Lylan MastermanNew York, New York, United States
Bio
Learn more about Lylan at www.lylan.com The "y" in Lylan is pronounced as a hard "i", so Lylan is: - L + island 🏝 , but without the d at the end or equivalently: - Lion 🦁 , but add an L between the two syllables (both descriptions should give you the same pronunciation) Lylan is an experienced operator, investor, and board member. As an investor over the last six years, Lylan has been a Principal, General Partner, and Venture Partner at White Star Capital and an Executive in Residence at Breakaway Growth. He has served as board member, observer, and advisor at several startups -- Drop Loyalty, Unacast, mnubo, Salesfloor, Immunio, Digg -- as well Raines International, a 50 year old executive search firm. Lylan previously led Product and Engineering organizations in his 15-year operating career, and most notably worked 4.5 years at aQuantive, acquired by Microsoft for $6.3 billion. Lylan is a Kauffman Fellow, an educational, networking, and leadership development program for venture capitalists. He is a first-generation high school & college graduate and holds a degree in Computer Science from the University of Waterloo and an MBA from Kellogg School of Management. Lylan has lived in Canada, and the east and west coasts of the US and has called New York home since 2011. Lylan has appeared on live TV on Cheddar and TDAmeritrade Network, has been interviewed in Inside The Mind of a New York VC, his writing has been featured in Business Insider, VentureBeat, Entrepreneur, and Thrive Global, and he has been interviewed in the podcasts Something Ventured, Venture Studio, and The Successful Pitch. In 2019, Lylan was selected as one of New York City's Top 50 NYC Movers & Shakers in technology and in 2020, Lylan was invited to the Quebec Government in New York's 80 for 80.
Social
Experience
Board Advisor
Raines International Inc.
May 2020 - Current
Angel Investor
Self-employed
May 2020 - Current
Venture Capital Fellow
Society of Kauffman Fellows
Jul 2014 - Current
The Fellowship has a world-wide network of innovation investors who provide smart, connected capital to fuel entrepreneurial change.
Venture Partner
White Star Capital
May 2020 - Dec 2020
General Partner
White Star Capital
Feb 2018 - May 2020
White Star Capital helps exceptional entrepreneurs build great technology companies. With a presence in Europe and North America and a truly global network, we invest in great teams and support them to scale globally.
Board Member
Unacast
Feb 2018 - May 2020
Unacast is the leading transparent and contextualized location data platform. We empower companies to make smarter decisions and build better products by providing the most accurate understanding of human activity in the physical world through the Real World Graph®. We believe that democratizing access to data is the currency of innovation, and we're on a mission to fix inaccurate and unverified location data to deliver unparalleled transparency and accuracy to our partners. Unacast is based out of NYC. Co-founders Thomas Walle and Kjartan Slette were also part of the founding team behind TIDAL, the music streaming company acquired by Jay-Z. Unacast has been awarded multiple awards for its platform, campaigns and company growth and culture.
Board Member and Observer
Salesfloor
Jun 2016 - May 2020
- Salesfloor has grown to a profitable technology platform with a world-class client base in North America and around the globe. We provide a mobile clienteling and mPOS platform designed for store associates. Our solutions empower associates to provide personalized service both in-store and online, improving the customer experience across all channels. With over 45,000 associates from leading retailers in apparel, beauty, jewelry and baby/toys, we are redefining the role of store associates."
Board Member and Observer
Digg
Apr 2016 - May 2020
I served on the board of Digg following its Series B, including a change of CEO and its acquisition.
Board Observer
IMMUNIO
Mar 2016 - Nov 2017
Immunio was acquired by TrendMicro in 2017 Immunio is a pioneer in real-time web application security (RASP), providing automatic detection and protection against application security vulnerabilities
Board Member and Observer
Drop
Oct 2015 - May 2020
Drop's last round was a $44m round. - At Drop, we’re on a mission to level-up consumer lives, one reward at a time. Through our personalized commerce platform, we intelligently surface the right brands, at the right time, to make our members’ every day a level better than it was before. Powered by machine learning, we match consumers with our over 300+ partner brands to satisfy two main goals: to earn points from their purchases and redeem them for instant rewards. Calling Toronto home but operating under a global mindset, Drop is building the next level experience for our 3 million+ members across North America, and most recently, the UK. Drop is comprised of top-tier, passionate, and diverse talent from a wide range of professional backgrounds, including fellow startups like Ritual and Shopify, to Fortune 500 companies like Amazon, Microsoft, Goldman Sachs, and Airbnb. We’re backed by top venture capital firms from Silicon Valley, as well as Canadian and global funds who’ve invested in now-household names, including Dollar Shave Club, Robinhood, Groupon, Snapchat, and more. We move quickly, but always ensure every voice at Drop is heard. Our culture is shaped by passion, hustle, and people who actually enjoy coming into work every day. Join us in revolutionizing personal commerce and building a next level rewards experience for everyone."
Board Observer
Mnubo
May 2015 - Feb 2018
In July 2019, mnubo was acquired by Aspen Technology Mnubo’s platform was designed to allow users to receive insights from IoT data captured from sensors, devices, machines, and equipment. Through its platform, users can view, manipulate, and analyze IoT data to build insights by training AI and machine learning models, using its IoT-specific libraries, and productizing results using the platform’s API and user interface.
Principal
White Star Capital
Jul 2014 - Feb 2018
White Star Capital helps exceptional entrepreneurs build great technology companies. With a presence in Europe and North America and a truly global network, we invest in great teams and support them to scale globally.
Technology Executive
New York City startups
Oct 2011 - Jun 2014
In 2011, I saw the the beginnings of a hockeystick in NYC's technology ecosystem. I moved to NYC and led multiple job functions, including Product, Engineering, User Experience, Ops, Documentation at three NYC startups: DoubleVerify, Maxifier, and StrikeAd. At each company, I worked with and at times managed international engineering teams spanning Tel Aviv Israel, Samara Russia, and Kiev Ukraine.
Venture Capital Senior Associate (summer)
Sierra Ventures
Jun 2009 - Aug 2009
As a Venture Capital summer senior associate, I sourced new investment opportunities, was an observer at board meetings for 2 digital media portfolio companies, and created a tool to help the firm identify startups that were gaining market traction.
Senior Program Manager
aQuantive
Mar 2004 - Aug 2008
- Co-led launch & growth of entrepreneurial first-version “Rich Media” product to 10% of division revenues ($15M of $150M) - Spearheaded software globalization & internationalization of flagship “Media Console” product. Project, when complete, had potential to generate revenues equal to US yearly revenues of $150M (prior to Microsoft's acquisition and change of our priorities) - Asked by management to take over leadership of underperforming “Customer Targeting” product team that had released 6 months late. Transformed team to exceed expectations and deliver on time - Defined user interface changes to Targeting product yielding 500% increase client productivity - Created new user interface model for redesign of division’s 8 products. Led cross-functional team of 15 to consensus on new model - Developed expertise in Agile practices, became a certified ScrumMaster by Ken Schwaber, trained on XP by Ron Jeffries, trained on Agile testing by Jim Shore, Agile estimation by Mike Cohn, discussed Agile UX with Jeff Patton - Consistently led the activities of 8 to 25 software developers
Program Manager
AskMe Corporation
Jan 2003 - Mar 2004
AskMe was a startup that created enterprise software that is known as an Employee Knowledge Network (EKN), similar to what Slack is today. We won several awards: "most promising company", "100 companies that matter", "newcomer of the year", and a big cover picture and article on the cover of the Seattle Times business section. Highlights: - Responsible for designing enterprise software in employee knowledge management and data mining to Fortune 500 companies - Reporting directly to CTO/co-founder, performed a complete redesign of flagship product
Program Manager
Microsoft Corporation
May 2000 - Nov 2002
I had 3 different jobs at Microsoft. Job #3: Program Manager for Visual Studio .NET Academic - Led the creation of Visual Studio add-ons and ASP.NET client-server applications to make it more appealing for colleges and universities to switch from Java to C# and .NET - Co-authored with a lawyer a new “shared source” license agreement - Active team player in defining strategy to encourage high schools to change their AP program from Java to J#. Job #2: Evangelist/Student Consultant for Microsoft Research - Evaluated students’ entrepreneurial projects and funded select projects with software and hardware - Presented first-version & beta products (VS .NET Beta, Embedded Developer Tools) at tech talks Job #1: Developer (co-op) in the California office for WebTV. - Led, designed, and developed in C++ a new feature for WebTV
Software Developer (Co-op)
Cypress Semiconductor
Aug 1999 - Dec 1999
Developed in C++ an application that updates clients' versions of Cypress Software
Software Developer (Co-op)
IBM
Jan 1998 - Apr 1998
Part of the Visual Age for Java (now Eclipse) team at Dave Thomas's OTI Labs, worked on the Simple Widget Toolkit (SWT) API
Little League Baseball Umpire
Little League International
1990 - 1996
This was a joy! From umpiring t-ball games all the way up to the Canadian national Little League Championship game. I was also promoted to a management role -- I'm not sure what title to use -- where I determined staffing of all games. One of the umpires was my father so I was, in effect, my dad's pseudo-boss :)
Education
Center for Venture Education
Kauffman Fellow, Venture Capital
Kauffman Fellows
Class 19, Venture Capital
Northwestern University - Kellogg School of Management
MBA, Venture Capital, Entrepreneurship, Finance
University of Waterloo
B.Math, Computer Science
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