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Director of Sales & Implementation



Sales & Business Development
Brooklyn, NY, USA
Posted on Wednesday, April 17, 2024
Full Time, Remote Position

About ChalkTalk

ChalkTalk is GitHub Copilot for teachers.

ChalkTalk uses student assessments to generate personalized digital courseware for every day in the course schedule. Every modular ChalkTalk lesson plan comes with editable teaching materials for the teacher, small group work and adaptive practice for students, and progress reports for administrators.

ChalkTalk is delivering improvement in student learning outcomes up to 6x, as measured by third-party test scores. It is currently used to power literacy and numeracy instruction district-wide at some of the largest US districts including 10 of the largest 100.

ChalkTalk currently has 35 employees. Check out this quickof our product and what we do from 2020: For a more updated list of our offerings, check out our website:

About The Role

ChalkTalk is seeking a Director of Sales & Implementation to help grow and lead our sales and implementation teams. In this position, you take over leadership and management of the Account Executive Team (currently managed by the CEO) and the Account Management Team (currently managed by the COO).

Chalktalk sold our flagship product by targeting high school ELA & math graduation tests. Now, we expanded to be a HS ELA & math that’s used as a core complement or supplemental program. We also added K-8 programs for math. We are used by over 100K+ students across 350+ schools in the US. We grew revenue organically by 2x+ every year since our launch in 2019, and are on track to hit ~$4.5M in 2024. We’ve closed district-wide partnerships with several of the largest school districts in the nation to individual schools from NY to Hawaii. We sell at the district level and follow a land-and-expand strategy, where we close large logos and grow them substantially with upsells/cross-sells to drive up NRR. Our sales are seasonal as per K12 sales cycle, and consultative in nature. Our buyer is typically the Director of Curriculum or Assistant Superintendent of Curriculum. Today, all sales are outbound and generated by your AEs who are full-cycle.

You will be leading a sales team of 3 Account Executives, 1 part-time Sales Enablement Associate, 3 Account Managers, and 1 RevOps. Our team is dispersed across the US. The three most important things we are hoping you can help us accomplish is (1) meeting our 2024 goals of 2x+ ARR growth with 130%+ NRR & 90% GRR (2) creating comradery and culture for a currently siloed team, (3) be a player-coach sales leader to the team, as we’re a bit too small for only a coach leader and a bit too big for only a player leader.


  • Lead and grow the sales and implementation teams
  • Drive and maximize revenue by iterating on sales methodology in order to optimize the funnel.
  • Set goals, expectations and quotas for the teams and enable them to achieve and exceed them.
  • Ownership of sales training and RevOps.
  • Create and execute on sales strategies including account-based strategies to help sales team meet their goals
  • Facilitate market research and creation of sales enablement materials in collaboration with others to help make AEs more productive
  • Set high-level vision; lead recurring meeting structure and sales process (pipeline review, deals review, sales velocity, …).
  • Iterate on framework & end-to-end process from lead generation to close to renewal and expansion
  • Organize and ensure adherence to the CRM (Hubspot)
  • Review call & Zoom recordings with the team and coach them on strategy and presentation
  • Leadership style compatible with an early-stage high-growth company environment: digging into the details with the AE or AM providing actionable support on the frontlines vs higher-level and process and strategic support only.


  • Has worked in a sales leadership position in a startup, very strongly preferably during its growth from $2M to $10M+
  • 5+ years enterprise B2B sales experience
  • Deep experience with Hubspot or other sales management platform
  • Has high retention rate among sales representatives
  • Delivers quota quarter over quarter
  • Outbound lead generation experience
  • Data/metrics-driven and process-driven, but also digs into account-based sales plans and helps with execution of individual deals.
  • Experience implementing sales methodology and establishing a culture of accountability
  • A disciplined self-starter with the ability to wear many hats
  • Prefer someone with K12 B2B enterprise sales experience, ideally on the ops side
  • Nice-to-have: has sold a suite of K12 C&I products, has successfully cross-sold C&I products, has experience in building separate customer-facing teams for separate functions.

Why work at ChalkTalk?

  • Mission: You want to help provide the best education possible to everyone on the planet.
  • Impact: In just 15 weeks, districts that bought ChalkTalk saw their students experience 2–6X MORE GROWTH ON OFFICIAL STATE TESTS compared to their peers who received 52 weeks of traditional classroom instruction. Big impact with vulnerable student populations.
  • Growth: Company has consistently grown, increasing revenue by double or more each year since 2019 and has 10 the largest 100 school districts in the US as customers.
  • Awards: Top 10 finalist at 700+ ASU GSV Cup 2020. Winner of FETC’s Best in EdTech 2021 alongside Microsoft & Lego. Winner of EdTech Week’s EdTech Cup in NYC 2022. HolonIQ’s North America EdTech 200 list for 2023.
  • Accelerators: AWS EdStart, OnRamp Education Accelerator, and Entrepreneurs Roundtable Accelerator (ERA) NYC
  • Competitive Compensation: Competitive salary, commission and equity offers
  • Benefits: Health, dental, and vision insurance. Unlimited PTO. 3-6 free counseling appointments through our EAP