Executive Hiring: Product

The guidance we will discuss here is focused on hiring a Product executive. This leader should be expected to have accountability and autonomy to drive the execution of the Product and platform (as the company expands) and integrate tightly with GTM and Engineering to make things happen.

Identifying Job Requirements

If your company is trying to hire a seasoned Product leader as a Product executive, or the candidate is considering other executive opportunities than the one you’re recruiting for the first time, it is most likely that the candidate will report to the CEO and be a peer to the CTO or VP of Engineering, regardless of what you call them. The ‘executive functioning’ skills of a Product leader include business and team leadership, cross-functional partnership, P&L management and operational rigor, and GTM or growth needs and awareness. 

A great question to ask before hiring any executive is: what 4 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-torque’ areas.

Your answer for the Product function should guide the search when writing the ‘what success looks like in this role’ part of the role description, and should involve, primarily:

• Continuously recruiting, leading, managing and retaining an exceptional Product team in a thoughtful and cost-effective manner.
• Ensuring close alignment with GTM, Growth, Customer Success & Support, and Engineering to build products users love, and help them price, promote, and place these products with the right users.
• Continuously monitoring the product feedback and feature prioritization process to ensure that you know what you should be building and why.

By far, the most important part of any leadership interview process is the working session (details below). This does the triple duty of assessing how the candidate collaborates with peers, assessing how quickly the candidate synthesizes the confluence of topics covered at the session, and assessing how deeply the candidate can cover the prescribed functional area that (s)he is interviewing for.

There are several key differences between hiring a Product leader for an early-stage company and one for a later stage company.

The Early-Stage Perspective

Typically, earlier stage companies have no PMs or are looking for a Product leader who is willing and able to be hands on. If this is a need/requirement, you’ll want to assess both the willing and the able part in the interview process. In this situation, the company should not be looking for someone who is excited to write PRDs, 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 everything? Usually, you’ll get a visceral reaction.

The Later-Stage Perspective

Later-stage companies have more organizational structure, more organizational and product complexity, and larger teams with a more diverse functional skill set. At this point, you should be looking for someone who understands how to orchestrate and navigate this complexity, but who can also make sure the organization stays nimble and doesn’t get ‘process overload.’ It’s tempting to want someone who has been there and done that several times - and there may indeed be someone who wants to do that again - but it’s also a great opportunity in the first chapter of the later stage journey to give an opportunity to a star step-up candidate who has seen great Product organizations at scale and with very capable executives who would be too senior for this job, but likely great mentors for this candidate.

Another dynamic that appears in later stage companies is the combination of Product and Engineering under one leader. This makes sense for platform and multi-vertical SaaS companies, and occasionally for a very specific, single-niche Consumer product (data-driven healthtech or fintech) but there are nuances to consider about the right executive leader for these particular role configurations.

Before jumping into the interview process, take the time to map out the ideal interview plan and process. After, consider utilizing the interview plan outlined below, which applies to both early-stage and scaling-stage leaders, as a foundational starting point.

Before Launching A Search

Before you actively interviewing candidates, there are several steps you should take: 

Gather Team Perspectives

Meet with the rest of the Executive, Engineering and Product teams to get their perspective on what to consider including in the candidate archetype. You may not necessarily agree with or use all of the feedback, but it’s important to allow them to feel like part of the process, as well as to ensure they know that the founders are taking responsibility for the eventual hire being successful.

Outline Candidate Qualities

Identify the qualities you are looking for in a candidate. These characteristics companies can include: New Product Strategy, UX & Design, User Research & Finding Product-Market-Fit, Product Analytics, Values Match, Domain Knowledge & Experience, and Managerial Competence.

Additionally, identify the hard requirements for the role. For example, is there a stage of company growth they must have been through? (e.g., 0-1, 10-50 employees, first PM experience, led a team of 5+, etc.) or must-have experience (e.g., Product Marketing, Design, Engineering, Gaming, Data Platform Products, etc.) It’s important to understand that each hard requirement narrows your potential candidate pool.

Draft an Inclusive Job Description

Build 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 message to your investors, trusted friends, and professional network, saying that you’re hiring a Product leader and link the role description. Importantly, state in the message whom you’re looking for, not what you’re looking for. For example, the role description will cover years of experience, level of technical expertise, etc., but the message should also address personal qualities and characteristics, such as detail orientation, growth mindset, being highly collaborative, and other personality traits and values you’re looking for in the human you want to hire.

Consult with Experienced Leaders

Meet with leaders who have done this job before to determine what is necessary and what is unnecessary to require in the role for your company, based on the calibration from these meetings with experienced leaders.

Engage with Search Firms

Have conversations with several search firms who have specific strengths in this area. Reference our guide on selecting the right search firm to assist in this decision.

Interview Plan

Regardless of which stage your company is at, the interview process for an early-stage leader and a scaling-stage leader should be roughly the same.

1. Initial Meeting with the 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. At this meeting, you’re leaning heavily on the company’s vision and its link to product vision, where the product is successful now, and what the potential is for the future with them in the role. You’re testing for alignment with company mission and vision (through their response to the pitch,) chemistry, and asking questions about the candidate’s general background.

During the point in the conversation where you’re talking about the company and the product, drop ‘breadcrumbs’ about what you need from this leader for the company to reach its full potential. These data should be related to the ‘what we’re looking for’ section of a job description.

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? What makes you say that?

2. Subsequent Meeting with the 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. At this meeting, you’re digging into who they are as a leader, what they have done and how relevant that experience is to what you are building.

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

Understanding Accomplishments

• ‍Question: What have you built that you’re most proud of? What made it work so well, and what pivots did you have to make along the way? How did you know when to pivot?

• Looking For: Ownership and accountability, but also (a) what the levers were for a successful product and how they built those levers, (b) what user/customer telemetry they built into their product process to know when and where to pivot, and (c) how decisive are they and what their process is for deciding.

Assessing Cross-Functional Collaboration

• ‍Question: What are some success stories of pairing closely with Engineering and Go-To-Market, and what did you and they do to make that partnership so successful? When did it go wrong, and how did you reorient?

• 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? What makes a great Product Manager and what do you look for that indicates a superstar PM?

• Looking For: In addition to great referrals, evidence of successful mentoring, coaching, and development of individuals who have gone on to achieve greatness.

3. Meeting with 2 Cross-Functional Peers (45-60 minutes each)

During these meetings, the candidate will meet with two leaders from cross-functional areas, such as VP Engineering, VP Sales/Revenue, VP Marketing, VP People, and 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 Product
• 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 long)

Ideally conducted in-person, this comprehensive and interactive session explores the three primary dimensions of Product's role within the company: Strategic, Tactical, and Operational.

• Strategic: Given the company's vision and what is known about the product’s user feedback, work through the current product strategy and how you’ll get more fidelity on features and the market.You should dig deep into the product process and how to know what not to do and build. It will also be a time to analyze competitive dynamics of the market and how to maximize moat.
• Tactical: Discuss what's working and not working well, and what you know about why. Part of this session should be about how to cement prioritization into the roadmap and increase velocity, how to cut through the noise in the development process, and what telemetry/tools the candidate would use to automate whatever can be automated.
• Operational: Discuss cross-functional alignment and what inter-team dynamics exist within Product. You are looking for a leader who can think practically about hiring, team organization, what things should (and shouldn’t) be automated, and how to approach the business as a whole.
  

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

Candidates who get to this point in the process should be considered finalists, and the team is primarily getting to know the candidate, how (s)he leads and manages, and giving the candidate context about the projects the team is working on.

At this meeting, the goal is really to ensure there is no sign of ‘organ rejection’, and that the Product leader and the team will work effectively together.

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:

• A summary of the candidate’s experiences (5-6 bullet points).
• Your disposition on them as a candidate; what you like, and any questions you have about them.
• How the candidate is feeling about the company, role, and team.
• How much of the meeting should be about selling the market, the company, and the team and how much should be vetting.
  

8. Closing

Closing a leadership candidate starts the moment you meet them, but the process is punctuated at the end. 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 Product 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 Product 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 Product 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?

Resource Allocation, Transparency, & Product Partnership

• ‍‍Give me an example of a time you realized that the existing Product 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?

Product Team Management

People Management - Thought Leadership

• ‍‍Give me an example of how you have inspired and motivated Product 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 Product

• Give me an example of how you mapped out Product plans and laid the groundwork on Product 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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