Josh Gillespie
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Josh Gillespie Email & Phone Number

Helping Underserved Communities Break into Tech ️‍🔥 | Founder @Losing by Design ⚡ | Enterprise GTM @Glassbox 🚀 | Founding AE @PandaDoc $0-$90M 🦄 | Sales Coach @AlwaysHired | 🧘 at AlwaysHired Sales Bootcamp
Location: San Francisco Bay Area, United States, United States 8 work roles 2 schools
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✓ Verified May 2026 3 data sources Profile completeness 86%

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Current company
AlwaysHired Sales Bootcamp
Role
Helping Underserved Communities Break into Tech ️‍🔥 | Founder @Losing by Design ⚡ | Enterprise GTM @Glassbox 🚀 | Founding AE @PandaDoc $0-$90M 🦄 | Sales Coach @AlwaysHired | 🧘
Location
San Francisco Bay Area, United States, United States
Company size
35 employees

Who is Josh Gillespie? Overview

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Josh Gillespie is listed as Helping Underserved Communities Break into Tech ️‍🔥 | Founder @Losing by Design ⚡ | Enterprise GTM @Glassbox 🚀 | Founding AE @PandaDoc $0-$90M 🦄 | Sales Coach @AlwaysHired | 🧘 at AlwaysHired Sales Bootcamp, a company with 35 employees, based in San Francisco Bay Area, United States, United States. AeroLeads shows a matched LinkedIn profile for Josh Gillespie.

Josh Gillespie previously worked as Sales Trainer at Alwayshired Sales Bootcamp and Founder at Losing By Design. Josh Gillespie holds Bachelor Of Arts, Philosophy from University Of California, Santa Cruz.

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AlwaysHired Sales Bootcamp

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Profile bio

About Josh Gillespie

Husband, Dad & Dog father.Avid basketball fan and rec-league player (retired).Philosophy student and Social Worker turned SaaS sales (circa 2008). I believe anybody can break into tech and all they need is an opportunity and mentorship to do so. Started my career in tech pre-IPO @Yelp (2008-09) > Startup GTM @Pinchit & Quote Roller (2009-2013) > 10 years as the top IC and Director of Enterprise Sales @PandaDoc from $0-$90M ARR (2013-2023) > Enterprise GTM at Glassbox (2024) > Trainer at AlwaysHired Sales Bootcamp (2024) > Founder, Losing by Design (now loading...). Over 2,000 logos won and counting.Check me out on "Around the Horn with Josh Gillespie vs. Morgan Ingram vs. Sam McKenna..." -https://www.pandadoc.com/library/webinars/sales-showdown/

Current workplace

Josh Gillespie's current company

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AlwaysHired Sales Bootcamp
Alwayshired Sales Bootcamp
Helping Underserved Communities Break into Tech ️‍🔥 | Founder @Losing by Design ⚡ | Enterprise GTM @Glassbox 🚀 | Founding AE @PandaDoc $0-$90M 🦄 | Sales Coach @AlwaysHired | 🧘
san francisco, california, united states
Website
alwayshired.com
Employees
35
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8 roles

Josh Gillespie work experience

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Sales Trainer

Current
Alwayshired Sales Bootcamp

San Francisco, California, United States

Pro bono work helping train and mentor 1st-time applicants for tech/sales.

Aug 2024 - Present

Founder

Current
Losing By Design

San Francisco Bay Area

Loading...

Sep 2023 - Present

Enterprise Gtm

Glassbox

San Francisco Bay Area

#1 Digital Experience Intelligence Platform in the world:https://www.g2.com/products/glassbox/reviews

Jan 2024 - Dec 2024

Enterprise Sales Director

Pandadoc

San Francisco Bay Area

Jul 2020 - Sep 2023

Mid-Market & Enterprise Sales Lead

Pandadoc

San Francisco Bay Area

Jan 2017 - Jun 2020

Founding Ae / Gtm Hire

Pandadoc

San Francisco

First AE sales hire: Sep, 2013.

Sep 2013 - Dec 2016

Head Of Sales

Pinchit

San Francisco Bay Area

Feb 2011 - Sep 2012

Account Executive

Yelp, Inc

San Francisco

Nov 2008 - Jun 2009
Team & coworkers

Colleagues at AlwaysHired Sales Bootcamp

Other employees you can reach at alwayshired.com. View company contacts for 35 employees →

YB Yunus Baş Yunus Baş Colleague at Alwayshired Sales Bootcamp Afyonkarahisar, Afyon, Türkiye, Turkey View → JH Joshua Hernandez Joshua Hernandez Colleague at Alwayshired Sales Bootcamp San Francisco Bay Area, United States View → LM Lisa Mayasari Lisa Mayasari Colleague at Alwayshired Sales Bootcamp North Sumatra, Indonesia, Indonesia View → MM Mostafa Magdy Mostafa Magdy Colleague at Alwayshired Sales Bootcamp New York, United States, United States View → MA Maria Angelita Señoron Maria Angelita Señoron Colleague at Alwayshired Sales Bootcamp Cagayan De Oro City, Northern Mindanao, Philippines, Philippines View → HK Hannah Kerrigan Hannah Kerrigan Colleague at Alwayshired Sales Bootcamp Tualatin, Oregon, United States, United States View → DF David Fierro David Fierro Colleague at Alwayshired Sales Bootcamp Santa Ana, California, United States, United States View → AA Ali Ahmad Ali Ahmad Colleague at Alwayshired Sales Bootcamp New York, New York, United States, United States View → SJ Samuel Jacobsen Samuel Jacobsen Colleague at Alwayshired Sales Bootcamp Hayward, California, United States, United States View → AA Antwan Alexander Antwan Alexander Colleague at Alwayshired Sales Bootcamp Atlanta, Georgia, United States, United States View →
2 education records

Josh Gillespie education

Education record

Ubc
FAQ

Frequently asked questions about Josh Gillespie

Quick answers generated from the profile data available on this page.

What company does Josh Gillespie work for?

Josh Gillespie works for AlwaysHired Sales Bootcamp.

What is Josh Gillespie's role at AlwaysHired Sales Bootcamp?

Josh Gillespie is listed as Helping Underserved Communities Break into Tech ️‍🔥 | Founder @Losing by Design ⚡ | Enterprise GTM @Glassbox 🚀 | Founding AE @PandaDoc $0-$90M 🦄 | Sales Coach @AlwaysHired | 🧘 at AlwaysHired Sales Bootcamp.

Where is Josh Gillespie based?

Josh Gillespie is based in San Francisco Bay Area, United States, United States while working with AlwaysHired Sales Bootcamp.

What companies has Josh Gillespie worked for?

Josh Gillespie has worked for Alwayshired Sales Bootcamp, Losing By Design, Glassbox, Pandadoc, and Pinchit.

Who are Josh Gillespie's colleagues at AlwaysHired Sales Bootcamp?

Josh Gillespie's colleagues at AlwaysHired Sales Bootcamp include Yunus Baş, Joshua Hernandez, Lisa Mayasari, Mostafa Magdy, and Maria Angelita Señoron.

How can I contact Josh Gillespie?

You can use AeroLeads to view verified contact signals for Josh Gillespie at AlwaysHired Sales Bootcamp, including work email, phone, and LinkedIn data when available.

What schools did Josh Gillespie attend?

Josh Gillespie holds Bachelor Of Arts, Philosophy from University Of California, Santa Cruz.

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