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City Sky

Team

Core Team

The core team brings deep expertise in digital trust and financial services, complementary skills/networks, and demonstrated operating acumen in building and operating successful businesses with decades of combined experience. 

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Jackie Shoback

Jackie is a seasoned C-Suite executive [CEO/CMO/COO] & operator with deep expertise in Financial Services, Go-to-Market, & Consumer Products. 

  • LinkedIn
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Howard Hall

Howard is a former serial tech entrepreneur and subject-matter expert on Digital Identity, Payments, Strategy and Corporate Development.

  • LinkedIn

Venture Partners & Advisors

Bringing a broad range of skills and experience, our venture partners & advisors drive a

high confidence in our portfolio selection as well as the success of our portfolio partners. 

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Claire Wadlington 

Claire has deep expertise with startup ventures and venture capital funds and merger & acquisition experience both as an investor and as a management team principal.

  • LinkedIn
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Mike Engle

Michael is a seasoned information technology executive and entrepreneur with expertise in Information Security, Business Development, and Product Design/Development. 

  • LinkedIn
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David Birch

Internationally-recognized Thought Leader in Digital Identity and Trust, Author of the Seminal “Identity is the New Money.”

  • LinkedIn
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Eve Maler

Globally-recognized Strategist and Author on Digital Trust/Identity, Security, Privacy, and Consent; President of Venn Factory, Former CTO of ForgeRock.

  • LinkedIn
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Matthew Thompson

Identity Industry Innovator and Security Expert with experience founding and leading New Identity Solutions; President at Socure; Former President and Cofounder of ID.me.

  • LinkedIn
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Chitra Nayak

Board Member, Infosys, Vimo; BCG Executive Advisor, Former COO Platform at Salesforce, Comfy, Funding Circle.

  • LinkedIn
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Andrew Shikiar 

Market development leader in Identity Management & Authentication;
Executive Director, FIDO Alliance.

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Clay Deutsch

Former CEO at Boston Private;

Financial Institutions Leader at McKinsey; Advisor/Investor With Multiple Pre-IPO Startups.

  • LinkedIn
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Luis Davila

Early Stage Operator with Cybersecurity; Enablement of High-Growth Digital Identity Companies; CEO at CTI Global.

  • LinkedIn
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Bart Van Rhijn

CFO at Nanobiotix; Serial Finance Executive with a Focus on Life Sciences and Healthcare.

  • LinkedIn
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William Carey 

Former CEO of AGF Investments US; Former President at Fidelity Retirement Co.; Institutional Wealth Services.

  • LinkedIn
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Jim Wodarski

Member at Mintz Levin (IP);

Patents and Intellectual Property.

  • LinkedIn
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Address

1380 Soldiers Field Rd Suite #3900

Boston, MA 02135, USA

Email

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© 2026 by 1414 Ventures. A Digital Trust Focused Firm

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