6 May 2021

Full-Time Know Your Team: Leadership Trainer/Coach

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Job Description

Headquarters: 100% Remote

URL: https://knowyourteam.com

Dear leadership trainer/coach who cares about furthering your impact on leaders,

If your dream is to help teach managers to become better leaders through a methodology that’s focused on bridging theory and practice, alongside a small team that values freedom, sustainability, and ownership, I’ve got good news for you… we’re hiring a Leadership Trainer/Coach at Know Your Team.

First, a quick introduction.

My name is Claire Lew, and I’m the CEO of Know Your Team. Our company, Know Your Team, is software that gives you the tools, training, and resources to become a better manager. Thousands of managers at companies like Airbnb and Dropbox use our software and attend our trainings every single week.

We were born from Basecamp back in 2014, and have been profitable since Month 1. We’ve been a 100% remote company for the entire time, and purposefully stayed small in headcount, and avoided traditional VC funding to enable us to stay focused on serving our customers to the highest quality. You can read more about our journey so far here. (We’re a bit of weird company, admittedly!)

Above all else, what motivates us at KYT is making progress toward our vision:  A world where bad bosses are the exception, not the norm. Imagine a world where leadership doesn’t have such a high learning curve. A world where anyone, anywhere, can become a better leader – with a little help from us 🙂

We believe if you help managers become better, everything gets better. An organization with better leadership achieves better outcomes and takes better care of its people. Helping people become better leaders might just be one of the most high-leverage ways to help the world.

For our own company, our vision is for KYT to be an independent, remote, profitable company that’s small in headcount but impacting tens of thousands (if not hundreds or even millions!) of managers, for 10 years and beyond. We want KYT to be a place where people come to do the best work of their lives – and continue to do the best work of their lives. Sustainability, and lasting in the long-term is a key part of success, for us.

So what’s the job?


You’ll teach and run our KYT Manager Learning Path trainings – which complement our KYT software platform – for our clients around the world, remotely via Zoom. This includes delivering our 90-minute foundational trainings on topics such as, “Foundations of Leadership,” “Giving and Receiving Feedback,” and “How to Coach and Motivate Your Team.” You’ll facilitate our 60-minute Masterclass and Capstone sessions that are focused on helping managers integrate and apply their learnings to their real-life situations. You’ll conduct thoughtful break-out sessions and answer managers’ questions accurately and clearly, citing useful examples and leadership research.

You’ll coach managers, one-on-one, on their greatest leadership challenges they’re facing via phone and email, for our clients who are enrolled in the 1:1 “office hours” coaching and “unlimited email leadership” components of our Manager Learning Path programs. You’ll ask meaningful questions to help a manager reframe their situation and share frameworks for them to better choose their own path for themselves.

You’ll run our Workshop Live! sessions for our KYT platform subscribers and audience members. These 60 to 120-min. sessions are attended remotely by hundreds of managers from all over the world, and are centered around topics such as, “How to Improve Morale in a Team,” “Best Practices for Remote Communication,” “How to Shift Culture”, and “Leading with Emotional Intelligence.”

You’ll contribute to the research, creation, and learning design of our trainings, helping us improve to include the latest leadership research and the most current learning science practices, and customize our content for each of our clients so there is an optimal mutual fit.

When you’re not preparing, delivering, or improving a KYT training, you’ll work on cross-functional projects that align with your skills and interests. Potential projects could include writing content for our KYT Leadership Guides and our KYT Leadership Blog, engaging with 1,000+ managers in our Watercooler leadership community.

High-level, here’s how you can expect to spend your time in a given week:

  • 70% – Preparing for and executing our training sessions and coaching. Our trainings occur Monday through Friday, from 8am to 5pm PT, and occasionally 6am – 8am PT. You’ll never run more than three training sessions in a single day. 
  • 30% – Working on cross-functional projects that align with your skills/interests that help more managers learn and benefit more from our KYT methodology.

The full-time salary for this role is $120,000 USD, with health benefits, and unlimited vacation. We try to do everything in our power to give you the trust, space and stability to do your best work. This is a full-time role, but we’d bring you on first as a contractor for the first month, to make sure you enjoy working with us and vice versa. And then if it was a good fit, we’d bring you on full-time. 

Together, we’d grow Know Your Team to improve the lives of hundreds of thousands (if not millions!) of managers every day.

Who I am looking for exactly?


I’m looking for an excellent verbal and written communicator. You are clear and precise when unpacking ideas, making the complex feel immediately digestible. Yet, you articulate ideas with warmth, friendliness, and thoughtfulness. To you, it doesn’t matter if you’re speaking or writing to a CEO or an intern:  You take the time and care to communicate what you truly mean, and deeply consider how it may be interpreted by the other person. You know that communication is more than the words themselves, but how your write, verbalize, or portray those words to others. The art of communicating well – both writing and speaking – is something you relish in, and enjoy improving at.

You’re a gifted teacher and coach.  People often seek out your advice and counsel because of your calm, nuanced approach. Nothing is what it seems on the surface, and you’re eager to start from “first principles” before projecting assumptions. You know how to read and interact with an audience – and one-on-one – respecting each person’s viewpoints, experiences, and boundaries, and never condescending. You enjoy being playful and using storytelling in your teaching, as you know how well that holding attention unlocks learning. You ask insightful, open-ended questions, to help people think for themselves – rather than telling them what to think.

You have direct leadership coaching experience and/or leadership experience. You bring case studies, examples, and situations from your own personal experience where leadership frameworks have worked – and not worked. You’ve perhaps even created a few leadership frameworks yourself, that you’re constantly refining to see how they hold true in the world (and you if yourself hold true to them! 🙂 )

Above all, you’re aligned with our methodology and believe in the vision of Know Your Team. You resist being prescriptive and “one-size-fits-all” – instead, you seek data and research, wanting to equip leaders with an array of frameworks for them to choose for themselves. You’ve personally experienced the steep learning curve to good leadership – and want to be helping as many managers as possible not suffer the same trials and pains that you did.

I’d love to hear from you. Here’s how you can apply:


If you’re interested in working together, apply here by May 20th, 2021, with the following information…
  • Please introduce yourself to us as a potential fellow KYT team member. What’s your story? 🙂 Writing is one of the top skills we prioritize as a company – particularly as a leadership trainer/coach. Feel free to take your time (we won’t begin reviewing applications until after the application due date of Thursday, May 20th.) Do take license to be creative, and include answers to these questions…
    • What made you want to apply for this role? Why do you think you’d be excited to work at KYT?
    • How would you describe your approach to teaching and coaching others?
    • Could you describe a time where you had to teach yourself a new skill in order to accomplish a job or project?
    • How do you define what it means to be an “effective leader”?
    • Please share a time when someone (i.e., a colleague, a client) came to you for leadership advice. What was the situation? What advice did you share with them? What was the outcome?
  • Please read this blog post, and then teach one aspect of the blog post content in a 2-minute video. Please feel free to choose any aspect of the blog post to teach – there is no “right” part to choose. We’re merely interested in your style, tone, and approach to teaching.  (The video can simply be filmed on a cellphone or laptop camera – nothing fancy. And, no need to create any accompanying slides + presentation – just a video would be great.)
We’re seeking a full-time leadership trainer/coach who would be available to run trainings anytime Monday – Friday 8am – 5pm PT, with the ability to run trainings during 6am – 8am PT, as necessary. Please include your location, and if you’d be able to fully cover those working hours.
We are a 100% remote company (and have been for the past 7 years), so location is not as important as mutual fit. That being said, we do prefer that your daytime hours overlap with Pacific Time working hours, as so to avoid any nighttime burnout.
Please apply here before May 20th. We’ll confirm that we’ve received your application within 48 hours. At the conclusion of the review process, we’ll respond to every application about the result and next steps. We appreciate your patience as we review each application carefully.
This is a unique opportunity to directly deliver, craft, and impact the learning journey of thousands of managers who want to become better. If you’re the right person for it, I’d be honored if we got help managers in this way, together.

Looking forward to hearing from you,

-Claire Lew
CEO of Know Your Team

To apply: https://weworkremotely.com/remote-jobs/know-your-team-leadership-trainer-coach

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Job Types: Full-Time.

Endless.

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