VP of Inside 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 complex, consultative deals. You know how to train others to close them. And you know how to design the infrastructure that makes repeatable performance possible. If you're looking for a sales leadership position where you drive enrollment outcomes from the ground up, this role is for you. If you're expecting to step into a fully built organization with established systems and a polished playbook, look elsewhere.
Alpha Anywhere delivers accelerated, personalized education that combines mastery-based academics with essential life skills. Students progress up to 2x faster in roughly 2 hours of daily focused work, supported by expert coaching from any location. Interested families enter our funnel through inbound channels and diagnostic assessments. Your mission is to convert that interest into durable enrollments—families who are the right fit and who stay committed.
This is a full-time, remote opportunity open to candidates worldwide. You will begin as a player-coach: personally conducting enrollment consultations, reviewing recordings, and troubleshooting funnel issues in real time. At the same time, you will architect an AI-augmented sales system—playbooks that work, CRM processes that flow, automation that performs, and enablement that accelerates new hire productivity and conversion.
If you're motivated by actual enrollment numbers, excited to build a scalable human-plus-AI operation, and ready to lead a team that builds genuine trust with families, let's talk.
What you will be doing
Personally conduct enrollment consultations with homeschool families and close enrollments in the core product by establishing clear fit between student needs and program capabilities
Review call recordings, conversation transcripts, and CRM funnel metrics to identify conversion drivers and retention predictors
Design and implement AI-enabled workflows that support call preparation, follow-up sequences, messaging personalization, lead qualification, and CRM task automation
- Inheriting a mature sales organization with established systems and ready-to-execute playbooks
- Optimizing for activity metrics such as call volume or demo counts while actual enrollments and retention remain stagnant
- Pressuring mismatched families into enrollment to hit short-term targets at the expense of churn, refunds, and cancellations
- Developing elaborate AI tools that sit unused or fail to produce measurable gains in conversion or rep efficiency
Key responsibilities
This position is accountable for generating consistent, growing Alpha Anywhere core product enrollments by designing and managing a scalable, AI-enhanced sales operation.
Candidate requirements
- Proven success in consultative, trust-driven sales involving high-consideration purchasing decisions
- Direct experience closing sophisticated deals, including discovery conversations, objection handling, and deal closure
- Documented ability to create or significantly refine a sales process that resulted in higher conversion or revenue
- Track record of managing a small sales team, covering recruitment, coaching, and performance oversight
- Proficiency in leveraging CRM funnel data to identify conversion obstacles and implement data-driven improvements
Nice to have
- Background selling education products, homeschool solutions, coaching services, or other parent-purchased offerings where fit and outcomes are critical
- Practical experience creating AI assistants, automation scripts, or workflow tools that enhance sales team output
- Skill in reviewing sales call recordings and distilling insights into simple, actionable playbooks that reps actually use
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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