People Operations Technical Assistant

About the Role

🚀 Want to join a team of A players in an exciting, high-growth, entrepreneurial environment?

We’re a small team solving big problems in the property management industry. Bootstrapped since 2013, we're passionate about helping small businesses simplify growth and streamline operations, providing the leading CRM in our space.

The long version of our story: Back when web 2.0 was a thing (get off my lawn!) LeadSimple’s founders started a lead generation business connecting landlords with property management companies. Witnessing the challenges lead buyers had closing deals led into a natural segue to build out an industry-specific CRM which became the de-facto industry standard. Fast forward to 2020 when we released a process/workflow suite to move from the sales side of our clients business into the heart of day-to-day operations. The market was hungry and responded aggressively to the new direction, which led us to double down with growth and additional product expansion.

Expectations for your first 90 days:

  • Own technical aspect of onboarding checklist. Participate in the orientation session, “Tech Teaching” to be of any needed assistance for new team members when setting up new accounts.
  • Independently own the creation and updating of weekly documentation and data for POPs and the Leadership team.
  • Complete full audit of the Zapier processes and suggest new uses for further automation.
  • Complete full audit of application process within LeadSimple and identify additional ways to further automate the process to reduce screening labor.

A day in the life of…

  • Monitors the output and processes of the People Operations department to identify areas that technology could solve, speed up, make more effective, and/or automate.
  • Works with the People Operations Coordinator to implement new tech options and troubleshoot all current pieces.
  • Efficiently generates documentation creation for the company and the department.
  • Identifies gaps and generates necessary suggestions to make workflow more efficient within the department, as well as LeadSimple across multiple platforms.
  • Schedules tasks, meetings, and to-do's on departmental task management software when needed by the department.
  • Conducts technical research and navigates platforms to enhance daily tasks and productivity for departments.
  • Acts as an internal IT provider of sorts, when needed, for new hires and current team members.
  • Train new hires and current team members on best practices for company technology platforms.
  • Troubleshoots and Identifies/Escalates Bugs


  • Monthly Friday Free Day
  • Company Holidays
  • Paid Time Off (in addition to the above)
  • Monthly Healthcare Allowance
  • Yearly Vacation Allowance
  • Fun and outcome driven work environment with a smart, hard working team
  • Location independence
  • Mission driven company and values-based culture

Please only apply if you:

  • Embrace new technology and can teach others effectively
  • Learn fast
  • Communicate crisply
  • Proactively seek solutions using technology
  • Stay calm under pressure
  • Own your outcomes
  • Have high standards for yourself and others
  • Embody emotional maturity
  • Bring an optimistic “can do” attitude
  • Supply your own internet and smartphone
  • Have 2+ years life experience with technology based problem solving (doesn’t need to be traditional work experience)

We have an amazing team of A Players and we’re ready to add more! Selected candidates might have written assessments and multiple interviews with different people. We’ll do whatever it takes to get the right person in the right seat.

If you think you would thrive in the above environment and make an impact for our customers, we’d love to talk to you!

In summary...

You can do it in an office

You can do it from home

We really don’t care

As long as it’s known 👇

What matters is this…

When the chips are down

And your back is against the wall

Can we count on you to make the right call?

Judgment, intuition, or care by another name

We call it “Owning The Outcome” - because it really is the whole game

Have the customers back, and they will treat you the same

If you can do that

Then we’re birds of the same feather

So come join our team and we’ll make music together.

Working at LeadSimple

LeadSimple is a B2B vertical SaaS company selling to SMB’s in the residential property management industry. Bootstrapped and profitable, we hit a new level of product market fit in 2022 resulting in +85% YOY growth. We’re small (30+ people), fully remote, kinda nerdy and really love SMB problems, real estate and punching above our weight class. If this sounds like your vibe - give us a shout!

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