There comes a point when having a founder, CEO, or engineering manager manage the technology function at a company becomes too large or too complex. This is the obvious point when it’s time to hire a VP of Technology.
But there are several other things to consider too.
The right time is influenced by revenue, funding stage, and team size. However, these factors alone don’t determine the time. The right time to hire a VP of Technology usually becomes clear through a combination of problems, including:
- Projects take longer to complete
- Engineering decisions depend on one person
- Technical problems keep interrupting strategic work
- No single leader is accountable for turning tech plans into results
Considering the right factors is critical when finding the right time to hire a VP of Technology. Because hiring a VP of Technology too early can add an unnecessary and very expensive layer of management the company does not need. Waiting too long can lead to missed deadlines, employee turnover, technical debt, security risks, and frustrated customers.
Here are 7 signs it’s time to hire a VP of Technology.
1. The Founder or CTO Has Become a Bottleneck
Often at the early stages of a company, the founder or CTO oversees the technical decisions. That usually works while the team is small and the company is establishing itself. But it starts to become a problem when the CTO becomes busier and, eventually, is spread too thin. At this point, engineers will have to wait for the CTO or founder to approve architecture decisions, solve delivery problems, review new hires, and coordinate with other departments.This waiting risks slowing down business and holding the company back.
The CTO or founder needs help. And it’s not because they’re not capable of doing the work. They are more than capable. The issue is that there’s no longer enough time in the day to do everything well.
When its’ time to hire the VP of Technology, they come on board are become responsible for the daily operation of the technology organization. This gives the CTO or technical founder more time to focus on long-term direction, major product decisions, investors, customers, and emerging technologies.
This is why hiring a VP of Technology at the right time is so critical. If you wait too long, then the core responsibilities of the CTO role may not get the attention they need. And since thoe core responsibilities are so important, you don’t want that to happen.
Key signal: If the company’s most senior technical leader spends most of the week resolving internal problems, the company may have outgrown its current structure.
2. Engineering Delivery Has Become Unpredictable
All companies have times when they are late on execution. But if you have a pattern of missed commitments and unpredictable delivery, then you may need an executive hire.
Common engineering delivery problems include:
- Deadlines changing without a clear explanation
- Teams starting more projects than they finish
- Product and engineering teams disagreeing about priorities
- Technical problems unforeseen and appearing late in development
- Leaders being unable to give customers or the board reliable timelines
A common mistake is that these indications are thought to signal the need for more engineers. However, it actually signals a need for strong operational leadership, and it’s time to hire a VP of Technology.
A VP of Technology creates clearer priorities, sets a dependable planning process, and holds teams accountable for delivery. The goal is not to eliminate every delay. It is to make delivery more consistent and ensure that risks are identified before they become emergencies.
Key signal: Engineering teams regularly miss deadlines, and company leaders can no longer confidently predict when important projects will be completed.
3. The Technology Team Has Outgrown Its Current Leaders
The time to hire a VP of Technology often becomes clear once the engineering organization reaches about 15 to 20 people. Or contains several teams and managers. There’s no exact number of employees that makes a VP of Technology necessary. It will depend on your organization's specific needs.
Essentially, it comes down to whether the team has become too complex to loosely, and informally manage. Problems with informal management arise when different teams:
- Choose conflicting tools
- Follow different development processes
- Solve the same problem more than once
Engineering managers may also need guidance that a busy founder or CTO cannot consistently give.
While size can be a key indicator, small organizations may find it’s time to hire a VP of Technology.
A smaller organization may need a VP of Technology sooner if it manages:
- Complicated infrastructure
- Sensitive data
- Multiple products
- Strict regulatory requirements
Key signal: As yourself, “Has leading this team become a full-time executive responsibility?”
4. Technical Debt Is Interfering With Growth
Technical debt is common and normal. Sometimes growing companies need to make short-term decisions to move faster. But problems begin when those decisions make future work slower, riskier, or more expensive.
Your company may find it’s time to hire a VP of Technology if:
- Engineers spend too much time fixing recurring problems
- Small product changes require extensive rework
- Outages or performance problems are becoming more common
- Nobody has the authority to prioritize foundational improvements
- The company cannot explain which technical risks matter most
If you’re wondering when you should hire a VP of Technology, for some companies it’s when they need someone to determine which problems should be prioritized. It can feel like everything needs to be addressed ASAP. A VP of Technology will have the skill to discern which needs to be addressed immediately and which can wait.
A VP of Technology can also create a realistic plan for improving the company’s systems without bringing product development to a halt. Hiring another developer may increase capacity, but it will not solve a lack of technical priorities or ownership.
Key signal: If it feels like a lot of decisions may actually be slowing the company down, it may be time the hire a VP of Technology.
5. The Company Is Entering a More Demanding Stage
A major business event can change what the company needs from its technology leadership.
For example, the company may be:
- Preparing for a new funding round
- Pursuing a large enterprise customer
- Expanding into a regulated market
- Completing an acquisition
- Integrating an acquired company
- Preparing for due diligence
- Scaling a product to serve significantly more users
These types of events place additional pressure on infrastructure, security, delivery, documentation, and reporting. Investors, customers, or acquirers may also want one executive who can both explain the company’s technical risks and take responsibility for addressing them.
The right VP of Technology gives the company a clear point of accountability during these types of transitions.
Key signal: Your company needs a point person to take responsibility for technical risks and communicate to investors, customers, or acquirers.
6. Technology Problems Are Affecting the Rest of the Business
A VP of Technology may be necessary when the rest of the company starts to notice technical problems or it starts to effect them.
For example, sales may be promising features without knowing whether engineering can deliver them. Product leaders may struggle to get reliable timelines. Finance may not understand rising technology expenses. Customer teams may be dealing with repeated performance issues without a clear resolution plan.
These problems need cross-functional collaboration and communication. The VP of Technology is the point person for these types of problems. They connect engineering decisions to business priorities. And they help other executives understand:
- What can be delivered
- What it will cost
- What could go wrong
- Which tradeoffs the company needs to make
That cross-functional leadership is one of the biggest differences between an experienced technology executive and a strong individual engineer or engineering manager.
Key signal: If the lack of cross-functional leadership is negatively impacting your company, it may be time to hire a VP of Technology.
7. No One Person Is Accountable for Technology Execution
Several people may share responsibility for technology without anyone truly owning the department or its outcomes.
The CTO sets the direction. Engineering managers oversee their teams. Product decides what should be built. IT manages internal systems. Security may sit with another leader or an outside provider.
Each person may be doing their job well, but problems can still fall between the gaps.
A VP of Technology creates a clear line of accountability across engineering delivery, infrastructure, technical operations, IT, and security.
The exact scope of the VP of Technology role should depend on the company, but the ownership must be clear before the search begins.
If every major technical problem leads to a debate over who’s responsible, the company likely needs stronger executive ownership.
Key signal: If there are multiple tech departments, without someone who is responsible for them, and things are starting to slip through the cracks, it may be time to Hire a VP of Technology.
When Is It Too Early to Hire a VP of Technology?
A company may not be ready for a VP of Technology if:
- It has only a few engineers
- Has not found product-market fit
- Still needs its senior technical leader to spend most of the day building the product
At this stage, a VP title can create more structure than the company needs. A strong engineering manager, technical lead, fractional technology executive, or experienced advisor may be a better fit.
It may also be too early if the company cannot define what the new executive would own. Hiring a VP of Technology without clear authority often creates conflict with the CTO, founder, product leader, or VP of Engineering.
Before beginning the search, the company should have a clear scorecard and scope for the role. They should be able to answer three questions:
- What problems must this person solve?
- Which decisions will this person have the authority to make?
- What should be measurably better within their first year?
If the leadership team cannot agree on those answers, it should define the role before recruiting candidates.
Should You Hire a VP of Technology, CTO, or VP of Engineering?
It’s time to hire a VP of Technology when the company needs an executive to run technology operations and turn strategy into consistent execution.
A CTO vs. an VP of Engineering is usually the better choice when the primary need is setting the company’s long-term technology direction, representing technology to investors or customers, or establishing the original technical vision.
A VP of Engineering over a CTO is typically the better fit when the need is concentrated specifically on engineering teams, hiring, performance, development processes, and product delivery. For example, a VP of Engineering often directs the architecture of AI scale.
Titles vary between companies, so focus on the work rather than the title. Our complete guide on how to hire a VP of Technology explains how these positions differ and how to define the right role.
Is Now The Time? Here’s When to Hire a VP of Technology
It’s time hire a VP of Technology when technology execution has become a full-time executive job.
If delivery is unpredictable, the CTO is trapped in daily problem-solving, technical risks grown, or the company is entering a more demanding stage, waiting can become more expensive than hiring. And it will almost always be more cost effective to hire for the right role, even it’s it a more expensive role, than to mishire for a lower level role that you don’t need.
The first step is deciding what your business needs this executive to accomplish.
Christian & Timbers’ technology executive recruiters help companies define, identify, and recruit senior technology leaders who fit their stage, strategy, and operating needs.
