I've seen some amazing startups grow from tiny beginnings to huge companies over the years. Take Facebook — it started as a way for college students to connect, and now it’s used by people all over the world. And Uber? It started with a few cars in San Francisco and grew into a service you can use in cities everywhere.
These success stories might make growing a startup look easy, but it's actually really tough. There are lots of challenges and important choices to make along the way. In fact, our report shows that 54% of entrepreneurs struggle with earning and maintaining finances and money.
I've gone through expert insights to figure out how to scale a startup the right way. We’ll talk about when it‘s time to grow, how to do it well, and what problems you might face. Whether you’re just starting out or already running a small business, knowing how to grow properly is super important.
Table of Contents
- What is Scaling?
- Types of Scaling
- When to Scale Your Startup
- 5 Scaling Challenges You Might Face
- How to Scale a Startup
- Scale When Your Systems and Team Are Ready, Not Just Your Ambition
What is Scaling?
Scaling in business is the ability of a company to grow its revenue at a faster pace than its costs. It involves expanding operations, increasing production or output, and entering new markets while maintaining or improving profitability.
Successful scaling requires refining systems, processes, and resources to accommodate growth without sacrificing quality or customer satisfaction.
Types of Scaling
When it comes to growing your business, there isn‘t just one way to do it. There are actually several different approaches to scaling, each with its own strengths and best-use scenarios. Understanding these different types can help you choose the right strategy for your company’s unique situation and goals.
Vertical Scaling
Vertical scaling increases the capacity of existing resources by upgrading current systems or improving employee skills. This approach is often simpler to implement, but further improvements eventually yield diminishing returns. Vertical scaling suits short-term growth or handling increased demand without major structural changes.
Horizontal Scaling
Horizontal scaling expands capacity by adding more units to the existing system. Like opening new locations, hiring more staff, or expanding product lines. Managing it can be a bit more complex, but it allows for unlimited growth. Scaling horizontally requires parallel systems and can be expensive. It's ideal for long-term growth strategies and provides better fault tolerance.
Diagonal Scaling
Diagonal scaling combines vertical and horizontal approaches. You improve existing resources while also adding new ones. It’s flexible and you can tailor it to your growth needs and maximize current resources while expanding capacity.
Functional Scaling
Functional scaling targets specific areas within a business for growth or improvement. It might involve expanding the marketing team, improving customer service, or developing R&D capabilities. With this approach, it is possible to target improvements and balance resources across different aspects of the operation. It's useful when certain functions limit growth or when entering markets that require specific knowledge.
Geographic Scaling
Geographic scaling involves expanding into new locations or markets to reach new customer bases and diversify market presence. It's a good way to protect against local economic fluctuations and find new talent. However, you have to adapt to different cultures, regulations, and market conditions — market research and localization strategies help with this.
.webp)
Free Business Plan Template
The essential document for starting a business -- custom built for your needs.
- Outline your idea.
- Pitch to investors.
- Secure funding.
- Get to work!
Download Free
All fields are required.
When to Scale Your Startup
Knowing when to scale your business is just as important as knowing how to scale a startup. Timing is crucial — scale too early, and you might stretch your resources too thin; scale too late, and you could miss out on valuable opportunities.
In this section, I’ll explore key indicators that suggest your startup might be ready to take the next big step.
1. When You Notice Repetitive Tasks That Could Be Automated
When we think about scaling a business, we often imagine big changes. But sometimes, the signs that it's time to scale are in the small, everyday tasks. Emil Hajric, CEO of knowledge base platform Helpjuice, offers an insightful perspective on this.
"There‘s ’micro-scales' that happen at every job role/process within a company,” Hajric says.
Hajric explains, if your support team tends to get the same questions, it might be time to “scale” it up by introducing a knowledge base. Another example, Harjric says, is if you're finding yourself spending 20% of your time as a CEO interviewing candidates. Then, it might be time to introduce a recruiter.
“My hot take is: It‘s time to scale once you’ve noticed a repetition that could be automated in one way or another,” Hajric says.
I think this idea of “micro-scaling” is powerful. The goal is to identify bottlenecks in your daily operations and find ways to streamline them. Here's how you can put this into practice:
- Audit your time. Keep track of how you and your team spend your days. Look for tasks that come up repeatedly.
- Identify automation opportunities. Could some of these repetitive tasks be handled by software or systems instead of people?
- Prioritize based on impact. Focus on automating the tasks that are taking up the most time or causing the most frustration.
- Start small. You don't need to automate everything at once. Begin with one or two processes and expand from there.
- Reinvest the time saved. Use the freed-up time to focus on tasks that contribute to your bottom line like acquiring new customers or improving product features.
2. When You're Seeing Tangible Impact on Customers
Your business is ready to scale when you're consistently seeing a measurable impact on your customers.
Jason VandeBoom, CEO of marketing automation platform ActiveCampaign, emphasizes this point. “One of the most impactful things that I found in building a business is the impact. If you can see the impact you’re having on brands throughout the world and on the teams themselves,” VandeBoom says.
How do you find out if this is the case? Look for concrete evidence in your customer data and feedback.
Are customers reporting specific productivity increases, such as saving 20 hours per week or completing tasks 30% faster?
Have they solved defined problems, like reducing inventory errors by 50% or increasing customer retention rates by 25%?
Are they achieving measurable goals, such as boosting sales by 40% or cutting operational costs by 15%?
This level of impact suggests you‘ve found a real market fit. Those numbers show your product isn’t just nice to have — it's becoming a necessity.
In my experience, there’s often potential for even greater growth when you see this kind of impact, and more customers could benefit from what you’re offering.
3. When You've Built a Strong Team and Culture
You know that feeling when everyone on your team just clicks? When ideas flow freely, problems get solved quickly, and there's a shared sense of purpose?
That‘s when you know you’ve built a strong team and culture. And it's also a sign that you might be ready to scale.
A solid team is one that works well together, adapts quickly, and is committed to your company‘s mission. When you’ve got that, you're in a great position to take on bigger challenges.
Think about it: Scaling means more work, more complexity, and probably more stress. You need a team that can handle that without falling apart. You need a culture that can absorb new people without losing its essence.
Spencer Rascoff, co-founder and former CEO of real estate marketplace Zillow, shared a great example of how a strong team and culture can drive quick changes in the Everything Marketplaces podcast.
When Zillow recognized the growing importance of mobile, they needed to pivot fast. Rascoff says he remembers sitting on his computer watching Steve Jobs' demo at WWDC. The iPhone had been out for about six months, but Jobs demoed the App Store.
“And he said in about six months, we’re going to add apps to this iPhone that, you know, nobody had yet. [...] I ran to my co-founder’s desk, you know, 50 people as with the whole company to mobile, like real estate shopping is the ultimate mobile experience,” Rascoff recalls.
Recognizing this opportunity, Zillow made a dramatic shift. The brand changed the name of the company literally, from zillow.com to Zillow.
“By the end of the week, we had declared that if I was in any product meeting or any meeting of any kind, and anyone showed me desktop screenshots before mobile screenshots, I would get up and walk out of the room, and the meeting would be over,” Rascoff retells.
That‘s the kind of rapid, company-wide pivot that’s only possible with a strong team and culture. Scaling up your startup might be a good idea if you're seeing this level of alignment and adaptability.
4. When You've Built Sufficient Liquidity in the Marketplace
In this context, liquidity means having enough active participants on both sides to ensure smooth transactions. While this concept is particularly crucial for marketplaces, it can also apply to other types of platforms or businesses where matching supply and demand is key.
For a marketplace to thrive, you need a healthy balance of supply and demand. This means having enough sellers or service providers to meet customer needs, and enough buyers or customers to keep those providers engaged and profitable.
Signs of good liquidity include:
- Quick matching between buyers and sellers.
- Consistent transaction volume.
- Low wait times for customers.
- Regular earnings for providers.
- Increasing user retention on both sides.
Without sufficient liquidity, users may become frustrated and leave, creating a negative feedback loop.
Marco Zappacosta, CEO of Thumbtack, a platform connecting customers with local service professionals, offers an interesting perspective on building liquidity on the Everything Marketplaces podcast.
"Creating liquidity is sometimes aided by being broader, right? Like because we were broader, we could leverage our efforts across more categories, we could actually acquire and attract more pros in any one category than any of our domains, sort of competitors,” he says on the show.
Zappacosta is referring to Thumbtack's strategy of offering a wide range of service categories rather than focusing on a single niche. This approach allowed them to build liquidity faster. Offering a wider range of services attracted more professionals and customers.
It may not be appropriate for all businesses to broaden categories, but increasing both supply and demand simultaneously is a valuable principle for many platforms.
Once you‘ve achieved strong liquidity, it’s a clear sign that your model is working. Users on both sides are finding value, and there‘s a steady flow of transactions. If you’re running a marketplace, a platform, or another type of business that matches demand and supply, this is the time to scale.
5. When You've Achieved Consistent Positive Cash Flow
Cash flow refers to a steady, steady stream of income that covers your expenses and then some.
Why is this important for scaling?
Growth usually requires investment. You might need to hire more people, upgrade your tech, or expand your marketing. All of that costs money. If you‘re consistently cash flow positive, you’re in a much better position to fund that growth.
Spencer Rascoff‘s experience with Zillow provides an interesting perspective on this. While he doesn’t directly mention cash flow, he talks about how they funded their growth.
“We did a $6 million pre-seed round from the founders. When we sold Hotwire for $700 million, I made $1 million as the co-founder. With that, I bought a $650,000-$700,000 house or used it as a down payment on an $800,000 house,” Rascoff says. The remaining $350,000 Rascof made from Hotwire was invested into Zillow’s pre-seed round.
While Zillow initially relied on investment, having consistent positive cash flow would have given them more options and stability as they scaled.
5 Scaling Challenges You Might Face
As your startup expands, you’ll face a new set of challenges that test even the most seasoned entrepreneurs. Our research shows that 23% of entrepreneurs face challenges in scaling their businesses.
What do you do? I‘ve gathered insights from industry experts who’ve been through the scaling process themselves. As you scale your startup, you'll likely encounter five major challenges — so here’s some expert advice on how to overcome them.
1. Maintaining Customer Focus as the Company Grows
As startups grow, one of the biggest challenges is keeping a strong connection with customers. This challenge intensifies as the company adds more employees, creates new departments, and potentially expands to new locations.
In the early stages, founders and small teams often have direct, frequent interactions with customers. However, as the company scales, these interactions can become less frequent and more removed. I’ve found this distance can lead to a disconnect between the company and its users' needs and experiences.
Jason VandeBoom highlights this challenge. He emphasizes how easy it is to lose touch with customers as a company grows and departments become more specialized.
“I think it’s challenging as you scale because as you scale, all of a sudden, it becomes more about functional roles. You start to get further and further away from the actual customer. And so I think the key for me is, how do we keep everyone as close to the customer as possible?” VandeBoom says.
VandeBoom stresses the importance of maintaining this connection at all levels of the organization, including leadership.
He adds, “If I‘m not talking to a customer, if I’m not directly interfacing with the customer in a given week, I'm just gonna get farther and farther away from myself, right?”
To address this, I recommend implementing:
- Regular customer feedback sessions. Schedule consistent times for team members across departments to speak directly with customers.
- Customer advisory boards. Create a group of key customers who provide regular input on product development and company direction.
- Internal customer storytelling. Share customer success stories and challenges across the organization to keep customer needs top of mind.
- Cross-functional customer interactions. Ensure that team members from various departments, not just sales and support, have opportunities to interact with customers.
- Lead by example. Executives should maintain regular customer interactions. As VandeBoom notes, “If I'm not talking to a customer, if I'm not directly interfacing with the customer in a given week, I'm just gonna get farther and farther away from myself, right?”
- Customer-centric metrics. Implement and track metrics that reflect customer success and satisfaction, not just company growth.
Growing startups can maintain their customer focus by prioritizing these efforts, ensuring that scaling doesn't mean losing touch with the very people they serve.
2. Changing Your Hiring Strategies
As your startup grows, one of the biggest challenges you‘ll face is adapting your hiring strategy. What worked when you were a small team of five won’t cut it when you're aiming for 50 or 500 employees.
This challenge is widespread among growing startups. In fact, during the growth and expansion stage, 24% of entrepreneurs struggle with recruiting and retaining talent. In my opinion, this statistic underscores the importance of developing a robust hiring strategy as you scale.
This is particularly true when it comes to scaling your sales team. As you expand, you‘ll need to develop a structured approach to hiring, training, and managing sales professionals who can drive your company’s growth.
In the early days, hiring often relied heavily on personal networks and a “hire smart people” approach. You were looking for jacks of all trades who could wear multiple hats and were passionate about your mission.
Marco Zappacosta from Thumbtack describes this evolution: "Early days, I think the main heuristic was trying to hire the smartest, hardest working people we knew.” Zappacosta notes that this works well for the first dozen or so hires, but it's not sustainable as you scale.
As you grow, you need to shift towards a more structured hiring process. This includes:
- Defining clear roles and responsibilities.
- Developing a formal recruitment process.
- Creating standardized interview procedures.
- Implementing proper onboarding systems.
- Focusing on cultural fit alongside skills.
You'll also need to start hiring for specific skills and experience rather than just general intelligence and adaptability. This shift can be challenging, especially for founders who are used to having a hand in every hire.
To navigate this transition successfully, Sheila Stafford, CEO of attendance solution TeamSense, offers valuable advice. "First, when it comes to finding talent, my advice is don't be penny-wise and pound-foolish, hire a great recruiting firm, and hold them accountable to delivering a funnel of exceptional talent,” Stafford says.
Stafford suggests using Mark Benioff's V2MOM model for setting and deploying company goals across the organization.
“The V2MOM setup ensures that the exceptional talent that enters the organization can quickly orient themselves to what is important to the organization, what are our major obstacles, and how we are ranking the priority of on-going work,” Stafford says.
3. Regulatory and Legal Challenges
When you expand operations, you'll inevitably encounter a more complex regulatory landscape. What might have been manageable at a smaller scale could become a major hurdle as you enter new markets, hire more employees, or introduce new products or services.
Failing to comply with regulations can result in hefty fines, legal battles, and damage to your reputation.
It can really slow you down and cost a bunch of money. You might need to hire lawyers, change how you operate, or put your growth plans on hold while you sort things out.
Spencer Rascoff from Zillow learned this the hard way when they tried to buy Trulia, a competitor. Here's how he described it:
“We spent 10 months arguing with the FTC, the Federal Trade Commission, that it wasn‘t going to create a monopoly. I believe, I believe there wasn’t agreement, I still believe it didn't create a monopoly... it took 10 months, and I think 26 trips to Washington and, you know, hundreds and hundreds of hours under oath.”
That's a lot of time and energy that could have been spent growing the business.
I recommend consulting with experienced lawyers specializing in startup and business law to ensure you understand and comply with relevant regulations. Create clear policies and procedures regarding intellectual property, data protection, employment practices, and contract management.
4. Evolving Leadership Roles
Initially, leaders often take on multiple roles — handling everything from product development to customer support. However, as the company grows, this hands-on approach becomes unsustainable and potentially detrimental to growth.
Your priorities shift to setting a clear vision. You want to build a scalable organizational structure and empower your team to take ownership.
Jason VandeBoom describes how his role has evolved as the company has grown.
"It‘s changed, and it’s just constant change. That‘s what makes it exciting. It’s about building a team close to the customer experience and the customer, and ultimately having to focus on different things over time. It's not up to any single individual anymore,” VandeBoom says.
According to VandeBoom, having the right people, building the right team, focusing on the customer, and problem-solving are where he spends most of his time today.
“It's very different from earlier on, where I would be actually writing code or doing something hands-on,” VandeBoom notes.
Your focus should shift from day-to-day operations to setting a clear vision, building a scalable organization, and empowering your team.
To navigate shifting priorities, I suggest you:
- Surround yourself with a team of talented individuals who complement your skills and share your vision. Delegate responsibilities, trust their expertise, and foster a collaborative environment where everyone feels valued and heard.
- Keep your team informed about your vision, goals, and challenges. Encourage open dialogue, feedback, and transparency at all levels of the organization.
- Reinforce your values, celebrate successes, and create opportunities for team bonding. A strong culture will keep your team engaged and motivated as you grow.
5. Navigating Funding
Startups often struggle to predict how much capital they'll need as they grow. Underestimating can lead to cash flow problems, while overestimating might result in unnecessary dilution.
Marco Zappacosta from Thumbtack highlights a crucial aspect of fundraising: “When you're raising your round, always know what the round after that one is interested in. Because you gotta put yourself in the mindset of these investors.”
Scaling means funding current operations as well as positioning yourself for future growth.
To navigate this challenge:
- Develop detailed financial projections.
- Include best-case and worst-case scenarios.
- Consider different growth trajectories.
- Factor in market conditions and competition.
- Plan for unexpected expenses.
Understanding what future investors will look for should shape your current fundraising strategy. It influences how much you raise now and how you allocate those funds.
Consider:
- Milestones you need to hit for the next round.
- Key metrics investors will focus on.
- How your current round will position you for future fundraising.
A forward-thinking approach helps you maintain momentum and avoid funding gaps as you scale.
How to Scale a Startup
Here are actionable tips and strategies based on insights from entrepreneurs and industry leaders.
I think it's also worth exploring resources designed specifically for scaling startups. For example, HubSpot offers a startup program that includes software and support tailored to the needs of scaling companies.
Focus on building capabilities and delegating founder-led tasks.
When it's time to scale, shift gears quickly. David Baum, CEO of content operations platform Relato, explains, "I think of scaling as a process of building capabilities and delegating most of what has been founder-led up to that point. The first problem to tackle is that the users you have won't be the same group you grow with.”
Baum notes that founders will go through family and friends quickly. The founders’ extended network of innovators is also quite small.
“Scaling involves engaging an early majority. That group of people aren't exactly the same as the innovators. They’re going to have a broader set of requirements and lots of objections you must handle in the product, terms, pricing, and with copy,” Baum says.
This perspective highlights a key aspect of scaling, in my opinion: evolving beyond the founder-centric approach that characterizes many early-stage startups. Here's how to put this into action:
- Identify founder-led tasks. Make a list of all the responsibilities currently managed by the founders.
- Prioritize delegation. Determine which tasks can be handed off to team members or new hires.
- Build new capabilities. Invest in systems, processes, and people that can take on scaled operations.
- Adapt to new customer segments. Recognize that your initial user base may differ from the broader market you'll target when scaling.
- Refine your offering. Be prepared to adjust your product, pricing, and messaging to meet the needs of a wider audience.
Scaling isn't just about doing more of the same. This often requires founders to step back from day-to-day tasks and focus more on strategic direction and team leadership.
While delegating is crucial, Baum also notes the importance of founders staying involved in key areas: “I believe the founders should stay deeply involved in marketing and sales through early growth.” This hands-on approach during the transition ensures the company's core vision and values are maintained as it scales.
Be prepared to pivot your business or target audience multiple times.
Scaling up means being flexible. Your initial business idea might not be the one that ultimately succeeds. Being ready to pivot — to change direction quickly — can be crucial for your startup's survival and growth.
Markets change, customer needs shift, and what seemed like a great opportunity at first might not pan out. That's normal in startups. The important thing is to stay adaptable and not get too attached to your original plan.
Pivoting could involve adjusting your product, targeting a different customer base, or even completely changing your business model. As you grow, you need to respond to what you learn.
Stay informed so you can pivot. Keep a close eye on:
- Customer feedback.
- Market trends.
- Your business metrics.
Spencer Rascoff's experience with Picasso, his fractional home ownership startup, illustrates how even experienced entrepreneurs need to be ready for multiple pivots:
According to Rascoff, his team found early product-market fit at Picasso, especially during the COVID quarantine when people wanted a second home. However, people eventually went back to work in offices, mortgage rates increased, interest rates increased, and tech stocks declined. The demand for second homes decreased.
“Suddenly, many of our customers felt less wealthy and said, ‘Well, I don’t need a Picasso anymore, or I don't want to spend a million dollars,’” Rascoff says.
Be honest with yourself about what’s working and what isn’t. I know it’s easy to ignore signs that change is needed, especially when you’re invested in your current path. However, recognizing the need to pivot early can save you time and resources in the long run.
Seek advice from other founders and functional leaders.
I believe one of the smartest moves you can make is to reach out to other founders who‘ve scaled their businesses. And functional leaders who’ve mastered specific areas like marketing, finance, or operations.
Most people love sharing their experiences. At the same time, Jason VandeBoom, the founder and CEO of ActiveCampaign, admits he didn't do this enough early on.
"One thing that I didn‘t do a lot of early on was reach out to other people. I thought they wouldn’t want to share or share reality. What I found was quite the opposite, both when it comes to founder-to-founder interactions and different functional roles,” VandeBoom says.
So, how do you go about this? Start by building your network. I suggest attending industry events, joining entrepreneurial groups, or reaching out on LinkedIn.
When you do connect, come prepared. Have specific questions ready. Maybe you‘re struggling with hiring for scale, or you’re unsure about entering a new market. Whatever it is, be clear about what you need help with.
Essentially, you want perspectives you might not have considered. Sometimes, the most valuable advice comes from someone seeing your problem with fresh eyes.
And here‘s a pro tip: don’t just seek advice from people in your exact industry. Cross-pollination of ideas from different sectors can lead to innovative solutions.
Launch a stealth brand to test concepts without drawing attention.
Launching a stealth brand can be a smart move when you're testing out new ideas or entering a competitive market.
So, what‘s a stealth brand? It’s basically a low-key version of your product or service that’s launched under a different name. It lets you test the waters without tipping off competitors or setting unrealistic expectations.
Spencer Rascoff, co-founder of Zillow, shared a great example of this strategy. "HomeAuction.com was the very first version of Zillow. We intentionally launched with that URL as a brand that nobody would pay attention to. We auctioned just one house,” he says.
This approach gave Zillow a chance to test their concept without drawing attention. They could learn from real users, spot potential issues, and refine their ideas before going big with the Zillow brand.
You don't want to stay stealth forever. Before you make your big move, give yourself some space to innovate and improve. When you nail your concept, you can reveal your true brand and scale up.
Just be sure to plan your transition carefully. You don‘t want to confuse or lose the customers you’ve gained during your stealth phase. Consider how you'll bring them along when you reveal your full brand and scale up your operations.
Focus on customer retention and expansion.
When you‘re trying to grow your startup, it’s easy to get caught up in chasing new customers. But keeping the customers you already have can be just as important, if not more so.
Think about it — it's usually easier and cheaper to keep a customer happy than to find a new one.
So, how do you do this? First, I recommend you make sure your product or service is top-notch. Then, listen to your customers. What do they like? What could be better? Use this feedback to improve.
Don't forget about expanding within your existing customer base. Can you offer them more services or products? This is often an easier sell because they already trust you.
Kyle Duffy, an investor at Gradient Ventures (part of Alphabet, Google's parent company), specializes in early-stage AI and machine learning startups in HubSpot’s Science of Scaling podcast. Drawing from his experience with portfolio companies, he points out a common pitfall in the podcast.
“Something that gets overlooked from the beginning is customer success. They see it as, ‘Okay, we need revenue, we need customers in the door.’ I don’t think there’s enough focus spent on how to expand customers that you already have,” Duffy says.
Duffy highlights how many startups, especially in the AI space, prioritize new customer acquisition over nurturing existing relationships. However, he argues that focusing on customer success and finding ways to expand your offerings to current customers can be a powerful growth strategy for early-stage companies.
If you’re looking for inspiration on how other startups have successfully scaled, I suggest you check out resources like HubSpot’s Scaling Showcase, which can provide valuable case studies and insights. Learning from the experiences of other founders who have navigated similar challenges can be incredibly helpful as you plot your own growth strategy.
A happy customer is more likely to stick around and even recommend you to others. So, while you‘re working on growing your customer base, nurture the relationships you’ve already built. Find the right balance between acquiring new customers and maximizing the value of your existing ones.
Scale When Your Systems and Team Are Ready, Not Just Your Ambition
As I've researched and written about startup scaling, one thing has become abundantly clear to me: For every successful startup that scales well, there are two or three others that stumble or fail in their growth attempts.
I‘ve seen countless examples of startups racing to scale based purely on ambition or pressure from investors, only to face serious operational issues or team burnout. On the flip side, I’ve observed companies that took the time to solidify their foundations before expanding, and they often navigated the scaling process much more smoothly.
Timing is crucial. The best time to scale isn‘t when the market seems hot or when competitors are growing rapidly. Instead, it’s when your own house is in order — when your systems can handle increased demand, your team is aligned and capable, and your core business model is rock solid.
Free Business Plan Template
The essential document for starting a business -- custom built for your needs.
- Outline your idea.
- Pitch to investors.
- Secure funding.
- Get to work!
Download Free
All fields are required.