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Real Estate Technology Brokerage

Sr. Manager / Director of HR Operations

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At Side, we believe everyone should own their path.

As the first company to design an end to end modern brokerage solution, Side is re-imagining the real estate industry from the ground up by combining innovative technology, creative branding expertise, and an experienced leadership team with a mission to empower the world’s leading real estate professionals to own their brand and better serve home buyers and sellers.

In the past three years, with an exceptional team of inSiders, we’ve processed $4B in transactions and raised over $60M in funding from top tier investors like Matrix Partners, Trinity Ventures, Sapphire Ventures, and 8VC.

At Side, you’ll have the opportunity to collaborate and innovate your way to success. Becoming an inSider means that you’ll be empowering business leaders to become business owners, all while forging your own path with like-minded entrepreneurs. Join us at Side and own your career, your impact, and your life.


We’re looking for a strategic and business-oriented HR operations leader who is eager to “roll up their sleeves” and drive innovative processes and insights that will ensure we are building a best in class People team. As the Senior Manager, HR Operations you will oversee our HR Systems and HR Programs and have strategic and operational oversight for systems & data, benefits, immigration, policy, process & compliance.

As the Senior Manager, HR Operations, you will not be satisfied with executing someone else’s playbook or simply writing one, but rather leading a team that will deep dive into existing HR processes and develop innovative improvement ideas for both current challenges and future problems we may encounter.

Success in this role is not just checking the box on a long task list, but getting to the “so what” and directing efforts to make sure we set the right foundation for our People team, partner functions, and ultimately the organization as a whole. The position is based in San Francisco and will report to the Head of TA and People.


  • You will partner closely with HR Business Partners and leadership to ensure that what we do connects the dots back to the needs of the business and employees and isn’t just process for process sake
  • You will be a leader amongst your Recruiting, Finance, Accounting, Legal and IT colleagues to ensure that there is clear communication, handoffs, collaboration and systems and workflow integrations amongst our G&A partner teams
  • You will deliver a comprehensive roadmap for process transformation and strong project and change management to execute against it resulting in automation, standardization, and centralization of HR processes and systems where possible
  • You will ensure compliance with applicable employment regulations and best practices that are highly aligned to meeting the needs of the business and improving the employee experience
  • Oversee the HR Programs and Operations team and the development and management of thoughtful, scalable, HR policies and processes that shape the employee lifecycle and are compliant, efficient, scalable, and reflect Side culture and values
  • Oversee the HR Systems team and the expansion and/or implementation of HR systems (BambooHR, LMS, etc.) ensuring high-quality data, consistent definitions, and reporting and analytics and business insights
  • Maintain knowledge and understanding of regulations, laws and industry best practices to ensure compliance with all applicable international, federal, state, and local employment laws
  • Partner with benefits brokers/vendors to review, update and administer benefits policies and programs, ensuring programs are competitive, compliant and scalable
  • Lead our immigration policies and programs, in partnership with legal counsel and recruiting
  • Partner with IT to create and oversee a technology roadmap across HR that will help provide a simple, scalable, automated and seamless experience throughout the employee lifecycle
  • Analyze data to track and report on the performance of our HR team against our internal and external goals and establish working norms and target SLAs / KPIs for the HR team


  • 8+ years of experience in HR/People Operations, preferably in a tech start-up environment
  • Experience managing people, preferably 5+ years
  • Proven track record of implementing and scaling people processes, operations, and systems
  • Advanced project management skills - ability to handle multiple projects at once and competing priorities. Organized, extremely detail-oriented and execution-focused a must!
  • Advanced knowledge of HR compliance, Federal and multi-state employment laws, best practices, and industry standards in a variety of HR processes including Leave of Absence, Workers Compensation, I-9 processing, and employee onboarding/offboarding
  • Employee Relations and management coaching experience helpful
  • Comfort and familiarity with HRIS (BambooHR preferred), LMS, Performance Management, project management software, and customer service/ticketing software
  • A flexible leader who can operate at a strategic level but also perform operational/tactical responsibilities
  • Superior communication skills and are comfortable talking to a wide range of people across all levels of the organization. Experience building relationships with employees, managers, and other peers
  • BA/BS degree required. Additional HR certifications and degrees are a plus but not required
  • Proven ability to take initiative, think on your feet, and make thoughtful fast decisions


  • Competitive salary
  • Equity options
  • Best-in-class benefits, including 100% healthcare coverage (medical, vision and dental)
  • Flexible PTO
  • Learning and development credit
  • Pet-friendly environment

Side at a glance

Real Estate Technology Brokerage

Side focuses on Real Estate and Website. Their company has offices in San Francisco. They have a mid-size team that's between 51-200 employees. To date, Side has raised $35M of funding; their latest round was closed on November 2019.

You can view their website at https://www.sideinc.com/ or find them on Twitter, Facebook, and LinkedIn.

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