Vice President of Sales
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 digital education for incarcerated people reduces recidivism and strengthens communities. Your leadership will directly translate into impact.
About Hustle 2.0
Hustle 2.0 is a fast-growing Public Benefit Corporation delivering transformational education across U.S. corrections. We’re pivoting from workbooks to a fully digital
EdTech model (SaaS licensing to correctional partners) and scaling to become the #1 digital education provider in corrections.
Role Snapshot
- Title: Vice President of Sales
- Team today: 6 Closers + 2 SDRs → scale to ~20 (10 Closers + 10 SDRs) in 12 months
- Ownership: Strategy, hiring, coaching, pipeline, forecasting, revenue
- Target growth: $2M+ in the next year
What You’ll Do
- Lead & inspire a global team of Closers and SDRs with rhythm, KPIs, and accountability.
- Recruit, onboard, train, and level up the org from 8 → ~20 reps.
- Own the numbers: forecasting, dashboards, funnel optimization (outreach → meeting → close).
- Coach for excellence: join calls, review emails, give sharp feedback.
- Operate as a HubSpot power user for pipeline, reporting, forecasting.
- Shape strategy with leadership & marketing (outreach, decks, messaging).
- Design comp plans & incentives to consistently hit aggressive but achievable targets.
What We’re Looking For
- Accountability hawk: daily standups, KPI enforcement, no excuses.
- Track record of growth: scaled teams that hit ambitious revenue goals.
- Proven leader: 5+ years managing 8–20+ sellers/SDRs (hiring, training, decisions).
- Analytical operator: digs into funnel conversion and adjusts early.
- Inspiring coach: tough, supportive, respected.
- HubSpot power user (dashboards, reports, forecasting).
- Strategic thinker who can zoom out and still execute.
- Mission-driven—sales as a force for transformation.
Work Hours
Full-time executive role (40h+). Must work U.S. business hours (EST/CST/PST) alongside correctional decision-makers.
Compensation
- OTE: $100K+ USD annually
- Base: $60–70K USD
- Performance Bonuses: $30–40K USD tied to team revenue & quota
Core Values (Hustle, Hope, Compassion, Impact, Candor, Ownership, Growth)
We value scrappiness, positivity, empathy, measurable impact, humble candor, accountability, and continuous improvement.
Equal Opportunity
We welcome teammates from diverse cultures and life experiences—including those with records of arrest or conviction.
Lived experience in the justice system is a strong asset.
Apply Now – Instructions
- Email your materials to fahim@hustle20.com with subject: “VP of Sales.”
- Include: Resume/CV, LinkedIn (and relevant links), 300–500 word cover letter 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?
- Confirm: “Yes, I am willing to work full-time U.S. business hours (EST/CST/PST) at an OTE of $100K.”
- Optional (strongly encouraged): a short cold email to a U.S. Sheriff or DOC leader requesting a meeting.