Director, People & Culture Jobs

Today, 60 million Americans work independently, and that trend is only accelerating. But benefits are tightly coupled with full-time, W2-based jobs. As a result, the millions of Americans who work independently are excluded from that financial safety net.
Stride is the world’s first benefits platform built specifically for contractors, part-timers, and the self-employed. We provide them all the same benefits you’d expect from a W2 job, like insurance, tax support, and discounts on products and services. In fact, since launching in 2014, Stride has helped over 3.5 million Americans save over $4 billion on their benefits and taxes.
We’re partnered with the top employers of non-benefited workers, including DoorDash, Uber, Postmates, MasterCard, Amazon, Aon, and Willis Towers Watson. We’re backed with over $86 million in capital by Venrock, New Enterprise Associates, Fidelity’s F-Prime Capital Partners, King River Capital, Mastercard, and Allstate.
And we’re growing! While we started off exclusively serving non-benefited workers, other companies in our space started knocking on our door to tailor our platform for their customers. Now we need outstanding people (like you!) to help us reach our mission and improve access to affordable benefits for all.
Cash Compensation Range: $204,000 - $227,000 + equity
We are seeking a Director, People & Culture to own the entirety of the Strider employee experience, from when a candidate first accepts their offer to join Stride, through to their last day with the company (and beyond that as a Stride Alumni!) Stride has committed to being a remote first organization, which has allowed for work from home flexibility, but has also come with a spate of new and unprecedented challenges - from having increasingly blurry boundaries between “work” and “life,” to building supportive and human relationships in a fully remote world. It is in this context that we’re looking for our Head of People.
You’ll partner closely with our Head of Talent Acquisition and our executive team to implement creative and new ways of thinking through the People-related challenges of the remote-first experience for our teammates. You love to bring creativity to your work to develop a world class, mission and values-driven culture, as well as teaching others and helping your team succeed.
Here’s an example timeline of your first year at Stride:
Within 1 month you’ll…

• Dive into our existing people processes - performance management, compensation philosophy, and other core policies and practices
• Learn about our core values, mission, vision, and company goals
• Meet your new teammates, learn what they do and what makes Stride a special place to work
• Meet the executive team and leaders across the organization, and begin building strong relationships with them
• Begin developing our People strategy that meets both the growth needs of our business and the strategic goals of the Talent function
• Identify gaps in existing processes that need to be addressed, and a relative prioritization to enrich our employee experience

Within 3 months you’ll…

• Establish KPIs that measure the success of People efforts across the organization
• Take a deep dive into the performance management process, understanding how we provide development opportunities to our team
• Review all dimensions of our compensation philosophy and practices to ensure alignment with core principles, and fairness and equity in their implementation
• Be introduced to a mentor / advisor in your field who can help further your career and shortcut some of the challenges you face in your job
• Overhaul our people-related systems to meet the needs of your strategy, and manage all day-to-day employee relations issues

Within 6-12 months you’ll…

• Feel excited to develop a growth plan for your next 6-12 months at Stride, and looking forward to growing your capabilities and furthering your career!
• Overhauled our performance management process to provide a more data driven and robust process
• Develop a plan to support managers with training and development, to enable more effective feedback and development across all levels of the organization
• Have implemented a robust and scalable strategy for driving personal performance and career development across the organization
• Be a valued and sought-after leader in our company, someone both leadership and your teammates trust to deliver on goals, provide sound counsel on organizational design, and contribute effectively to company strategy
• Train the organization on how to effectively partner with People to yield the best outcomes, gaining buy-in and commitment across the organization

Helpful Information
This resource will help explain Stride’s Compensation Philosophy and compensation practices, and will answer some common questions you might have.
Stride’s Compensation Philosophy utilizes a National Payscale, which is designed to fairly and equitably pay employees based on their performance and impact regardless of geographic location. For employees in the United States, our National Payscale leverages San Francisco Bay Area market data to determine our compensation bands for cash, commissions, or bonus (if applicable) and equity.
Unless otherwise noted, the cash compensation above is the total salary and does not include a bonus. In addition to cash compensation, all full-time Striders will be given stock options to participate in Stride’s equity incentive program. We want all Striders to be an owner of the company, value that ownership, and be able to participate in any future positive outcomes for the company.
Individual compensation packages are based on a few different factors unique to each candidate, including their skills, experience, qualifications, and other job-related reasons. Our compensation ranges are designed to be competitive, equitable, and growth-oriented.
We know that benefits are also an important piece of your total compensation package. To learn more about what’s included in total compensation, check out some of the benefits and perks Stride offers to all US-based employees.
At Stride, we believe in compensating Striders in ways that are true to their value in the marketplace, that inspire and motivate the team to execute our vision, that shape behavior toward productively building and sustaining Stride's culture, and that support the risks and rewards of a fast-growing technology company.
We know the confidence gap and imposter syndrome are a real thing. This can get in the way of meeting incredible candidates, so please don’t hesitate to apply — we’d love to hear from you!
If you are interested in learning more about us, you can check us out on- Built In, The Muse, Stride in the News, and Additional Press.
Stride is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.