Head of Sales, Prologue, US

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+ plus years in B2B SaaS Sales with 4+ plus years building or leading sales teams
• Consistent success closing complex, multi-stakeholder district deals
• 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 matt@prologuerecruit.org with your resume.

All conversations stay confidential 🚀