Senior Director, Services

BetterLesson - Cambridge, Massachusetts - Full time

About BetterLesson:

BetterLesson trains K-12 teachers for the modern classroom: learner-centered, culturally responsive, and individually personalized. Instead of the existing conventional (and ineffective) format of professional development for educators—filling an auditorium for a day of snooze-worthy slides and lectures—BetterLesson supports teachers with bi-weekly 1:1 coaching for their entire school year, leveraging our technology to study actual classroom performance, to set customized strategies relevant to each teacher and school district, and to access a nation-wide network of similarly progressive teachers as well as a deep database of lessons. Combining these elements creates a system that has off-the-charts teacher love (our data shows teachers love BetterLesson more than Apple users love their iPhones), high administrator engagement, and, most importantly, results that really help change classroom practices for the better.

We design and tightly control every aspect of the system in-house: the content of the teaching pedagogy, the delivery of services to all teachers and district leaders, and the software engineering of our web and mobile apps. BetterLesson has raised over $35M of venture capital and grant funding, serves over 70 school districts and other partners, and is expanding quickly.

We are currently a small and growing team of teaching theory aficionados, educational opportunity devotees, and software development masterminds. We place tremendous value on our company’s roots and culture: a precisely refined mix of individualism and common purpose. 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 join a small team, have flexible hours, and make a big impact.

About The Job:

As Senior Director of Services, you will oversee the management of our coaching operations, designing strategy and supporting the delivery of all coaching and consulting services to teachers and school district leaders. This is a very fast-paced, hands-on role, responsible for establishing and optimizing the operational structures and systems necessary for the rapid scaling of our service delivery while maintaining a very high level of quality. These responsibilities are critical to our company creating a world-class instructional coaching force and achieving our target levels of impact on teachers and students. If you’re the consummate “doer,” in addition to being a skilled and attuned leader, this might be your next gig!

You will focus on five main functional areas:

  1. Working with our coaching team to develop and define the key components of successful coaching delivery, and supporting and empowering the success of that team.
  2. Recruiting, hiring, onboarding, and managing the ongoing development of hundreds of top coach contractors who will work with both teachers and instructional leaders. We are rapidly scaling our contractor-based coaching model, and you will oversee the continued growth.
  3. Developing and refining the products, processes, and logistics to manage the deployment of our in-person workshops and on-demand instructional coaching model as it scales.
  4. Analyzing and optimizing the experience for teachers and instructional leaders that we coach to maximize educator delight and student impact.
  5. Overseeing regulatory and legal functions to ensure that we abide by the contractor and employment laws of every state in which we work.

You are:

  • a proven leader with outstanding management and interpersonal skills;
  • a clear and professional communicator, both verbally and in writing;
  • able to work in partnership with all levels of the organization;
  • operationally focused and experienced with rapidly scaling a team;
  • driven by client satisfaction and able to effectively leverage client feedback;
  • analytically oriented with strong decision-making and problem-solving abilities;
  • passionate about education and BetterLesson’s social mission; and
  • comfortable embracing the experimentation, risk, speed, and failure inherent to startup hustle.

You will:

  • lead a team that recruits, onboards and manages hundreds of instructional coaches;
  • manage the business aspects of coaching delivery (margin, utilization and satisfaction);
  • develop and refine short and long-term business and org structure strategy, and execute against it;
  • work closely with our product operations team to create the systems necessary to manage the full life-cycle of coach experience;
  • collaborate with our product team around end user (teacher or instructional leader) experience and ways to maximize their delight;
  • collaborate with our sales team to optimize incentives for coaches and ROI for district partners to drive revenue growth;
  • liaise with outside counsel to ensure complete compliance with employment laws; and
  • recruit top operational and instructional talent to join the team.

You have:

  • a Bachelor’s degree;
  • professional experience in the education space;
  • 8+ years of management and operations experience, preferably with 3-5 years in management consulting and 3-5 years in an industry operations management position; and
  • experience building and refining complex logistical systems and processes.

You potentially even have:

  • direct understanding of on-demand “gig economy” service models.

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Experience Level

Senior Level


BetterLesson trains K-12 teachers for the modern classroom: learner-centered, culturally responsive, and individually personalized.

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