- Cal Henderson is the cofounder and chief technology officer of Slack, acquired by Salesforce in a $27.7 billion deal last year and boasting more than 2,500 employees and 142,000 paid customers.
- He talked with Insider about his early career ambitions — making video games — his thoughts on remote work and workplace norms, and the company's goals and initiatives for the new year.
- Henderson's advice to other leaders and companies during this time is to be "organizationally agile."
- "It's about how quickly you can actually change direction, and that kind of alignment is hard to do without strong relationships," he said.
- Visit Insider's homepage for more stories.
Cal Henderson never envisioned being in the position he's in now: cofounder and chief technology officer of one of the most in-demand workplace apps around — Slack, which reported revenues of $630 million in 2020 and was recently acquired by Salesforce for an impressive $27.7 billion. What he helped start in 2009 (then incorporated as Tiny Speck, Inc.) with a team of eight has grown to more than 2,500 employees, with over 142,000 paid customers using the platform.
Initially, Henderson told Insider, he just wanted to make video games. A British expat who's lived in the United States for over 15 years, Henderson started this venture in the early 2000s alongside Slack cofounders Stewart Butterfield (now CEO), Eric Costello, and Serguei Mourachov. Their video game efforts eventually evolved into the creation of photo-hosting platform Flickr, which Henderson built the design and infrastructure for. In 2005, Flickr sold to Yahoo for a reported over $20 million.
Henderson then moved from Vancouver to San Francisco, and after a few years the foursome of Henderson, Butterfield, Costello, and Mourachov tried again to make games. It was another miss.
"In both cases of Slack and Flickr, we started companies to do something totally different," Henderson told Insider. "And I didn't foresee being a leader of a company at the scale we're at today, either. I always thought I'd be creating software for someone else."
As CTO, Henderson said his day is very much oriented around Slack's platform — the company is in some ways the biggest customer of itself. Still, he's aware of the need to disconnect from it, and said he's generally not reachable outside of work hours.
"I have my 'do not disturb' sign on, especially when I'm with my kids," he said, adding that he believes the "always on" attitude is more about corporate culture, less about tools like Slack.
What's missing in today's remote work
Slack's relevance has only grown as a result of the pandemic, with the company adding 12,000 net new paid customers in the fiscal quarter ending October 31, 2020, up 140% year over year. For many, like Henderson, it's become the only real-time connection to colleagues.
"In many ways, the pandemic accelerated changes that were already happening," he said. "And why work in the future is going to be so different is because now people understand it's possible to work in a distributed manner and still be productive. Now that we've seen it's possible, you really can't put the genie back in the bottle."
Henderson initially thought working remotely wouldn't provide the same productivity seen at over a dozen of Slack's global offices. But when the company, like others, had to switch to being remote overnight, he said his skepticism was tested.
It's an "extreme situation," he added. "People are not working from home in the normal sense, it's during a global pandemic, so they can't see family or friends, they can't get out of the house, they can't meet up with people for a meeting — it's the worst possible version of working from home," he said.
He thinks there are also downsides with a fully distributed, remote setup.
"What's really missing is the collaborative work opportunity, which often means employees huddled around a whiteboard or in a conference room of some sort," Henderson said. Also missing, he said, is the more "subtle cultural aspects, like the serendipitous meetings of talking to someone in the elevator or sitting next to them at lunch or running into them in the hallway."
Henderson thinks when we reach the post-pandemic period (whenever that may be) is when people will get a better impression of what working remotely really looks and feels like.
Building new norms
Henderson said that one of the biggest mistakes many made at the beginning of the pandemic was trying to shift real-world working habits and practices to the virtual space. "Zoom fatigue is real," Henderson said.
In response, he said, Slack is developing more features which will help with asynchronous communication and act as an alternative to endless video calls.
One of the new features is called Huddles, which allows users to start a spontaneous voice call in a channel that anyone can jump into. The other feature is video stories, where users can create and post short video messages in the channel. The company hasn't announced when these features will be available to the public.
Henderson said that similar to how the rules around email have evolved, Slack is a fairly new communication medium that needs to establish its own expectations in the workplace.
"It took a decade for people to build cultural norms around what the expectations around replying to email was, or whether or not it is fine to send someone an email at night," he said.
Looking and planning ahead
Henderson said the Salesforce acquisition will have no impact on Slack's neutrality, explaining that the company has 2,400 different apps in its public directory and works with thousands of services including Salesforce, Microsoft, and Google.
"The acquisition is much like what happened when Salesforce acquired Mulesoft two years ago, in that Mulesoft, like Slack, is a platform that integrates with a ton of different bits of software," he said. The goal for Slack, he said, is to work with every piece of software, whether it comes from the Slack and Salesforce family or anyone else.
He added what will change will be with the integration of Salesforce products such as Sales Cloud, Service Cloud, and Commerce Cloud. But many Slack customers are also Salesforce customers, he said, so the focus will be on making things work even better together.
Henderson plans the goals of the company for the next six months, then 18 months. Then he asks himself what he's doing that week, day, or during a particular time block that advances those goals. He said he concentrates on the things with the highest leverage that will drive the business forward, rather than trying to do whatever is needed, when it's needed.
"It's really easy to fall into the trap of always being busy, and you can feel busy but never get anything done," he said. "There's a never ending series of things you could be doing or responding to, especially as an organization becomes more complex."
Henderson's advice to other leaders and companies is to be "organizationally agile."
"It's about how quickly you can actually change direction, and that kind of alignment is hard to do without strong relationships," he said.
But for companies like Slack, success is also based on creating software that people want to use.
"Creating software means you can have an impact on millions of lives," Henderson said. "That's super exciting for me and why I'm still here."
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