Executive Search

A strong engineering leader is a critical hire for any scaling startup. Developing an interview process that tests for core technical skills, strong leadership ability, and the ability to inspire and develop a team will ensure you hire a seasoned leader who can grow with the business.

Interview Plan

Initial Screen

• ‍Time: 45-60 minutes‍
• Interviewer: CEO‍
• Goal: Initial conversation to discuss high-level background & engineering leadership philosophy. Partial selling motion.

First Onsite

Sell Meeting

• Time: 45-60 minutes‍
• Interviewer: Co-Founder/ Board Member‍
• Goal: Sell meeting to discuss the vision of the company and the executive role.

Cross-Functional Partnership

• ‍Time: 60 minutes‍
• Interviewer: CEO, Head of Product, or PM‍
• Goal: Discussion on cross-functional leadership & product partnership.

Engineering Management

• ‍Time: 60 minutes‍
• Interviewer: CEO, Head of Product, or PM‍
• Goal: Discussion on engineering management and technical acumen.

Second Onsite

Culture Interview

• ‍Time: 45 minutes‍
• Interviewer: HR Leader or Cross-Functional Team
• ‍Goal: Opportunity to sell company culture and identify if the candidate would add to it.

Leadership Principles

• ‍Time: 45 minutes‍
• Interviewer: CEO or Other Executive‍
• Goal: Discussion on leadership values and team-development

People Management

• ‍Time: 60 minutes‍
• Interviewer: CEO, Head of Product, or PM‍
• Goal: Discussion on ability to hire and develop teams.

Executive Interview

• ‍Time: 45 minutes‍
• Interviewer: CEO‍
• Goal: Highlight any yellow flags, selling the opportunity and discussing the long-term company plan.

Closing

Dinner/Drinks with Founders and/or Board Members

• ‍‍Can be done via Zoom

1:1 Meetings with Other Key Decision Makers

• As needed

Interviewing Best Practices

1. Gauge the candidate's ability to manage, oversee, and scale HR operations - payroll, benefit, compliance, onboarding, etc.
2. Assess what programs the candidate has instituted at their current company to increase employee satisfaction, productivity, and tenure.
3. What experience does the candidate have opening new offices or building remote teams? What type of training programs have they instituted for managers and leaders?
4. Can the candidate make the executive team and company smarter about HR strategy? Great HR leaders should use metrics to drive decisions.

Example Interview Questions

Initial Screen

• Organization Management Strategy: Walk me through an example of building a highly functional and efficient engineering organization?
• Organization Management Strategy: 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 at its largest state?
• People Management - Building & Maintaining Trust: Give me an example of how you built trust with an existing engineering team.
• People Management - Building & Maintaining Trust:  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?
• People Management - Scaling Engineering Teams:: 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.
• Organizational Management - Retention & Team Culture: 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.
•  Recruiting - Trusted Recruiting Advocate: 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.
• Diversity & Inclusion Advocate: What were the major challenges in diversity? How did you solve for them? What was the impact of this and how was it measured? What did you learn?

First Onsite - 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?
• Resource Allocation, Transparency, & Product Partnership: 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.‍
• Project Management: 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?‍
• Recruiting - Scaling Teams: 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?‍
• Resource Allocation & Budgeting: 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?

First Onsite - Engineering Management

• People Management - Thought Leadership: Give me an example of how you have inspired and motivated engineering teams.
• People Management - Thought Leadership: 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.‍
• Organizational Management - Operationalizing Engineering: 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.‍
• Technical Problem Solving: 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.‍
• Technical Competency & Curiosity: 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?‍
• Operationalizing the Engineering Team: Can you give me an example of how you helped to transform an underperforming team into a high-performing team?‍
• Operationalizing the Engineering 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.‍
• Technical - Quality 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?

Second Onsite - Culture

• Relationship with Co-Workers 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: Seek 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.‍
• Question: 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.

Second Onsite - Leadership Principles

• Delegation: Give me an example of when you decided to delegate a responsibility rather than doing it yourself.
• Delegation: 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.‍
• Accountability & Transparency: 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?‍
• Team Development: 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.‍
• Customer Success: 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?‍
• Technology Obsession: 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?‍
• Superpowers: How have you helped your team to develop their own superpowers?

Second Onsite - 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?
• Recruiting & Business Alignment: 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?‍
• People Management - Promotions: 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 a 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).‍
• People Management - Internal Mobility: 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)‍
• People Management - Measuring Success: 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?‍
• People Management - Difficult Conversations: What about this was challenging for you? What did you do? What was the end result of this process? What did you learn?

Second Onsite - Executive Interview

• Company Vision & Execution: Share your company vision over the next 1 - 2 years, and long-term. Describe the execution plan
• Company Vision & Execution: 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
• Concerns or Thoughts: 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?

Closing

• Dinner with Founders/ Board: Talk through any reservations or hesitations about the company/role. Sell the long term vision and upside in the opportunity as well as the impact engineering will have.
• ‍1:1 Meetings: Resolve outstanding yellow flags or concerns by the candidate by connecting them with the appropriate people.

There are 3 main functions recruiters and HR leaders oversee - recruiting, human resources (HR), and people strategy. Every recruiter and HR leader will have different strengths and focus areas. It's important to hire the right type of leader based on your stage, company size, and goals.

In general, most companies should have at least one people leader by the time they hit 50 employees. However, depending on your growth, location, employee-base, and goals you might need to hire earlier or a larger people team.

People Focus Areas

Recruiting

• Identifying Candidates
• Outreach & Messaging
• Closing Candidates
• Managing Offers
• Supporting DEI efforts

HR

• Payroll
• Benefits
• Compliance
• Performance Management

Strategy & Programs

• Headcount strategy & Org Design
• Compensation & Leveling
• Manager Training
• Culture & DEI
• Remote Team Support

People Team Timeline

Your people team should grow and evolve in tandem with your organization. Early-on focus on on bringing in a rockstar individual contributor recruiter who can help hire your core team and build very basic processes. As your organization grows, bring on HR experts who can help shape the company culture and institute scalable programs.

<25 Employees

Recruiter

• Hire a recruiter if planning to hire more than 15 employees throughout the year
• Leverage a PEO or 3rd party to manage payroll, benefits, & compliance

>50 Employees

Recruiter, HR, or  Hybrid

• If planning to hire more than 25 employees, hire 2+ recruiters
• If your employee-base is distributed, remote, or heavily sales-focused, consider bringing in an HR or hybrid leader to manage complexity

50-100 Employees

Recruiter & HR

• Companies with 50+ employees should bring on an HR Leader to develop programs to support employees and future growth
• Companies at this stage will likely also have 1-2 recruiters

100-300 Employees

Recruiting Team & HR Team

• Depending on their knowledge of recruiting, an HR leader might oversee the growing recruiting team

300-500 Employees

Geo-Focused Recruiting Team & HR Team

• Effective recruiting teams are generally function & geography focused
• At this stage the HR team should have grown to 3+

500+ Employees

Expanded Recruiting & HR Teams

• The recruiting team will include sourcers, coordinators, recruiters, & managers
• HR team might include Total Rewards, HRBPs, DEI leads, & L&D

Hiring a Recruiter

One of the highest-leverage hires a startup can make is a strong in-house recruiter. A great recruiter can save countless hours and money by managing hiring efforts, setting up basic interviewing and on-boarding infrastructure, building an employer brand, and developing company culture.

Every recruiter will have different focus areas, strengths, and interests. It’s important to ensure their strengths fit your company needs. There are generally 3 types of recruiters that you will find in the market. Strengths, weaknesses, and which companies each is best for is outlined below:

Pure Recruiter

Description:

A pure recruiter is an individual contributor focused purely on recruiting and sourcing and generally has little to no HR experience. They specialize in either tech or non-tech roles and do best in higher volume, straightforward environments. They might come from a late stage startup or large public company.

Pros:

• Great at spinning up candidate pipeline and usually have a strong focus on volume.
• They typically have a deep knowledge of a specific industry or vertical and will come with an existing network they can tap into.

Cons:

• Generally, not focused on strategy or metrics.
• They usually solely focus on filling roles and won’t be helpful in developing headcount plans.
• They will not have experience setting up and driving process.
• Most pure recruiters will come into a company that already has an ATS (applicant tracking system), interview process, and employee referral program.
• It can take them a lot longer to identify when and how to implement these processes.

Best For:

Companies that have a high volume of similar roles to fill and a founder who is willing to manage the strategy aspect of the recruiting function. Also a fit for rapidly growing companies with an existing recruiting leader.

Head/ Director of Talent - Hybrid

Description:

A hybrid recruiter enjoys both hands-on recruiting and the strategic aspects of hiring. They typically have a keen eye for metrics and have experience implementing an ATS, building basic interview processes, and running hiring manager training. They might come from an early or mid-stage startup and may have been the #2 on a fast-growing team.

Pros:

• They have highly relevant startup experience and have seen common challenges faced at early-stage companies.
• They usually will have an area of expertise but have hired across a lot of different roles, both tech and non-tech.
• They have experience working with minimal budgets and have a “scrappy” work-ethic.
• They will have experience reporting on hiring metrics and can use them to improve the hiring process.

Cons:

• These recruiters can be hard to find, as most people fall into the first two categories.
• Expect to pay a premium. Although they might be coming in as an IC, recruiters with previous startup experience are in high-demand and are commanding $160–200k salaries.

Best For:

Companies who are looking to hire for the next 18+ months and need help setting up hiring best practices. Hybrid recruiters are best fits for founders who want to bring in a strategic partner who will up-level the executive team’s knowledge about hiring.

VP of Talent - Strategist

Description:

A strategist will often have a manager, director VP, or “head of” title. They will currently manage a team, drive strategic recruiting and/or HR initiatives, and haven’t been hands-on with recruiting in the past 6 months. They might come from a mid-stage to late-stage startup and usually have been a first in-house recruiter in the past.

Pros:

• Strategists are ideal for rapidly growing companies who need help setting up hiring and basic HR infrastructure.
• They have seen a company scale from sub 50 and can help you anticipate and prepare for the common challenges companies face as they grow.
• They have a strong focus on strategy and metrics. They “report-up” well and can help you develop a headcount plan that’s tied to business initiatives.

Cons:

• Typically haven’t had to focus on hands-on recruiting in quite some time.
• Will quickly want to hire a team and are usually unhappy in transactional roles.
• They won’t stick around long if they remain an individual contributor for more than a few months.

Best For:

Companies who are going to quickly scale and have budget to hire a small recruiting team within the next 6 months.

Interviewing a Recruiter

Goal:

• Understand their past experience with the full hiring process - sourcing, messaging, interviewing, closing, and partnering hiring managers.
• Determine their aptitude and desire to work within this role. Candidates who are more focused on HR and programs tend to be unhappy and unsuccessful in recruiter roles.

Process:

• Develop an interview process that mirrors the common skillsets required by the job.
• Recruiters should interact with a cross-functional set of the team - hiring managers, team members, executives, etc.
• Phone Screen - 45 min-1 hour with the hiring manager.
• Onsite Interviews - 4 total interviews (1 hour each) with team members

Common Mistakes:

• Not understanding candidate motivations- they need both the skillset AND the desire to get really hands-on.
• Transactional questions-  ie. only asking about hiring goals, roles filled, time to fill, etc,. Make sure to explore why decisions were made and how the candidate made their teams smarter about hiring.

Interview Topics:

Use situational/behavioral interview questions to assess their skill set. Mirror the actual role as closely as possible.

• ‍Identify & Engage: Gauge candidate's ability to assess a role, define requirements, identify candidates and develop messaging.
• Interview & Qualify: Determine if the candidate can build an effective interview process. This includes recruiter screen, onsite interviews, and building interview training.
• Closing Candidates: Can the candidate convince top talent to join the company? Ask  them to pitch their current company, sell the vision, and talk about equity/ value.
• Strategy & Metrics: Can the candidate make the executive team and company smarter about hiring? Great recruiters should use metrics and A/B testing to drive decisions.

Hiring an HR Leader

HR leaders can give companies the strategic leverage to scale headcount, open new offices, increase employee productivity, and influence retention. Most companies should consider, bringing in an HR leader between 50-100 employees.

Depending on the complexity of HR needs (remote, distributed, sales-heavy, etc.) there are different profiles of HR leaders that might be most impactful. Plan to hire someone who’s background fits your company growth goals for at least the next 18+ months. Similar to recruiters, there are also 3 types of HR leaders. Strengths, weaknesses, and which companies each is best for is outlined below:

HR Generalist

Description:

An HR Generalist is an individual contributor focused purely on HR operations and administration. They generally have little to no recruiting experience. They are typically great at basic compliance, payroll, benefits administration, and project managing existing programs (onboarding, manager training, performance reviews, etc). HR Generalists might have worked at a large company in the past or been part of a large team.

Pros:

• Great at managing highly hands-on HR operations.
• Typically don't have deep knowledge about recruiting or building new programs from scratch.

Cons:

• Generally, not focused on strategy or metrics.
• They usually solely focus on actioning HR tasks.
• Due to their experience at large companies or within large teams, they aren't always up to date with new or upcoming HR-tech and usually have limited experience selecting any of these solutions.

Best For:

Early-stage companies with a strong recruiting leader who understands HR or growing companies with an existing HR leader.

Head/ Director of HR

Description:

An experienced HR leader that has worked at a startup in the past. They will bring knowledge about HR operations, strategy, and building culture and teams. They might have a passing knowledge or interest in recruiting, but are typically most focused on HR and people strategy.

Pros:

• Experience managing dynamic people programs at a growing startup.
• Knowledge of best-in-class and emerging HR-tech. Experience selecting these types of tools in the past.
• Aptitude for developing manager training, onboarding programs, DEI initiatives, custom performance reviews, etc.

Cons:

• Generally, not focused on recruiting and may or may not have participated in executive headcount planning meetings in the past.
• Can bring tactical knowledge and bridge the HR gap for rapidly growing companies, but they usually don't have deep enough experience leading teams to oversee both recruiting and HR teams.

Best For:

Companies that have complex HR needs - remote, distributed, sales-heavy. Best paired with an experienced recruiter as a peer.

VP of People

Description:

An experienced HR leader who has managed HR and recruiting teams in the past. Ideal candidates will have worked at a startup at some point, but will also have worked at several large companies. Ideal candidates will also have helped to start and scale remote, distributed, and/ or global offices.

Pros:

• Experienced leaders who have seen a variety of iterations of company-building.
• Will have the ability to oversee all people functions - both HR and Recruiting
• Experience building complex people programs - custom manager training, remote onboarding, multi-year compensation plans, etc.
• Will have experience working closely with the C-Suite on roadmapping and strategy.

Cons:

• Generally, have not been hands-on with managing tactical HR operations in a long time.
• Will want to come into an existing team and will want to continue to build it. Will be unhappy in transactional roles.
• Will want to be part of the executive team and participate in all strategy meetings (this is actually a great thing, but be prepared to give this person the ability to influence decisions).
• Will want to oversee recruiting in addition to HR.

Best For:

Companies that have an existing people team, are rapidly scaling, and need to build out their recruiting, HR, and people strategies.

Interviewing an HR Leader

Goal:

• Understand their past company experience - specifically focus on size of company, complexity of HR and people initiatives, and ability to manage teams.
• Determine their aptitude and desire to work within this role. These roles are generally all-consuming and exhausting.
• You are looking for someone who has experience managing through difficult situations and overseeing long-term programs.

Process:

• Develop an interview process that mirrors the common skillsets required by the job.
• People leaders should interact with a cross-functional set of the team - hiring managers, team members, executives, etc.
• Phone Screen - 45 min-1 hour with the hiring manager.
• Onsite Interviews - 4 total interviews (1 hour each) with team members.

Common Mistakes:

• Not understanding candidate motivations- they need both the skillset AND the desire to get really hands-on. Watch out for people that have moved between companies every year. These roles are hard and HR leader attrition can be hard on company morale.
• Over indexing on historical questions-  ie. only asking about past companies and experience vs. how they would build out programs for your company. Make sure to explore why past decisions were made and how the candidate would institute programs and plans at your company.

Interview Topics:

Use situational/behavioral interview questions to assess their skill set. Mirror the actual role as closely as possible.

• HR Operations: Gauge candidate's ability to manage, oversee, and scale HR operations - payroll, benefit, compliance, onboarding, etc.
• Culture & Programs: What programs has the candidate instituted at their current company to increase employee satisfaction, productivity, and tenure.
• Team Building: What experience does the candidate have opening new offices or building remote teams? What type of training programs have they instituted for managers and leaders?
• Strategy & Metrics: Can the candidate make the executive team and company smarter about HR strategy? Great HR leaders should use metrics to drive decisions.

Example Interview Questions

Recruiter Interview Questions

• Assess Motivations: What do you not have today that you need in your next role?
• Scope of Role: Tell me about the scope of your role and your most important contributions.
• Sourcing: Tell me about your sourcing process.
• Sourcing: Where do you find candidates?
• Sourcing: What is the breakdown of your pipeline (% sourced, inbound, agencies, etc.)?
• Company Pitch: What can you tell me about your business, and how recruiting is a key driver to your success.
• Company Pitch: How is your company differentiated?
• Company Pitch: What is your current company's long term vision?
• Identifying & Engaging: Walk me through your typical new role kickoff meeting.
• Identifying & Engaging: How do you build a candidate engagement strategy?
• Interviewing & Qualifying: Walk me through your current interview process? What works about it and what would you change?
• Interviewing & Qualifying: How have you trained teams to interview more effectively? What framework did you use?
• Closing Candidates: Walk me through a recent, difficult offer you made and how you were able to close the candidate.
• Closing Candidates: Tell me how you talk about the compensation, value of equity and your strategy for closing candidates.
• Tools & Systems: What tools have you used that have made you successful?
• Tools & Systems: If you had to pick just 1 tool to get you started here, what would it be?
• Leadership: Tell me about your leadership style.
• Leadership: What was the team structure?
• Leadership: How involved have you been in interviewing & training new recruiters?
• Strategic Impact & Metrics: How have you shaped your company’s recruiting strategy?
• Strategic Impact & Metrics: How have you used data to inform your decisions?
• Strategic Impact & Metrics: Walk me through your impact on headcount planning and organizational design (only for Hybrid candidates).

HR Interview Questions

• Assess Motivations: What do you not have today that you need in your next role?
• Scope of Role: Explain your role and the most impactful initiatives you have lead.
• Scope of Role: How hands on are you with HR operations?
• Scope of Role: How have you contributed to org design & workforce planning?
• HR Operations: Who manages day-to-day HR operations?
• HR Operations: What is your strategy for scaling the management of payroll, benefits, & compliance across a rapidly growing organization?
• Remote Work & Distributed Teams: Tell me about your company's philosophy and current structure around remote work.
• Remote Work & Distributed Teams: Tell me about some of the key factors that you've found make remote or distributed teams successful.
• Culture & DEI: How is your company's culture unique?
• Culture & DEI: What are some strategic programs you have implemented to build company culture?‍
• Culture & DEI: What is your company's philosophy about DEI? What strategic initiatives have you implemented around this?
• Performance & Manager Training: What did the performance review process look like when you first joined the company? What does it look like today?
• Performance & Manager Training: Tell me more about your company's manager training programs. Who runs them?‍
• Adversity: What are some of the most difficult challenges you've encountered over the past 18 months? How did you overcome them?
• Leadership: Tell me about your leadership philosophy.
• Leadership: What team structure would you implement to achieve our goal of X?
• Leadership: How do employees connect with your vision?
• Strategic Impact & Metrics: How is HR a key driver in the success of your business?
• Strategic Impact & Metrics: How have you used data to inform your decisions?
• Strategic Impact & Metrics: Where does the company HR strategy come from? How are decisions made?

The VP of Finance will serve as a key member of the leadership team with responsibility over all aspects of the finance department and operations. This is a high visibility role that requires strong communication with cross-functional partners across the business.

When hiring, look for strategic and analytical insight, at all levels of the organization, and someone who can help transform the team, product offerings, and the company.

Hiring Scorecard

Experience

• Proven senior finance executive with a successful track record serving as a finance leader within relevant companies that have successfully grown from early stage to broad commercial success. Relevant companies could exist within Cloud Native, Devops, Analytics/Data, Open Source ecosystems.  
• Leader & mentor. Has built, scaled, and managed best-in-class finance organizations.
• Excellent FP&A abilities with a strong strategic mind. Doesn’t just think about the numbers but more broadly understands how a finance leader should help support business decisions through financial modeling, pricing, etc. Can clearly serve as a strong business partner to the senior team & CEO.  
• Comprehensive knowledge and successful experience in fundraising, capital markets, working with potential and existing investors, etc.  
• Key personal traits: Passionate, Mission Driven, Thorough, Intelligent, Strategic, Forward-thinking, Tactical, Collaborative. Leads by example; a positive voice in the Company.

Accountability

Leader/ Builder

• Act as an internal and external voice of the company relating to financial operations.
• Build all internal infrastructure to effectively oversee fiscal activities including budgeting, forecasting, reporting, auditing, financial systems, etc.
• Optimize and manage processes, reporting mechanisms, dashboards, etc., to help the Company make informed business decisions.

Operational/Knowledgeable

• Develop strong operational intelligence to drive valuable insights for financial, cost, and expenditure management.
• Single point of contact for the Company and Board relating to all financial questions.
• Has the intellectual ability to quickly understand the nuances & complexities of our specific business model.

Business Partner

• Serves as the key strategic financial partner to Jack.
• Partner with the executive leadership team to help shape the Company’s profitability and direction as we strive to achieve growth from current state to $XXM over the next 3 years.

Communicator

• Honest and straightforward communicator who projects confidence and instills trust across every level of the organization and all external parties.
• Comfortable in giving and receiving feedback, both positive but more importantly, constructive criticism.  
• Brings out the best in themselves and those around them.

Example Job Description

VP Finance

About the Role

COMPANY  is looking for a VP of Finance who has experience building and running a financial team and can take our $XXM company to the next level.

The VP of Finance will serve as a key member of our leadership team with responsibility over all aspects of our finance department and operations. This is a high visibility role that requires strong communication with cross-functional partners across the business. We value strategic and analytical insight, at all levels of the organization, and will depend on your work to help transform our team, product offerings, and the company.

About COMPANY

What you will do

• Drive COMPANY ’s strategic financial planning; prepare budgets by establishing schedules; collecting, analyzing, and consolidating financial data; forecasting revenue and expenses, and recommending plans
• Prepare reliable current and forecasting reports
• Recommend investment strategies by considering cash and liquidity risks
• Control and evaluate COMPANY ’s fundraising plans and capital structure
• Ensure cash flow is appropriate for our operations
• Oversee preparation and delivery of annual, quarterly, and monthly financial statements and related analyses to the management team, investors and Board of Directors
• Review daily/weekly/monthly sales performance, highlighting material variances to expectation and resulting actions required. This includes defining, refining, and interpreting the financial impact of KPIs
• Oversee and optimize all aspects of finance operations
• Develop and maintain a high performing finance organization by hiring, training, mentoring, and retaining top talent
• Update and implement all necessary business policies, accounting practices, and financial controls

What Will Set You Up For Success

• Proven experience as a senior finance officer
• Experience working at a high-growth start up, preferably with a Cloud native organization
• Relishes the ten thousand foot view as well as rolling up sleeves to see the five-foot view
• Excellent knowledge of data analysis and forecasting methods
• In-depth knowledge of corporate financial policy, law, and risk management practices
• Comfortable with ambiguity; strategic thinking and problem solving
• Excellent communication skills
• A track record of close partnership with senior leaders of an organization, influencing business decisions and strategy
• Developing high performing teams, fostering collaboration, and creating a learning culture to stay ahead of the growth curve