Neil Wainwright

Trailblazer
DISC Type : ID

CEO at CiraSync

Toronto, Ontario, Canada

Overview

Neil Wainwright is a serial entrepreneur and the CEO of CiraSync, with over 30 years of experience in technology leadership at firms like IBM and Lotus. He is also the founder of UpHabit, a relationship management app. He holds a BSc in Electrical Engineering from Queens University and is a mentor at the Creative Destruction Lab.

Outside of his professional roles, Neil is a husband, a father to three children, and an owner of two dogs. He has a keen interest in consumer technology and user interface design, particularly within the automotive space, and is a passionate advocate for products that offer a seamless user experience.

He contributed a chapter on CRMs to a book focused on accelerating startups, sharing his lessons learned with other entrepreneurs.

Personality Overview

Achievement-Oriented

Persuasive

Charismatic

They will bat for you if they come to believe in you.  They prefer to ensure that they are in control of the situation. They are charming and can persuade others to support their decisions.

Topics They Care About

Enterprise Productivity
As CEO of CiraSync, he focuses on solving foundational business challenges like syncing contacts, calendars, and notes across enterprises to improve efficiency.
Relationship Management
He founded the UpHabit app to help professionals develop and nurture their network after personally experiencing the challenge of losing contact with 2, 000 accounts.
Startup Mentorship
As a founder and associate at the Creative Destruction Lab, he actively coaches and mentors the next generation of Canadian entrepreneurs.

Media Appearances

Neil has no verified media appearances

Work History

6-2024
CEO at CiraSync
10-2017
Founder, CEO at UpHabit
9-2017
G7 Founder & Associate at Creative Destruction Lab
9-2016
CEO at Tech CEO & Associates
3-2017 - 9-2024
Board Member at Peerscale

Education

1980 - 1984
BSC from Queen's University

More Information

Social Presence :

Prographics :

Exp : 9 Location : Toronto, Ontario, Canada Job Level : Leadership Designation : CEO at CiraSync
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Insights For Selling To Neil

During A Call Or A Meeting

DO's

  • Build a trustworthy relationship while keeping the product center-stage
  • Keep your pitch focused on the impact but nurture the relationship too
  • Display high self-confidence and expect them to have a strong personality.

DONT's

  • Don’t force involvement of other stakeholders unless it is critical
  • Do not look like someone who doesn’t know what they are talking about
  • Avoid unnecessary negativity or slowness

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Neil is

  • Relationship and product conviction matter equally, followed by a sense of achievement.
  • Will you ever get a clear answer from Neil

  • If they are not convinced, they will say no though in a friendly way.

Insights For Deal Planning

    How fast (or slow) will Neil move?

  • They can make decisions quickly if they develop trust in you and conviction in the product.
  • Can Neil take some risk or not?

  • If necessary, they will be ready to take risks.

You And Neil

Personality Compatibility


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