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Sourcing, Interviewing and Interview Questions for a Head of Software Engineering

April 21, 2024

Hiring a Head of Software Engineering is a critical decision that can significantly impact the success and innovation of your tech company.

At Recruiting from Scratch, we’ve helped many of our clients successful hire for Heads of Software Engineering (in addition to other Heads of Engineering roles).

Below, we’re sharing how to effectively source and evaluate a Head of Software Engineering, along with some potential interview questions.


Sourcing Heads of Software Engineering

LinkedIn is a powerful tool for recruiting top talent, especially for a senior-level position like Head of Software Engineering. Here’s a few of the ways we’d recommend sourcing for Heads of Software Engineering if you’re just starting out:

Use advanced search filters on LinkedIn: Start with LinkedIn’s advanced search filters to narrow down candidates by location, current company, experience, and more. Keywords such as "Head of Engineering," "Software Development Leader," or even “CTO” (if recruiting from smaller companies), and similar titles can identify potential candidates.


Similarly, we also recommend using filters to look for specific technologies your team uses, or you know you will be using. You don’t want to get down the interview process and realize that someone will have not have adequate experience with the tools you need.


Leverage LinkedIn Recruiter: This premium tool offers more robust search capabilities and outreach potential. It allows you to save searches and even get recommendations for candidates who might not be actively looking but match your criteria.


Finding the right mix of experience during interviews

The experience required for a Head of Software Engineering goes beyond technical skills. However, for example, at smaller companies, we find that Heads of Software Engineering often need to be comfortable with being individual contributors, as they may need to produce work themselves as the company is growing.

Here’s some of the qualities our recruiters always look for in Head of Software Engineering candidates:


Proven leadership: Look for candidates who have experience leading engineering teams. Think about the size of the team you want them to manage. Do they have experience managing teams close to that size?

Evidence of mentoring team members, managing through challenging product launches, and strategic leadership can be crucial here.


Technical expertise: As mentioned, candidates should have a strong background in software development with expertise in the technologies your company uses. They should also be adept at architecture and possibly have experience managing large-scale systems.


Sometimes, we work with clients who are super interested in a candidate because they come from a well-known company or worked on a well-known product. But during the interview phase, you should spend time reviewing their abilities. Do they have the technical expertise they mention on their resume? Or did they work “with” teams who used this technology, or “managed projects” that used a particular language? Pay attention to the wording they use to describe their involvement.


Business acumen: A suitable candidate should demonstrate an understanding of business operations and how they align with engineering efforts. Experience in budget management, strategic decision making, and stakeholder management is valuable.


Look for candidates who have worked cross-functionally, and how/if they have worked with other teams. Terms like “stakeholder management”and “cross-functional teams” are often used at larger corporations, but we also find that smaller companies need team players who can manage stakeholder relationships as well (such as the CEO, or founders/investors). They need to be able to speak to their work and communicate well – whether this is for an audience of 10s of people or just one or two.


Innovative thinking: A Head of Software Engineering should be forward-thinking and innovative, capable of anticipating tech trends and adapting strategies accordingly. Do they talk about their work on LinkedIn? Or do they share what they do on a personal website?Look for these indicators. If they don’t share their work publicly, ask more detailed questions about this during the interview.


The right mix of “job-hopping” on their resumes: Most of our clients want to see reasonably long tenures at roles, where people have built products and teams over time at their companies and seen projects through. Conversely – it can also be a “red flag” if a candidate has stayed at a company too long, and their industry knowledge is limited only to what they’ve learned at that company.


As you’re starting to interview candidates, pay attention to the length of their tenures, but also ask about their accomplishments within these roles. Even if they were in a role for a short amount of time – did they achieve what they set out to achieve? Or if they were in a role for a longer period– did they have some great achievements, or were they working on less-than-impressive projects?


Every company is different, so “job-hopping” has a different definition for any person you ask. However, we recommend asking candidates why they left certain roles, especially for roles between 2020-present. It could be they were laid off due to circumstances outside their control, for one or more roles they’ve held over the last several years due to the changing tech environment.


Some suggested interview questions for Heads of Software Engineering.

 1. Below are some interview questions we suggest asking Heads of Software Engineering candidates. We’ve asked variations of these questions for our own candidates.


2. What tech stacks do you use or have the most experience with?


3. Is there anything you don't use in terms of tech stacks?


4. Why do you think you'll be a good fit for this role?


5. Explain a project where you felt you made the most impact?


6. What sizes of teams have you worked on?


7. What are the two or three most important things you're looking for in your next job?


8. Do you have any experience at a start-up or smaller company? How large were they when you joined and/or left?


9. Could you give a breakdown of the percent of time you spent doing technical work vs. the percent of time you spent doing non-technical work in your last role?


10. What's the largest user end-user base you’ve ever supported? OR – how many people used the product at your last company?

Interested in learning more about the roles we hire for? Check out our roles page, or contact Recruiting from Scratch to speak with someone

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