Head of Sales

Lucky Little Learners (LLL) creates fun, rigorous, research-aligned classroom resources and curriculum for K–2 teachers. Their mission is simple: less time prepping, more time connecting with students. They give teachers the tools they need to be great!

LLL is hiring their first Head of Sales to bring their products to schools and districts across the United States. Teachers already find and love them on their own. This role turns that grassroots demand into school- and district-wide purchases.

As LLL’s only salesperson, you’ll do the work yourself: prospecting, running demos, and closing deals. At the same time, you’ll put the sales processes in place that the business will run on. You’ll own the playbook, the pipeline, and the numbers from day one.

This is a remote role with very little travel. Expect a handful of conference and vendor-show trips a year, not a territory on the road.

What you’ll do

Sell

• Own the full sales cycle for school, district, and campus licenses of All Access: prospecting, discovery, demos, quotes, POs, and close.
• Run a high-velocity, transactional motion: many deals in flight, short cycles, and fast follow-up.
• Turn the existing teacher base into warm leads, partnering with marketing to find schools where teachers already use LLL.
• Sell confidently to principals, curriculum directors, and district leaders, speaking to K–2 math and literacy outcomes and the science of reading.
• Represent LLL at a few select conferences and vendor shows each year.

Build

• Build the sales function from zero: process, pricing and quoting workflows, CRM, and reporting.
• Write the playbook: ideal customer profile, outreach sequences, demo flow, objection handling, and procurement guides.
• Forecast revenue and report pipeline and results to leadership.
• Feed what you hear from schools and districts back to our curriculum and product teams.

What you bring

• 3+ years selling into K–12 school districts. Early elementary (K–2) experience is ideal.
• A track record of building a sales function from zero at a smaller organization, not only selling within an established team at a large company.
• Transactional sales experience: you’re comfortable managing a high volume of deals with short cycles.
• Working knowledge of how schools and districts buy: budgets, funding sources, POs, and procurement timelines.
• Comfortable as a team of one: you’ll do all the selling yourself while building the processes behind it.
• Strong organization and comfort with data, and forecasting.
• Clear, warm communication that resonates with educators.

Bonus points

• Former classroom teacher, principal, or curriculum director (a strong plus).
• Familiarity with the science of reading and structured literacy.
• Existing relationships with K–2 decision-makers.
• Experience selling digital subscriptions or site licenses.

Lucky Little Learners creates fun, rigorous, research-aligned classroom resources and curriculum for K–2 teachers. Their mission is simple: less time prepping, more time connecting with students. They give teachers the tools they need to be great!

Everything they make is digital. Their core offering is their All Access membership, which gives teachers unlimited downloads from the full library of 30,000+ resources, which includes a K–2 math curriculum and a 1st–2nd grade literacy curriculum. More than 300,000 teachers and districts use LLL across the country!

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