Montgomery Ostrander

Commander
DISC Type : D

Sales Performance Director at Sandler

San Diego, California, United States

Overview

Montgomery Ostrander is a Sales Performance Director at Sandler who uniquely integrates his background as a clinical psychotherapist to enhance sales performance. A graduate of USC and Pepperdine University, he has been awarded "Best Tech Sales Trainer" and is described by colleagues as insightful, empathetic, and creative.

His history as the founder of a successful residential care enterprise for elderly and dementia patients highlights a passion for healthcare and social causes. This experience, combined with his masters in social work, reflects a deep interest in applying psychological principles to solve real-world challenges.

He founded and grew a residential care business for the elderly, generating $1. 4 million in revenue in its first fiscal year.

Personality Overview

Impact-Driven

Decisive

Strong-Willed

More than the product, they care about the impact of the product.  They like to move fast and expect the same from others. They prefer to be the ones controlling the conversation or defining the terms.

Topics They Care About

Sales Psychology
He merges clinical psychology with sales, using psychodynamic principles to move beyond scripts and improve team performance through a deeper understanding of human behavior.
Sandler Methodology
As a certified Sales Performance Director at Sandler, he is a dedicated practitioner and teacher of the Sandler methodology, which he views as the gold standard.
Performance Coaching
He focuses on enhancing team results through 1: 1 coaching, role-playing, and creating detailed training materials to close skill gaps and drive revenue growth.

Media Appearances

Montgomery has no verified media appearances

Work History

2-2025
Sales Performance Director at Sandler
6-2024 - 7-2025
Director of Sales Operations at SS&C Technologies
8-2022 - 6-2024
Sr Sales Enablement Manager, Global at Netradyne
2-2018 - 10-2020
Director of Sales And Business Development at Hospice of the North Coast
3-2012 - 4-2021
Founder at Family Residential Care

Education

2012 - 2013
Master of Social Work - MSW from University of Southern California
2011 - 2012
Master of Science - MS from Pepperdine University Graduate School of Education and Psychology

More Information

Social Presence :

Prographics :

Exp : 25 Location : San Diego, California, United States Job Level : Mid-senior Designation : Sales Performance Director at Sandler
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Insights For Selling To Montgomery

During A Call Or A Meeting

DO's

  • Make sure that you circle back fast on any action items, it wins their trust
  • Get to the point quickly instead of spending time doing small talk
  • Be respectful but crisp

DONT's

  • Do not back off when challenged, respond with a confident, objective answer instead
  • Do not spend too much time focusing on product tech or features
  • Avoid being too verbose

When Cold Calling

When Writing An Email

While Negotiating & Closing

    The secret to closing fast with Montgomery 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 Montgomery

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

Insights For Deal Planning

    How fast (or slow) will Montgomery move?

  • They can reach decisions fairly quickly if they are convinced.
  • Can Montgomery take some risk or not?

  • They don’t mind risks but can be quite binary about them.

You And Montgomery

Personality Compatibility


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