Who We Are

Executive Team

Sam Shank


A travel-obsessed serial entrepreneur, Sam previously founded and was CEO of DealBase.com, a travel deals search engine, and was CEO of TravelPost.com, a hotel reviews site. SideStep acquired TravelPost.com and Sam stayed on as VP of business development until its fortunate acquisition by Kayak. Sam also worked in comparison shopping at Excite, CNET and NexTag. Not at all surprisingly, he was an assistant to Wes Craven on the film Scream. He HotelTonights at the Ace New York.

Jared Simon


The office’s music police chief, Jared oversees supplier relations and operations. He previously was VP of corporate development at online-video production and distribution pioneer TurnHere. He also helped launch the hotel business at Orbitz.com and served as general manager of the company’s Lodging.com brand. Before he realized life was supposed to be enjoyable, he worked in corporate finance and investment banking at Credit Suisse First Boston and Budget Group, Inc. He HotelTonights at the Hollywood Roosevelt.

Chris Bailey


A master in the art of proper espresso preparation, Chris built HotelTonight’s first iOS app and backend systems, and continues to drive architecture and strategic technology. He was previously CTO of DealBase and prior to that, architect and senior computer scientist at Adobe Systems. He has led many engineering teams, been involved with several startups, and done a variety of consulting. He HotelTonights at Hotel Zetta in San Francisco.

Sam “Mac” MacDonnell


A builder of technology and teams that deliver innovative mobile experiences since before mobile was cool, Mac was previously Director of Engineering for Core Technology at Autodesk. He also managed and architected mobile services at Adobe and Macromedia. Realizing early on that he was not going to make the PGA Tour, he earned his coding stripes at various startups and companies developing connected services in gaming, mobile, aerospace and telecom. He HotelTonights at the W in San Francisco.

Tony Grimminck


An avid cyclist and champagne backpacker who has roamed through 5 of the continents, Tony focuses on driving profitable growth at HotelTonight. He previously was the Senior Director of Finance, Strategy and Corporate Development at StubHub, an eBay Company and prior to that an investment banker at Goldman Sachs and J.P. Morgan. Tony started out his career as an officer in the Australian Army getting a taste of alternate lodging whilst on operations in Africa, East Timor and the Middle East. He HotelTonights at Farmhouse Inn in Sonoma.

Ray Elias


An avid snowboarder and runner, but not at the same time, Ray is responsible for brand, communications, customer acquisition and customer retention. Ray was previously CMO at StubHub, acquired by eBay in 2007, and led search marketing at Esurance, which was acquired by Allstate in 2011. He was named “40 Under 40” by Sports Business Journal in 2013. He began his career in the late nineties with early stage Internet start-ups in the Action Sports and Health and Fitness verticals. He HotelTonights at h2 Hotel in Healdsburg.

Karen Klein


Karen took the leap from tech company lawyer to travel company lawyer in 2001 and hasn’t looked back. After taking Orbitz through multiple sales and a second IPO, she joined Kayak.com where she had fun helping build the business, completing another IPO and selling the company to Priceline. When she isn’t lawyering she travels to as many beaches as possible with her family and is a diehard fan of her beloved Packers and Badgers. She HotelTonights at Cavallo Point Lodge in Sausalito.

Amanda Richardson


Amanda heads up Data and Strategy at HotelTonight (when she’s not daydreaming about becoming a travel writer). Previously a Blockbuster shelf-stocker, hedge fund analyst, SVP Product at Snagajob, and Head of Product and Design at Prezi, Amanda loves making users happy and inspiring them to have great adventures. She HotelTonights at Calistoga Ranch (and any hotel that welcomes her Wheaten Terrier, Finnegan).

Amir Segall


A multilingual world citizen and music and football (soccer) fanatic, Amir divides his team between our offices around the world leading our international operations and growth efforts. Before joining HT, he held several leadership positions in fast-growing web companies, such as Operations Director for Western Europe at Groupon and Co-Founder and Managing Director of Zalando France. Prior to that he was also a management consultant and an officer in the Israeli Air Force. He HotelTonights at the Hoxton Holborn in London.

Jeff Ehrenberg


Jeff is focused on creating phenomenal experiences for people at work. At HotelTonight he leads the People Team and is responsible for creating an experience that attracts, develops and continually motivates the team to achieve big things through a focus on HR, technology and places. Jeff's prior experience in HR was at Google, where he built out several divisions from the ground up, and at IBM. He HotelTonights wherever his current mood compels him to go.

Kalpana Chandrasekhar


Kalpana heads up Customer Experience at HotelTonight where she focuses on delighting our customers. Previously, she worked in consumer insights marketing at American Express in New York, and then joined SurveyMonkey to help build out their enterprise businesses in San Francisco. When she's not working, she's hiking, baking, karaoking or planning her next international trip. She HotelTonights at any place she hasn't been before.


Board Members & Advisors

Brian O’Malley


Brian is a partner at Accel Partners, where he focuses primarily on internet and software investments. Prior to Accel, Brian spent 10 years at Battery Ventures where he originally led the seed round at HotelTonight. While at Battery, Brian was involved in the IPOs of Bazaarvoice (BV) and Skullcandy (SKUL), while also leading several investments in the mobile ecosystem besides HotelTonight, including Prismatic, Sosh, Sprig and Viddy.

Rick Lewis


Rick is a General Partner at USVP, focusing on software, mobile and e-commerce businesses. He has been involved in over a half-dozen successful exits at USVP including Instantis (acquired by Oracle), MeetMe (NASDAQ:MEET), Trunk Club (acquired by Nordstrom), Trusteer (acquired by IBM), Victrio (acquired by Verint) and Yammer (acquired by Microsoft). Rick currently serves on the boards of leading software companies like Act-On Software, ThreatMetrix and Wayin, and innovative consumer services companies like Pluto TV and Primary.com.

Roger Lee


Roger invests in great entrepreneurs building innovative companies across the software and consumer landscape. His investments include Angie’s List (IPO), Blue Jeans Network, BlueKai, FreeWheel, Gainsight, Groupon (IPO), Kontagent, Lotame, Narrative Science, PrimeRevenue, TrialPay and World Golf Tour. Before joining Battery as a general partner, Roger spent 10 years as an entrepreneur and operator. Most recently, he was co-founder of Corio, a leading managed service provider that was acquired by IBM.

Amy Bohutinsky


Amy is chief operating officer of Zillow Group, a portfolio of the largest and most vibrant real estate and home-related brands on Web and mobile, including consumer brands Zillow, Trulia, StreetEasy and HotPads.

As chief operating officer, Amy oversees Zillow Group’s people organization (HR, recruiting and learning & development), as well as marketing, communications and consumer care. Amy joined Zillow pre-launch in 2005, as one of the company’s earliest employees, and built the marketing and communications functions from the ground up. Prior to becoming COO, Amy served as Zillow Group’s chief marketing officer, leading brand strategy, growth, marketing and consumer care for the company’s flagship Zillow brand.

Before Zillow, Amy was on the founding team at discount travel site Hotwire, where she ran communications. Amy began her career as a broadcast journalist, working for various CBS, NBC and ABC affiliates.

Howard Love


Howard is a life-long entrepreneur who has been starting and running companies for almost 30 years. Among them: Inmark Development (RogueWave), MarketHome (CLAC), GetawayZone (EXPE), PageWise (Demand Media), FlexJobs.com and LoveToKnow.

Barry Sternlicht


Barry is the founder, chairman and CEO of Starwood Capital Group, the private investment firm focused on global real estate, hotel management, energy, infrastructure and securities trading. During his previous tenure as CEO of Starwood Hotels & Resorts, he created W Hotels and built the St. Regis Hotels brand from a single hotel to a global brand.




Battery strives to invest in cutting-edge, category-defining businesses in markets including software and services, Web infrastructure, consumer Internet, mobile and industrial technologies. Founded in 1983, the firm backs companies at stages ranging from seed to private equity and invests globally from offices in Boston, the San Francisco Bay Area and Israel.


Founded in 1983, Accel Partners is a leading venture capital and growth equity investment firm, working with entrepreneurs to build world-class businesses. Accel manages over $6B globally using dedicated teams and market-specific strategies for local geographies, with offices in Palo Alto, London, New Delhi, Bangalore and China, through a partnership with IDG-Accel. Accel has helped entrepreneurs build over 300 successful companies, many of which have defined their categories, including Facebook, Groupon, Comscore, AdMob, Diapers.com (Quidsi), Glam Media, Etsy, Kayak, Angry Birds (Rovio), Macromedia, MetroPCS, Playfish, QlikTech, Rapt, Real Networks, Redback Networks, Riverbed, SunRun, UUNet, Veritas and Walmart.com, among others.


First Round Capital is a seed-stage venture capital firm dedicated to helping talented entrepreneurs build great companies. First Round Capital’s portfolio is a community of web-enabled businesses led by entrepreneurs, guided by an active partnership and connected through a technology platform designed to support companies throughout their growth. The firm’s current portfolio includes StumbleUpon, OneKingsLane, Bazaarvoice, Modcloth, RockMelt, Uber and Square. First Round Capital invests nationally with offices in San Francisco, New York and Philadelphia.


U.S. Venture Partners (USVP) is a leading Silicon Valley venture capital firm, partnering with entrepreneurs to transform their ideas into world-changing companies. USVP has invested in over 400 companies spanning three decades, including: Box, Castlight Health, Check Point Software, Concur, GoPro, Guidewire Software, HotelTonight, Imperva, InsideSales.com, Intersect ENT, Omada Health, OncoMed, SanDisk, Sun Microsystems, Trunk Club, Trusteer, Yammer and Zerto. USVP focuses on early-stage start-ups that transform cybersecurity, enterprise software, consumer mobile and e-commerce and healthcare. The USVP team consists of former entrepreneurs, technologists, corporate executives and financial professionals who assist with strategy, scaling, team building, product development and business development. USVP is based in Menlo Park, California.


Coatue Management is a global investment manager with approximately $7.5 billion under management focused on public and private companies in the technology, media and telecommunications industries. Founded in 1999 by Philippe Laffont, Coatue has offices in New York City and Menlo Park.


GGV Capital is a $1.6 billion expansion stage venture capital firm focused on the US and China. Based in Silicon Valley (Menlo Park) and Shanghai, China, the firm operates as a single team across the world’s two largest economies. GGV portfolio companies include Alibaba Group, AthenaHealth, Buddy Media, Isilon, Meilishuo, Pandora Media, Qunar, SoundCloud, Square, SuccessFactors, Youku/Tudou, UCWeb, YY and 21ViaNet.

Rich Barton


Co-founder and executive chairman of Zillow, Rich also served as CEO from 2005, when the company was founded, until September 2010. Before co-founding Zillow, Rich founded Expedia.com. Started within Microsoft in 1994 and spun out in 1999 as a public company, Rich served as president, CEO and board director until 2003. Rich also co-founded and serves as non-executive chairman of Glassdoor.com and is chairman of Trover LLC. Rich is also a venture partner at Benchmark Capital and is on the boards of directors of Netflix, Avvo, RealSelf.com and CommonSenseMedia.Org.

Hugh Crean


Currently an entrepreneur in residence at General Catalyst Partners, Hugh was president and CEO of Farecast, which was acquired by Microsoft in 2008. Hugh joined the Microsoft search team as general manager/principal engineering manager, focused on the development and launch of Bing Travel. Before Farecast, Hugh was senior vice president of business development at National Leisure Group (NLG), vice president of product and corporate development at Priceline and vice president of strategic analysis for Citigroup’s Advanced Development/e-Citi division.

Erik Blachford


Currently Venture Partner at Technology Crossover Ventures, Chairman at Butterfield & Robinson, Inc. and executive chairman at TerraPass, Inc., Erik was formerly the chief executive at TerraPass, Inc., Expedia, Inc. and IAC/InterActiveCorp’s travel division, IAC Travel. Erik currently serves as a board director at Butterfield & Robinson, TerraPass, Zillow and Glassdoor.com.