Head of Sales, Alpha Anywhere (Remote) - $150,000/year USD

You close high-trust deals yourself. You coach others to replicate that success. And you design the system so performance doesn’t rely on individual heroics. If you want to own enrollment growth from end to end in a sales leadership role, this is worth your attention. If you’re looking to step into a mature organization with established playbooks already in place, this role is not the right fit.

Alpha Anywhere delivers accelerated, personalized learning for families who want mastery-based academics and life skills at home. Students progress up to 2x faster in roughly 2 focused hours per day, supported from any location by proven coaching methods. Interested families arrive through inbound channels and diagnostics. Your mission is to convert that interest into committed enrollments with strong alignment and minimal refund exposure. This is a full-time, fully remote position available worldwide.

You begin as a player-coach: you will personally conduct enrollment consultations, review call recordings, and troubleshoot funnel breakdowns. At the same time, you will construct an AI-augmented sales engine—clear playbooks, CRM workflows, automation, and rep training that lift conversion and accelerate onboarding for new hires. If you want accountability tied to real enrollments, the opportunity to build a scalable human + AI system, and the chance to lead a team that earns family trust, we should talk.

• Conduct enrollment consultation calls directly with homeschooling families and close core product enrollments by establishing clear student-program alignment.
• Review call recordings, transcripts, and CRM funnel metrics to identify the patterns that reliably drive conversion and long-term retention.

Operating a fully formed sales organization that already has mature processes and finished playbooks. Optimizing for vanity metrics such as call volume or demo counts while actual enrollments and retention remain stagnant. Forcing misaligned families into the funnel to boost short-term volume at the cost of churn, refunds, or cancellations. Developing elaborate AI tools that go unused or fail to deliver measurable gains in conversion or rep efficiency.

This role is accountable for delivering consistent, growing Alpha Anywhere core product enrollments by building and managing a scalable, AI-enhanced sales engine.

• Proven track record of high achievement in consultative sales involving trust-based, high-consideration buyer decisions.
• Direct experience closing complex deals, including conducting discovery, managing objections, and securing commitments.
• Documented ability to design or significantly enhance a sales process that measurably increased conversion and/or revenue.
• Background leading a small sales team, including responsibility for hiring, coaching, and managing performance.
• Proficiency using CRM pipeline data to identify funnel constraints and implement measurable performance improvements.

• Background selling education services, homeschooling solutions, coaching programs, or other parent-driven offerings where fit and outcomes are central.
• Practical experience creating AI copilots, automation tools, or workflow systems that enhance sales team productivity.
• Ability to analyze sales call recordings and distill insights into clear, actionable playbooks that teams actually use.

Bring accelerated learning home with personalized academics and life skills. Combine the power of at-home learning with Alpha’s proven coaching to unlock success in academics and beyond.

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $75 USD/hour, which equates to $150,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly.