Daniel Chait is sitting in his rented home on Long Island instead of his old office on the 11th floor of a tower in the Flatiron district of New York. Chait has moved out of Manhattan with his family in the wake of Covid-19, one of billions of people around the world working remotely.

We are dressed almost identically, both of us in dark sweaters and light blue shirts. “I got the memo for the required outfit,” Chait laughs.

The chief executive and co-founder of Greenhouse has raised more than $110 million for his business since 2012 and his hiring software company has grown explosively since it started. It has more than 4,000 customers. Many of its big-name clients have significant presences in Dublin – Stripe, Intercom, Pinterest, and Hubspot.

Chait graduated from the University in Michigan in computer science in in 1995 and is down-to-earth rather than the cliched twenty-something Silicon Valley founder – all frenzy and fire.

Last January, Greenhouse opened its first international office in Dublin to oversee its European, Middle East and African operations. Chait hired industry veteran Colm O’Cuinneain from LinkedIn to lead his team here. With Covid-19 causing unemployment to spike around the world, it seems like a good time to talk to the founder of a recruitment company working with some of the most interesting and resilient firms in the world.

Why persistence pays when raising funds

Daniel Chait founded Greenhouse in 2012 after spending almost a decade with Lab49. Chait had cofounded Lab49 and helped build it into a decent business working with investment banks and hedge funds.

He spent a lot of his time trying to hire talented people and, over time, realised how hit-and-miss recruitment was. He knew how much a bad hire could hurt a business, and how much a good hire could bring.

In a 2013 interview, Chait outlined the problem he wanted to solve: “What makes a company great at recruiting and how can we automate that?”

In 2011 Chait sold his stake in Lab49 and ploughed the money into setting up Greenhouse. This brought him for the first time to Sand Hill Road, an arterial road in Silicon Valley along which are based some of the biggest venture capital companies in the world.

“This is not only a societal ill, and discriminatory, but it is bad for business. It squanders tonnes of human potential every day.”

Daniel Chait

“I showed up there as sort of an outsider,” he told me. “It was hard. If you are a 27-year-old computer scientist from Stanford, then venture parties know how to look at you.

“If you’re not, it is not easy… I had built a pretty successful global company in New York in the financial services industry, but we were niche. When I got out to Sand Hill Road, I am just one guy with PowerPoint, and they see a hundred of me a day.

“I was describing some of the stuff we had done (with my old business). We had worked with big customers like Morgan Stanley. It almost felt like it didn’t seem real to them.”

Some of the venture capitalists he met couldn’t believe he had bootstrapped his old business rather than burning through external money. “It didn’t connect,” Chait reflected.

Eventually, Greenhouse got traction. In late 2013 Social and Capital, founded by early Facebook executive Chamath Palihapitiya, and a group of angels, put up $2.7 million.

What advice would Chait give any Irish founders trying to raise in Silicon Valley? “I would say to Irish entrepreneurs it is all about persistence, persistence, persistence. I can’t tell you the number of ‘Nos’ I got.”

Five years later in July 2018, Greenhouse raised a $50 million series D round led by Riverwood Capital. At that stage the tech press were tipping Greenhouse as a future unicorn. But for Chait the reality of fundraising was not so easy.

“At that point we had tens of millions in revenue and hundreds of employees. We were kind of well-known for what we did,” Chait said.

“But when I raised that round of funding, we had 35 firms tell us no. Back when I was a guy with a PowerPoint – you would look at a company that has already succeeded and you think ‘Wow they must have no problems whatsoever. They have it all figured out.’ Not really! It is constantly a struggle.”

The squandered potential of unconscious bias

Recruitment, Chait said, has had to adapt to Covid-19 as hiring goes remote. “It has accelerated changes that were already happening,” he said.

“People feel when they meet someone in person that they can tell a lot about them, but the truth is and the science shows, that that is actually not true.

“Signals can be really misleading, and it is hard to judge individuals. A lot of the time when people get comfortable in a face-to-face interview it is ‘Hey you and I went to the same school. We dress alike and we look alike. He seems like a good guy so he gets the job.’ Obviously that is incredibly unfair and ineffective.”

Chait said Greenhouse tried to help companies find the best talent and one of the ways it did this was through an approach that rooted out unconscious bias. Movements like Black Lives Matter only reinforced the need for this approach.

“Don’t just spray and pray. You need to custom tailor your approach to each role. Read up on what is going on.”

Daniel Chait

“When we started this company in 2012, we knew that more inclusive hiring was integral to better hiring,” Chait said. “People mistake background markers or appearance for real talent.

“This is not only a societal ill, and discriminatory, but it is bad for business. It squanders tonnes of human potential every day.

“This year there was a big societal shift and awakening (in response to BLM). People are more interested and more motivated now. We have a whole rank of tools just around combating implicit bias.

“The science is really interesting about how those biases work and how you combat them. I will give you one example…If I was to say to you to close your eyes and imagine a genius you’d probably picture in your head Albert Einstein. Most people do.

“So you implicitly associate this idea of a genius with the idea of a white man. It is just there. It does not mean you are a bad person. But getting past those ideas and getting to the core of who this person is I am interviewing and how do I know if they’re right for the job is a real skill in its own right.

“Letting the interviewer say grade a work sample irrespective of who sent it in is a great way to remove bias. Obviously, Greenhouse has a lot to do in collecting the right amount of data and letting our customers see what is happening in their recruitment funnels.”

Working with Irish unicorns

The scale that Greenhouse is helping companies hire is huge. In 2019 its customers hired 450,000 employees sifted from more than 45.5 million applications, while more than nine million scorecards were used to rank hires.

Is Greenhouse making inroads to Irish firms or is it mainly working with US multinationals?

“We have local sales representatives, and we are definitely starting to get business in the local area,” Chait said. “Learnupon (which raised $56 million in October) comes to mind.”

Greenhouse also has close links with two Irish unicorns. Stripe’s head of people Maia Josebachvili, who was recently promoted to a new role in M&A and investing, spent the previous four years of her career with Greenhouse. Intercom, another customer of Greenhouse, shares a mutual investor in Social Capital. 

“There is a sort of community of leaders and companies who have really changed how they hire and how they relate to their talent,” Chait said. “We just sort of discovered it and they discovered us. A lot of (new customers) come from a growing awareness in more and more businesses around the need to hire differently.

“It is a persistent and incredibly costly problem hiring the wrong person. We say our mission is to help every company become great at hiring.”

LinkedIn, Chait said, had replaced the old-fashioned Rolodex: “Everyone now has a Rolodex with hundreds of millions of names.”

Finding the right people and getting them to apply was part of what Greenhouse did. Another was making the hiring experience good for talented people.

“Today people in the job market have tonnes and tonnes of control. If you don’t impress them and stand out you’ll never get them,” Chait said. Greenhouse also helped companies make decisions around hiring.

“In the couple of hours I have to decide on hiring I am making what ultimately becomes a $1 million bet on your capabilities,” he said. “It is hard to hire because a lot of biases creep in and you have a limited amount of time.

“The last thing we do is around operational excellence. Data and infrastructure and technology make recruitment work better. If you make a bad hire it is super costly. To make smart decisions you need good data to help.”

The future of work, and outlook for the office

Remote working, Daniel Chait maintains, has made the talent pool wider for employers. “It used to be that being within a commute from your desk was very important. That is not a constraint anymore,” he said. “Companies are waking up to the idea that they can really hire great people everywhere.”

“I am a huge believer that there is amazing talent everywhere and increasingly now those opportunities are available to those same people. For companies it is a big shift. I am not going to hire only in my local community now. I am going to hire people anywhere in the world.”

Chait said it was too soon to predict the death of the office. “There is less pressure on companies to return to how it used to be. Companies don’t have to make this big investment in real estate and force everyone to come in every day when we know we don’t have to do that. I think a lot of the thing about remote work is here to stay but certainly not all of it.”

What advice would you give someone looking for a job?

“Most of the time when someone applies for a job, they don’t get it.  Our customers are interviewing 20, or 30, or 50, or 100 people for just one job. If you are a job seeker you need to look at many, many jobs,” he said.

“But don’t just spray and pray. You need to custom tailor your approach to each role. Read up on what is going on in a business. Try to say something meaningful about that when you apply and say something meaningful about yourself. Don’t just have it be generic chat. There is tonnes of that and people get better and better sifting through it.”

What does it take to be hired by Greenhouse? “I am less focused on where you are from or where you worked in the past. To me it starts with values,” Chait said.

“We have all kinds of people in the company doing all kinds of things. The one thing they have in common is they look at our company values and they go ‘Yeah, that’s how I am going to live and work.’ It is not for everyone. Most people won’t work for Greenhouse but for the ones that do look at our company values.”

What advice would you give employers hiring? “I would say seize the opportunity. One thing that I have seen is that (employers) err on the side of pattern matching for roles.

“So if I am hiring somebody for a certain type of job I want to know have they done that exact job at a company like ours? But maybe there is this amazing person for that job who just got laid off from a role in a different part of the country who has the skills and the talent and who with a little bit of training can become a really unique member of your team.

“This is someone that your competitors aren’t looking at, that no one else is looking at. A bit of advice would be to see this moment as an opportunity and expand out your definition of what you look for when hiring and improve your capability when making those decisions for yourself and assessing on your own who is the right talent for your team.”

“It is not just about looking at the resume, if you do that you are giving yourself a real edge.”