Hustle 2.0: Vice President of Sales

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Job Overview

Hustle 2.0 is looking for a dedicated Vice President of Sales who will not only drive revenue but also lead a team towards meaningful change. The organization is a Public Benefit Corporation that aims to deliver transformational education to incarcerated individuals. This role goes beyond traditional sales leadership; it focuses on making an impactful difference in people's lives, interrupting cycles of incarceration, poverty, and violence.

Company Background

Hustle 2.0 is a fast-growing company particularly focused on the education sector within the criminal justice system. As they transition into a digital EdTech provider, Hustle 2.0 provides educational courses that reduce recidivism and improve reentry outcomes into society. They envision becoming the #1 digital education provider in corrections, selling licenses for their online courses to correctional partners across the U.S. At present, the organization has around eight sales team members and plans to grow to 20 within the next year.

Position Responsibilities

As the Vice President of Sales, you will have a range of responsibilities that shape the sales organization:

  1. Lead and Inspire: You will manage a global sales team, driving accountability and monthly quota attainment.

  2. Scale the Organization: Recruit, onboard, train, and transition sales team members as the organization grows.

  3. Own Revenue Growth: You will be responsible for revenue forecasting, optimizing the sales process, and maintaining KPIs.

  4. Coaching: You will actively review performance metrics and provide constructive feedback to develop skills among your team members.

  5. HubSpot Mastery: Familiarity with HubSpot is crucial for overseeing metrics and pipeline management.

  6. Develop Sales Strategies: Collaborate with leadership and marketing to create effective outreach strategies and messaging.

  7. Growth Targets: Set compensation plans and incentives that align with achieving aggressive revenue targets.

Qualifications and Skills Needed

To be a strong candidate for this position, you should possess the following skills and qualifications:

  • Experience in Sales Management: A minimum of 5 years managing sales teams of 8 or more, with a history of driving performance and growth.
  • Analytical Skills: Be comfortable digging into performance metrics and adjusting strategies accordingly.
  • Leadership Qualities: You should inspire others, enforce performance standards, and promote a culture of accountability.
  • HubSpot Proficiency: A solid understanding of HubSpot for pipeline and reporting is crucial.
  • Mission-Driven Outlook: A desire to create social impact through your work.

Nice-to-Have Skills

The following additional skills and experiences can set you apart:


  • Background in SaaS or EdTech sales.
  • Strong writing and marketing abilities.
  • Experience with strategy creation for presentations.

Work Environment and Compensation

This position is a full-time role, requiring a minimum commitment of 40 hours per week. The work hours align with U.S. business hours to correspond with correctional decision-makers across the nation. Compensation comprises:

  • Base salary: Between $60,000 and $70,000 per year.
  • Performance bonuses: An additional $30,000 to $40,000 based on team revenue. Thus, on-target earnings (OTE) for this role exceed $100,000 annually.

Core Values of Hustle 2.0

Hustle 2.0 looks for candidates who resonate with their core values, which include:

  • Hustle: Show resourcefulness and urgency in all tasks.
  • Hope: Maintain positivity and gratitude.
  • Compassion: Understand the challenges faced by stakeholders.
  • Impact: Strive to leave everyone better than they found them.
  • Candor: Uphold open and honest communication.
  • Ownership: Be accountable for your actions.
  • Growth: Pursue continuous improvement.

Hustle 2.0 embraces diverse backgrounds, actively encouraging individuals with different life experiences, including those with criminal histories, to apply.

Application Process

If you feel you fit the qualifications and can resonate with the mission of Hustle 2.0, they encourage you to apply. The application materials required include:

  1. Resume detailing sales leadership experience.
  2. LinkedIn profile and other relevant professional links.
  3. A cover letter (300-500 words) explaining your interest and relevant experiences.
  4. Confirmation of readiness to work full-time hours at the stated compensation level.

This is a pivotal opportunity to leverage your sales expertise while working for a mission-driven organization aiming to transform lives in the corrections space.



This job offer was originally published on weworkremotely.com

Hustle 2.0

Anywhere in the World

Sales

Full-time

October 10, 2025

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