Head of Sales $150,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Description
You know how to close deals that require trust. You know how to train others to do it well. And you know how to design a system where success doesn't hinge on individual effort alone. If you're looking for a sales leadership position where you're accountable for enrollment growth from start to finish, this role is worth your attention. If you're expecting to step into a polished organization with a fully documented playbook, this opportunity isn't the right fit.
Alpha Anywhere delivers accelerated, personalized learning designed for home environments, combining mastery-based academics with essential life skills. Students progress up to 2x faster in approximately 2 concentrated hours daily, supported from any location by experienced coaching. Families discover us through inbound channels and diagnostic tools, arriving with genuine interest. Your responsibility is converting that interest into enrolled students who are well-matched to the program and unlikely to request refunds.
This is a full-time, fully remote position available to candidates worldwide. You'll begin as a player-coach with direct involvement: personally conducting enrollment consultations, reviewing call recordings, and addressing funnel breakdowns as they occur. At the same time, you'll construct an AI-enhanced sales infrastructure—actionable playbooks, CRM processes, automation layers, and training resources that elevate conversion performance and accelerate onboarding for new team members.
If you're prepared to be held accountable for actual enrollment outcomes, to architect a scalable human-AI hybrid system, and to lead a team that builds genuine trust with families, we'd like to speak with you.
What you will be doing
Conduct enrollment consultation calls directly with homeschooling families and finalize core product enrollments grounded in clear alignment between student needs and program capabilities
Review call recordings, transcripts, and CRM funnel metrics to identify the behavioral and messaging patterns that influence conversion and long-term retention
Design and implement AI-supported workflows covering call preparation, follow-up sequences, messaging templates, prospect qualification, and CRM process automation
Recruit, train, onboard, and manage a compact enrollment team through structured pipeline reviews, individualized deal coaching, and performance tracking against conversion benchmarks
Collaborate with the marketing function to refine qualification standards, optimize messaging, and strengthen the inquiry-to-diagnostic-to-consultation pathway
What you will NOT be doing
- Overseeing a mature sales organization with established systems and fully documented operational playbooks
- Prioritizing activity metrics such as call volume or demo counts while actual enrollments and retention figures remain stagnant
- Forcing mismatched families into the funnel to artificially boost numbers, resulting in churn, refund requests, or early cancellations
- Developing elaborate AI infrastructure that remains unused or fails to produce measurable gains in conversion rates and rep efficiency
Key responsibilities
This role is accountable for generating consistent, growing Alpha Anywhere core product enrollments by establishing and managing a scalable, AI-augmented sales operation.
Candidate requirements
- Documented history of exceptional performance in consultative sales involving trust-intensive, high-stakes purchasing decisions
- Direct experience closing sophisticated deals and managing discovery conversations, objection handling, and deal closure
- Verified success in designing or significantly enhancing a sales methodology that produced measurable increases in conversion rates and/or revenue
- Background managing a small sales team, encompassing recruitment, coaching, and performance oversight
- Advanced capability in leveraging CRM pipeline data to identify funnel inefficiencies and implement demonstrable improvements
Nice to have
- Background selling educational services, homeschool programs, coaching offerings, or similar parent-decision services where program fit and outcomes are critical
- Direct experience creating AI assistants, automation scripts, or workflow tools that measurably enhance sales team productivity
- Proficiency in reviewing recorded sales calls and translating observations into straightforward, actionable playbooks that teams actually adopt
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style screening interview.
Cognitive aptitude test.
Prove real-world job skills.
Interview with the hiring manager.
Pass proctored test.
Accept job offer.
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