Our focus

Intelligent sales acceleration

Ensight partners with insurance carriers and national distributors to provide next-generation SaaS based sales and data acceleration platforms that make selling insurance simpler, more profitable & a better customer experience.

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Get to know the team

Nothing works better than just improving your product.

About Bill

Prior to Ensight, Bill was a leader in the San Diego venture capital (VC) community with Tech Coast Angels, acting as an investor, board member, and advisor for several businesses in the cyber security, consumer product, and communications technology sectors.

As CEO of Anonymizer (2000-2011), Bill led the firm in the cyber security sector, providing subscription services to the U.S. government and large enterprise customers for online covert communications and non-attribution/identity services for cyber operations against opponents such as foreign opponents, terrorists, and hackers.

Innovation is the ability to see change as an opportunity - not a threat.

About Matt

Over the past decade, Matt has led various marketing divisions and strategy/innovation programs at global financial services provider Zurich Insurance Group, a market leading commercial property & casualty carrier in the insurance sector. He has led critical strategic marketing and business strategy projects across the Consumer, Small Business, Corporate Enterprise and Public Sector markets. 

Prior to Zurich Insurance, Matt spent a decade in Silicon Valley, leading marketing for two network security start-ups focused on Virtual Private Network (VPN) and digital certificate based authentication services. Matt has a B.A. in Literature & Economics from Boston College, an M.B.A. from London Business School (LBS), and an M.A. International Relations from the London School of Economics (LSE).

To create, one must first question everything.

About Heidi

Prior to joining Ensight, Heidi spent 14 years overseeing Life and Annuity sales and operations for Simplicity Life, with an expertise in defining Life and Annuity product offerings, pricing strategies and go-to-market models that drive profitable growth.

She has been a driver of critical organizational strategy and implementation with an emphasis in building highly effective teams in operations, finance, sales and distribution, and product marketing. She is passionate about collaborating with key stakeholders to optimize the business process and technology stack to ensure a seamless customer journey.

We cannot solve a problem by using the same kind of thinking we had when we created them.

About Tim

Tim has over 20 years of experience building and taking to market innovative enterprise software products. His emphasis has been on data intensive and analytics based solutions within the financial services, telecommunications, and insurance industries.

Tim started his career as a software engineer developing real-time transactional fraud solutions. Prior to joining Ensight, he has worked in various business and technical roles at both startups and large corporations, including FICO/HNC Software, Visa Europe, Opera Solutions, and Renovate America.

Change within an industry is never comfortable, but it’s always inevitable.

About Ryan

Ryan has a broad background across technology startups and the financial markets. He started his career in the New York area as an analyst at an investment bank and a hedge fund. He eventually relocated to California and become involved with several technology startups, in both founding and consulting roles.

He has extensive experience across marketing, analytics, sales, finance, strategy and operational functions. He holds a B.S. in Economics from the State University of New York.

current role
  • Chairman, President, and Chief Executive Officer of American Assets (NYSE: AAT)
  • Founder and Chairman of the Board of Insurance Company of the West (ICW)
  • Chairman of the Dean’s Advisory Council of the Rady School of Management, UCSD
previous roles
  • Chairman of Western Financial Bank (1982-2006)
  • CEO of Western Financial (1994-1996; 1998-2006)

About Ernest

Throughout his career, Mr. Rady’s business leadership has been leveraged in a number of endeavors and affiliations. His interests have spanned ownership positions in a range of categories, including beverage wholesaling, radio stations/ telecommunications towers, oil and gas. Mr. Rady has significant experience serving on boards of both U.S. and Canadian companies. He has been both an entrepreneurial and philanthropic leader of his adopted community and state. He owns and has invested in an array of California-based businesses employing thousands. His charitable endeavors have focused on education, the health and well being of children, and scientific research.

current role
  • CEO of Rady Asset Management
previous roles
  • Senior Portfolio Manager of Rady Contrarian Long/Short Fund
  • Senior Portfolio Manager of Long-Only Rady Opportunistic Fund
  • CEO of MyOwnCIO

About Harry

Harry was the Senior Portfolio Manager of the Rady Contrarian Long/Short Fund and the Long-Only Rady Opportunistic Fund that was ranked in the top 1% by PSN Informa for the 1-, 2-, 3-, 5-, and 15-year periods in the Large Cap Value space.  He was also CEO of MyOwnCIO – an outsourced Chief Investment Officer service for ultra-high net worth investors.  Prior to establishing Rady Asset Management, Harry served as the CIO of a multi-billion dollar financial, investment, and real estate conglomerate.  He was also an investment analyst at a quantitative hedge fund.  Harry serves on the board of trustees and is Chairman of both the Investment and Information Technology committees for Rady Children’s Hospital.  He is also on the Board of Directors of the Rady Children’s Institute for Genomic Medicine.  Harry is a member of the Dean’s Advisory Council for the Rady School of Management at UCSD.  Harry is also a member of the UCSD Foundation Board of Trustees.  He is also a frequent guest on CNBC and is regularly interviewed by Barron’s, Forbes, WSJ, and other financial publications.  Harry received his MBA from the University of Southern California.

current role
  • Board member of KinderCare Education, Rosetta Books, and Ensight
  • Advisory Board to Julius, Thuzio, and MD Revolution
previous roles
  • Chairman of the Board and CEO of Vistage International (2004-2013)
  • CEO of Hoyts Cinemas Corporation
  • President of USA Networks International
  • Executive VP, International, of News Corporation and Fox Television International
  • President of CBS/Fox Video International

About Rafael

Rafael Pastor has an extensive and diversified track record in both running successful businesses and advising business leaders. His career has spanned the media/entertainment, education, and business/financial services sectors. He now serves on a variety of Boards and as an Advisor.

Rafael started his career as an attorney, first at the Wall Street law firm of Hawkins, Delafield and Wood and then as Associate General Counsel at CBS Inc. He earned a BA from Columbia University and a JD from NYU School of Law.

current role
  • Executive Chairman of tab32
previous roles
  • Director of Community Dental Network
  • President and CEO of First Dental Health

About Michael

Dr. Grossman founded the first dental preferred provider organization in California, was director of Community Dental Network, and President of Dimension Dental Services. He was also founder, President, and CEO of First Dental Health, developing an innovative fee-for-service point of service platform. First Dental Health was sold to Principal Financial Group in 2012. Today, Dr. Grossman is the Executive Chairman of tab32, the #1 free cloud based dental software and practice management company.

current role
  • Independent Senior Advisor, Deloitte Center for Regulatory Strategies
  • Member of the Board of Directors of The Doctors Company
previous roles
  • Managing Director and Global Insurance Regulatory Leader, Deloitte
  • Superintendent, New York State Insurance Department
  • Member, New York State Assembly and Deputy Minority Leader

About Howard

Howard Mills is a retired Deloitte Managing Director and Global Insurance Regulatory Leader and currently serves as a Senior Advisor at the Deloitte Center for Regulatory Strategies. Prior to joining Deloitte in 2007, Mr. Mills served as Superintendent of the New York State Insurance Department. During his tenure as Superintendent, he led the Department’s transition to conducting risk-based examinations, was a leader at the National Association of Insurance Commissioners on issues such as principles-based reserving for life insurance companies, terrorism risk insurance and disaster preparedness. He was active at the International Association of Insurance Supervisors, was a member of the Presidential Financial and Banking Information Infrastructure Committee, served as co-chair of the International Commission on Holocaust Era Insurance Claims and testified before Congress on matters impacting the insurance industry. Mr. Mills is a Governance Fellow at the National Association of Corporate Directors and has over 30 years of experience serving on the boards of numerous not-for-profit organizations.

Currently, he serves on the Board of Directors of the Insurance Federation of New York and as a Trustee of the Griffith Insurance Education Foundation. Mr. Mills was elected to three terms in the New York State Assembly and rose to become the Deputy Minority Leader. He was also elected to three terms as Supervisor of the Town of Wallkill, NY. He has been an adjunct instructor of political science at Mount Saint Mary College and Orange County Community College. Mr. Mills earned a Bachelor of Arts degree in political science from Marist College and a Master of Arts degree in public administration from The American University. He completed a one-year non-degree course of study in politics, philosophy, and economics at Mansfield College, Oxford University.

current role
  • Managing Director & Co-founder of DaggerBoard Advisors
previous roles
  • CEO of Ad-Juster (2017 - 2020)
  • President of Content Monetization at NetSeer (2013-2017)
  • Executive Vice President at Software Equity Group (2010-2013)
  • CEO of Alignent Software (2004-2007)
  • CEO & Co-founder of Cardiff Software (1991-2004)

About Dennis

With over 25 years’ experience in the software industry as an executive, advisor and entrepreneur, Dennis has made a major impact at many emerging tech companies with four successful exits in his career. Dennis has unique expertise in combining technology with go to market strategies across a wide array of software companies.

Dennis brings an unparalleled track record of building, growing and transforming B2B SaaS companies and a unique combination of expertise in areas such as business strategy, implementation, market strategy, product development and financing. He has an uncanny ability to identify and establish long rewarding products and sales relationships.

As an accomplished CEO, Dennis has been successfully operating in a highly entrepreneurial mode, while remaining focused on customer needs, business fundamentals and ROI.

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