Director 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 high-stakes deals on your own. You have the skill to coach others through the same process. And you understand how to design systems that deliver results without relying on individual heroics. If you are looking for a sales leadership position where you will own enrollment growth from start to finish, continue reading. If you are seeking to step into an established organization with a fully developed playbook already in place, this opportunity is not the right fit.
Alpha Anywhere delivers accelerated, personalized learning at home through mastery-based academics combined with life skills coaching. Students are able to learn up to 2x faster in approximately 2 focused hours per day, from any location, supported by experienced coaching. Families come to us with interest generated through inbound channels and diagnostic tools. Your responsibility is to convert that interest into committed enrollments characterized by strong alignment and minimal refund exposure.
This is a full-time, fully remote position available to candidates worldwide. You will begin as a player-coach with direct responsibilities: you will conduct enrollment consultations personally, review call recordings, and troubleshoot funnel breakdowns. At the same time, you will construct an AI-augmented sales infrastructure: actionable playbooks, CRM processes, automation frameworks, and enablement resources that elevate conversion rates and accelerate onboarding for new team members.
If you are prepared to be evaluated on actual enrollments, design a scalable human + AI system, and lead a team that builds trust with families, we are eager to speak with you.
What you will be doing
Conduct enrollment consultation calls directly with homeschooling families and secure core product enrollments grounded in clear student-program alignment
Review call recordings, transcripts, and CRM funnel data to identify the patterns and behaviors that increase conversion and long-term retention
Design and implement AI-supported workflows for call preparation, follow-up sequences, messaging frameworks, lead qualification, and CRM automation
- Overseeing a fully mature sales organization that already has established processes and completed playbooks
- Focusing on vanity metrics such as call volume or demo activity while actual enrollments and retention remain stagnant
- Forcing misaligned families into the funnel to boost short-term volume at the cost of churn, refunds, or cancellations
- Developing complicated AI infrastructure that remains unused or fails to produce measurable gains in conversion or rep productivity
Key responsibilities
This role is accountable for generating predictable, growing Alpha Anywhere core product enrollments by designing and managing a scalable, AI-enhanced sales operation.
Candidate requirements
- Documented history of excellence in consultative sales involving trust-based, high-consideration purchasing decisions
- Direct experience closing complex deals and managing discovery conversations, objection handling, and deal closure
- Demonstrated success in designing or significantly enhancing a sales process that resulted in improved conversion and/or revenue outcomes
- Background leading a small sales team, including responsibilities for hiring, coaching, and managing performance
- Advanced capability using CRM pipeline analytics to identify funnel inefficiencies and implement measurable enhancements
Nice to have
- Background selling education services, homeschooling programs, coaching offerings, or other parent-driven solutions where outcomes and alignment are critical
- Practical experience developing AI copilots, automation scripts, or workflow tools that enhance sales team productivity
- Confidence analyzing recorded sales calls and translating findings into straightforward, actionable playbooks that get adopted
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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