Head of Sales

RevPilots; United States; Remote; USD 175,000 - 225,000; Full time

Job summary

Join a mission-driven EdTech company as the Head of Sales, shaping the future of how K-12 districts implement innovative learning solutions. This remote role offers the chance to create impactful revenue strategies and lead a talented team committed to educational excellence.

Benefits

Equity participation

15 vacation days (increases to 20 after 3 years)

14 company holidays annually

6 sick leave days with reimbursement for health insurance

Sabbatical after 48 months

Community giving days

Paid bereavement days

Qualifications

• 10+ years in sales leadership roles, with 5+ years in senior positions.
• Experience selling to K-12 districts with strong negotiation skills.
• Expertise in building and leading national sales teams within SaaS or EdTech.

Responsibilities

• Design and lead sales strategy, focusing on K-12 markets.
• Build, coach, and manage a high-performance sales team.
• Utilize HubSpot CRM for pipeline management and reporting.

Skills

Sales Leadership

Edtech Experience

Coaching Teams

Data Analysis

Education

Bachelor's or Master's degree

Tools

HubSpot CRM

Sales Automation Tools

Job description

Executive Leadership Role | Sales & Revenue Operations | K–12 EdTech Location: Remote, USA

About Our Client

Our client provides a learning platform redefining how students prepare for life beyond school. Through their unique offerings, they help students discover who they want to be — not just what they want to do.

Our client sells to K–12 districts across the U.S. with personalized, competency-based learning that builds agency, SEL skills, career awareness, and workforce readiness.

The Opportunity

We are hiring a transformational Head of Sales to architect, lead, and scale a national sales organization, that drives adoption of our offerings across K–12 school systems.

Reporting directly to the President & CEO, this executive will be accountable for all aspects of sales leadership — from territory design and pipeline generation to sales team performance and operational systems. You’ll build a modern revenue machine rooted in strategy, data, and disciplined execution.

This role is ideal for a high-performing sales leader with deep edtech experience who thrives in building systems, coaching teams, and winning in complex, consultative sales environments.

Executive Mandate

• Own the full top-of-funnel through close: Sales strategy, pipeline, team performance, forecasting.
• Master and operate all Sales Operations infrastructure — especially HubSpot CRM.
• Drive high conversion and disciplined execution through coaching, analytics, and leadership.

Core Responsibilities National Sales Strategy & Execution

• Design and lead the go-to-market strategy across core K–12 regions, aligning with education funding cycles and procurement rhythms.
• Create territory plans, account segmentation models, and goal frameworks to drive pipeline velocity and market penetration.
• Lead execution of sales campaigns, RFP submissions, and multi-year contract development in collaboration with Marketing and Product.
• Build, coach, and lead a high-performance sales team with a focus on middle and high school districts.
• Create and manage team structures, hiring profiles, and compensation models that reward high-value execution.
• Run weekly 1:1s, deal strategy sessions, and performance reviews to ensure high accountability and active coaching.
• Develop and maintain sales playbooks, proposal templates, objection-handling guides, and pitch decks customized to district buyers.
• A/B test messaging strategies, refine value articulation, and embed learnings into team development.
• Collaborate with Product and Marketing to ensure tight alignment between positioning, market needs, and buyer behavior.
• Fully own the HubSpot CRM: pipeline management, automation, reporting dashboards, territory views, and quota tracking.
• Drive CRM hygiene and reporting accuracy across the team to ensure forecast confidence and transparency.
• Establish and maintain a complete Sales Operating System, including cadence rituals, dashboards, and performance metrics.

Ideal Candidate Profile

Required Experience

• 10+ years of progressive sales leadership experience, with 5+ years in a senior executive capacity.
• Extensive experience in K–12 education sales, navigating district-level sales cycles, public procurement, and multi-stakeholder negotiations.
• Proven success building, leading, and scaling national sales teams within a SaaS or EdTech company.
• Strong understanding of state funding (ESSA, CTE, Perkins, etc.) and the district buying process.

Required Technical Mastery

• HubSpot CRM: Advanced expertise — including pipeline structure, reporting, automation workflows, forecasting, and team performance dashboards.
• Proven ability to wrangle data to create a sales advantage — whether identifying conversion gaps or surfacing top-performing playbooks.
• Comfortable working cross-functionally with Marketing and Product on messaging and field enablement.

Leadership Attributes

• Strategic and operational — can think in quarters but lead in weeks.
• High EQ team builder who creates psychologically safe, accountable teams.
• Data-first mindset: believes performance starts with clean inputs and transparent reporting.
• Inspirational and trusted communicator — with internal teams and external education leaders alike.

Reporting Structure

• Reports to: President & CEO
• Cross-Functional Partners: Marketing, Product, Revenue Operations

Location: Remote USA

• Salary: $175,00 + performance-based incentive compensation
• Equity participation aligned to company growth
• Remote-first work model across the U.S.
• Vacation: 15 days per year, increasing to 20 after your third year
• Holidays: 14 additional company holidays annually
• Sick Leave: 6 sick days + up to $800/year in health insurance reimbursement
• Sabbatical: 4 weeks unpaid leave after 48 months
• Community & Climate Support:
• 1 Giving Back Day per year
• 1 Bad Weather Day per year
• Bereavement: 2 paid days off per year for the loss of a loved one — including pets

Why Join?

This is a rare opportunity to build the revenue engine of a mission-driven edtech company poised to redefine how future readiness is taught in America. You’ll shape how districts discover and implement our offerings — and in doing so, help students nationwide discover who they are and how they want to live.

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Industries

  Technology, Information and Internet, Education, and Software Development

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Inferred from the description for this job

Medical insurance

Vision insurance

Paid maternity leave

Paid paternity leave

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