While we know most of our clients don’t necessarily turn to us for growth, it is always in the back of founders’ minds. Growth is the dream, but structured, sustainable growth is the goal. As the co-owner of WorkBetterNow, I’ve had a front-row seat to the challenges—and the rewards—of scaling a business, and I’ve seen how having the right infrastructure, team, and strategy in place prevents growth from turning into chaos. 

While growth brings new opportunities (for us, that meant placing 114th in the INC 5000!), it also introduces complexity—more customers, bigger teams, and greater operational demands. Without the right systems and support, businesses can quickly become overwhelmed. 

I’ve seen businesses scale the right way, and I’ve seen businesses try to grow too fast, only to crash and burn. The difference is in the culture, preparation, and the ability to delegate effectively to the right people. Whether you’re an entrepreneur looking to expand or a business owner ready to take things to the next level, this checklist will help you scale sustainably and successfully. 

1. Start with a Clear Growth Strategy

Scaling isn’t just about doing more—it’s about doing the right things, at the right time, in the right way. At WorkBetterNow, we follow the Entrepreneurial Operating System (EOS), a framework that helps businesses set and achieve their biggest goals. A major part of our growth strategy is our biannual leadership retreats, where we collectively identify the big projects we want to tackle next. We just got back from Jamaica, and our next big focus? Improving how we communicate with our clients.  

Before expanding, take a step back and define your growth plan: 

• Are you focusing on acquiring new customers, increasing revenue per client, or expanding into new markets? 

• Do you have the infrastructure to support growth, or will your current systems crack under pressure? 

• What challenges will arise as you scale, and how will you address them? 

Every successful business has a blueprint for growth. Mapping out your goals and anticipating obstacles ensures you scale with intention, not just ambition. 

Once you've identified your growth strategy, break it down into actionable steps. If your goal is market expansion, conduct thorough research on customer demand, competition, and potential challenges in the new market. If your focus is increasing revenue per client, consider refining your offerings, improving customer retention, or adding complementary services. The key is to be specific—vague goals lead to scattered efforts, while a structured plan keeps your growth on track. 

Additionally, make sure your strategy aligns with your core values and long-term vision. Scaling for the sake of growth alone can lead to operational chaos, loss of brand identity, or financial instability. Thoughtful planning ensures your business not only grows but thrives. 

2. Get Your Finances in Order

Scaling requires investment—whether it’s in hiring new team members, upgrading technology, or increasing marketing efforts. Cash flow problems can derail even the most promising businesses, so before scaling, ensure your financial foundation is solid. 

• Are your revenue streams stable and profitable? 

• Do you have access to funding, such as business loans, investors, or grants? 

• Can you predict financial trends and expenses for the next 12-24 months? 

Having a strong financial plan in place allows you to grow with confidence, knowing your business won’t be stretched too thin. 

3. Optimize Your Operations

Your current processes may work fine for where you are now, but can they handle double or triple the workload? Scaling efficiently means refining your operations before you hit growing pains. 

Look at your workflows and identify areas where automation and delegation can improve efficiency. Tools like AI-powered scheduling, automated invoicing, and CRM systems can free up time and reduce errors. 

And when it comes to delegation, businesses and business owners that scale successfully don’t try to do everything themselves. That’s where WorkBetterNow comes in. With WBN Certified Professionals™, companies gain access to top-tier remote talent in marketing, accounting, HR, and more—without the cost and complexity of traditional hiring. 

WBN CPs are highly skilled professionals who are thoroughly vetted and work same time zones as U.S.-based businesses. They help tackle time-consuming tasks and ensure that core business functions continue running smoothly as your company grows. Instead of spending months on recruiting and onboarding, WBN CPs can be up and running quickly, providing immediate support and long-term value to your organization. 

4. Build the Right Team

Your team will make or break your ability to scale. As your business grows, you’ll need more hands on deck, but hiring quickly without strategy leads to inefficiencies. 

Paying attention to your team means having meaningful conversations, ensuring upskilling opportunities, and making career development a priority. When employees see a clear path for internal mobility and growth within your company, they are far more likely to stay for the long run. Investing in your team’s professional development not only increases retention but also strengthens your company from the inside out. 

But scaling doesn’t just test your operations—it tests your company culture. Growth can fracture what once felt tight-knit and aligned. As you grow, your values, communication style, and leadership habits need to scale with you. That means being intentional about the kind of culture you want to maintain and making sure that every new hire and internal shift supports that vision. Otherwise, culture becomes an accidental casualty of growth, and that can hurt your business more than any missed KPI. 

Dan Martell puts it best: 'Don’t hire people to grow your business, hire people to buy back your time.' As a leader, your job isn’t to do everything—it’s to focus on the high-impact work that drives growth. The right hires free you from the day-to-day grind, allowing you to focus on strategy, innovation, and scaling sustainably. 

Rather than hiring reactively to fill gaps, take a proactive approach: 

• Identify the key roles essential for scaling. 

• Determine which tasks should be handled in-house versus outsourced. 

• Ensure new hires align with your company’s culture and long-term goals. 

Many businesses struggle to find skilled professionals who are cost-effective and available when needed. That’s why so many companies turn to WBN’s Talent as a Service (TaaS) model. With WBN CPs, our clients quickly onboard highly skilled remote professionals, keeping operations smooth while reducing overhead costs.  

At WBN, we chose to work exclusively with highly skilled professionals from Latin America. Why? Because they align with U.S. time zones, making real-time communication seamless. They share cultural similarities that enhance collaboration and customer service. And they bring strong English proficiency, ensuring clarity in every interaction. 

By combining a strong team with optimized operations, your business will have the foundation it needs to scale efficiently and successfully. 

5. Strengthen Your Brand and Marketing

Scaling isn’t just about internal growth—it’s also about ensuring your brand presence expands alongside your business. More customers mean greater visibility, which means your marketing needs to work harder than ever. 

Make sure your brand is positioned for scale: 

• Is your website optimized for conversions? 

• Do you have a solid content marketing strategy in place? 

• Are you leveraging social media, email marketing, and SEO effectively? 

A strong brand builds trust, and trust leads to sustainable growth. Don’t just focus on getting new customers—nurture existing ones and turn them into loyal advocates. 

6. Prioritize Customer Experience

A common mistake businesses make when scaling is letting customer experience slip. As demand grows, response times slow down, service quality declines, and customers start to feel like just another number. 

The best way to prevent this? Build systems that ensure consistent, high-quality service, no matter how big your business gets. This includes: 

• Streamlining customer service with chatbots, ticketing systems, and clear response protocols. 

• Regularly gathering customer feedback and making data-driven improvements. 

• Implementing loyalty programs to encourage repeat business. 

At the end of the day, happy customers drive long-term success. As you grow, never lose sight of the relationships that got you there. 

7. Expand Your Network and Partnerships

No business scales in a vacuum. Growth often comes from strategic partnerships, collaborations, and strong industry connections. 

As a consultant for the Small Business Development Center and the Goldman Sachs 10,000 Small Businesses Program, I’ve worked with countless entrepreneurs who transformed their businesses simply by expanding their network. 

For me, being part of peer groups like Birthing of Giants, EO, and ProVisors has been a game-changer. These communities have provided not just support but also invaluable opportunities for collaboration, fresh perspectives, and business growth. 

I always recommend seeking out joint ventures with businesses that complement yours—it’s one of the fastest ways to expand without massive capital investment. Leveraging affiliate marketing and influencer partnerships can also broaden your reach and introduce your brand to new audiences. 

The right partnerships can accelerate your growth without requiring massive capital investment. Look for opportunities that align with your goals and bring mutual benefits. 

8. Track Your Metrics and Stay Agile

Scaling is a continuous process, not a one-time action. What works today may not work tomorrow, which is why the EOS system we operate on has us tracking key performance indicators (KPIs). 

Ask yourself: 

• Are you hitting your revenue and profitability targets? 

• What’s your customer acquisition cost vs. lifetime value? 

• Are your operational processes still efficient, or do they need tweaking? (Hint: your operational processes constantly need tweaking and should be reexamined at least twice a year.) 

Successful businesses don’t just set a plan and stick to it no matter what. They adapt, refine, and improve as they grow. 

Scale Smart, Not Fast 

Scaling isn’t just about doing more—it’s about doing more of the right things with the right people. At a certain point, it’s not just about how you grow, but who helps you grow. That’s the core idea behind Who Not How: instead of asking “How do I fix this?” start asking “Who can help solve this?” Whether it’s building internal leadership, bringing on WBN CPs, or hiring a consultant to shore up your systems, growth depends on surrounding yourself with the expertise your business needs next—not just trying to figure it all out on your own. 

And yes, sometimes the “who” is a one-time consultant. Other times, it’s someone who becomes an extension of your team. Either way, the goal isn’t to carry the weight alone. 

At WorkBetterNow, we’re passionate about helping small and midsized businesses grow with intention. Our clients are building incredible companies, and we’re proud to be one part of the larger ecosystem that makes sustainable scaling possible. 

If you’re thinking about growth, think beyond headcount or revenue. Think about your team, your culture, and the structure you’re building for the long haul. Sustainable growth isn’t just possible—it’s entirely doable when you’ve got the right people in your corner. 

If you’re looking to scale without the headache of hiring, WorkBetterNow can help. Our Certified Professionals™ provide expert support in key areas like administration, marketing, and finance, so you can focus on growing your business while we handle the details. 

Ready to take your business to the next level? Let’s make it happen.  

WorkBetterNow (WBN) provides outstanding remote talent to small and midsize businesses. WBN’s highly skilled and pre-vetted Latin American professionals are hand-matched for each client’s unique needs. Hundreds of growing businesses turn to WBN to unleash their potential through our exceptional talent, ease of hiring, and ongoing support. Request a consult today!