Vice President of Sales

Headquarters: 6400 S Fiddlers Green Cir. , Ste 300 #504 Greenwood Village, CO 80111 USA
URL: https://www.hustle20.com/

Are you ready to build and lead a world-class sales team … while making a massive difference?

This is not your typical VP of Sales role. At Hustle 2.0, sales leadership isn’t just about hitting numbers—it’s about changing lives. Our programs help interrupt generational cycles of incarceration, poverty, and violence. Because of your leadership, Hustle 2.0 graduates will be the first in their families to go to college, and the last in their families to go to prison. You’ll be driving growth for a company where sales directly translates into impact, giving voice and opportunity to people who are too often forgotten.

About Hustle 2.0

Hustle 2.0 is a fast-growing Public Benefit Corporation that delivers transformational education to incarcerated people across the U.S. Our courses and digital programs reduce recidivism, improve reentry outcomes, and help build safer, stronger communities.

We are at a pivotal moment: transitioning from a workbook-based model into a fully digital EdTech provider. Our future is SaaS—selling licenses for online courses to correctional partners nationwide—and we’re scaling rapidly with a vision to become the #1 digital education provider in corrections.

We’re seeking a world-class Vice President of Sales to own and scale this transformation. Today, our team includes 6 closers and 2 SDRs; within the next year, we expect you to build and lead a high-performing team of ~20 (10 closers and 10 SDRs). This is a defining leadership role: you’ll set strategy, drive revenue growth, and build the sales engine that powers our national expansion. Bonus points if you bring SaaS or EdTech experience—but above all, we’re looking for a proven sales leader who can scale a team and deliver results.

What You’ll Do

• Lead & Inspire: Manage and motivate a global sales team of closers and SDRs, driving accountability, consistency, and quota attainment every month.
  
  

• Scale the Org: Recruit, onboard, train, and (when necessary) transition team members to build a high-performance sales organization—growing from 8 to ~20 in the next year.
  
  

• Own the Numbers: Take full responsibility for revenue growth and forecasting. Track daily/weekly/monthly metrics, enforce KPIs, and optimize the sales funnel from outreach → meeting → close.
  
  

• Coach for Excellence: Set the standard by jumping on calls, reviewing emails, and providing sharp feedback that develops skills and raises performance across the team.
  
  

• HubSpot Mastery: Use HubSpot to oversee pipeline, reporting, and forecasting. You don’t need to be a CRM admin, but you must be a power user who lives in the data.
  
  

• Shape Strategy: Partner with leadership and marketing to refine outreach campaigns, sales decks, and messaging—ensuring the team delivers personalized, effective outreach at scale.
  
  

• Drive Revenue Growth: Build comp plans, create incentives, and foster a culture that delivers aggressive but achievable growth targets—$2M+ in the next year.

What We’re Looking For

• Accountability Hawk: You live in the numbers. You set a daily rhythm of accountability (standups, KPIs, funnel reviews) and enforce performance standards without excuses. Direct, fair, and consistent.
  
  

• Track Record of Growth: You’ve led teams that hit aggressive revenue targets—and you know how to replicate that success.
  
  

• Proven Sales Leader: 5+ years managing teams of 8+ sellers/SDRs, ideally scaling to 15–20+. You’ve hired, trained, developed, and, when necessary, made tough calls to keep the bar high.
  
  

• Analytical Operator: You don’t just look at top-line numbers—you dig into the funnel, spot weak conversion points, and adjust strategy early. Data isn’t optional; it’s how you lead.
  
  

• Inspiring Coach: You set high standards and hold people to them, but you also invest in their growth. Tough, supportive, respected.
  
  

• HubSpot Power User: You live in HubSpot for pipeline, reporting, and forecasting. You’re don’t need to be an admin, but you’re fluent in building dashboards and making the data actionable.
  
  

• Strategic Thinker: You can zoom out—partnering with leadership and marketing to sharpen messaging, outreach, and decks—while keeping the team executing at ground level.
  
  

• Mission-Driven: You want your skills to matter. At Hustle 2.0, sales doesn’t just drive revenue—it transforms lives.

Non-Negotiables (must-haves):

• ​​Exceptional English fluency and communication.
  
  

• Daily accountability + KPI enforcement.
  
  

• Analytical, metrics-driven leadership.
  
  

• HubSpot fluency (pipeline, reports, dashboards).
  
  

• Experience managing 6–10+ people.
  
  

Nice-to-Haves:

• SaaS/EdTech or government sales background.
  
  

• Strong writing/marketing chops.
  
  

• Slide/Deck strategy skills.
  
  

Work Hours

This role requires working U.S. business hours (EST/CST/PST). Our entire sales team works these hours to align with correctional decision-makers across the country.

This is a full-time executive role (minimum 40 hours/week, often more). We’re looking for a highly ambitious, driven leader who thrives in a fast-paced, high-accountability environment and is excited to put in the work to scale a sales org from 8 → 20+.

Compensation

• On-Target Earnings (OTE): $100K+ USD annually
  
  

• Base Salary: $60–70K USD
  
  

• Performance Bonuses: $30–40K USD, tied directly to team revenue and quota attainment

This is a rare opportunity to earn U.S.-level VP compensation while working remotely, leading a global team, and making a measurable difference in the world.

Core Values

As we evaluate potential teammates, we look for alignment with Hustle 2.0’s core values: 

• Hustle: Our can-do attitude, resourcefulness, curiosity, initiative, urgency, and scrappiness result in a high sense of hustle in everything we do.

• Hope: We choose positivity daily, show gratitude, and embrace a better future—even in the face of unrelenting negativity.

• Compassion: We empathize with our stakeholders’ pain and distress, taking actions daily to partner with them in transforming their futures.

• Impact: Caring for our stakeholders leads us to strive to leave everyone we interact with better than we found them.

• Candor: We value open and honest communication that is humble, helpful, immediate, and constructive.

• Ownership: We’re committed to excellence and generating positive outcomes. We’re accountable for the results of our actions.

• Growth: We pursue growth by having the resolve to improve and transform, intellectually, creatively, and professionally.

Equal Opportunity at Hustle 2.0

Hustle 2.0 is proud to be an equal opportunity company. We currently have team members in six countries, and we actively welcome people from diverse cultures, backgrounds, and life experiences to join us.

We are also a rare employer that doesn’t just accept applicants with criminal histories—we value them. Having lived experience in the justice system is not a requirement for this role, but it is a major asset. People who have been incarcerated bring unique insight into the system we serve, and we see that as a strength, not a barrier.

In fact, this role can be an ideal fit for individuals who were incarcerated in the U.S. and later deported—because you understand firsthand the realities of incarceration and reentry. We celebrate transformation, resilience, and second chances, and we want to work with people who have turned their lives around and now want to help others do the same.

At Hustle 2.0, we believe that true diversity includes lived experience, and we strongly encourage candidates of all identities, nationalities, and backgrounds—including those with records of arrest or conviction—to apply.

Apply Now – Instructions

If you are a proven sales leader who thrives on accountability, growth, and impact, we’d love to hear from you. Apply today and help us build the #1 digital education program in corrections.

Send all application materials to fahim@hustle20.com, and in the subject line, write “VP of Sales.”

To be seriously considered, please follow these steps carefully (we only review complete applications):

Step 1 – Required

• Resume or CV – Detailing your sales leadership experience.
  
  

• LinkedIn profile (and other relevant professional links).
  
  

• Cover Letter (300–500 words) answering:
  
  

• Why do you want to join Hustle 2.0?

• How have you built and scaled a sales team before?

• How do you enforce accountability while keeping your team motivated?
  
  

• Comp Expectation Confirmation – Please confirm: “Yes, I am willing to work full-time U.S. business hours (EST/CST/PST) at an OTE of $100K.”

Step 1.5 – Optional (Strongly Encouraged)

Writing Sample – Draft a short cold email you’d send to a U.S. Sheriff or DOC leader introducing Hustle 2.0 and requesting a meeting. This helps us see your communication style and polish.

Step 2 – By Invitation

Candidates who stand out in Step 1 will be invited to submit a short (3-minute) video answering  a handful of questions about your leadership style, sales philosophy, and interest in Hustle 2.0. A simple phone or laptop recording is fine—no editing required.

To apply: https://weworkremotely.com/remote-jobs/hustle-2-0-vice-president-of-sales