Natasha Hipwell

Enigma
DISC Type : cdi

Personal Lines Sales Executive at Gallagher

Naples, Florida, United States

Overview

Natasha is a dual-licensed professional in Southwest Florida, serving as a Personal Lines Sales Executive at Gallagher and a Real Estate Agent with Realty ONE Group. She leverages a unique background that includes over a decade in insurance, digital marketing for Fortune 500 companies, and a Business Management education from Edison State College.

Originally from Ontario, Canada, Natasha is a dedicated, family-oriented professional. A significant personal passion is martial arts; she is a 4th-degree black belt and previously ran a family martial arts school. She is community-driven and focuses on building meaningful connections in her professional and personal life.

Unique fact: Natasha is a 4th-degree black belt in martial arts.

Personality Overview

Hard To Convince

Challenger

Persuasive & Assertive

They are generally strong communicators and are not easy to convince.  They are likely to ask many questions and look heavily for supporting proof as well as information. They can sound friendly and charming but can quickly change gears to become inquisitive and probing

Topics They Care About

Southwest FL Real Estate
As a real estate agent with Realty ONE Group in Naples, she actively helps families buy and sell homes in the local market.
Personal Risk Management
Her role as a Personal Lines Sales Executive focuses on providing clients with tailored homeowners, auto, and boat insurance solutions.
Martial Arts
She is a 4th-degree black belt and has experience running a family martial arts school, indicating a deep, long-term passion.

Media Appearances

Natasha has no verified media appearances

Work History

1-2026
Personal Lines Sales Executive at Gallagher
8-2025 - 1-2026
Personal Lines Sales Executive at AssuredPartners
3-2025
Real Estate Agent at Realty ONE Group
12-2018 - 9-2019
Personal Lines Team Leader at IRMSinc
7-2018 - 12-2018
Account Coordinator at IRMSinc

Education

1-2025 - 1-2025
Real Estate Sales Associate License from Larson Educational Services
Business Management from Edison State College

More Information

Social Presence :

Prographics :

Exp : 14 Location : Naples, Florida, United States Job Level : N/A Designation : Personal Lines Sales Executive at Gallagher
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Insights For Selling To Natasha

During A Call Or A Meeting

DO's

  • Build rapport slwly without rushing, it will come handy to handle hard questions later
  • Be prepared for a mix of questions and inquisitiveness, answer them in the tone in which they have been asked
  • Leverage 'negging', or the art of asking negative questions like "you must not be convinced yet..."

DONT's

  • Avoid long presentations and just 'high-level' value proposition, dive into the details
  • Don’t brush off any concerns, take all questions seriously. They are easily deterred
  • Don’t try to rush them into a decision, provide all necessary information first

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Natasha is

  • Proven value, strong objective evidence are important for them, rapport can impact decisions a little.
  • Will you ever get a clear answer from Natasha

  • They are practical and friendly, but can give a clear response with a little prodding

Insights For Deal Planning

    How fast (or slow) will Natasha move?

  • They like to be detailed, so unless they develop strong conviction, they can take their time to arrive at decisions
  • Can Natasha take some risk or not?

  • They evaluate their decisions systematically and do not take risks that often, unless you can get them to develop strong conviction

You And Natasha

Personality Compatibility


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