VP 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 excel at closing consultative, high-trust deals. You know how to coach others to replicate that success. And you understand how to systematize results so they don't rely on individual heroics. If you're looking for a sales leadership position where you own enrollment growth from start to finish, read on. If you'd rather step into a mature organization with established playbooks already in place, this role won't be the right fit.
Alpha Anywhere delivers accelerated, personalized learning at home—combining mastery-based academics with essential life skills. Students progress up to 2x faster in approximately 2 focused hours per day, learning from anywhere with expert coaching support. Families reach us with genuine interest through inbound channels and diagnostic assessments. Your responsibility is to convert that interest into committed enrollments that demonstrate strong fit and carry minimal refund risk.
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 funnel breakdowns as they occur. At the same time, you'll design an AI-enhanced sales infrastructure—clear playbooks, streamlined CRM processes, intelligent automation, and enablement resources that boost conversion and accelerate new hire productivity.
If you're ready to be held accountable for actual enrollments, construct a scalable human + AI system, and lead a team that builds genuine trust with families, let's talk.
What you will be doing
Conduct enrollment consultation calls directly with homeschooling families and convert them into core product enrollments grounded in clear student-program alignment
Review call recordings, transcripts, and CRM funnel metrics to identify the conversion and retention drivers that matter most
Design and implement AI-powered workflows covering call preparation, follow-up sequences, messaging cadences, qualification steps, and CRM automation
Hire, onboard, coach, and manage a compact enrollment team through structured pipeline reviews, deal-level coaching, and conversion performance tracking
Collaborate with marketing to refine qualification standards, optimize messaging, and enhance the inquiry-to-diagnostic-to-consultation pipeline
What you will NOT be doing
- Overseeing a fully developed sales organization with polished processes and pre-built playbooks already in place
- Focusing on vanity metrics such as call volume or demo activity while actual enrollments and retention remain stagnant
- Pressuring mismatched families into the funnel to artificially boost numbers, leading to churn, refunds, and cancellations
- Developing elaborate AI systems that go unused or fail to deliver measurable gains in conversion or rep efficiency
Key responsibilities
This role is accountable for generating predictable, accelerating enrollments in Alpha Anywhere's core product by designing and leading a scalable, AI-enhanced sales operation.
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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