A SaaS Founder’s Guide to: Hiring a Head of People

A SaaS Founder’s Guide to:
Hiring a Head of People

This is Part 3 of Mainsail’s How-to-Hire Series: A SaaS Founder’s Guide to Building Out Your Leadership Team. Read why we put together this resource for growing SaaS business and how to navigate it here.

Within the leadership suite of a growing SaaS company, the Head of People role is one of the most impactful hires you can make. This individual will be a strategic partner to the CEO — helping set the company vision and drive company culture — as well as a hands-on operator, responsible for creating and disseminating your business’s processes for recruiting, onboarding, management and growth.

With the right hire, a Head of People can become a backbone of your organization, shaping culture, defining the employee experience and enabling your organization to scale.

Drawing from our experiences, this is Mainsail’s guide for when to hire a Head of People, what to look for in a candidate and how to structure the position for success.

When to hire a Head of People

The short answer to, “When should I hire a Head of People?” is simple: sooner than you think.

We often see companies prioritize hiring heads of sales, finance or product ahead of a dedicated people leader, as those roles tend to have clearer short-term ROI. However, at an early growth stage, your people are just as critical an asset as your intellectual property. With a strong Head of People in place, you can ensure your team is well structured and properly supported, enabling scalable growth.

Specifically, we suggest making this hire once you reach 40-50 full time employees. (As a guideline, plan to add another HR team member for every additional 50 full-time employees.)

Here are a few signs you’re ready to hire a Head of People:

The CEO is overloaded with HR minutia. Early on, the CEO acts as the Head of HR, making all people-related decisions. As the company grows, it becomes increasingly impractical for the CEO to manage HR and run the company. A trusted Head of People can take on these responsibilities, freeing up space for the CEO to focus on growth.
Your hiring processes are immature. In the beginning, hiring “familiar” candidates—those from existing networks—is common and often effective. But as you scale, this approach limits growth and can lead to an insular culture with underqualified hires. To scale, you are going to need professional hiring tools like position specs and interview scorecards, managed by a seasoned leader.
Your company culture is undefined. If employees can’t articulate your company values, or if you notice inconsistencies in how your managers handle challenges, it’s a sign you need a cohesive cultural framework.
You’re starting to see an impact on employee retention. Without standardized hiring and onboarding processes, managers will create their own systems, resulting in inconsistent evaluation criteria, training programs and career progression paths. Eventually, this can lead to an increase in mis-hires and a decrease in employee retention.

A Head of People can make a massive impact in your organization by bringing professionalism and structure to your people processes. They can elevate the quality of new hires, improve retention, strengthen career paths and fortify company culture — all while giving the CEO back time they need to run the company.

Hire the right level leader and structure the position

This role is more than a recruiter, an HR manager or even an HR generalist. While your Head of People must have a solid grasp on the tactical mechanisms of HR, their true value lies in building scalable people programs and being a strategic leader.

For this reason, we suggest hiring a VP-level leader who can serve as a trusted partner to the CEO. Given the significance of the decisions they will be supporting, this person needs to have “been-there-done-that” with enough seniority and wisdom to navigate complex scenarios with both emotional and intellectual intelligence.

Look for candidates who have experience at the scale you are targeting to reach. For example, if your company is growing from 50 to 300 employees, your Head of People should have successfully managed similar growth and built scalable systems in a comparable environment. While not required, familiarity with the software industry or M&A experience can be valuable as well.

In terms of leadership structure, have your Head of People report directly to the CEO. This sends a clear signal that you view people management as a strategic function, not just a cost center. When treated as a strategic partner, your Head of People can challenge workforce planning assumptions and contribute to discussions about organizational design. In addition, by reporting to the CEO, the Head of People can be sure that people strategy is integrated with the overall goals of the business.

Characteristics to look for and how to evaluate them

A great Head of People can balance strategic vision with tactical execution, moving seamlessly between long-term planning and day-to-day implementation. In interviews, pay close attention to their ability to pivot between these two worlds, as versatility is crucial for success.

Beyond that, we suggest you look for these key traits in your interviews:

Business acumen. Do they have a sophisticated understanding of business metrics and can they speak the language of the executive team? This person is going to need to collaborate with the CEO daily, so they need to hold their own both in terms of business planning and human capital strategies.
Data-driven. How have they previously used data — such as employee Net Promoter Scores or engagement surveys — to measure and improve employee satisfaction? Can they speak to the data fluently and do they demonstrate an understanding of how to use data to implement and measure change?
Process-oriented. Assess their experience creating repeatable, scalable processes for hiring, onboarding and performance management. Ask for specific examples where they implemented systems that were successfully adopted across the organization.
Culture keeper. Ask them to tell you about culture-building initiatives they’ve led in the past, and how they measured success. Can they foster a high-performance culture? Will they vibe well with your CEO?
Even-keeled problem solver. People management is rife with complex challenges. Does this person demonstrate adaptability, creativity and resilience, even in high-pressure situations? Look for someone with a calm, even demeanor who can navigate tricky situations with grace and confidence, knowing they will be working at all levels of the organization.

It goes without saying that this person also needs to have mastered the core competencies of HR, including recruiting, talent development, performance management, benefits/compensation, employee relations and conflict resolution. Be sure to assess for these basics in the interview by (for example) asking how they set goals, track progress and reward achievements.

Roadmap for the first 18 months

In the first 18 months, your Head of People is going to be busy building systems and supporting the company culture and vision. Here are a few specific things they should be able to speak to:

Revisit company values, culture and mission. Assess the company’s mission statement and core values. Ensure they are clearly articulated and woven into the organization’s processes, communications and culture.
Conduct an audit of existing HR processes and systems to identify gaps, inefficiencies and areas for improvement across all people operations, from recruitment to offboarding.
Create or refine key processes (hiring, onboarding, performance reviews). Standardizing these processes ensures consistency, improves efficiency and enhances the employee experience across all departments.
Implement or optimize core HR infrastructure and tech tools to streamline operations and improve data-driven decision-making.
Develop a strategic HR roadmap aligned with company goals. This should outline key initiatives, timelines and expected outcomes, serving as a guide for the contribution to overall business objectives.
Establish metrics for measuring employee engagement and satisfaction. Regular pulse surveys or annual engagement surveys can provide data-driven insights into company culture and areas that need attention.

Charting the course for people excellence

A great Head of People can have a meaningful impact on the very heart of your organization: your employees. A successful hire, followed by a successful first 18 months, can lay the groundwork for long-term organizational health for your entire workforce.

Approach this hire with discernment and try to find a thoughtful visionary who can help craft your people strategy, challenge your assumptions, and act as a catalyst for employee engagement so your talent and business goals align as you grow.

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