Hightail – Why Work For Us?


We are a technology company built around engineers, developers and operations working in small, independent teams where everyone is expected to voice opinions and have a material impact. We earn a real and sustainable revenue, and with a goal of doubling our user base quickly, everything we do focuses on scaling for massive growth.

Our number one priority is making Hightail a great place to work because we believe a great culture attracts great people who create great products. We like passionate, creative, wicked smart folks who take the initiative and don’t ever want to hand it back.​​​​​


​​​​Get it done on your computer​​​​

​​Hightail exists to make your life easier. It works where you work by plugging in to the applications and tools you use everyday or get our desktop app to access your folders with one simple clic​​k.​​​​


​Hightail for Mac​​

Drag and drop files and folders to Hightail from your Finder. All changes are instantly updated so you can share the latest version with anyone.

​​Hightail for Windows​​

Easily manage and share files and folders right from your desktop. Changes are instantly updated so you will always see the latest version.



Hightail exists to make your life easier. Desktop access to all your folders with one simple click.​​​​

​​​Hightail for Outlook​​

Add the power of Hightail to your email. Send large attachments the reliable way without leaving your mailbox. Windows XP or higher.

​​Hightail for Outlook (Beta)​​

Access all your Hightail folders right from your mailbox. Email large attachments the reliable way and automatically store files you receive. Beta release for Windows XP or higher.


Hightail Express sits on your desktop and springs into action with one simple click so you can send large files faster than ever.​​

Access the latest version of your document, presentation or video on your tablet to add ideas whenever inspiration strikes. Changes are instantly synced so you'll see them when you're back at your desk.​​

​​​​Get it done on the go​​​​

Access the latest version of your document, presentation or video on your tablet to add ideas whenever inspiration strikes. Changes are instantly synced so you'll see them when you're back at your desk.​​


​​It Starts with You​​

Hightail's mission is to revolutionize the way people share and store their life's work. We're looking for the right mix of talent, attitude and passion. We are a technology company built around engineers, developers and operations working in small, independent teams where everyone is expected to voice opinions and have a material impact.

Our number one priority is making Hightail a great place to work because we believe that great culture attracts great people who create great products. We like passionate, creative, wicked smart folks who take the initiative and don’t ever want to hand it back. If that sounds like you, and you want a career-changing experience in an exciting and growing industry, find your next great opportunity here.

To learn more about us, head over to our ​Hightail blog​.​​​


​​Brad Garlinghouse​​

​​Chief Executive Officer​​

​​​​​​​Brad believes that a truly successful company begins with its employees and the culture they build together as a team. Great people build great products and great people gravitate towards great company cultures.​​​​​​

It’s a philosophy that Brad has cultivated throughout his career, from management stints at SBC Communications and @Home Network to his time as CEO of Dialpad Communications. As a Senior Vice-President at Yahoo!, Brad was responsible for all of the company’s communications products. His transformation of that group’s culture gave teams ownership of their products and encouraged experimentation that led to notable successes, including both Yahoo! Mail and Yahoo! Messenger becoming the clear leaders in their respective spaces.

Most recently, Brad was President of Consumer Applications at AOL where he transformed its Silicon Valley operations, expanding the reach of its existing products and reinvigorating mobile and social strategy.

He holds a BA in economics from the University of Kansas and an MBA from Harvard.


​​​​Kiersten Hollars​​

​​Vice President, Corporate Communications​​

Kiersten’s golden rule of communications is: always be honest. It’s how she builds trusting relationships with the reporters, editors and publishers who will help her spread the Hightail story around the world.

Having spent her entire professional life in the Bay Area, Kiersten has naturally developed a strong tech industry network. It helped her when she was one of the first few dozen employees at PR startup OutCast Communications and when she took on the task of promoting Yahoo!’s tech credibility in a world dominated by Google. Kiersten’s strategies at Yahoo! were so successful, she was made Communications Director for all of Yahoo!’s communications products. Her love for the challenge of working for the underdog continued during a stint at AOL.

Most recently, Kiersten was a partner at Andreessen Horowitz, overseeing marketing for the venture capital firm’s portfolio companies.

Kiersten holds a BA in communications from St. Mary’s College of California.

​​Matte Scheinker​​

​​Chief Product Officer​​

Matte is driven by an obsession to understand the design decisions behind products and the specific human needs they represent. It’s a desire that guides his Hightail product strategy—every feature and experience his team creates must solve real problems.

His early days as an interaction designer at printing startup Liveprint showed him how truly empathizing with a customer’s needs is the key to building better experiences. After joining Yahoo in 2001 he started to look at the bigger picture, building teams that applied his user-focused philosophy to helping products like Yahoo! Mail and Messenger become the world’s leading communication tools.

Most recently, Matte was Vice President of Consumer Experience and Commerce at AOL where he was responsible for building and developing the product teams on key projects, including the redesign of TechCrunch and the launch of Patch user blogs.

Matte has a BA in Psychology from the University of Maryland.

​​​​Ned Sizer​​

​​Chief Financial Officer​​

Ned likes to say that he spends Hightail's money as if it’s his own. He wants everyone at the company to embrace the principle that every investment, large or small, must align with Hightail’s strategic, cultural and financial goals.

This fiscal discipline was honed during a decade at Ford Motor Company where Ned developed his finance leadership and analytical skills before a move to Siebel Systems gave him a first taste of the tech world. His ability to implement effective strategic planning frameworks and integrated systems enabled Ned’s next companies Macromedia and Omniture to scale and grow quickly, leading to his major roles in Macromedia’s acquisition by Adobe and Omniture’s successful IPO.

Most recently, Ned led finance and analytics at Ancestry.com, building a very successful performance based culture and facilitating the company’s private equity transaction.

Ned has a BA in History from DePauw University and an MBA in Finance from Miami University.

​​Eric van Miltenburg​​

​​Senior Vice President, Business Development, Corporate Development and International​​

Eric leads Hightail’s development charge with his unique ability to successfully connect businesses, people and things that at first glance don’t appear to be an obvious match.

This talent first became apparent when he began applying his traditional business school training to cultivate B2B relationships in the cutting-edge dot com world, starting in the 90s at NETCOM Online and later for @Home Networks. The value of his strategic insights and commercial connections brought Eric to Yahoo! where he led a number of key initiatives, including a groundbreaking long-term partnership with the leading U.S. newspaper consortium.

Most recently, he was Senior Vice President of Business Operations for AOL’s Consumer Applications Group, directing crucial monetization initiatives and the acquisition of innovative startups.

Eric has a BA in Mathematical Economics from Pomona College and an MBA from the Tuck School of Business at Dartmouth College.

​​Lynne Collins​​

​​Vice President, Human Resources​​

Lynne is on a mission to foster a company culture at Hightail based simply on love: you should love what you do and you should love where you work.

Throughout her career Lynne has made a real impact in the tech world and beyond through her exceptional ability to build a company's image and culture from the ground up. As a PR consultant she was instrumental in online retailer Overstock.com's meteoric rise from launch through IPO and onto billion-dollar business, before she moved into the recruitment world with boutique executive search firm Exceptional People Inc.

Most recently she was Head of West Coast Recruiting for AOL, partnering with some of Silicon Valley's most talented executives to build world-class teams amidst fierce competition from the industry's big players.

Lynne has a BA in English from California Polytechnic State University.

​​Abhay Rajaram​​

​​Vice President, Customer Success​​

Abhay loves to learn new things and knows that no one can teach him more about Hightail than its customers. Ensuring their voice is heard and problems are solved is what drives his Customer Success team.

His eclectic career includes engineering and marketing management positions at 3Com Corporation and Wipro Technologies before he became senior product manager at IronPort Systems. This array of experience and knowledge is invaluable in understanding how Hightail can meet the diverse needs of its customers.

Most recently, Abhay managed product operations, strategy, pricing and training for Cisco’s Security Technology Business Unit.

Abhay holds a BS in Computer Science from the National Institute of Technology, India and an MBA from the University of California at Berkeley.

​​Jeff Schmidt​​

​​Senior Vice President, Sales​​

Jeff builds teams with a transparent approach to sales. Long-lasting customer relationships are built on trust so a successful sales team is not only direct about your service’s benefits but also about how you deal with challenges.

This belief was confirmed during his time at IBM’s Coremetrics where customers routinely told him only his company actually delivered what everyone else promised. Never wanting to over-sell an average product has compelled Jeff to only work for best-in-class organizations, such as WebEx, Blue Pumpkin Software and Octel Communications.

Most recently, Jeff was Chief Revenue Officer at marketing intelligence firm, Pivotlink.

Jeff holds a BA in Speech Communications from California State University, Northridge.

​​Mike Trigg​​

​​Chief Marketing Officer​​

Mike manages all marketing, lead generation and e-commerce activity at Hightail.

His background includes a variety roles from start-ups to Fortune 500 companies across both enterprise and consumer segments. Prior to Hightail, Mike founded an online gaming company called Spitball Entertainment and was VP of marketing and business development at hi5 (sold to Tagged), one of the world's largest social networking sites, where he helped launch the company's games portal, virtual currency, and original social game titles.

Previously, Mike was VP of marketing and interim CEO of Spoke, a social networking site for sales professionals. He co-founded Truviso (sold to Cisco), a real-time web analytics provider. He also was VP of product management and corporate marketing at Epiphany, a leading provider of marketing analytics and web personalization (sold to Infor), and an early employee of Octane Software prior to the company's acquisition by Epiphany. Earlier, Mike held communications, marketing and product management positions at 3Com and MCI, and was a press secretary in the U.S. Senate. He is also a board member and past president of the Palo Alto Community Fund.

​​Mike holds a B.A. from Northwestern University and M.B.A from the University of California at Berkeley.​​​​

Hightail employees frequently join together in helping our community by fundraising and volunteering time to community projects.  Below are some of the community projects that Team Hightail has contributed to.

Family Supportive Housing

Family Supportive Housing provides a full spectrum of services to hundreds of people for whom overcoming poverty, hunger and homelessness is a daily struggle. Team Hightail split into two groups: one group helped in the kitchen to prepare dinner and other food prep for the rest of the week, and the other group organized the donations that they receive.


Loaves & Fishes Family Kitchen

Loaves & Fishes Family Kitchen is committed to providing no cost, hot nutritious meals and support services in a dignified, safe and caring environment. Team Hightail helped prepare and serve a nutritious meal to senior citizens and homeless individuals in the community.


Guadalupe River Park Conservancy

The Conservancy has already collected hundreds of pounds of debris from the Guadalupe River this season! Team Hightail collected 10 bags of trash, a shopping cart full of tires and a mattress! The river runs from Alviso to the Bay and by keeping the riverbank clean, we keep trash out of the Bay too. 



As a RAFT volunteer, everything you do helps to support educators and saves them time and money. The  Hightail team sorted and packed construction paper, numbers, letters and art material into packets, then assembled mini-Science projects using recycled items into a math-like bingo game & a space ship science experiment. They also cut gauze into 4 x 4 squares to help with another science project for the kids, whereby the the gauze is used to sift strawberry puree & collect DNA from it.  Cool stuff.


City Parks Dept of San Jose

We signed up to help make Vista Park clean and green with the City Parks Dept of San Jose. The park needed to be weeded and then have the new shredded bark spread out in the non-grassy area.  It was 3 hours of dusty, dirty hauling and raking, but they made a huge dent in this project for the park!


Hightail Reviews

81 Reviews
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Recommend to a friend
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Ranjith Kumaran
6 Ratings
  • Helpful (1)

    Meet the new boss, same as the old boss

    • Comp & Benefits
    • Work/Life Balance
    • Senior Management
    • Culture & Values
    • Career Opportunities
    Current Employee - Systems Administrator in Campbell, CA
    Current Employee - Systems Administrator in Campbell, CA

    I have been working at Hightail full-time (more than a year)

    Positive Outlook
    Approves of CEO
    Positive Outlook
    Approves of CEO


    Original founder Ranjith Kumaran has returned, cleared house at exec level, and laid off half of workforce. I label this a pro because major change was inevitable, and better to bite the bullet now rather than wait until the piggy bank is empty and the bubble has burst. Ironically, the company was spread too thin under Brad Garlinghouse, focusing on branding while the product went stagnant, growth went flat, and the tech organization operated without leadership, vision, or priorities. End result - a "lipstick on a pig" platform that is lagging behind the competition in terms of features, yet overly complicated and unreliable. It’s so bad that many employees recommend and prefer Dropbox or Google. Yeah, I said it.

    To the former CEO’s credit, he did build a positive culture that recognized top performers, and the company still can boast that it values employees, offers excellent benefits (401k match is the only thing missing), is light on politics, and offers two excellent locations in Campbell's Pruneyard or San Francisco's SOMA district. Hightail is currently doing a full product reboot, and believe it or not, there is reason to be upbeat on its future. In two years of working here, this is the first time I would recommend it to a friend.


    The middle management layer was purged in 2013, and this has created a very flat structure. While that’s refreshing in some ways, it also repeatedly creates situations where problems and responsibilities lack ownership and folks at the Director and VP level get overwhelmed. There’s also a long history of bad processes, sloppy or non-existent project management, over-promotion as means of retention, not to mention two acquisitions intended to add talent that really just created conflict. Despite the recent overhaul, most employees are complacent to these problems and it will take additional staffing changes to undo them.

    Advice to Management

    When hiring leaders, make sure they have people under them who can effectively champion projects and see them to the finish line. Otherwise, good ideas ultimately end up as junk in the tech debt pile.

Hightail Interviews

Updated Mar 30, 2015

Interview Experience

Interview Experience


Getting an Interview

Getting an Interview


Interview Difficulty


Interview Difficulty




    Software Engineer Interview

    Declined Offer
    Positive Experience
    Average Interview
    Declined Offer
    Positive Experience
    Average Interview


    I applied through a recruiter. The process took a weekinterviewed at Hightail (Campbell, CA) in March 2015.


    I applied via LinkedIn, and was approached by a recruiter and then scheduled a phone interview through the same recruiter.
    Next came the Phone Screen, general questions and several technical questions asked.
    After, another Phone Screen took place, and more technical questions asked.
    After, an onsite interview consisted of several different engineers you will be working with each asking different questions for 45mins each.

    Interview Questions

    • If you are applying as a Javascript Engineer, it will be necessary to review vanilla JS, scope, oojs, the use of popular js libs, css, sass, angular, html   Answer Question

Hightail Awards & Accolades

Something missing? Add an award
Top 100 Companies, OnDemand, 2013
HOT 100, JMP Securities, 2013
Nominee, Webby Awards, 2012
Deloitte Technology Fast 500™, Deloitte, 2012
Gold Award, Stevie Awards, 2012
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Additional Info

Website www.hightail.com
Headquarters Campbell, CA
Size 50 to 149 Employees
Founded 2004
Type Company - Private
Industry Information Technology
Revenue $10 to $25 million (USD) per year

Hightail's mission is to revolutionize the way people share and store their life's work. Founded in 2004, Hightail was working in the cloud before the term was even coined. At first our service (then called YouSendIt) was a simple way to send the large attachments that email couldn’t process, but we’ve since grown to offer robust online file storage, sharing and management capabilities to more than 43 million customers.

We are a technology company built around engineers, developers and operations working in small, independent teams where everyone is expected to voice... More

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