Head of People

Stride Benefits

United States Remote

Full time

People Operations / Mid/Senior level

Mar 23

This job is no longer accepting applications.

We are seeking a Head of People 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…

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

Within 3 months you’ll…

  • Take a deep dive into the performance management process, understanding how we provide development opportunities to our team
  • 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
  • Review all dimensions of our compensation philosophy and practices to ensure alignment with core principles, and fairness and equity in their implementation
  • Establish KPIs that measure the success of People efforts across the organization

Within 6-12 months you’ll…

  • Have implemented a robust and scalable strategy for driving personal performance and career development across the organization
  • Develop a plan to support managers with training and development, to enable more effective feedback and development across all levels of the organization
  • Overhauled our performance management process to provide a more data driven and robust process
  • Train the organization on how to effectively partner with People to yield the best outcomes, gaining buy-in and commitment 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
  • 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!

We’re excited that you’re looking to Stride for your next employment opportunity. We take that decision seriously and want to provide you with an opportunity where you can grow meaningfully in your career. We support a flexible work structure with headquarters in San Francisco, along with the option to establish your own fully remote office. We look forward to hearing from you!

About Stride

Our mission at Stride is to build the world’s first benefits platform designed for the independent workforce, and we’re looking for amazing people (like you!) to help us do it. Today, 60 million Americans are working independently - in gig work or otherwise - and that trend is only accelerating. For many Americans, benefits are tightly coupled with their full-time, W2-based jobs where they receive group-based benefits. For the 60M Americans working independently and outside of that safety net, they need to find medical coverage on their own. That’s where Stride comes in. We make it incredibly easy and intuitive to find the best and most affordable health care coverage for independent workers and their families, including dental, vision, life, accident, and disability coverage. All the same benefits you’d expect from a W2 employer, but built specifically for independent workers. 

Stride partners with the world’s leading platforms and employers of non-benefited workers including DoorDash, Uber, Postmates, MasterCard, Amazon, Aon, Keller Williams and others to help them provide their workers access to affordable health and wealth benefits and perks. The company is backed by Venrock, New Enterprise Associates, and F-Prime Capital Partners.

Notable Press

Born Digital: "Mastercard, Stride Partner for Gig Worker Benefits"

Fast Company: "Ahead of its IPO, Postmates starts offering no-strings perks for couriers"

The New York Times: "It’s Not Just You: Picking a Health Insurance Plan Is Really Hard"

Business Insider: "Stride Health Secures $23.5 Million in Series B Funding"

Perks & Benefits

In addition to the satisfaction you’ll receive from helping Americans obtain a financial safety net regardless of their employment, full time employees are eligible for the following benefits and perks:

  • Competitive salary: Stride is dedicated to fair and equitable compensation. At Stride, our compensation philosophy is based on a National Pay model with all salary bands mapping back to San Francisco bands. This means that you can live anywhere in the U.S. without having to worry about location-based salary adjustments.
  • Health, Dental, and Vision plans with employees covered at 100% and dependents covered at 70%
  • 12 weeks of paid bonding leave for birthing and non-birthing parents, inclusive of adoption and fostering
  • Employer paid One Medical membership
  • Flexible paid time off
  • Quarterly company-wide mental health days
  • 2 weeks of company-wide end-of-year refresh time
  • 401k management platform (we do not currently match)
  • Equity Package
  • Employee Assistance Program
  • Company-wide in-person retreats, as conditions permit
  • $100/month work from home stipend
  • $75/month wellness stipend
  • $1,000/year learning and development budget

We’re excited that you’re looking to Stride for your next employment opportunity! We take that decision seriously and want to provide you with an opportunity where you can grow meaningfully in your career. While we’re reviewing your application, you can read some of our press coverage here - https://www.stridebenefits.com/press

Candidates must be legally eligible to work in the United States. Stride is an equal opportunity employer.

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Stride Benefits

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