Executive Hiring: People Leaders

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?

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