Senior Customer Success Rep. - "Pilot"

Mid / Senior Positions Open

November 2, 2020

Working at LeadSimple

Are you looking for fully remote, fast paced, fun, and meaningful work?

LeadSimple is a fully remote company working in the property management space. We help entrepreneurs harness new technology to streamline their businesses. We believe in taming small business chaos. We don’t just provide a software product, we aggressively work to “own the outcome” and make our clients successful.

Role Description

🚀 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.

Fully remote and fully engaged, you can read more about our company culture here.

Senior Customer Success Representative

The Senior CSR, or “Pilot” as we call it internally, helps customers turn aspirations into reality by translating their business goals into a fully implemented solution inside of LeadSimple. They’ve mastered both the product and the art of navigating priorities and challenges with business owners. From conception to execution to team roll out they hold the customers hand each step of the way.


  • Consultative - You know how to translate customer challenges into an elegant solution - even when that means pushing past surface feedback and uncovering deeper needs.
  • Owns The Outcome - We don’t leave people hanging, we climb down the cliff face, pull them up and hand them a flask and healthy snack when we get to the top.
  • Comfortable with ambiguity - Sometimes you won’t know the answer. Sometimes there will be a bug you’ve never seen and on rare occasions, in essence the fecal matter will hit the oscillating device. Do you panic or hide? OR can you project confidence and hold space for people while answers are still forthcoming?
  • Attention to detail - You’re down to learn the nitty gritty of the product knowing that our customers run the business on this software and small errors can be costly for them.
  • Mindset - A balance of coachability and confidence - think MJ pre bulls championship run.

Key Outcomes:

  • Project discovery process results in well defined and useful project scope
  • Project implementations end with high levels of customer satisfaction and long term account engagement
  • Personal and team capacity is managed to be able to handle process proposal target each month
  • Employ highly consultative style to discover additional unmet needs and new use cases that generate additional implementation projects

Benefits and Perks:

  • Early Off Fridays (every other Friday afternoon off)
  • 3 Weeks Paid Vacation (in addition to the above, but includes local bank holidays)
  • Healthcare Allowance
  • Vacation Allowance
  • Fun and relaxed work environment with smart, caring people
  • Location Independence
  • Mission driven company and values-based culture

Please only apply if you can:

  • Embrace new technology 
  • Learn fast
  • Communicate crisply
  • Be proactive
  • Own the outcome

Selected candidates will be invited to a 30-minute call, followed by a 90-minute structured interview.

If you enjoy owning the outcome for customers, influencing product, and honing your craft, 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?

Judgement, 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.

How to Apply

If you believe you fit the description above and this type of career and working environment would be suited to you, contact us for more information on the application process and how to initiate it. We're looking forward to hearing from you!