In nearly every industry, the workload fluctuates. It's normal to have occasional periods of high stress. However, when the team constantly works overtime, accumulates technical debt, and encounters sluggish communication and decision-making, you might face the challenges of a company that has outgrown its size.

As a startup starts to scale, the roles of each team member naturally transform. For instance, the CTO's focus shifts from hands-on technical involvement to a more strategic function. As the team expands, people management takes on greater significance. Undertaking this transition is far from simple. Frequently, companies seek external assistance during this phase. Introducing a CTO coach can facilitate the transformation from an early-stage startup team to a more organized scale-up organization.

So, how do you know it's time to move on to the next stage?

Reading tip: This is how we help SaaS teams

How do you know when your team is ready to scale?

Increased Workload and Overwhelming Tasks

Your team consistently works overtime. The rates of sick leave have risen, in part due to burnout. Elevated stress levels burden the team's atmosphere.

Frequently, deadlines are narrowly met or missed, causing a backlog of tasks to accumulate. You might see this as a temporary situation ending once Project X or Release Y is finished. But think about how long it's been going on. If it's been like that for several months, and it's hard to figure out when it will stop, your team really needs more help right away.

Strained Leadership and Decision-Making

As your company expands, new tasks and responsibilities emerge. Are roles distinctly defined? Does your existing leadership team entirely cover responsibilities? Or did team members take up additional duties they're not completely proficient in?

Are decisions getting passed around between different stakeholders, stuck in a "not-my-responsibility zone," and blocking progress?

Are managers grappling with a lack of strategic focus due to operational overload? Is everyone just too busy?

If you identify such bottlenecks, your company might need to add more leadership to support the team better. An early-stage start-up CTO might not be a good fit for a scale-up CTO position. You may need to review the organizational structure and assess which roles must be filled.

Seeking guidance from an experienced startup leader who has effectively managed scaling businesses in the past can prove immensely valuable.

Missed Business Opportunities 

Sometimes, we simply have to say No to a client or an opportunity.

If the reason isn’t strategic, you are losing money due to a lack of staff! 

Even if you currently can't hire for a full-time position, you still have the option to engage a freelancer, or you can partner with an external business to offer services you can't provide in-house under your own brand, allowing you to maintain client relationships and build a reputation in the industry.

Innovation is put on hold

Can you still invest time in exploring new features and product enhancements? Is your team's current level of research and development enough to stay ahead of the competition in the future?

 Can your company pursue innovative strategic initiatives, or is everyone just too busy? 

While these activities might be temporarily put on hold during an emergency, they should never be ignored if you want to stay competitive in the long run. If you don't quickly expand your team when needed, your competitors will soon launch what you didn't have time to build.

Declining Productivity and Quality

Your clients are complaining about a decline in quality. A growing number of bugs require attention, all while technical debt continues to accumulate.

In this context, it's crucial to investigate the cause of the problem:

Is your team taking shortcuts to meet stringent deadlines?

If you want to build a reputation for high quality, investing more resources in quality assurance and fixing bugs is crucial.

Skill Gaps and Lack of Expertise

Skill gaps within your team can slow down your growth. You might be missing the specialized expertise needed to handle certain projects and smoothly explore new technologies and markets.

Occasionally, enlisting external consultants is a good choice. However, if you find your core competencies dependent on outsourcing firms, consider bringing in team members who have these skills in-house. Ensuring your consultants pass on their skills to your internal team is essential.

(Madewithlove’s engineers commonly guide our client's teams to ensure they can function autonomously after we’re gone.)


The main signs that show it's time to expand your team, like having too much work, decreasing quality, missing skills, and decision-making problems, aren't always noticed immediately. Sometimes, they're seen as temporary or just part of the way things are.

To ensure your company doesn't overlook these signals, consider getting help from an experienced coach. Madewithlove can assist you with technical due diligence and CTO mentoring to proactively help you spot and address these problems, making it easier to grow your team successfully.