Head of Sales

Prologue; United States; Remote; USD 150,000 - 200,000; Full time

Benefits offered by this job

Market-competitive base

OTE and meaningful equity

Full benefits

Job summary

An innovative K12 LMS company is seeking a Founding Head of Sales to lead the sales strategy and build a high-performing team. This remote-first role requires extensive K12 EdTech sales experience and a proven track record in B2B SaaS sales. The successful candidate will partner closely with leadership and set the standard for execution and culture. The position offers competitive compensation and equity options.

Qualifications

• 8+ years in B2B SaaS Sales with 4+ years building or leading sales teams.
• Mastery of K12 buying cycles including RFPs.
• Strong executive presence and ability to inspire and coach a team.

Responsibilities

• Design the full GTM playbook for K12 districts and state agencies.
• Own the forecast, pipeline hygiene, pricing, and deal strategy.
• Recruit, train, and lead AEs across segments.

Skills

K12 EdTech sales experience

B2B SaaS Sales

Executive presence

Salesforce CRM discipline

Tools

Salesforce

HubSpot

Outreach

Clay

Job description

Direct message the job poster from Prologue

Overview

Prologue has been retained by a fast growing K12 LMS company at Series A. The product is becoming a market leader and is already winning multi-year district contracts. We are hiring a Founding Head of Sales to own new ARR, build the sales motion from zero to one, and scale a high-performing team across Enterprise and Mid-Market K12. You will report to the CEO, partner closely with Product, Marketing, and RevOps, and set the standard for execution and culture.

What you will do

• Design the full GTM playbook for K12 districts and state agencies
• Own the forecast, pipeline hygiene, pricing, and deal strategy in Salesforce
• Recruit, train, and lead AEs across Enterprise and Mid-Market segments
• Drive enterprise pursuits with ACVs of 200K plus and multi-year terms
• Navigate RFPs, board approvals, procurement, security reviews, and legal
• Build channel and SIS partnerships that accelerate district adoption
• Collaborate on demand generation with Growth Marketing and RevOps
• Establish metrics for win rates, cycle times, and 3x pipeline coverage

What you have

• K12 EdTech sales experience is required
• 8+ years in B2B SaaS Sales with 4+ years building or leading sales teams
• Mastery of K12 buying cycles including RFPs and state adoption processes
• Proven playbook development, from ICP and territories to comp and quotas
• CRM discipline in Salesforce and familiarity with tools like HubSpot, Outreach, and Clay
• Strong executive presence and the ability to inspire and coach a team

Nice to have

• LMS or adjacent learning ecosystem background
• Experience with SIS integrations and channel partnerships
• Prior founding or early-stage operator experience

Outcomes in your first 12 months

• Hit or exceed your new ARR target with 3x qualified pipeline coverage
• Hire and onboard the first wave of AEs with clear territories and quotas
• Reduce average sales cycle time and increase win rates
• Land flagship district logos and referenceable case studies
• Stand up a forecast rhythm and deal review cadence with the CEO

Location

United States. Remote first with periodic travel to customers and company offsites.

Compensation

Market-competitive base, OTE, and meaningful equity. Full benefits. Final package aligned to experience.

If interested in the position:

Apply directly on LinkedIn, DM us directly, or email [e-mail] with your resume.

All conversations stay confidential

Seniority level

• Mid-Senior level

Employment type

• Full-time

Job function

• Business Development and Sales
• Industries

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