Ryan Jacobson

Commander
DISC Type : D

Acquisition Specialist at Pie Insurance

Greater Chicago Area, United States

Overview

Ryan Jacobson is an Acquisition Specialist at Pie Insurance, focused on driving strategic growth through agency and broker partnerships for workers compensation. She has an extensive background in talent acquisition, previously serving as a Recruiting Manager at The Jacobson Group. Ryan holds a Bachelor of Science from the University of Illinois Chicago.

Outside of work, Ryan has a significant green thumb, owning more than 100 indoor plants. She is focused on personal well-being through fitness and goal setting to maintain a healthy work-life balance. Her favorite movie is "The Devil Wears Prada" and she enjoys cheesecake.

Unique fact: Ryan is a dedicated plant enthusiast who cares for a collection of over 100 plants.

Personality Overview

Candid & Clear

Very Quick

Impact-Driven

They respond better to strong and respectful interactions.  They do not care very much about building rapport or relationships. They are less concerned about the product and more about its potential impact.

Topics They Care About

Agency Partnerships
Her current role at Pie Insurance involves identifying and securing agency, wholesaler, and broker partnerships to expand the company's national footprint.
Small Business Insurance
Her professional headline and role are centered on providing workers' compensation insurance solutions specifically for small businesses.
Talent Recruitment
Managed a recruiting team and oversaw the entire hiring process in her previous long-term role as Recruiting Manager at The Jacobson Group.

Media Appearances

Ryan has no verified media appearances

Work History

2-2025
Acquisition Specialist at Pie Insurance
9-2020 - 8-2024
Recruiting Manager at The Jacobson Group
1-2019 - 9-2020
Assistant Research Manager at The Jacobson Group
1-2018 - 1-2019
Lead Researcher, Talent Delivery at The Jacobson Group
3-2017 - 1-2018
Senior Recruiter at The Jacobson Group

Education

2012 - 2014
Bachelor of Science (B.S.) from University of Illinois Chicago
2010 - 2012
Associate of Arts and Sciences (A.A.S.) from Illinois Central College

More Information

Social Presence :

Prographics :

Exp : 15 Location : Greater Chicago Area, United States Job Level : Junior Designation : Acquisition Specialist at Pie Insurance
URL has been copied!

Insights For Selling To Ryan

During A Call Or A Meeting

DO's

  • Be respectful but crisp
  • When negotiating terms, help them build an impression that they are the ones calling the shots
  • Use phrases like ‘it’s your decision’, ‘strategic impact’ etc.

DONT's

  • Avoid being too verbose
  • Do not hesitate from asking counter questions, just avoid challenging their authority
  • Don’t be in a rush to invite them for a social meet and greet

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Ryan is

  • Conviction around the impact matters the most to them, followed by a sense of achievement and ROI.
  • Will you ever get a clear answer from Ryan

  • If they are not convinced, they will say no without any hesitation.

Insights For Deal Planning

    How fast (or slow) will Ryan move?

  • If convinced, they can reach decisions quite fast.
  • Can Ryan take some risk or not?

  • They do not shy away from taking risks, but can be quite binary about them.

You And Ryan

Personality Compatibility


Other Pie Insurance Employees

Explore more public profiles from related professionals at the same organization.

More Profiles

Discover additional public profiles from our index.

Search more profiles

Looking for someone else? Search here for anyone.

Or visit Humantic AI to know more.