Head of Sales

Direct message the job poster from Prologue

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 Rev Ops, and set the standard for execution and culture.

• 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 Rev Ops
• Establish metrics for win rates, cycle times, and 3x pipeline coverage

• 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 Hub Spot, Outreach, and Clay
• Strong executive presence and the ability to inspire and coach a team

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

• 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

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

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

Apply directly on Linked In, DM us directly, or email matt with your resume.

All conversations stay confidential

• Mid-Senior level

• Full-time

• Business Development and Sales
• Industries

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