I'm Claire Lew, CEO and Co-founder of Know Your Team. AMA!

Howdy all! :wave:

I’m Claire Lew, is the CEO of Know Your Team – a software tool that helps managers become better leaders. Our software has helped over 15,000 people in 25 countries at companies like Airbnb and Kickstarter. And, our blog is read by hundreds of thousands of people all over the world. We have a bit of a unique origin story, as well, as we’re a spin-off company of Basecamp.

My mission in life is to help people become happier at work. I’ve spent the past almost 10 years speaking internationally on how to create more open, honest workplace environments, and have been published in Harvard Business Review, CNBC, Inc, Fortune, among others. I also served as an adjunct professor of entrepreneurship at my alma mater, Northwestern University.

I’m happy to chat about anything and everything related to being a new founder and/or first-time leaders: Remote leadership, coaching employees, giving feedback, holding effective 1:1s, delegating well, managing performance issues, building trust in a team, setting vision + direction, etc.

I’ll be here on Thursday, April 9th at 10AM PT, to answer your questions :zap:So looking forward to it!


Note: This AMA is closed for new questions, but you can check out the existing conversations below.

In this AMA, we had Claire Lew — the co-founder and CEO of an amazingly lean startup, Know Your Team, a passionate advocate for happier workplaces, and a brilliant illustrator and painter — share her thoughtful insights on how to test and create a pricing model that works for you, marketing when your product is a good-to-have, building a lean and remote team, and more. Dive in!

AMA Index (Claire’s brain-pickings) :brain:

(founding insights, opinions, and observations; deftly examined and articulated)

Claire’s take on their unconventional pricing models and how software, community, and education come together in the current form
On eschewing “judo solutions”
How to position a product so it IS a must-have
What explains Know Your Team’s content prowess; “The short answer is that I wrote every week and published on our blog, for the past 6 years”
Pressing suggestions on making the remote transition
How measuring remote performance isn’t different, why 360 evaluations can be a hit or a miss, and dealing with the managerial chasing habit
Product improvement and prioritization, what Know Your Team focuses on
How Claire approaches the written word; “I think there is no replacement for reading others’ work as a way to become a subject-matter expert”

Further reading/listening/pondering from the interwebz :open_book:/:headphones:

(Other insightful excerpts drawn from blog posts, interviews, and conversations)

On building a profitable with a lean team of 4:

  • “For me, I got into this whole starting-a-business thing because I wanted to do it on my own terms: Small in headcount, big in impact, independent, profitable. Life is short. Why build a business any different from your vision for it?”

  • “…what I realized is that a lot of times, as founders and as entrepreneurs, we gravitate toward the things that we can control. So we like fixing bugs, we like tweaking the UI, design because we can control that, we can build the features, we can mock up a page. But we don’t like talking to customers because who knows that the customer is going to say. That’s so out of our control, so out of control. We don’t like thinking or analyzing the marketing because, oh my gosh, who knows what that’s going to say and tell us? That’s so outside of our control. So I think for us as founders, it’s important to reflect. And I struggle with this every day of remembering that where our natural tendency is is to move towards the things that we think we can control and to turn our backs towards the things that we feel are out of our control.”
    Source: Blazing New Trails with a Small Team with Claire Lew of Know Your Company

On communicating authentically with your audience:

“The fact that something takes longer and requires a little more effort matters less to me. What matters is that we’re trying to communicate authentically with whoever is kind enough to lend us their time. Even if it’s not “perfect” quality or the most efficient thing to do… So what? If it shows you care, I say do it.”
Source: Why I illustrate all our blog posts, as a CEO

On changing and solidifying your culture:

“Changing your company culture also isn’t about just changing the espoused values and beliefs. Saying at all-company meetings, “We believe in honesty and transparency” or writing “We believe in diversity and inclusion” on your career website doesn’t automatically make those things true. Changing your company culture is about tapping into the core beliefs of each individual, understanding what their basic underlying assumptions are, and creating an environment where those can be listened to, brought together, and reacted to.”
Source: The Culture Cliché

Stay in touch: :sunny:

You can follow Claire to stay updated with her discoveries and insights:

  1. Claire on Twitter
  2. Claire on LinkedIn
1 Like

Glad to have you on Relay, Claire! :slightly_smiling_face:

Thanks for taking the time!

Being a value-based pricing geek, I’m forever curious about pricing models that different companies experiment with. Even in its previous form, KnowYourTeam had a very unique model, where you had people pay a fixed sum upfront instead of a recurring charge. And the current one, where you offer education and community, as an integral part of the product is as fascinating.

— How did you arrive at such a unique value metric when most other products in your category price using almost the same, conventional ways?

— How did you think about the benefits and the trade-offs of transitioning to the existing version? Also, how deeply do the three offerings — community, education, and software — feed into each other?


Thanks for doing this session, Claire!

There’s much to learn from all that you’ve shared over the years about how you’ve shaped the company and how doing that, in turn, has shaped you as a leader. As a fellow founder, I’d love to learn how your thinking has evolved around:
— Constraints. (Given that KnowYourTeam has scaled successfully with such a lean team; and bootstrapped for such a long time as well.)
— And impact. (As you’ve dedicated almost a decade to address a single pressing challenge across different mediums, from public speaking to writing and from consulting to building SaaS products.)

I love what you said about founders gravitating towards things we can control :slight_smile:



Hi Claire,

Thanks for taking time to help us out through this AMA.

One question that i am struggling with and i see that you have mastered well is, how to sell your product or service, which is otherwise considered as a good to have and not really a must have. I am always confronted with educating the buyers a lot in the non-material value (eg culture) that one product offers, which can have a profound impact in their material outcome. In short, how to best manage your sales cycle and conversions when your product/service is not a direct contributor to buyers EBITA / Balance sheet?

looking forward to understand your experiences.

Thanks much,
@Logesh, @Deepika


Hi Claire,

Thanks for doing this AMA!

I was amazed to read that you built a super efficient inbound engine that was predominantly fuelled by educational content coupled with organic distribution on different channels. Also that you ran almost no ads.

How did you make that happen? And what were the top 3 strategies that worked for you?

Thanks! :slight_smile:


Hi Claire,

Have enjoyed reading your blog posts and the occasional podcast appearances over the years. Thank you for creating wonderful content that is super useful for managers.

What advise would you have for companies/ companies which are now going through a sudden and forced remote work situation. Especially for a small team like ours where everyone misses the collegial atmosphere and spontaneity (and the water cooler moments) of a physical workplace.

As a CEO running a very lean time, would be curious to know how you split your time between various functions and responsibilities.


Hi Claire,

Thanks so much for doing this AMA. It was great to read your story and learn that you do it with just 4 people. Thats just brilliant! I would like to know and manage my team better and have the following questions

  1. We have been working remotely for 2 weeks now and it’s likely to continue for a while as is the case across the world. We are tempted to offer it as an option to people who want it and are good at it even after we get back. How do you evaluate which people do well? How would you make sure that the remote employee stays connected with the business and continues to grow?
  2. I have yearly 1:1s with all of our staff. I would like to make them quarterly with their managers and be a 360 evaluation as well. What is the best way to make sure this is a success?
  3. We have a 100+ person organization and one of the biggest issues our managers share is that they have to follow up with people on their tasks. How do we get out of this chasing habit that we have got ourselves into?

I noticed that you have an inbound engine with no ads and a very small team! Thats very cool. How does your onboarding process work? Is it product led or people led?

Thanks for your insights.


Hi Claire,

Thanks for doing this AMA.

As a (kind of) new founder, I’m eager to see answers to many questions here.

Specifically, I’d love to understand how your early decisions around pricing models & value definition were and how they evolved as you built up a larger customer base.



Hello Claire,

Thanks for doing this AMA; it’s wonderful to see the work Know Your Team is doing.

How do you ensure high user engagement and satisfaction with your product? How did you prioritize content and community needs? Was it only user interviews or other inputs? How did these strategies inform your business model?



Hi Claire,

I have another one:

Reading from your work, what shines through each and every insight you share, is the fact that you’ve dedicated years to understanding the same subject.

For founders who’re just beginning to approach content as a way to reach their audience, where and how do you think, they should begin on the ladder of getting to insights?

Thank you for your time! :raised_hands:


Thanks for these questions, Krish!

For your first question:

As you mentioned, the original pricing model of Know Your Team (back when it used to be called Know Your Company) was that we charged $100 per person one-time – and that’s it. So if you had 25 people, KYC would cost $2,500 for your team. The reason we’d set up this pricing was because we wanted to encourage people to think of KYC as a program – an investment you made in getting feedback + encouraging your team to be open and honest. We felt with a typical monthly subscription model, it’d be too easy to say “you know what, it’s $10/mo, and it’s just this app I turn on and then do nothing with…” Rather, we wanted leaders who purchased KYC to think, "I invested $2,500 in this, so now I want to take real actions to encourage honest feedback at our company. For us, it was about aligning behavior with the price.

We decided to change this pricing model when we turned Know Your Company into Know Your Team, because the audience and the behavior we wanted to promote changed. Know Your Team is for managers – and if the product were to cost thousands of dollars, that would make it inaccessible to them. Additionally, it’s the manager herself (or himself) who is benefitting from KYT – and so we decided to charge per manager instead of per user. So today, KYT costs $30/mo per manager. Again, it was about aligning audience + behavior with the price.

For your second question:

Transitioning from KYC to KYT was definitely a big leap for us – we re-built the product and created new marketing, new pricing, and new onboarding for essentially a new company, with only 2 people and in less than 1 year. But for us, that cost of time, effort and energy was worth the potential upside, which was serving a customer segment (new managers) who were unserved. So when we were making the decision, we kept going back to the core question: “What’s the real problem we’re solving, and for who?” It may seem cliché or even pedantic, but for us, all decisions around should we do X or Y with the transition came down to getting super clear about the exact problem we were trying to solve – and for who, first.

The 3 offerings of community, education, and software all feed into each other quite deeply. For example, the software is heavily influenced by the education and the community insights. And the software enacts the recommendations made in the education and the community. At the same time, in future iterations of KYT, my vision is to have the 3 components more deeply integrated.


Hey Rajaraman – thanks for these kind words.

My thinking around constraints and impact have been definitely evolved over time – and also in some ways, haven’t changed much :slight_smile: Specifically…

Constraints have become something that I’ve changed my reception of, I think, slowly over time. Previously, I think I’d always been searching for the “judo solution” amidst constraints. That is, how can you get the maximum outcome by doing the least? And while that’s a useful frame for some problems, I think other times, in the face of certain constraints, it’s frustrating. For example, when you’re faced with certain constraints in your business (e.g., capital, people, time), yes, you can totally seek out the minimum thing to do that gets you the maximum effort. But also, I think if you want to create something special or meaningful, sometimes you have to accept that the constraint just means something will take more time – and that’s okay.

I think as entrepreneurs, when we’re faced with constraints, self-imposed or not, we can be hungry for the “hack” or elevator that zooms us up to the top. But when we don’t find that, it haunts or burdens us. Instead, I think realizing that amidst constraints, something will just take longer, is an important truth to accept. A perfect example of this I think is the writing we do on our blog. I could’ve looked for the judo solution for creating organic traffic (e.g., hire content writers + editors) – but I had a specific vision for what I wanted the content to be. And I knew that we had the constraint of cash. As a result, I’ve chosen over the past 6 years to write every single one of our 100s of blog posts myself (with maybe ~4 exceptions). And we’ve gotten incredible traffic because of it + built a loyal audience. But it also took 6 years. And I wrote everything. There was no “judo solution” because of the constraint, and I chose to be okay with that because of the vision I had in mind.

Regarding impact, I’ll say this is likely something that view hasn’t changed on. For me, personally, it’s what’s driven me to focus on this single problem (helping managers become better) for, as you noted, almost 10 years now! And for me, it’s simply because, contributing to solving a problem that is meaningful to myself and others is, well, what helps me feel alive :slight_smile: That’s my wellspring of motivation. I think for other founders, theirs may be different – which is 100% great! But for me, recognizing that impact is my source of motivation has helped sustain and guide me in the work I do.


Hey Logan and Deepika,

Great question. I approach this from 2 angles:

#1: Find a way to position your product so it IS a must-have + directly contributing to buyer’s balance sheet. This usually means a few options. You can:

  • Position your product to only a segment of your original audience that feels the need, stronger than anyone. (E.g.: We specifically seek out working with new managers because they are feeling the pains of not knowing what to do as a manager. As a result, KYT is a must-have to them, versus someone who has been managing a team for 5+ years).
  • Show how your product affects your buyer’s balance sheet. (E.g., We have a One-on-Ones Tool that talks about how 89% of managers see better performance from their team when they’re doing regular one-on-ones).
  • Change your product so it delivers on a promise that affects your buyer’s balance sheet. (E.g.: We have a Heartbeat Check-in that saves our managers hours of times every week. And for managers, time = money.)

#2: Appeal to the most painful, frustrating moments that your customers are facing – and then alleviate them. A product doesn’t feel like a must-have if the customer isn’t feeling the problem strongly enough. So then you’ll need to ask yourself:

  • Are we tackling a painful enough problem? Or is there a different one we should tackle? (E.g., We used to be focused solely on tackling “lack of team feedback” as the problem – but then realized “accidentally becoming a bad boss” was a more painful problem. So then, we rebuilt the product to be what it is today.)
  • Are we focused on a customer segment that is actually truly feeling this exact problem? Similar to what I described above, you might not be focused on the right people – and perhaps there’s another subset of users who is experiencing the pain + frustration that your product will alleviate.

Hope this helps! Best of luck to you.


Hey Aditi – thanks for these questions.

The short answer is that I wrote every week and published on our blog, for the past 6 years :slight_smile:

The less glib answer is that we focused on a few things…

  • Being consistent. Audiences accrue when there’s an expectation built up that a person has something valuable to say. That expectation can only happen if there’s been enough past experiences of value to go back and reference. As a result, a huge part of building an effective inbound engine is consistently producing value, over time. This could be as simple as writing one blog post per week (that’s where I started). Do that for at least 6 months consistently, promote it consistently, and you’ll slowly start to see that expectation build up… and an audience very slowly start to emerge.
  • Optimizing for SEO. This is the obvious one. But for us, boy, did it pay off. I didn’t have any prior experience with SEO and learnt everything by devouring books and articles. You don’t need to hire a SEO specialist or firm to get started. It’s very possible to learn yourself. A few book that I read when getting my feet dirty with SEO:
  • Writing on topics that people want to most learn about. The topic itself that you choose is critical. As a result, I would pay attention to what pain points our audience + customers would mention, what other news outlets are writing about, what is trending on Twitter, etc. to get a sense of what the most burning topics people wanted to learn. One of the best ways to do this is to use an SEO tool like SEMrush (that’s the one that we use) to look at keyphrases volume search. Additionally, I would “test” topics by tweeting about them, or talking about them in live presentations – and if something resonated particularly well, it’d be the foundation of a blog post that I’d then write.

Hey Vengat – thank you for these words!

Regarding the transition to remote work, I have many suggestions, but these I’d say are the most pressing:

  • Focus on making communication expectations clear. Specifically: Match the message to the channel. For example, is it clear what communication channel (e.g., Slack, Basecamp, email, Zoom, etc) should be used if something is urgent? Or what about if someone is going to be offline? Creating some sort of shared document on what these communication expectations are is key. Here are a few examples:

  • Be extra intentional with social interaction. As you mentioned, this is the biggest thing that folks miss in moving to remote work is the sense of rapport. To account for this, you’ll want to consider setting up things like a buddy system, or having a dedicated non-work channel for talking about things like pets etc., or doing virtual coffee or board game hang outs. In Know Your Team, we have something called a Social Question which we designed for this exact purpose, that you might find useful.

  • Automate your status updates. With remote teams, it’s a burden to hold meetings to figure out what everyone is working on – you’ll waste precious time. Instead, find a way to have a system that proactively asks + shares what everyone in the team is working on. We use the Heartbeat Check-in here at KYT to do this, internally.

  • Give an abundance of trust. When you’re remote, it’s easy to wonder, “Is my team working?” You’ll want to nix that nagging paranoia, because (1) you never can really know, even if folks are in person (2) what you should ultimately care about is the results, and (3) extra pressure + surveillance, especially when remote, hurts a team’s performance. Instead, focus on creating clear systems of communication + proactive sharing of progress, and trust your team to do the work you hired them to do.

For a deep dive, you may want to check out these free resources, as well:

In terms of how I split my time as a CEO, one caveat: My role is likely a little different than other CEOs because I execute all of our content. As a result, I spend about 20% on team communication, alignment, conversation, strategy, 20% talking to customers, 60% writing + researching our content, as well as any growth experiments we’re running.

More broadly, CEOs we’ve surveyed tend to focus mainly on three things: (1) Recruiting / Hiring, (2) Long-term vision, and (3) Communication.


Hey Ravi – thanks for your questions.

  1. The best way to evaluate people is based off the work/output they produce versus the expectations agreed upon for them. Remote work isn’t any different than in-person work in that performance = the actual results that the person produced. In terms of making sure that remote employees stay connected with the business, you’ll want to: (1) Clearly define what you mean by “connect with the business”. Do you mean feel connected to the vision? To the people? To the work? (2) Create systems + cadence of interactions that reinforce the intended outcome. For example if you want people to feel more connected to the company vision over time, you’ll want to hold 1:1 conversations to figure out what are people’s personal visions, and how do they align / match up to the team’s vision. Or, if you want people to feel connected to their coworkers over time, you’ll want to invest in opportunities for social interaction (e.g., buddy system, virtual coffees, our Social Question in KYT).

  2. 360 evaluations can be hit or miss depending on how you do them. One consideration is to keep in mind that they take a lot of time, depending on how many people you have – so quarterly might in fact be too often. The most common frequency we see is 2X a year. (If you have 100+ people, I’d recommend no more than 2X a year) You’ll want to make sure these 360 reviews are NOT tied to compensation, so people don’t feel pressure to weight + bias their reviews. Instead, communicate the underlying purpose to be reflection + improvement. Lastly, ensure that a self-review is included in the 360 – it enables the person themselves to take stock of their own performance and calibrate how they’d like to move forward in the coming months/years.

  3. I hear you on the chasing habit :slight_smile: One of the best ways to avoid this is (1) ensure that expectations for sharing progress is clear and (2) create an opportunity for your team to proactively share progress. For the latter, we here at KYT internally use our Heartbeat Check-in for this. Every morning, via Slack or email, a check-in is sent out that asks, “What did you work on yesterday, and what are you working on today?” Folks can fill the Heartbeat out that day when it best suits them. And after they do, the answers are shared with everyone. No one is interrupted. And everyone – not just you as the leader – get to benefit from seeing the answers. This way, you’re creating a shared expectation of distributing information for everyone’s benefit – not running around and chasing folks to figure out is something is done :slight_smile:

Regarding onboarding, it is mainly product led in that we have a guided tour + onboarding videos. We also offer personal 1:1 calls with me, on a limited basis, for folks who want great support and guidance.

Thanks for these questions, again, and best of luck to you!


Hey Jay!

Thanks for this question. I answered something similar for Krish here, if you wanna take a look – hope it’s helpful! :


Hey Meghana – thanks for these great questions.

We focus on a few things to determine how to improve the product + what to prioritize…

  • Talking to customers. This is a pretty obvious one – but there’s really few things that replace getting on the phone to understand how someone is using the product, what they’re liking, etc. I in fact offer 1:1 onboarding calls for a limited number of slots as a way to both help the customer and for us to gather this info.
  • In-app surveys. In our product itself, we ask folks how willing they are to recommend KYT, and this gives us a sense of satisfaction overall.
  • Email surveys to customers. Depending on how someone answered our in-app survey, we’ll often follow up with a more detailed survey asking the specifics of what they like + don’t like with the product. Then we can segment + find intriguing insights, for example: “Oh, people who feel neutral about KYT don’t use X, Y, and Z parts of the product.”
  • Anectodal feedback. We get quite a few emails from folks, unprompted, telling us what they love about the product – or what they’d like to see in addition to it. We pay attention to the underlying reasons there, and the frequent + valence of that feedback.

Hey again, Aditi!

Thanks for this question.

I think there is no replacement for reading others’ work as a way to become a subject-matter expert – and to improve your own writing. I read and research A LOT to really get a vantage point on a subject before writing on it. I also pay attention to the way good writers write. Other than simply practicing writing and doing it yourself, reading is likely the best way to get there.

Hope this helps!