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Reclaim.ai, an intelligent calendar assistant and time management platform, aims to help deskbound workers take back their schedules.

COURTESY GRAPHIC: RECLAIM.AI - Calendar tool company Reclaim.ai has received a $4.8M seed funding round. tHE The tool analyzes calendar content. It can move meetings and appointments around depending on their priority.

Calendar tool company Reclaim.ai has received a $4.8M seed-funding round, the Portland-based company announced Wednesday, May 26.

Reclaim's goal is to reclaim working people's time with an orderly calendar. It uses artificial intelligence to learn users' priorities, Reclaim.ai's CEO Patrick Lightbody explained to the Business Tribune. (The domain suffix AI stands for artificial intelligence.)

For example, if workers in a software company repeatedly cancel meetings about designing new product features and instead attend sales meetings, a report would suggest they are focusing on the short term rather than long-term goals. It gives insight that would be harder to collect in conversation or by surveys.

Individuals can use it, too. The app shows a calendar in a browser. Adding a meeting to Reclaim syncs within about 15 seconds to the user's main calendar, such as Google Calendar, and vice versa.

Users can schedule some of the usual events of the day, such as exercise, lunch and a twice daily half-hour for catching up on email. If you schedule a meeting that conflicts with lunch, lunch moves into a different time slot within a two-hour window. The software learns when users regularly postpone meals, exercise or certain meetings.

COURTESY: RECLAIM.AI - 'Our main mission is helping our customers be the best version of themselves professionally,' said Reclaim.ai CEO Patrick Lightbody. The tool learns which meetings workers are skipping or kicking down the road, and helps prioritize them or report on their priority to the corporation.  (The domain suffix AI stands for artificial intelligence.)

Calendar management a part-time job

With working from home becoming common and days consisting of a stream of Zoom meetings, Slack chats, texts, calls and emails , mastering a calendar without the cues of office mates has become a challenge.

Lightbody admitted as much to the Tribune. "On one of our very first meetings with a potential investor, we showed up on the wrong day," he said.

The firm's staff and funders have roots in Jive, New Relic and Puppet, but now are in contact with even more tech stars. The round is led by Index Ventures, whose institutional participants include Gradient Ventures, Flying Fish, Operator Partners and Calendly.

The funding has a northwest involvement, with early investor Flying Fish, located in Seattle, coming back for more.

Strategic investors, who can provide know-how, access and networking power, include Jason Warner, CTO at Github; Sue Khim, CEO at Brilliant.org; Alex Solomon, Co-Founder & CTO at PagerDuty; Kenny Van Zant, former Head of Business at Asana; and Yvonne Wassenaar, CEO at Puppet.

"Index Ventures set things like terms and price, and they did introduce us to quite a number of investors, many of which participated in the round," Lightbody said. "But we also found some of our own to participate. For example, Calendly (out of Atlanta) was one of our own connections."

Reclaim touts itself as an "intelligent calendar assistant and time management platform." The company's own study claims that users get 40% of their time added back into their work day.

Reclaim will use the $4.8 million to hire product managers, developers and sales staff. Its customers number 4,000 companies worldwide, including Uber, Netflix and Equinox.

Lightbody said they could have closed the round two or three months sooner, "but we really wanted to have a more interesting, diverse, broad range of reach with our investors. We purposely took our time to go out and find a lot of angels and smaller funds that strategically aligned with what we're doing."

Reclaim had a "pre-seed" round $1.5 million. "That included a few of those early angels like Jim, my old boss (from New Relic) as well as Flying Fish."

Most of the money will be spent on hiring new staff. "Engineering salaries in the Portland area can range anywhere from $80,000 early in your career to upwards and beyond $200,000 for very senior architects and senior engineering leaders," Lightbody said.

He noted that the big cloud vendors, such as Amazon, Microsoft and Google, give startup credits to acquire them as customers.

"I think, in our case, it's up to $100,000 of basically free credits for hosting and cloud services. Startups like ours often are not spending much on actual hosting in the near term. I'm sure their goal is to get you to get you hooked on it so that you're spending it down the road. But for now, our overall expenses are pretty low beyond headcount."

They can work remotely but he would prefer them in North America for the time zone.

Startups get all sorts of free offers. The credit card Brex comes with discounts on services such as customer service software called Intercom (a chat window that pops up on the right side of a browser). Startups in incubators get deals on software and rent, but Reclaim did not go the incubator route. The company started in Lightbody's garage on the west side of Portland. The staff of five recently met for their first all-together, in-person meeting in his home since the start of the pandemic in early 2020. For now they don't need a separate office.

COURTESY GRAPHIC: RECLAIM.AI - Calendar tool company Reclaim.ai has received a $4.8M seed funding round. The tool analyzes calendar content and can block out times as busy until something more urgent comes along than eating or exercising.

Product, product, product

For Reclaim, 2020 was all about making sure that had a product with a market fit, something users would use and love.

The company grew out of working at medium-sized software companies.

Reclaim is free in 2021 but will start charging in 2022, around $10 to $20 a month, per user. The product does not work with Microsoft Office 365/Teams yet, but they will use the new funding to chase that market.

"Microsoft has open APIs (application programming interfaces) to encourage the startups like ours," Lightbody said. "That's what we use for Google as well, and our customers authorize Reclaim to access their calendar and to take action on their behalf."

COURTESY: RECLAIM.AI - Henry Shapiro, co-founder of Reclaim.ai.

Three things

The product does three main jobs. One, it watches your personal calendar and blocks out time for work and personal commitments. The example Lightbody gave is someone settling into the dentist chair and getting a message saying, "Where are you? We have a meeting now."

One customer is the Chief Product Officer at the Dallas Morning News, who has to keep the online news flow moving.

"We do it in a very privacy-forward way, where you don't have to share your personal details with your work environment. You probably wouldn't want to put a job interview and invite your work address to that particular meeting; that would be fairly awkward," Lightbody noted.

The second feature, Habits, involves reminders for people to make time for their daily routines, such as exercise and replying to emails. Lightbody said that while C suite executives have personal assistants to keep their calendars straight, middle and upper managers are on their own but are pulled in different directions by the product and the staff. He felt this at New Relic, which then was a company of 1,500 people.

'Be where they are'

"Where the AI starts to play into our company name is we don't mark that time necessarily as busy. So the event is on your calendar, but it might initially appear as free. And that's important, because anyone who's trying to schedule time with you using one of these scheduling services like Calendly … it's basically a just-in-time defense," Lightbody said. "You're trying to get the best of both worlds: availability to do your job and time to focus on you."

The third feature is Tasks, launched in August 2020. It's similar but works for recurring daily or weekly events.

"If you need six hours to write an article, (in a normal calendar) a reminder often comes too late. Reclaim is constantly looking out weeks ahead and finding time to get the work done in a way that doesn't disrupt your availability."

So, if you have two hours set aside for writing for three weeks, and choose to take a meeting instead of writing for two hours, Reclaim looks ahead and schedules two hours in another spot.

"We learned from our work at New Relic we should meet the users where they are. And where they are is often their current tool: your calendar app, or typing and chatting in Slack. We should be where they are, rather than asking them to come to us."

He added, "We're living in a world of intense distraction and growing complexity. Our ambition is to help people like you and me — and any kind of busy professional — be the best version of themselves."


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