Director of Sales, Alpha Anywhere (Remote) - $150,000/year USD
Skills
About This Role
Overview
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
Director Of Sales 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.
Basic 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 Requirements
- 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
About Alpha Anywhere
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.
There is so much to cover for this exciting role, and space here is limited.
Hit the Apply button if you found this interesting and want to learn more.
We look forward to meeting you!
Working with us
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.
Consult www.crossover.com/help-and-faqs for more details on this topic.
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