Training Specialist
Posted on Indeed on Apr 08, 2021

At Side, we believe everyone should own their path.

Side is the only real estate brokerage platform exclusively for the nation’s best agents. Based on its belief that homeownership is a fundamental human right, we provide top-performing real estate agents, teams, and independent brokerages with the best system, support, and service, in order to elevate the experience and results of buyers and sellers.

Led by experienced industry professionals and world-class engineers who develop technology designed to improve agent productivity and enhance the client experience, Side is backed by over $200M in funding from top-tier venture capital firms including Coatue Management, Sapphire Ventures, Trinity Ventures, Matrix Partners, MetaProp, and other real estate investors. Headquartered in San Francisco, Side currently has operations in California, Texas, and Florida, with plans to expand nationwide

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.


The Training Specialist will deliver and integrate enterprise-level software training modules to both internal and external stakeholders at Side. S/he will leverage strong communication and relationship building skills to partner with the Onboarding, Customer Success and Product teams, identify training requirements, craft solutions, and deliver the resulting modules through a variety of means.


    • Provide leadership, technical project coordination, and consultative services; liaise with cross-functional work teams, key stakeholders and subject matter experts at an enterprise level to develop course specifications and gather course content
    • Project manage, develop, and deliver technical process end-user course content and train-the-trainer content for multiple user personas and a variety of levels and roles in instructor-led, virtual, eLearning, and recorded formats
    • Collaborate with Head of Learning & Development to create curriculum with certification paths for customers, both business best practices and technical
    • Deliver projects, content, and training that enable customer success, change management and adoption
    • Manage course content for technical software products and ensure that up-to-date knowledge is conveyed for each release
    • Work with leadership to understand and coordinate onboarding and ongoing training needs for customer-facing employees
    • Continue to evolve training curriculums based on feedback and research
    • Keep up to date on trends and developments in the industry that can better improve the overall program
    • Organize and conduct seminars/trainings for individuals local and in remote locations. Expected travel once it is safe.


    • 5-7+ years of deep experience effectively managing training projects, software-user curriculum design, development, and delivery with a range of customer stakeholders within the Real Estate industry
    • High level of flexibility, creativity and dependability required.
    • Superior business writing and technical writing skills required
    • Ability to deliver technical training to a variety of audiences and adapt delivery as needed is required.
    • Bachelor’s degree with coursework in Communication, Business, Education, Real Estate, or a related field preferred
    • Knowledge and understanding of learning principles and training techniques
    • Proficiency in administering Learning Management Systems (LMS) preferred


    • Competitive salary
    • Stock options
    • Best-in-class benefits, including 100% healthcare coverage (medical, vision and dental)
    • Flexible PTO
    • $1,000/yr for learning and development
    • Pet friendly environment

Side is dedicated to working with the highest skilled people from the most inclusive talent pool feasible. We maintain that diversity in all aspects leads to positive change, solutions and innovation for our customers and career fulfillment for our employees. All qualified individuals are encouraged to apply.

Side uses the E-Verify employment verification program.

Our stewardship of the data of many of our customers means that a background and DRE license check is required to join Side. We will, nonetheless, consider qualified applicants with arrest and conviction records in accord with applicable law, including the San Francisco Fair Chance Ordinance.

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