Senior Director of Sales

BetterLesson - Cambridge, Massachusetts - Full time

About Us

BetterLesson empowers K-12 teachers to build a modern classroom: learner-centered, culturally responsive, and personalized. Instead of the conventional format of professional development for educators, BetterLesson supports teachers in a way that’s personalized and continuous -- utilizing a mix of virtual 1:1 coaching, virtual PLC coaching, remote workshops, and in-person workshops, all supported by the BetterLesson Lab. We match each teacher with a world-class coach and then leverage our technology to suggest customized teaching strategies, to qualitatively and quantitatively measure impact on student learning, and to continuously improve teaching practice through rapid iteration. This process leads to off-the-charts teacher love (our data shows teachers love BetterLesson more than Apple users love their iPhones), high administrator engagement, and, most importantly, dramatic teacher and student growth.

We design and tightly control every aspect of the system in-house: our coaching methodology, the content behind our pedagogical viewpoint, the delivery of our services to all teachers and district leaders, and the software powering our web and mobile apps. BetterLesson has raised over $30M of venture capital and grant funding, serves over 100 school districts, sees 850K+ monthly active users accessing our online lessons and strategies, and is expanding quickly.

We are a growing team of teaching practice gurus, educational opportunity devotees, and product development specialists. We place tremendous value on our company’s roots and culture: a shared passion to transform professional learning for educators at scale and a sense of urgency to achieve this vision. All candidates should have the experience, competence, and enthusiasm to dive in headfirst and rapidly solve complex, exciting, and interconnected problems. We feel we offer a unique opportunity to lead a growing team, have flexible hours, and make a massive impact on our education system.


Not your average sales leader? Great! We’re not your average sales team! We have a crew of incredibly skilled and experienced Directors of Partnerships, each owning a territory, who have done an incredible job building a culture of learning on the sales team; mentoring one another, codifying learnings across regions, deeply investing in the mission to bring continuous, personalized PL to every district, and driving more than 2x growth year after year.

We’re looking for an exceptional leader, committed to learning-by-doing, and continue to accelerate our growth and impact! Our Co-Founder has served as interim sales leader, shoring up our go-to-market strategy and sales process. And we’re now more than ready for a leader who can dedicate their full time to the leadership and support of this team; providing both the operational and strategic thought-partnership we need to fly even higher.

The right candidate will be passionate about and driven by BetterLesson’s mission to provide personalized professional development for educators so that they can create joyful, rigorous and engaging student-centered learning environments for all students.

You are

  • Experienced in supporting teams of high-performing, highly-experienced sales executives by taking a personalized approach to support and dedicating yourself to clear and open communication;
  • Skilled at cross-functional collaboration and people management; taking a learner-stance when approaching systems development;
  • A strong and warm relationship builder and communicator with a keen ability to engage a diverse cross-section of internal and external stakeholders;
  • Adept at managing teams to design and execute against revenue targets and key deliverables, using data to inform decisions at every turn;
  • An exceptional strategic thinker and leader with strong planning, organization, and detail-driven implementation skills;
  • Committed to a lead-by-doing attitude, open to some amount of travel to attend prospect and customer meetings, and actively helping to drive sales;
  • Driven to succeed on behalf of kids;
  • You are highly motivated, kind, and operate with integrity that aligns with BetterLesson’s core values.

You will

  • Dive into a learn-by-doing onboarding process, getting up to speed quickly and efficiently while digging right into the work of leading your team;
  • Work with the existing cross-functional leaders to learn the product, GTM strategy, and sales process;
  • Work particularly closely with our Growth Operations team to analyze various data sets in order to surface trends and insights, telling a clear, data-informed story around process optimization;
  • Establish the right (likely variable) cadence for connecting directly with our Directors of Partnerships, working with the Co-Founder/COO to gradually transfer support;
  • Support Directors of Partnerships with their Territory Planning, ensuring they have everything they need to execute against those plans, and strategizing around specific opportunities;
  • Oversee all strategic planning, including prospecting and hiring of new territory reps;
  • Be responsible for continuing to concretize the sales process, iterating on our already-strong approach to SalesForce use, our Ideal Customer Profile, and our Unique Value Proposition;
  • Work cross-functionally -- with marketing, partner success, services, etc. -- to connect up and execute against your team’s aspects of the go-to-market strategy;
  • Bring a genuine learner-stance to everything you do!

You have

  • A minimum of 8-10 years of leadership experience, preferably within k-12;
  • 5-8 years of Consultative Sales and/or Customer Success leadership experience, within a high-growth environment;
  • A track record of leading sales teams that meet and exceed revenue targets, on-time and with predictability;
  • A believable, impossible-to-miss passion for equity through education, and teacher support as a promising vehicle for that equity;
  • Lovely Additions: You have experience managing high-performing teams to do complex, solutions-selling to k-12 district leaders, around a tech-enabled services offering. ;)

We can offer you

  • the opportunity to work with an awesome team to solve important problems;
  • a competitive salary;
  • health benefits;
  • generous equity;
  • a great office space near Harvard Square in Cambridge (and part-time remote flexibility);
  • a flexible schedule and vacation policy; and
  • the opportunity to spend everyday working with school- and school system leaders to improve outcomes for teachers and students.


  • Cambridge, MA preferred. Open to partially remote for the right candidate!

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Experience Level

Senior Level


BetterLesson empowers K-12 teachers to build a modern classroom: learner-centered, culturally responsive, and personalized.

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