Success story with

"UpCounsel's matches are so precise that I don’t have to spend my time reviewing multiple proposals by attorneys who may not be a good fit. When I have a legal need, my account manager just shoots me off to the right folks."

Sean Conway

Pillow CEO & Co-Founder

Pillow, founded in 2014, was acquired by Expedia Group and continues offering short-term rentals for multifamily properties, allowing building owners and property managers to have control and transparency while enabling their residents to rent their units sites such as Homeaway, VRBO, and Airbnb.


How does Pillow benefit by working with UpCounsel?

Why Pillow CEO Sean Conway uses UpCounsel Enterprise:

1. Cut Costs. Sean cut 60% of his legal bill by moving 80% of Pillow’s legal work to UpCounsel.

2. Quality Legal Advice. Sean says he finds the same quality attorneys he finds at his big law firm.

3. Improve Efficiency. An account executive helps Sean save time on recruiting by hand-selecting candidates who are the the best fit for his business and unique legal needs.

of Legal Work to UpCounsel to Start
of Legal Work within 1st Year
Savings on Employment

The challenge

Before finding UpCounsel, Pillow Homes CEO Sean Conway had been relying on a big tech law firm to cover all of Pillow’s basic business law needs. He was satisfied with the firm’s work but not the large legal bills, lagging responses from his attorneys and the amount of his time he had to spend overseeing legal projects.

These were big problems for Sean because Pillow had taken off in the past year, and he was doubling down on scaling the company – including doubling headcount. He needed to be able to focus his time and money on projects that had an impact on the company’s bottom line.

UpCounsel attorneys charge $200-250 per hour, whereas Pillow’s law firm charges $400-600 per hour.

He needed a solution to cover his basic business law needs, but Sean didn’t want to spend his time finding, vetting and onboarding new attorneys or transferring Pillow’s legal projects from his law firm to a new provider. While imperfect, Pillow’s law firm did know his company’s business.

An Enterprise customer now, Pillow first started out using UpCounsel’s marketplace in 2013 when an urgent legal project came up. Sean didn’t want to spend thousands of dollars to ask his law firm to provide a simple contract review, and he didn’t have time to wait for his law firm to turn it around.

He says UpCounsel attorneys are able to grasp an understanding of his business model and legal needs quickly – meaning he doesn’t have to spend his time onboarding them – and charge significantly less than his big law firm. He turned over 20 percent of his work to the UpCounsel marketplace.

Pillow Sent 20% of its Legal Work to the UpCounsel Marketplace and reversed the division of work after signing up for UpCounsel Enterprise.

But as his company grew, Sean wanted legal to be taken care of with as little effort as possible. He was working with several lawyers at UpCounsel to secure total coverage of his legal needs and wanted support coordinating his relationships.

Sean turned to UpCounsel’s Enterprise product. Pillow has needs in more than one legal area, so Sean decided to use UpCounsel Enterprise. He worked with an account manager to customize his legal team to meet Pillow’s core legal needs: immigration, contract management and real estate.

The solution

The UpCounsel account manager then hand-selected candidates for him based on his business model and legal needs and quickly delivered three attorneys – with biographies, pricing and an offer of a free phone interview. He spoke with them and then selected the attorneys that matched his budget and his needs.

What’s more, he loved the quality of the matches.

“When I have a legal need, my account executive just shoots me off to the right attorney that perfectly suits my needs every single time.”

“It’s great to have an expert hand-selecting the best potential candidates for my needs,” Sean says. “I’m confident in the quality of the attorneys my account manager delivers because I know they’ve been vetted.”

He adds, “The matches are so precise that I don’t have to spend my time reviewing multiple proposals by attorneys who may not be a good fit. When I have a legal need, my account manager just shoots me off to the right folks.”

Sean says when a one-off legal need comes up, he can reach out on Slack to his UpCounsel account manager, who can draw from the attorney community to immediately find him three choices of attorneys who are a good fit for his company and the specific project. UpCounsel’s community offers access to attorneys across multiple legal areas, and he likes that he can effortlessly find someone to handle any legal project.

Pillow Sends 80% of its Legal Work to UpCounsel EnterpriseThe new distribution of work has helped Sean cut thousands of dollars from his legal budget.

Sean likes that he has the flexibility to choose each of Pillow’s attorneys – rather than being introduced to a partner at the law firm who may or may not be a good fit for his business’ unique legal needs.

“I don’t have options when I work with my law firm,” he says. “I’m just told this is the person you’re going to work with. With UpCounsel, I have buy in.”

Sean’s favorite part of using Enterprise? The invoice he receives at the end of each month. Sean says “cost saving was my number one priority for my legal operations.”

UpCounsel attorneys typically charge $200-250 per hour, whereas his law firm charges $400-600 per hour. A project that costs $5,500 at his law firm costs about $2,250 on UpCounsel, according to Sean.

Pillow Saves More than $3k on Employment by using All Access

He says that it’s no longer cost prohibitive to send a contract to an attorney to review.

“I used to say, we don’t really need to check out that contract. Is it really worth $1,300 to make sure this basic business contract is correct?,” Sean says. “Now my contracts are reviewed by a legal expert. We’re not just reactive to problems. Which is especially important with due diligence matters.”

The transparency of the invoice also saves Sean hours of his time. UpCounsel breaks down each call, email or other task needed to get a project completed. He says this makes it easy for him to verify the output for every hour.

He used to feel that he needed to oversee calls with his team to make sure time at $400 per hour is used effectively. Now he takes a step back and lets each team handle their legal needs directly.

UpCounsel Enterprise now handles 80 percent of Pillow’s legal needs while his law firm is now handling 20 percent, and Sean has cut 60 percent of his legal budget.

“The matches are so precise that I don’t have to spend my time reviewing multiple proposals by attorneys who may not be a good fit.”

“Entrepreneurs are always looking for ways to save money without sacrificing quality,” Sean says. “The attorneys on UpCounsel are the same quality attorneys that I’d expect to find at a big law firm.”

Sean feels confident using the platform because of UpCounsel’s vetting process and his ability to see client reviews of each attorney. With Enterprise, he has an UpCounsel team on-hand to cover all of his basic business law needs.

UpCounsel Enterprise is so easy to use and the matches are so precise that moving more of Pillow’s legal work away from his much more expensive firm was seamless, he says. His account manager handled everything.

Sean uses UpCounsel Enterprise as legal services provider that acts as a complement to Pillow’s big tech law firm.

Sean says that technology makes it easy for him to move work away from his law firm. From UpCounsel Enterprise to eShares to Zenefits, Sean isn’t afraid to look beyond the status quo.

Pillow Homes Logo

Pillow is a hospitality company that makes it easy to manage rental properties and share your home with travelers.

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