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 can close high-trust deals yourself. You can coach others to do the same. And you can build the system so results don’t depend on heroics. If you want a sales role where you own enrollment growth end-to-end, keep reading. If you prefer inheriting a mature org with a finished playbook, this is not for you.
Alpha Anywhere brings accelerated learning home with personalized, mastery-based academics and life skills. Students can learn up to 2x faster in about 2 focused hours a day, from anywhere, backed by proven coaching. Families arrive with interest through inbound demand and diagnostics. Your job is to turn that intent into committed enrollments with strong fit and low refund risk.
This is a full-time, fully remote role open globally. You start as a hands-on player-coach: you will personally run enrollment consultations, listen to call recordings, and fix what breaks in the funnel. In parallel, you will build an AI-enabled sales engine: practical playbooks, CRM workflows, automation, and rep enablement that raise conversion rates and ramp new hires fast.
If you want to be measured on real enrollments, build a human + AI system that scales, and lead a team that earns trust with families, we want to meet you.
What you will be doing
Run enrollment consultation calls with homeschooling families and close core product enrollments based on clear student-program fit
Analyze call recordings, transcripts, and CRM funnel data to find the patterns that drive conversion and retention
Build and deploy AI-assisted workflows for call prep, follow-ups, messaging, qualification, and CRM automation
Coach, hire, onboard, and manage a small enrollment team using pipeline reviews, deal coaching, and conversion metrics
Partner with marketing to improve qualification criteria, messaging, and the inquiry-to-diagnostic-to-consultation funnel
What you will NOT be doing
- Managing a fully built sales organization with mature processes and established playbooks
- Chasing vanity metrics like call counts or demos while enrollments and retention stay flat
- Pushing wrong-fit families through the funnel to inflate volume and create churn, refunds, or cancellations
- Building complex AI systems no one uses or that do not measurably improve conversion and rep productivity
Key responsibilities
This role exists to deliver predictable, accelerating Alpha Anywhere core product enrollments by building and leading a scalable, AI-enabled sales engine.
Candidate requirements
- Demonstrated track record of high performance in consultative sales with trust-based, high-consideration decisions
- Experience personally closing complex deals and handling discovery, objections, and closing
- Proven ability to design or materially improve a sales process that increased conversion and/or revenue
- Experience leading a small sales team, including hiring, coaching, and performance management
- Strong ability to use CRM pipeline analytics to diagnose funnel bottlenecks and drive measurable improvements
Nice to have
- Experience selling education, homeschooling, coaching, or other parent-driven services where outcomes and fit matter
- Hands-on experience building AI copilots, automation, or workflow tooling to augment sales productivity
- Comfort analyzing sales call recordings and turning insights into simple, adopted playbooks
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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