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Head of People Ops & Insights

Los Angeles, CA +5

🚀 Whatnot

Whatnot is a livestream shopping platform and marketplace backed by Andreessen Horowitz, Y Combinator, and CapitalG. We’re building the future of ecommerce, bringing together community, shopping and entertainment. We are committed to our values, and as a remote-first team, we operate out of hubs within the US, Canada, UK, and Germany today.

We’re innovating in the fast-paced world of live auctions in categories including sports, fashion, video games, and streetwear. The platform couples rigorous seller vetting with a focus on community to create a welcoming space for buyers and sellers to share their passions with others.

And, we’re growing. Whatnot has been the fastest growing marketplace in the US over the past two years and we’re hiring forward-thinking problem solvers across all functional areas.

About the People Team

The purpose of the Whatnot People Team is to make Whatnot an inclusive, remote-first destination where all employees feel respected, valued, and empowered to do their best work. We accomplish this goal by hiring top talent, investing in growth and development, championing diversity, and recognizing and rewarding impact at Whatnot.

💻 Role

We’re looking for an experienced and creative leader, with keen business acumen, to join our growing People team at Whatnot! As the Head of People Operations, Technology & Insights, you will report to the Chief People Officer and be a key member of the People Leadership team. Our People Operations function will be critical to building a high-performing culture, attracting and retaining the excellent people we will need in order to deploy Whatnot’s mission at scale. 

As our first Head of People Operations, Technology & Insights, you will have a proven track record of leading teams to success, a passion for technology, and a commitment to building a great workplace culture. You will be responsible for leading, shaping, and scaling all human resources systems and processes.

These systems and processes are essential components of Whatnot’s operating system. Getting them right will require you to be a strategic partner in defining, documenting, and bringing to life our culture of high-performing innovation and delivery.

This will involve building and running the systems, structure, and team needed to independently drive the development and execution of strategic initiatives to continuously improve employee onboarding and offboarding, feedback and decision making systems and insights, technology solutions and operations, compliance, policy and procedure administration, and more. 

We expect you to be our internal subject matter expert on all things “HR.” You have thoroughly studied best practices, but understand that each company and situation is unique. Rather than relying on a rigid playbook, you believe in delivering sensible solutions that are tailored to the specific needs and challenges of Whatnot. Getting things done is in your DNA, and you will execute quickly and excellently.

You understand the importance of building reliable processes enabled by best-in-class technology. Finally, you thrive in a creative, scrappy, and collaborative environment in which the best ideas change the company’s direction on a regular basis.

  • Crisp communicator at all levels both internally and externally
  • 5+ years of experience in people management; experience being a player/coach, and owning some of the hard things with your team
  • An unyielding passion to provide the ultimate employee experience, and serving as a model of Whatnot’s values in the experience of cross functional partners working with the team
  • IPO-to-Public experience a plus 

👋 You

Curious about who thrives at Whatnot? We’ve found that low ego, a growth mindset, and leaning into action and high impact goes a long way here.

  • As leader of this function, you will play a pivotal role in shaping Whatnot’s future and charting the course to drive data-informed decision-making across all People team areas
  • You will lead the team responsible for all things related to our HR systems, analytics, and the operations to support all of Whatnot from overseeing the development and optimization of people technology solutions, to surfacing the insights and analytics to support leaders across the company, to simplifying processes that support managers and employees alike
  • Attract, lead, and inspire a team of leaders and individual contributors who are highly technical, analytical, and operational
  • Sponsor the development and implementation of a comprehensive people systems infrastructure and roadmap, becoming the central owner across various enterprise and productivity tools across the People team
  • Develop and implement a comprehensive people technology strategy that aligns with the organization's Talent and business goals
  • Ensure that People technology systems comply with data privacy and security regulations and maintain the highest standards of data protection
  • Coordinate our teams to deliver scaled programs and projects (e.g. systems implementation, M&A, internationalization) and innovate at speed with a smooth, end-to-end user experience
  • Lead cross functional People projects aimed at improving operational efficiencies and enhancing the employee experience across key user journeys
  • Collaborate with stakeholders across the People team, as well as cross functional partners in Finance, Accounting, Security, IT, and beyond to ensure alignment and optimization of technology and operations efforts across Whatnot

Preferred Qualifications & Leadership Capabilities

  • 10+ years of progressive experience in people operations, consulting, or related areas at innovative companies with outstanding People functions
  • A strong operational background with the ability to leverage technology in building an efficient user experience.
  • Demonstrated experience in taking things from “scrappy” to “scaled” in a high growth, fast paced environment
  • Experience in systems implementation that includes integration across business systems beyond the People team, such as Finance, Corp Eng, and IT
  • Experience with leading large-scale, complex change and transformation
  • Demonstrated expertise in people analytics and the ability to digest data and pull out insights, but also understand where the data comes from and how to optimize systems to support its digestion
  • Experience with influencing and partnering with senior leaders to help drive their people strategy and increase business results


For US-based applicants: $285,000/year to $330,000/year + benefits + stock options

The salary range may be inclusive of several levels that would be applicable to the position. Final salary will be based on a number of factors including, level, relevant prior experience, skills and expertise. This range is only inclusive of base salary, not benefits (more details below) or equity in the form of stock options.

🎁 Benefits

  • Flexible Time off Policy and Company-wide Holidays (including a spring and winter break)
  • Health Insurance options including Medical, Dental, Vision
  • Work From Home Support
  • $1,000 home office setup allowance
  • $150 monthly allowance for cell phone and internet
  • Care benefits
  • $450 monthly allowance on food
  • $500 monthly allowance for wellness
  • $5,000 annual allowance towards Childcare
  • $20,000 lifetime benefit for family planning, such as adoption or fertility expenses
  • Retirement; 401k offering for Traditional and Roth accounts in the US (employer match up to 4% of base salary) and Pension plans internationally
  • Parental Leave
  • 16 weeks of paid parental leave + one month gradual return to work *company leave allowances run concurrently with country leave requirements which take precedence.


Whatnot is proud to be an Equal Opportunity Employer. We value diversity, and we do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, parental status, disability status, or any other status protected by local law. We believe that our work is better and our company culture is improved when we encourage, support, and respect the different skills and experiences represented within our workforce.

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