inbox overflows, all your marketing wins will unravel. Test site speed. Set up fallback offers. Have contingency plans in place.

6. After the Rush: Don’t Just Collapse — Analyze

Once the dust settles, great founders don’t just rest — they review:

• What channels drove the most profitable sales?

• Which offers converted best?

• How did new customer LTV compare to past BFCMs?

They turn results into insights, and insights into better decisions for next year.

Final Word: BFCM Is a Test of Operational Excellence

Founders who win Black Friday & Cyber Monday treat it like a campaign, not a gamble. They plan deep, execute fast, and always keep one eye on long-term brand health.

Whether you’re selling rugs, SaaS, or subscriptions, the formula remains the same:

🎯 Warm your audience early
📦 Know what you can deliver
🔁 Think beyond the first purchase

You don’t need a massive team or VC backing to win BFCM. Just a playbook — and the discipline to follow it.

Need help fine-tuning your BFCM plan? Drop us a line — or steal our checklist and build your own.