A remote-first operational excellence strategy: Ken Weary of Hotjar

Most companies arrived at remote work by accident in 2020. Hotjar chose it in 2014, from an island where everyone already lived within driving distance of each other. That decision is the foundation of the operational excellence strategy Ken Weary describes here, and it is why the company had nothing to scramble for when the rest of the world was learning on the job.

Weary is COO at Hotjar, the product experience insights company, which had over 200 employees and was acquired by Contentsquare shortly before this conversation. Before Hotjar he spent 11 years in corporate product and IT roles at Safeco and Liberty Mutual, responsible for allocating $180 million in annual IT spend. He is also a full-time digital nomad, more than 2,700 consecutive days into traveling with his family, and was in Portugal at the time of recording.

Hired because of a travel blog

Weary's background spans nonprofits, startups, scale-ups, corporate roles, independent contracting and running his own business, which is part of what appealed to Hotjar's founder David Darmanin.

The other part was the blog. Weary had been a digital nomad for about eighteen months and had been writing about it. At some point in the interview process, Darmanin told him that if he could work out the logistics of traveling with a car through Central America, he could probably handle scaling Hotjar.

He joined as VP of Operations and held that title for years before it became COO. His description of the change is one plenty of operators will recognize: the role itself did not really change. The purview and accountability grew until the title needed to catch up.

The uber project manager

Asked whether he is a mile wide and an inch deep, Weary says mostly yes, with one exception.

The thing he has always done, in every job, is manage projects. He describes his role at Hotjar as being the company's uber project manager, looking across everything, assessing risk and opportunity, making sure the right resources are in place, and then acting as train master to keep things moving.

The subject matter of any given project, legal, financial or otherwise, is a mixed bag where his depth runs out quickly. The skill is the constant.

What sits under him is finance, legal and compliance, anything regulatory, all of people operations from recruitment through the full employee lifecycle, and then everything miscellaneous, which he defines with admirable honesty as anything his boss does not want to do. Internally they call that business operations.

His observation about the role generalizes across this entire show. There is no common definition of what a COO owns, which makes it genuinely hard to find a peer group. Two people with the same title routinely discover they have almost nothing in common.

Privacy as a design position

Regulation is the one area where Weary has gone well past an inch deep, out of necessity.

GDPR was not part of the company's vocabulary when he joined. Now it is GDPR plus CCPA in California, LGPD in Brazil, and draft legislation in more than a dozen other countries, on top of continual reinterpretation of the original rules.

Hotjar's approach has two halves.

The first is genuine agreement with the premise. Weary says they believe the spirit of the regulation is right, that individuals should control what happens to their data. That belief is not decorative. It is what makes it straightforward to get engineers and marketers behind the work rather than treating compliance as friction.

The second is a deliberate standard. Hotjar decided early to hold itself to what Weary calls the gold standard, meaning the German interpretation, on the reasoning that Germany is an important market for them and that meeting the strictest reading means meeting essentially every other jurisdiction. They pair that with an outside privacy practice they engage regularly, both for interpretation and to flag new legislation around the world.

Doing due diligence on your acquirer

This is the most valuable thing in the episode, and it should be standard practice.

The Contentsquare relationship started long before the deal. When Darmanin founded Hotjar, he deliberately reached out across the behavioral analytics industry to build rapport with competitors and their CEOs, including Contentsquare's founder Jonathan Cherki. They stayed in touch for years, comparing notes, and gradually established that they were not really full competitors. Contentsquare served enterprise, Hotjar served SMB.

Interest surfaced periodically and never went anywhere until Contentsquare made a concerted approach and eventually an offer. The strategic logic was funnel coverage. A business can start on Hotjar for free and grow, and between the two companies the combined offering covers the whole range, with each the leader in its segment.

Then came the part worth copying. As a term in the original letter of intent, Hotjar negotiated the right to run diligence on Contentsquare.

What they investigated is exactly what a team should want to know. Cultural fit. How the acquirer actually operates. Whether this was a cannibalization, meaning whether Contentsquare would simply take the customers and move on. What Contentsquare's own employees thought, including their employee opinion scores. Weary's plain version of the question: are they a bunch of jerks or not.

He also supplies the argument that makes it negotiable rather than presumptuous. These deals are usually cash plus stock. If you are accepting equity in a company, you are making an investment decision, and making one blind is not defensible. The counter, if the acquirer resists, is simply that you need to know what you are being given. Contentsquare accepted without needing it.

Weary describes the resulting couple of months, with each side diligencing the other, as grueling. But the framing he ends on is the right one. Before the board decided, the question they were answering was whether this was a good place for their team, more than anything else.

A why, and a just cause

Hotjar's stated reason for existing is to inspire change through empathy, which sounds abstract until Weary connects it to the product.

His starting point is that heat maps and session replay, on their own, do not amount to much. The company is fans of Simon Sinek's argument that you need a why and a just cause behind it, so they went looking for the larger version.

The mechanism is a chain of empathy. The product lets a site owner understand what is frustrating their users and what those users love. That understanding gets passed back to future visitors in the form of a better experience. Multiply it across the web and you have changed something bigger than any one company's conversion rate. Weary says it drives how they design and improve the product.

What they found in Contentsquare's vision statement was effectively the same idea in different words: improving experiences for customers who then improve experiences for their own customers.

Running the business while selling it

Weary's account of managing diligence is unusually practical.

First, an observation about where the burden lands. Diligence is mostly about people, finance and legal. Nobody looked at how the product functions or reviewed the code. So more than 80% of the work came to him and his teams.

Second, secrecy. Under tight NDA, they kept the number of people involved deliberately small, and his reasoning is the correct one. Acquisitions frequently fail. If you spin up the whole team on a possibility that evaporates, you have lost their focus and left them running what-if scenarios about their own jobs.

So he delegated, telling his team only that David or the incoming CEO had asked him to handle something and that he would be out of certain meetings.

What made him the right person to lead it is worth noting. He was the fourteenth person to join Hotjar, so he knew the history, the internal processes, and where everything was buried, which meant he could both run diligence and personally source most of what it required.

The unexpected outcome is the part I would underline. Leaning on his team taught him how much of the day to day did not need him, and how much more of his role should be strategic. They did not make mistakes, and the business kept scaling through the process without him.

It still cost an enormous amount of evening and weekend work, which he treats as simply the cycle.

Nomad logistics, described honestly

Weary travels with his wife and two children, then 16 and 12, who have been on the road for more than half their lives.

He is candid that the acquisition and full-time travel only coexisted because of timing. COVID had halted travel, so they were not moving. Had they been mobile, he would have had to stop, because work has to be the priority for a nomad to stay afloat. His mother-in-law came from the US to Portugal to co-parent while he was buried.

His definition of the lifestyle is location independence, professionally and personally, and the mechanics are all about reducing variance.

They slow travel, staying at least a month in one place. They only move on weekends or planned holidays, never mid-week, because the context switching is too disruptive and the internet at the next place is an unknown until you are in it.

The family operates on explicit norms. When he is working, he is working, and interruptions are for emergencies, the same courtesy extended to his wife's calls and the children's schoolwork.

And they travel with their own mesh network, because the recurring failure is not bad internet, it is a decent connection behind a poor router that only works in the living room. Michael's own kit history, laptop stand, router, a 25 foot ethernet cable and eventually a power strip, suggests this is a known progression.

Why hybrid will not work

Hotjar was founded remote-first in 2014, and the detail that makes it a real decision rather than a convenience is that the founding team all lived in Malta. Meeting daily would have been trivial. They concluded that scaling the business required being remote, so they started remote on a small island.

Everything followed from that. Documented processes, centralized so there is always a reference point. A recruitment process built to hire remotely from the beginning. Weary's point is that they have only ever been iterating on a system built with the right assumptions, unlike companies that were thrown into remote from an office.

His position on hybrid is blunt: an experiment that will completely fail.

The argument is about culture. Once you offer the choice of office or home, you fracture the culture by default. Then, when people pick their days, they end up in the office with the people they already click with and not the others, which fractures it further. His summary is that trying to have both is like going out all night and expecting no hangover.

He is careful to say he has nothing against in-person companies, has worked at them, and thinks they are good for many people. He just does not think you get to blend them.

Replacing serendipity with intent

Michael raises the standard objection: remote loses the hallway conversation. Weary's answer starts by questioning the premise.

In an office, proximity produces the connections with people near you. But the colleague on another floor or in another building, the one you actually ended up close to, came from a company meeting, a birthday, a social or a happy hour. Something organized created that.

So the remote answer is intentionality, and Hotjar's implementations are specific.

Houses. Everyone who joins is sorted into a house, in the Harry Potter sense, by a sorting hat they built. Each house is around five people deliberately mixed across departments, tenures and backgrounds. It functions as an internal support group and a cross-company shortcut, so if you need to know what is happening in marketing, someone in your house can tell you. Houses then become the unit for internal fundraising decisions and team-building contests.

Culture Jar. With around 220 people across 35 countries, sessions where people present their own cultural traditions, especially around holidays, with slides, dress and dance. Weary's assessment is that it is powerful and that he never had anything like it in an office.

The rest is opportunistic. A Halloween costume contest on video, which he points out allows creative things that are impossible in person. A Secret Santa across 35 countries.

His most important point is about motive. Retention at the time was in line with previous years, and he is explicit that this is not why they do any of it. If you run these activities to reduce attrition, they are inauthentic and people can tell. You do them because they are fun and because the team wants them. The test before introducing anything is whether it fits the culture and whether the team will enjoy it, not whether it will help hiring or retention.

And they kill things that do not work. Some initiatives were shut down because the team did not enjoy them, others started strongly and fizzled. There is no forced team bonding.

The 5 things I took away from this conversation

1. Negotiate the right to diligence your acquirer, in the letter of intent. Weary's justification is airtight: if part of the consideration is stock, you are making an investment, and nobody invests blind. It gives the selling team real information about whether this is a good place for their people, which is the question that actually matters.

2. Pick the strictest jurisdiction and build to it. Hotjar meets the German interpretation of privacy law and treats everything else as covered. That is a far cheaper operating posture than tracking dozens of regimes separately, and it turns compliance into a design constraint rather than a permanent scramble.

3. Remote-first is a decision, not a circumstance. The founding team lived on the same small island and chose remote anyway, because they knew it was required to scale. Everything Hotjar does well here, documented process, remote-native recruiting, deliberate culture, follows from making that call before it was forced.

4. Serendipity in an office is also manufactured. This reframing is the strongest counter to the hallway argument I have heard. Your best cross-company relationships came from an organized event, not proximity. Remote companies just have to be honest that the organizing is the mechanism.

5. Culture activities must not be justified by retention. The moment you tell people the sorting hat exists to keep them, you have ruined it. Weary's standard, do it because it is fun and kill it when it stops being fun, is what keeps it real, and the retention benefit arrives only as a byproduct.

FAQ

What does a chief operating officer do in a company like Hotjar? At Hotjar the COO owns finance, legal and compliance, regulatory matters, all of people operations from recruitment through offboarding, and a business operations bucket covering anything else that needs an owner. Weary's broader point is that there is no standard definition of the role, which makes finding genuine peers difficult.

What does an operational excellence strategy look like at a remote company? Documented and centralized processes so there is always a single reference point, a recruitment process designed for remote hiring rather than retrofitted, and deliberate culture mechanisms replacing what proximity would otherwise supply. Hotjar built all of this from 2014 because it chose remote before it was necessary.

Should a company being acquired do due diligence on the acquirer? Weary argues yes, and negotiated it into Hotjar's letter of intent. The team assessed cultural fit, how the acquirer operates, whether the deal was a cannibalization, and what the acquirer's own employees thought. The negotiating argument is that a cash and stock deal makes you an investor, and investing blind is not defensible.

Does hybrid work? Weary does not think so. His argument is that offering a choice fractures culture by default, and that letting people choose their office days means they see only the colleagues they already get along with. He respects fully in-person companies and fully remote ones, and thinks the blend gets the benefits of neither.

How do you keep a distributed team connected across many countries? Through explicit structures rather than hope. Hotjar sorts everyone into small cross-departmental houses that serve as support groups and activity units, and runs sessions where colleagues present their own cultural traditions. Crucially, these are run because people enjoy them, and are discontinued when they stop working.

Also mentioned

• Hotjar and its acquisition by Contentsquare
• GDPR, CCPA and Brazil's LGPD, the privacy regimes Hotjar tracks
• Simon Sinek on having a why and a just cause behind it
• Malta, where Hotjar's founding team lived and chose to work remotely anyway
• GitLab's handbook, the public reference point for remote-first operations
• Ken Weary on LinkedIn, and the Hotjar blog for material on how the company operates remotely

Listen to the full episode

Ken Weary on Between Two COO's

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