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Vice President, Sales - US Region
67,000 school districts. 50 million students. One platform that changes everything.
- Boston, Massachusetts
- Hybrid (Office/Remote)
| Reports To | Chief Marketing Officer (CMO) |
| Direct Reports | Sales Managers, Account Executives, Sales Development Representatives, Partnerships/Channel Managers, and Bid/RFP resources as the function scales |
| Location | Boston, Massachusetts (US Office) | Work from Office only |
| Coverage | United States region with national market development responsibility |
| Travel | Up to 30% for district meetings, leadership meetings, partner engagement, and strategic business development |
| Compensation | Competitive and attractive executive compensation with base salary plus an attractive commission structure |
About the Company
TutorCloud.AI is building the most advanced AI-powered tutoring platform in the world. One that delivers personalized, Socratic, one-on-one instruction to every K–12 student for less than the cost of a single textbook. No human tutors. No scheduling. No waiting lists. Just an AI tutor that knows every student’s name, remembers every misconception, and never gives up on any child.
We’re looking for the sales leader who will put this platform in every school in America.
The Opportunity:
This is not a VP Sales role at a mature company optimizing an existing playbook. This is a founding commercial leader building the entire US go-to-market engine from scratch; The team, the territories, the partnerships, the RFP machine, and the revenue model that will scale from $0 to $50M+ ARR.
You will be the first senior hire in the US. You will report directly to the CEO. You will have the authority, the budget, and the mandate to build something that matters.
What You Will Own
- Full P&L ownership for US revenue: from pipeline generation to close to renewal.
- Building and leading the US sales organization: Sales Managers, Account Executives, SDRs, Partnerships & Channel Managers, and RFP/Bid support.
- The go-to-market strategy for K–12 school districts, charter networks, state agencies, and strategic ecosystem partners (LMS providers, assessment companies, MTSS platforms).
- District-level enterprise sales: complex, multi-stakeholder deals involving superintendents, curriculum directors, CTOs, and school boards.
- RFP and procurement leadership: identifying, qualifying, and leading responses to district and state RFP opportunities, including ESSA evidence positioning and Title I/Title IV funding alignment.
- Strategic partnerships: Clever, ClassLink, Canvas/Google Classroom integrations, and co-selling relationships with complementary EdTech platforms.
- The narrative: how TutorCloud.AI is positioned in analyst briefings, conference keynotes, district showcases, and media coverage.
What Makes This Role Extraordinary
1. Timing
The post-ESSER era is forcing districts to cut human tutoring programs that cost $25–45/hour/student. We offer the same quality at $3–8/student/month. You are selling a 10x cost reduction into a market with an urgent, visible pain point.
2. Product
Unlike every competitor, TutorCloud.AI uses zero human tutors. The AI teaches using the Socratic method, adapts in real time to each student’s level, and covers every subject K–12 including AP, SAT/ACT, world languages, and computer science.
3. TAM
The US K–12 EdTech market exceeds $295 billion in 2025 and is growing at 13%+ CAGR. AI-powered tutoring is the fastest-growing segment.
4. Impact
Every deal you close means thousands of students get a personal AI tutor who never gives up on them. This is a commercial role with a humanitarian outcome.
What You Bring
- 8+ years of progressive sales leadership in K–12 EdTech, with at least 3 years at VP/SVP level or equivalent.
- Proven track record of building and scaling B2B SaaS sales teams from early-stage to $20M+ ARR in the K–12 district market.
- Deep Rolodex: existing relationships with superintendents, CIOs, curriculum directors, and procurement officers across 50+ districts.
- Experience navigating the K–12 procurement cycle: RFPs, pilot programs, board approvals, state adoption lists, and multi-year contracts.
- Understanding of ESSA evidence requirements, Title I/Title IV funding streams, and how districts justify EdTech investments post-ESSER.
- Experience selling into or alongside LMS platforms (Canvas, Google Classroom, Schoology), SIS providers (PowerSchool, Infinite Campus), or assessment companies (NWEA, Renaissance, Illuminate).
- A builder’s mentality: you’ve built a team before, not just inherited one.
Compensation & Benefits
- Base salary: $180,000–$250,000 (commensurate with experience and track record).
- Commission/bonus: Aggressive, uncapped commission structure tied to revenue milestones. Realistic OTE of $350,000–$500,000+ in Year 1 for exceptional performance.
- Equity: Meaningful equity stake, you are a founding executive building a category-defining company.
- Premium healthcare: Medical, dental, vision. Company-paid life insurance and long-term disability.
- Cell phone stipend, generous PTO, 12 paid holidays.
- Annual conference budget for ISTE, ASU+GSV, CoSN, FETC, and key industry events.
| Executive Influence | Work directly with the CEO and leadership team on growth strategy, market expansion, and commercial decision-making. |
| Career Exposure | Gain visibility with enterprise customers, investors, strategic partners, and major EdTech industry forums. |
| Mission & Impact | Contribute to a business that helps schools deliver better student support through AI-enabled tutoring innovation. |
| Ownership & Growth | Build a national sales function with significant strategic ownership and strong long-term leadership runway. |
How to Apply
Please submit your resume, LinkedIn profile to [email protected] with the Subject Line “VP Sales – US Region – [Your Name]”
Include a brief note (not a cover letter, a note) answering one question: What is the largest K–12 district deal you personally led from qualification to close, and what made it successful?
Equal Opportunity Employer
TutorCloud.AI is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.
