Cash Flow

9 Cash Flow Management Tips for a Seasonal Business

I once worked for a company in Queenstown, New Zealand, that provided a hot pool experience. During the busy ski season, we were always fully booked. Unfortunately, once the season ended, tourists left, demand dropped, and revenue plummeted, highlighting the need for better cash flow processes.

Running a seasonal business can sometimes feel like riding a financial rollercoaster. One minute, you’ve got more customers than you can handle, and the next, you’re calculating how much cash you’ll need to keep the lights on during your off-season. Welcome to the wild world of cash flow management, where even the best businesses can hit a cash flow crisis without the right planning.

This guide is here to help you move from reactive to proactive when it comes to managing cash flow. Whether you run a landscaping service, freelance year-round, or own a hot pool business in Queenstown, you’ll find strategies that help you handle cash inflows and outflows, maintain healthy cash flow, and sleep better at night.

Is Your Business Seasonal?

You might be surprised to learn how much money can be saved through effective cash flow management.

The term “seasonal business” typically brings to mind ski resorts, ice cream trucks, and snowplow services. But any business that experiences cash flow fluctuations due to budget cycles, consumer behavior, or even weather patterns can qualify as seasonal.

If you’ve ever looked at your cash flow statement and asked, “Why is this month bone-dry compared to last?” you’re already in seasonal territory. Freelancers, tax preparers, digital marketers, and even e-commerce sellers face the same ebbs and flows.

The Strategic Importance of Healthy Cash Flow

Cash flow management is more than just tracking income and expenses. It’s the engine behind your business’s financial health, the key to surviving unexpected expenses, and a lifeline when net income is low or delayed.

Here’s why mastering your company’s cash flow matters:

• It ensures business continuity even during slow periods.
• It lets you make informed financial decisions about hiring, inventory, and capital expenditures.
• It helps you avoid negative cash flow events like missed accounts payable deadlines or late payment fees.

You have a clear understanding of how money flows in and out of your business, in real time.

In short, effective cash flow management = freedom.

The advice here will apply to any small business that experiences significant cash flow fluctuations.

Let’s discuss cash flow strategies for your seasonal business, including the importance of timely payments.

1. Forecast Cash Flow Like a Finance Pro

Cash flow forecasting is one of the most powerful tools in your financial toolbox. Yet many seasonal business owners skip it, or worse, rely on gut instinct instead of data. Don’t be that business.

A well-structured cash flow projection is like a GPS for your company’s financial journey. It tells you exactly when cash inflows are expected, how much you’ll need to cover your cash outflows, and whether you’ll face negative or positive cash flow in the months ahead.

In fact, according to J.P. Morgan Chase’s “Cash Flow Playbook” (2022), 82% of small businesses cite poor cash flow management as a major contributor to business failure, and yet only 40% actively engage in forecasting or budgeting activities. That gap is where your opportunity lies.

Where to Start With Cash Flow Forecasting

Begin by collecting your financial statements, especially your cash flow statement, income statement, and balance sheet. These will provide insights into past operating cash flow and help you model future behavior.

Next, build a cash flow forecast that spans at least 12 months. Map out:

• expected cash inflows: customer payments, retainers, off-season promotions, passive income, etc.
• expected cash outflows: rent, utilities, contractor wages, insurance, capital expenditures, etc.
• timing of accounts receivable collections and accounts payable obligations
• known or predictable peaks and valleys (e.g., ski season ends in April, holiday e-commerce spikes in Q4)

You don’t need a finance degree to do this, just a solid accounting tool. (For example, the real-time reports and at-a-glance dashboard in FreshBooks can help you optimize cash flow, track cash flow trends, and make informed financial decisions all year long.)

Real-Time Visibility = Financial Agility

With proper forecasting, you won’t be caught off guard by a surprise tax bill, a dip in revenue, or an increased cash outlay for raw materials. You’ll also be in a better position to take advantage of early payments or negotiate favorable payment terms with vendors, two underused strategies that directly impact cash flow.

And when it’s time to meet with a bank, investor, or lender? Your forecasts will demonstrate your business’s financial performance, planning prowess, and significance in your industry.

2. Go All In During Peak Season

The most effective way to survive seasonal slowdowns is to dominate when business is booming. Your peak season is your golden window to generate not just revenue, but the reserve cash you’ll need to weather downturns, manage operating expenses, and invest in strategic tasks for long-term growth. Think of it as a financial squirrel strategy: gather aggressively when the nuts are falling so you’re not starving come winter.

This approach is key to maintaining positive cash flow when demand drops. Strong peak-season performance can minimize your reliance on loans or credit lines, giving you greater flexibility, better margins, and more control over your working capital.

Strategies to Maximize Cash Inflow During Busy Periods

Here are several tactics to optimize cash flow and build financial momentum during high-earning months:

• Increase your average transaction value. Bundle services together or upsell complementary products. For example, if you run a landscaping business, offer seasonal maintenance add-ons (e.g., mulching or irrigation checks) alongside your base package. Higher-value orders translate directly into increased free cash flow.
• Pre-book clients for slower months. Encourage clients to schedule future services while you’re top of mind. Sweeten the deal with early-bird discounts or limited-time bonuses. This approach brings in quick cash now and promotes year-round stability
• Offer retainers or subscriptions. Turn one-time clients into long-term partners. A social media consultant, for instance, might convert seasonal campaign work into a year-round monthly content package. Retainers stabilize income and create predictable net flows, even during off-months.
• Use volume to negotiate supplier terms. If you’re ordering in bulk during the busy season, leverage that purchasing power. Negotiate discounts or improved payment terms with vendors. This reduces your cash outflows and helps you manage accounts payable more efficiently.
• Front-load major projects. Aim to tackle large, high-margin projects during peak demand when clients are more motivated to buy and less price-sensitive. This increases net income and adds breathing room for the slow months ahead.
• Build demand with urgency-based marketing. Limited-time offers, seasonal exclusives, and countdown campaigns can help drive urgency and spike sales when you’re already operating at high velocity. The more revenue you capture now, the less you’ll worry about future financial challenges.
• Tighten your billing cycles. During peak season, prioritize short billing windows and strict payment terms. The faster you’re paid, the more excess cash you’ll have to reinvest—or set aside for when the calendar flips and things quiet down.
• Consider a short-term loan. Getting a loan just before or during peak season allows you to optimize and boost different aspects of your business to ensure you’re able to grab every bit of revenue and growth available.

Why Going All In Works

High-season sales don’t just bring in revenue, they reduce your risk exposure. A flush cash reserve means you won’t have to rely on short-term financing to pay expenses, cover unexpected costs, or keep up with capital expenditures. It also allows you to say “yes” to strategic investments like equipment upgrades, marketing campaigns, or new hires when your competition is forced to sit still.

The key is effective cash flow management: being intentional about how, when, and why your money is earned and spent. With the right planning and execution, you can transform your peak season from a cash grab into a full-blown growth strategy.

3. Adjust Your Marketing Strategy Ahead of Off-Season

As a freelance writer, my slow season is from December to January. During the year, I’m constantly cold emailing to market my services and find new clients.

I ramp up my efforts as I near my slow periods. I tell clients that I’m booking my schedule for those months, creating a sense of urgency in my communications: They should book me now if they want my services. Because many other writers slow down their marketing efforts as the winter holidays approach, despite business slowing, I’m able to capture a portion of the market.

Depending on the nature of your seasonal business, you may consider giving off-season discounts or targeting a different region or demographic. Be sure to explore flexible and affordable marketing strategies like social media.

Don’t wait for the phone to stop ringing before you act. Plan 2 to 3 months ahead and adjust your messaging to keep cash inflows coming.

Things to try:

• Pre-sell seasonal packages. (“Book your spring landscaping now and save 10%.”)
• Promote early payment discounts or referral bonuses to keep the pipeline warm.
• Focus on retention marketing, email your current customers with exclusive offers.

Bonus tip: Turn quiet time into strategic tasks like inventory management, performance reviews, or updating your financial statements.

4. Generate More Revenue from Existing Clients

Your existing clients are a goldmine because you already have a relationship with them. Use that relationship to upsell your current services and increase your customer lifetime value (CLV).

You could, for example, build a tiered pricing model for your services by:

• Bundling services together. For example, if you run a content marketing agency that focuses on writing content assets, you could also include SEO research and marketing strategy as you realize your clients are doing this in-house.
• Packaging different service levels. Here you present (usually 3) packages alongside each other, each with different deliverables and pricing. Prices should increase from lower- to higher-tier packages in line with incremental value. For example, a landscaper could create these 3 service tiers:
  1. Starter package for $1,800 (grading and sodding)
  2. Mid-range option for $2,200 (grading, sodding, and general maintenance)
  3. Premium package for $2,800 (grading, sodding, general maintenance, and specialized services)
• Package how you deliver your service process. For example, a designer could package all the steps involved in building a website, from the client briefing to creating wireframes to delivering the final project and having a project post-mortem.

Beyond upselling, you can also get clients on a retainer to guarantee a certain income. Such guaranteed income ensures a consistent cash flow.

Your goal: Increase customer lifetime value (CLV) while reducing the cost of new client acquisition.

5. Get Paid Faster

Cash stuck in accounts receivable = money you can’t use. Slow payments hurt your cash flow categories and can push your business into negative cash flow.

Delays in client payments can have a devastating effect on cash flow for a seasonal business owner. It may not concern you when business is thriving, but if your slow period is imminent, it can become a serious concern. After all, expenses remain even when cash isn’t coming in. You don’t want to be in a position where you can’t pay staff, bills, and outstanding debts.

The solution is to speed up payments and make sure you collect all outstanding payments from clients. Here are some ways you can make sure your invoices get paid on time:

• Send invoices immediately, as soon as you’ve completed the work. It seems obvious, but far too many service professionals fail to send invoices on time.
• Show courtesy in your invoices, as it increases the percentage of invoices paid on time by 5%.
• Provide clear payment terms upfront, specifying the exact number of days within which the client should pay you. Make sure these payment terms are included in all contracts and client agreements.
• Send a gentle reminder before the invoice is due. FreshBooks lets you automate payment reminders, so you don’t need to worry about crafting delicate emails and engaging in awkward money talk.
• Send late-payment reminders. Sometimes clients miss payment deadlines because they get busy, and all they need is a gentle nudge. FreshBooks allows you to set late-payment reminders that run on a schedule.
• Make it easy for clients to pay by accepting multiple forms of payment, such as credit cards and checkout links.
• Reward clients for early payment with a discount.
• Make sure invoices are correct to avoid back and forth with a client. Watch for common errors, like incorrect PO numbers, not specifying the payment due date, or sending the invoice to the wrong person!

And if you find yourself continually chasing late payments, perhaps it’s time you asked for an upfront deposit.

Cite-worthy tip: According to Fundbox, the average small business has $84,000 in unpaid invoices at any time (Fundbox, 2023), and small businesses in the U.S. are owed $825 billion in unpaid invoices overall. Don’t be that business.

6. Diversify Your Core Offering to Extend Your Market

Some seasonal businesses will close during the off-season, while others remain open. If you’re the latter, consider increasing your income in that period by adding extra services beyond your core business.

However, the service you offer must be in line with your brand so that consumers can see the association. Think about what your customers need in the off-season.

For example, as a landscaper, you could offer snow removal services during winter. As a tax accounting professional, outside the tax season, you could provide financial advisory services, bookkeeping services, management consultant services, and financial advice for companies issuing share capital or merging.

Suppose you’re a location-dependent seasonal business like a lawn care or landscaping company. You could expand your market to reach new customers by offering online consultations and landscape design services year-round. You could also use online remote collaboration tools like Zoom to discuss landscaping plans, present virtual landscape designs, and even offer online courses.

Digital services give you flexibility without a massive increased cash outlay.

7. Partner With Opposite-Season Businesses

Think peanut butter and jelly. Or snow plows and lawnmowers.

One often-overlooked but highly effective cash flow management strategy for seasonal businesses is partnering with a business that thrives during your off-season. These partnerships are not only practical, they can also be mutually profitable and key for maintaining healthy cash flow year-round.

Let’s say you operate a lawn care business that hums from April to October. Come winter, things slow down. Meanwhile, a snow removal company is ramping up operations in exactly the same timeframe. Instead of scrambling to pivot, why not collaborate?

Or maybe you’re a tax accountant flooded with work from January to May. Partnering with a financial coach or small business advisor whose services are in demand during the summer and fall months can be a win-win. By aligning your calendars and your clients’ needs, you both benefit from improved cash flow and a more stable revenue stream.

The Cash Flow Perks of Strategic Partnerships

When structured well, these seasonal pairings help businesses:

• Smooth out cash flow fluctuations. By aligning with another company’s peak, you help fill in your revenue valleys and reduce the impact of cash flow slowdowns.
• Increase cash inflows through joint promotions and bundled service packages.
• Tap into new customer bases without expanding overhead.
• Reduce operating costs by sharing marketing expenses or operational resources.
• Make informed financial decisions based on predictable income during off-peak periods.

These collaborations don’t just help you avoid negative cash flow during slow periods, they offer proactive, low-cost ways to optimize cash flow processes without taking on increased cash outlay or risky investments.

Practical Ways to Make It Work

Here’s how to maximize the impact of a seasonal partnership:

• Cross-promote each other on websites, social media, newsletters, and even invoices.
• Share client lists or referrals (with permission) to extend your reach and reputation.
• Create seasonal bundles (e.g., “Spring yard cleanup + Winter driveway clearing”).
• Split advertising or event costs to stretch your marketing dollars.
• Offer co-branded discounts to customers who use both services.

If your partner is based in a different geographic region, you can even stagger marketing pushes so one of you is always generating buzz and income while the other rides the slower season.

Collaborations like these help protect your business against future financial challenges and minimize the likelihood of cash flow issues that so often derail seasonal entrepreneurs.

So next time you’re looking to improve cash flow, don’t go it alone. Look sideways, your perfect seasonal counterpart might just be a DM away.

8. Get Ruthless With Cost Control

When income slows, cash outflows become a major liability.

Operating expenses remain even when revenue falls. That’s not to mention that you’ll sometimes incur extra expenses (e.g., maintenance) to prepare for the next season.

But that doesn’t mean you can’t control and reduce costs to soften the blow of reduced income. Here are ways to do that:

• Hire part-time employees for the busy season.
• Instead of hiring full-time staff, consider hiring contract staff.
• Communicate with vendors to negotiate better payment terms.
• Lease equipment through skip payment leases and step payment leases.
  • Skip-payment leases allow you to make payments in peak season and stop payments in slow times.
  • Step-payment leases require payment throughout the year. You either start with a higher monthly payment that decreases with time or a lower monthly payment that increases with time.
• Make the most of your office space. For example:
  • Negotiate with the owner of your building to increase rent in peak season and reduce it during the off-season.
  • If you don’t need office space in the off-season, negotiate a shorter lease.
  • If you own the offices but don’t need them in the slow period, let another company rent.
• Ask yourself: Do you even need office space? It may be that your entire team can work remotely year-round

A lean operation means you’ll have enough cash to weather any storm.

9. Find Repeat Clients to Carry You Through the Off-Season

When business slows down, your bills don’t. That’s why repeat clients—sometimes called anchor clients—are invaluable for maintaining positive cash flow and ensuring business continuity during your off-season.

These clients provide a consistent, predictable stream of income that can support your operating cash flow, reduce your reliance on last-minute projects, and help you avoid financial trouble when cash inflows are limited. With a strong anchor client base, you’re less likely to scramble for working capital, delay paying invoices, or take on increased cash outlay just to stay afloat.

But strong anchor clients don’t appear by accident. You build them through trust, reliability, and value.

How Repeat Clients Improve Cash Flow Management

From a cash flow management perspective, recurring clients offer massive benefits:

• They make your future cash flow more predictable.
• They reduce the cost (and stress) of constant new client acquisition.
• They allow you to make more informed financial decisions about staffing, marketing, and inventory management.
• They generate free cash flow that can be reinvested into strategic tasks or set aside to handle unforeseen expenses.
• They boost your company’s ability to manage both high and low seasons without financial strain.

Tactics to Win—and Keep—Anchor Clients

Here are a few simple but powerful ways to find and grow long-term client relationships that help you optimize cash flow and stabilize revenue:

Upsell services to existing customers

If you’ve already done good work and built trust, don’t let the relationship stop at one invoice. Offer upgrades, additional services, or new packages that extend the lifecycle of the partnership.

For example:

• A web designer might offer monthly maintenance packages after launch.
• A landscaping company could transition clients into seasonal contracts.
• A freelance writer could pitch a blog retainer or newsletter management.

These add-ons generate cash inflows while minimizing human intervention in the sales process.

Tap into your clients’ networks

Repeat clients are often your best marketing tool. Once you’ve established a strong relationship, let them know you’re looking to expand. Ask if they can recommend you to peers, partners, or friends.

You might say:
“If you know anyone looking for [your service], I’ve got a few openings coming up and would really appreciate the referral.”

This simple ask can lead to a chain of clients who share similar timelines, industries, or payment terms, helping you build a roster that reduces financial risks across the board.

Formalize the relationship with retainer agreements

Retainers lock in steady revenue and give you instant visibility into the next few months’ financial outlook. This not only helps you plan for debt repayments or capital expenditures, but also supports paying vendors and maintaining strong supplier relationships without overextending your working capital.

Plus, with the right systems in place (like FreshBooks or another cloud-based platform), you can set up early payments, track accounts receivable, and automate billing to reduce cash outflows caused by inefficiencies.

Keep the Cash Flowing for Your Seasonal Business

No matter how wild the peaks and valleys, you don’t have to let cash flow issues control your business. With the right tools and habits, you can:

• Improve cash flow management.
• Plan for unforeseen expenses.
• Make smarter, informed financial decisions.
• Sleep well, knowing your company’s cash flow is under control.

The goal isn’t just survival. It’s confident, intentional growth, even when your business has a built-in off-season.

Ready to conquer cash flow management in your seasonal business? What strategies do you use?

This post was updated in May 2025.