Director 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 built on trust. You know how to teach others to do it too. And you know how to design a system that scales without relying on constant firefighting. If you're looking for a sales leadership role where you own enrollment outcomes from top to bottom, read on. If you'd rather step into a mature organization with all the infrastructure already in place, this role isn't the right fit.
Alpha Anywhere delivers accelerated, personalized learning at home—combining mastery-based academics with essential life skills. Students can progress up to 2x faster in approximately 2 focused hours per day, learning from anywhere with expert coaching support. Families discover us through inbound interest and diagnostic assessments. Your responsibility is to convert that interest into enrolled students who fit the program well and are unlikely to request refunds.
This is a full-time, fully remote position available to candidates worldwide. You'll begin as a player-coach: personally conducting enrollment consultations, reviewing recorded calls, and addressing breakdowns in the conversion funnel. At the same time, you'll construct an AI-enhanced sales engine—developing actionable playbooks, CRM processes, automation tools, and enablement resources that increase conversion and accelerate new hire onboarding.
If you want to be held accountable for actual enrollments, design a scalable human-plus-AI system, and manage a team that builds genuine trust with families, let's talk.
What you will be doing
Conduct enrollment consultation calls with homeschooling families and close enrollments for core products based on clear alignment between student needs and program capabilities
Review call recordings, transcripts, and CRM funnel metrics to identify the patterns and behaviors that increase conversion and improve retention
Design and implement AI-assisted workflows for call preparation, follow-up sequences, messaging, lead qualification, and CRM automation
- Overseeing a fully developed sales organization with established systems and completed playbooks
- Focusing on surface-level metrics like call volume or demo counts while actual enrollments and retention remain stagnant
- Pressuring poorly matched families into enrollment to boost short-term numbers and trigger churn, refunds, or cancellations
- Creating elaborate AI tools that go unused or fail to deliver measurable gains in conversion or rep effectiveness
Key responsibilities
This role is accountable for generating predictable, growing Alpha Anywhere core product enrollments by developing and managing a scalable, AI-enabled sales operation.
Candidate requirements
- Proven history of excellence in consultative sales involving trust-based, high-consideration buying decisions
- Direct experience closing complex deals and managing discovery conversations, objection handling, and deal closure
- Documented success designing or significantly improving a sales process that resulted in higher conversion and/or revenue
- Track record of leading a small sales team, including responsibility for hiring, coaching, and managing performance
- Strong capability to leverage CRM pipeline data to identify funnel issues and implement measurable process improvements
Nice to have
- Background selling education services, homeschooling solutions, coaching programs, or other parent-focused offerings where fit and outcomes are critical
- Practical experience developing AI copilots, automation systems, or workflow tools that enhance sales team productivity
- Confidence reviewing sales call recordings and translating findings 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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