Executive Hiring: Engineering

This guide focuses on hiring an engineering executive. In most cases, when a company has a co-founding CTO, they naturally assume responsibility for the company's technical vision and architecture. However, as the engineering team expands beyond a certain threshold (this threshold will vary from CTO to CTO), it may become necessary to hire an operational engineering leader. This leader will oversee the day-to-day operations of product development and provide guidance to the development team.

Reporting & Responsibilities

If your company is looking to hire an experienced engineering executive, they will likely report to the CEO and work alongside the CTO, regardless of the specific title (e.g., VP of Engineering, SVP of Engineering). The necessary "executive functioning" skills for this role encompass not only technical abilities but also strong leadership qualities. These include managing business and teams, forming cross-functional partnerships, overseeing profit and loss (P&L), maintaining operational rigor, and being attuned to go-to-market or growth strategies. The required technical skills vary based on the company's stage and the existing team's expertise. Meanwhile, the CTO's role emphasizes foresight "seeing around the corner" in technology and ensuring the product architecture is scalable, extensible, and leads the market.

Identifying Job Requirements

A great question to ask before hiring any executive is: what four things need to happen in the next four years for this company to win the space? From there, you can ask the same question of each function and ensure that all of the functional leaders are focused on the 'highest-value" areas.

For the Engineering function, your answer should guide the search and be reflected in the "what success looks like in this role" part of the role description. This should include the following:

Recruiting & Leading‍

Continuously recruit, lead, manage, and retain a top-notch Engineering team.

Aligning with Other Departments‍

Ensure seamless alignment with Go-To-Market, Growth, Customer Success & Support, and Product Management to create products that users will love.

Maintaining Engineering Hygiene‍

Monitor the software development and release process regularly to ensure optimal engineering practices and remove any obstacles to collaboration and innovation.

Decision Making‍

Collaborate with the CTO (when applicable) in build-vs-buy decisions, focusing on the core product's strength.

Early-Stage Perspective

It's important to recognize the distinct differences in hiring an engineering leader for an early-stage vs. a later-stage company. These distinctions often lie in the levels of experience required, the specific challenges faced, and the alignment with the company's growth stage and direction.

Typically, earlier stage companies have smaller engineering teams and need a leader who is willing and able to be hands on technically. If this is a need/requirement, you’ll want to assess both the willingness and the ability pieces in the interview process.

In this situation, the company should not be looking for someone who is excited to code, but is willing and able to do it if the need arises. A very easy filtering mechanism is to simply ask the question: "We’re an early-stage company with a small team now that will be growing over time. Are you interested in rolling up your sleeves to help with the building, including contributing code when needed?" Usually, you’ll get a visceral reaction.

Later-Stage Perspective

Later-stage companies typically exhibit more organizational structure, increased product complexity, and larger, more diverse teams. When hiring an engineering leader for scaling company, it's essential to look for a candidate who can manage this complexity without inhibiting agility and innovation. They should have the ability to balance the need for structure without succumbing to "process overload."

While it might be tempting to hire a seasoned veteran who has navigated these waters before, consider the unique opportunity that this stage offers for promoting a rising star. Look for someone who has observed great engineering organizations at scale and who may have been mentored by executives with more experience than the current position requires. This approach might unearth a candidate with fresh perspectives and an eagerness to grow.

A specific dynamic often seen in later-stage companies is the merging of Product and Engineering under one leader. This organizational structure may be suitable for platform and multi-vertical SaaS companies, and occasionally for niche Consumer products such as data-driven healthtech or fintech. However, this structuring decision should not be made lightly. Understand the particular needs and nuances of your organization to determine the right executive leader for these combined roles.

Whether you determine you need a seasoned veteran or a up-and-coming rising star, thoughtful consideration of the above factors will ensure you make a hire that will scale with your business in both the short and long term.

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Before jumping into the interview process, first work on mapping out the ideal interview plan and process. Consider the perspectives on the ideal profile from the existing team, fully leverage your board professional networks, tap into perspectives from tenured leaders, identify ways to appeal to a diverse set of candidates, and engage with specialized search firms.

Before you officially release a role description to the market, there are several steps you should take:

Gather Team Perspectives

Before even drafting a role description, meet with the full executive and engineering teams to gather their thoughts. Though you might not agree with all feedback, involving them fosters collaboration and ensures that everyone knows the founders are invested in the hire's success.

Draft an Inclusive Job Description

Create a role description that is flexible and resonates with a diverse set of candidates. Limit the requirements to 5-6 key points about what success looks like in the role.

For instance, instead of stating, “Has 10+ years of experience leading teams of 100+...", consider phrasing it as “Has experience leading large teams building highly available products at global scale.” This approach opens doors for strong candidates from various backgrounds, making the process more inclusive.

Reach Out to Your Network

Send a targeted message to investors, friends, and professional contacts, announcing the role. Focus on the personal qualities and values you're seeking, like a growth mindset or collaboration skills. Link the role description, but let the message speak to the character of the individual you aim to hire.

Consult with Experienced Leaders

Meet with professionals who have previously filled the role. Their wisdom will help you distinguish between necessary and unnecessary requirements, tailored to your company’s unique needs.

Engage with Search Firms

Converse with search firms that specialize in this area. Trust in the partner leading your search is fundamental to a successful relationship and outcome. Reference our guide on selecting the right search firm to assist in this decision.

Interview Structure

Regardless of whether the CEO or the CTO is conducting the interview, and irrespective of the company's current stage, the interview procedure should be roughly the same.

1. Initial Meeting with Hiring Manager (45-60 minutes)

This first meeting should be focused on 75% selling the company and its vision, and 25% on vetting or interviewing the candidate. Here's how you can structure it:

Alignment Check‍

Test for alignment with the company's mission and vision by observing their reaction to the pitch. This part of the conversation helps gauge the candidate's chemistry with your organizational goals and culture.‍

Background Inquiry‍

Spend some time asking about the candidate's general background. This can give you insight into their previous experiences and how they might fit into your team.

Strategically Drop ‘Breadcrumbs’‍

As you discuss the company and the product, subtly introduce key details about what you expect from this leader. Link these 'breadcrumbs' to the specific requirements outlined in the "what we're looking for" section of the job description. This can help you assess how well the candidate resonates with the role's requirements.

Vetting Questions to Ask‍

• Tell me about yourself and what you love doing.
• What about this company is intriguing to you?
• Given what I’ve told you we are looking for in this role, how closely do you feel that it fits what you’re exceptional at?

2. Subsequent Meeting with Hiring Manager (45-60 minutes)

The second meeting shifts to a more rigorous skills assessment, allocating 25% to selling the opportunity and 75% to vetting and interviewing. The focus here is to unearth insights into the candidate's leadership abilities, achievements, and their relevance to your organization.

Here's a deeper look into the main areas to probe:

Understanding Accomplishments

• ‍Question: What have you built that you’re most proud of?‍
• Looking For: Ownership, accountability, why the achievement mattered, and a balanced attribution of success ('we') and shortcomings ('me').

Assessing Cross-Functional Collaboration

• ‍Question: Who are the cross-functional leaders you’ve worked closely with that you were the most successful partnering with? What are some success stories, and what did you and they do to make that partnership so successful?‍
• Looking For: Self-awareness, understanding of natural collaboration, and the flexibility to adapt their leadership style.‍

‍Identifying Preferred Team Operating Modalities

• Question: What team operating modalities do you thrive in? Why is that? What teams did you work in that you didn’t thrive in, and what did you do about it?
• Looking For: Introspection, self-identification of their optimal work environments, and proactive problem-solving when in less compatible settings.

Evaluating Mentoring and Coaching Abilities

• Question: Who are the best people you’ve managed and mentored to be exceptional? How did you get the best out of them, and coach them to get the best out of themselves?
• Looking For: Evidence of successful mentoring, coaching, and development of individuals who have gone on to achieve greatness.

3. Meeting with Two Cross-Functional Peers (45-60 minutes each)

During these meetings, the candidate will meet with two leaders from cross-functional areas, such as VP Product, VP Sales/Revenue, VP Marketing, VP People, VP Finance/CFO. These sessions should be a balanced mix of both interviewing and selling the opportunity (50% interviewing, 50% selling).

At this meeting, each functional leader should talk with the candidate about:

• What they view as a great partnership with engineering
• What is working well now, and what needs changing
• Where they see the future of their function 

4. Working Session with Key Stakeholders (2-3 hours)

A working session with the VP of Product, VP of Sales/Revenue, and the most senior technical members on the team is a critical stage in the assessment process. Ideally conducted in-person, this comprehensive and interactive session explores the three primary dimensions of Engineering's role within the company: Strategic, Technical, and Operational.

Strategic Dimension

• Focus: Aligning the technology strategy with the overall company vision.
• Strategy: Workshop the key success steps related to the company's ‘four things in four years’ objectives, identifying what needs to go right to achieve them.
• Assessment: Evaluate the candidate's ability to switch contexts frequently and partner with cross-functional leaders to leverage technology for non-technical success factors.

Technical Dimension

• Focus: Assessing and planning for technical success.
• Strategy: Discuss current technical strengths and weaknesses, as well as strategies for immediate improvements and future growth.
• Assessment: Look for a leader who understands the limits of their abilities but takes responsibility for problem-solving and guides the team toward technical success.

Operational Dimension

• Focus: Navigating the practical aspects of managing an engineering team.
• Strategy: Explore cross-functional alignment, current inter-team dynamics with Engineering, and practical aspects like hiring, team organization, automation, and business alignment.
• Assessment: Seek a leader who thinks pragmatically about the operational aspects of Engineering, balancing efficiency, effectiveness, and alignment with business objectives.

5. Meeting with Direct Reports (30-45 minutes each)

This stage of the interview process should be reserved for finalists. The meeting is a crucial opportunity for the engineering team to become acquainted with the candidate and understand their leadership and management style. It also provides the candidate with a chance to learn about the projects and responsibilities of the team.

Understanding Leadership Style

• Goal: Assess the candidate's leadership approach, communication skills, and ability to manage a team.
• Strategy: Engage in discussions that allow the team to observe how the candidate approaches leadership, mentoring, and collaboration.

Team Integration

• Goal: Ensure compatibility between the candidate and the team, looking out for potential friction points or signs of what might be termed 'organ rejection'.
• Strategy: Share information about ongoing projects, team dynamics, and expectations to see how the candidate might fit within the existing structure.

Candidate Exploration

• Goal: Provide the candidate with a comprehensive view of the team's work, challenges, and culture.
• Strategy: Invite questions and curiosity from the candidate, encouraging them to delve into the specifics of the team's operations and objectives.

6. Soft Close

After this meeting, if the sentiment is that a candidate is the top candidate and the one the company wants to try to close, the CEO should have a direct conversation with the candidate about why that is, and ask “if we gave you an offer you could accept, would you accept it?” If not, find out what ‘stands between now and yes’, and focus on answering those questions and addressing any concerns. 

7. Meeting with One or More Board Members

Meeting with one or more Board members can be a compelling part of the closing process and may encompass selling, vetting, or both, depending on the situation. To ensure that Board members are adequately prepared for this meeting make sure to prep each Board member with a candidate prep sheet beforehand:

Candidate Overview‍

Provide a succinct summary of the candidate's experiences that are relevant to the position. This should be brief, consisting of 5-6 bullet points, and highlighting their major accomplishments, skills, or attributes.‍

Your Insights & Assessment‍

Share your personal views on the candidate, highlighting what has impressed you, and mentioning any reservations or specific questions that you would like the Board to explore. This section sets the tone and gives context to Board members about what to look for.

Candidate's Perspective‍

Give a brief overview of how the candidate perceives the company, role, and team. This insight can help Board members to understand the candidate's mindset and enthusiasm for the opportunity.

Meeting Focus & Objectives‍

Specify the proportions of the meeting that should be allocated to selling the market, company, and team versus vetting the candidate.

8. Closing

The closing process should be high-touch and personalized. Deliver the offer over dinner or drinks and focus on building a bon with the candidate to humanize the company. Learn about the candidate's family, hobbies, history, etc. You'll be working closely together and want to build trust from day 1.

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We've aggregated a number of questions our experienced CEOs have used to hire great executive teams over the years. For any questions or support in the hiring process, please reach out to Lightspeed's executive talent team here.

General Organizational Questions

Organization Management Strategy

• ‍‍Walk me through an example of building a highly functional and efficient engineering organization?
• ‍‍What was the largest challenge of building the team that you were trying to address?
• How did you overcome this?
• What did you learn?
• Is there anything you would have done differently?
• What was the size of the team in its largest state?

People Management - Building & Maintaining Trust

• ‍‍Give me an example of how you built trust with an existing engineering team.
• ‍‍What was the “trust” challenge you were trying to address?
• What did you do?
• What was the result?
• What did you learn?
• How did this apply with other trust issues?

People Management - Scaling Engineering Teams

• ‍‍What types of professional development and leveling programs have you helped to create?
• What was the “trust” challenge you were trying to address?
• What did you do?
• What was the result?
• What did you learn?
• How did this apply with other trust issues?

Organizational Management - Retention & Team Culture

• ‍‍Give me some examples of the types of retention programs you have implemented.
• At the time, what challenges were you solving for with these programs?
• How did you accomplish this?
• What resources were available to you?
• What was the overall impact of these programs and how was it measured?

Recruiting - Trusted Recruiting Advocate

• Give me an example of how you have partnered with recruiting teams.
• What were the major challenges in hiring?
• How did you partner with recruiting to address them?
• What was the structure of the partnership?
• What were your contributions and what did you learn?

Diversity & Inclusion Advocate

• ‍‍Give me an example of how you helped to create an inclusive & diverse workplace.
• What were the major challenges in diversity?
• How did you solve them?
• What was the impact of this and how was it measured?
• What did you learn?

Cross-Functional Partnership

Resource Allocation, Transparency, & Product Partnership

• ‍‍Give me an example of a time you realized that the existing engineering team was unlikely to meet the deliverables for a new roadmap?
• ‍How did you address this and who were the key stakeholders?
• What solution(s) did you come up with and how did you mobilize them?
• What was the end result?
• Is there anything you would have done differently?‍

Project Management

• ‍‍Give me an example of how you ensured alignment and accurate schedules during a release.‍
• What are the challenges of instilling project management discipline within a team?
• What are some examples of how you have solved for this?
• How did this apply in other areas of alignment and scheduling?‍

Recruiting - Scaling Teams

• ‍‍What’s the largest team you helped to grow?‍
• What were the challenges and how did you identify them?
• How did you address them?
• What was the overall impact and how did you measure it?
• How did this apply to other areas in hiring?‍

Resource Allocation & Budgeting

• ‍‍Can you give me an example of a time you had to evaluate between the benefits and tradeoffs of hiring for full-time employees versus contractors?‍
• At the time, what challenges were you solving for with these programs?
• How did you address these through hiring?
• What resources were available to you?
• What was the overall impact of this decision?

Engineering Management

People Management - Thought Leadership

• ‍‍Give me an example of how you have inspired and motivated engineering teams.
• What was challenging about inspiring and motivating the team?
• How did you solve for this?
• What was the impact of the strategy and execution?
• What did you learn?

‍Organizational Management - Operationalizing Engineering

• Give me an example of how you mapped out engineering plans and laid the groundwork on engineering deliverables.‍
• ‍What challenges are you solving for when developing these plans?
• What considerations do you evaluate between?
• How do you help to ensure the team’s ability to execute on these plans and align them to specific projects?‍

Technical Problem Solving

• Give me a specific example of a time that you improved operational inefficiency for your team.‍
• ‍What challenges within operational inefficiency were you solving for?
• How did you address them?
• What was the impact of the improvement and how was it measured?
• How did this apply in other areas of operationalization?‍

Technical Competency & Curiosity

• Tell me about how you ramped up on the tech stack and architecture at your current company.‍
• ‍To what extent are you technically hands on today?
• How do you decide when to delegate vs when to directly contribute to a project?
• How hands on would you like to be?‍

Optimizing the Engineering Team

• Can you give me an example of how you helped to transform an underperforming team into a high-performing team?‍
• ‍How did you identify the challenges in performance?
• How did you address them?
• What was the overall impact and how was it measured?
• How did this apply to other areas of company performance?‍

Technical - Quality Solutions

• Give me an example of how you ensured and scaled high-quality end-to-end solutions.‍
• ‍What were the challenges and how did you identify the solution(s).
• What was the overall impact and how did you measure it?
• How did this apply to other areas of quality?

Culture

Relationship with Coworkers

• Tell me about the team you’ve been working with recently.
• What are the different people’s roles?
• Who do you work with day to day?
• Ideal Response: The main purpose of this question is to determine whether the candidate had abrasive or adversarial relationship with former coworkers.‍

Empathy, Transparency

• ‍‍‍Tell me about a time when you saw conflict within your team.
• How did it come about?
• How did it get resolved?‍
• Ideal Response: Look for willingness to change one’s perspective based on this new information, and involves compromising with the other side based on new information learned.‍

Empathy, Courage

• You want to introduce a new process to improve some aspect of a workflow but your team is resistant to the idea.
• How would you handle this situation?‍
• Ideal Response: Their approach should begin with a genuine desire to understand why the others are hesitant to take the new approach.‍

Courage

• Tell me about a time you disagreed with a direct report and successfully alleviated concerns/pushed forward with your idea.‍
• Ideal Response: Candidate concretely recounts an example in which they pushed forward with an idea, was able to understand and empathize with why others were hesitant, and was able to use those learnings to come up with a compromise or concessions.‍

Empathy

• ‍‍Can you tell me about a time when you helped a direct report to grow professionally?
• Ideal Response: Candidate should talk about a specific, convincing instance where the candidate helped employees to develop their career and why doing so is important to them.‍‍
• Tell me about a time you interacted with a customer.
• How did you communicate?
• What did you learn from them?‍
• Ideal Response: Candidate describes iterating on a product based on new input from a customer, and shows a large degree of customer empathy and a genuine desire to understand why a customer feels a certain way.‍

Continuous Improvement

• Can you tell me about a time you received feedback that was impactful for you
• Ideal Response: Candidate should be able to recount specific instances in which they channeled the feedback into concrete actions or responses.‍

Well-Rounded

• What is one thing you are most excited about coming to a small startup?
• What is one thing you are nervous about when joining a small team?‍
• Ideal Response: Candidate ideally offers specific elements they are excited and nervous about respectively, demonstrating they have been thinking about this in their search process.‍

‍Curiosity, Always Improving

• What’s the coolest thing you learned in the past year?
• When did you feel it “clicked” for you?‍
• Ideal Response: Communicates how this specifically was a ‘light bulb’ moment for them and expresses a positive interest and attitude towards continually learning new things.

Leadership Principles

Delegation

• Give me an example of when you decided to delegate a responsibility rather than doing it yourself.
• What was the challenge you were trying to address?
• What did you do?
• What was the result?
• What did you learn?
• How did it apply to other areas of working with delegating?‍

Accountability & Transparency

• Give me an example of a time when your engineering team was behind on their deliverables.‍‍
• What was the challenge you were trying to address?
• What did you do?
• What was the result?
• What did you learn?
• How did it apply to other areas of project schedules?‍

Team Development

• Give me an example of how helped to generate growth opportunities on your teams?‍
• What was the challenge you were trying to address?
• What did you do?
• What was the result?
• What did you learn?
• How did it apply to other areas of professional development?‍

Customer Success

• Give me an example of building trusted relationships with customers and technology partners.‍
• What was the challenge you were trying to address?
• What did you do?
• What was the result?
• What did you learn?
• How did it apply to other areas of customer and partner relationships?‍

Technology Obsession

• Can you share an example of a time that you employed a creative solution, mobilized a team around the vision, and why it was impactful to a specific customer?‍
• What was the challenge you were trying to address?
• What did you do?
• What was the result?
• What did you learn?
• How did it apply to other areas customer management?‍

Superpowers

• ‍What’s your superpower?
• Can you share an example of using your superpower/strengths to help your team?
• How have you helped your team to develop their own superpowers?‍

People Management

Recruiting & Business Alignment

• Give me an example of a time that you proactively anticipated the needs of a growing business?
• How have you addressed this through organizational management and recruiting?
• What was the challenge you were trying to address?
• What did you do?
• What was the result?
• What did you learn?
• How did it apply to recruiting and organizational management?‍

People Management - Promotions

• ‍Give me an example of when you knew that an engineer was ready to be promoted to a manager?‍
• Ideal Response: The answer to this should reflect a growth mindset, going above and beyond to create opportunities for growth for their teams and placing a high value on this.
• What signals do you expect to see from an engineer that should be promoted?
• Have you helped to create the next line of managers at your current company?
• What does this process look like?‍

People Management - Internal Mobility

• Give me an example of how have you assisted a member of your team to transition to another department or team (ex: from engineering to product or from systems engineering to frontend).‍
• What was the reason for the transition and what about it was challenging or significant?
• How did you help to set the employee up for success?
• What was the impact of this change?
• What did you learn?‍

People Management - Measuring Success

• Give me an example of how you measure the success of direct reports?
• Failure?
• Give an example of how you managed a low performer out of the organization (firing).‍
• What is challenging about measuring success and failure?
• What indicators do you measure or look for?
• How did you determine when a low performer should be transitioned out of the organization?
• What was the impact of this?‍

People Management - Difficult Conversations

• Give me an example of a situation where an engineer wanted to become a manager but is better suited as an IC at the current time?‍
• What about this was challenging for you?
• What did you do?
• What was the end result of this process?
• What did you learn?

Executive Function

Company Vision & Execution

• Share your company vision over the next 1 - 2 years, and long-term.
• Describe the execution plan.
• Share your vision for engineering over the next 1 - 2 years, and long-term.
• How will this position help drive the execution of this vision?
• How does this align with the vision of their next role?
• Any concerns or misalignments?‍

Performance Expectations

• Describe the performance expectations for the role, how they will be measured, and evaluated.
• Ask if this is consistent or different from their current position.‍
• Any concerns, red or yellow flags about the team, company, or overall opportunity?

‍Candidate Questions

• Give the candidate an opportunity to ask any questions they may have - leaving no loose ends.
• Is there anything that’s unclear?

Working Session

Working Style & Communication

• ‍Ideally, in the working session you will tackle 2-3 key challenges the engineering team is trying to solve.
• You will be able to observe how the candidate navigates varying viewpoints and drives the team/group to a decision. 

Technical Decision Making

• Through the discussion, you should be able to observe the candidate’s technical understanding of key problems, as well as any strongly held technical opinions (about technologies, approaches, etc.). 

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