Chief of Staff

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.


Hankering for a chance to lead and learn across 6 functional teams within a high-growth start-up? We are seeking a highly competent executor with tremendously good judgment (and a sense of adventure!) to support and extend our Co-Founder and COO as we continue to build on 2018’s fast growth and level-up operations to support significant upticks in sales and partnerships.

Primarily this position will own strategic projects and support day-to-day awesomeness across the Sales, Marketing, Customer Success, People Operations, Growth Operations, and Finance teams, with a particular focus on systems and strategy within our Sales team. Additionally, this critical leadership role will necessitate close collaboration with our Product and Services teams, as we continue to fine-tune and creatively evolve our broader, go-to-market strategy.

The right candidate will be passionate about BetterLesson’s mission to provide personalized professional development for educators so that they can create joyful, rigorous and engaging student-centered learning environments. You are driven to succeed on behalf of kids; you are analytically inclined; and you are highly motivated, kind, and operate with integrity that aligns with BetterLesson’s core values.

You are:

  • a proven leader who can strategize, implement, improve, and manage both new and existing ideas and tactics;
  • ready to take each day as a grand adventure, embracing failure with an eye towards quick iteration and the next right thing to try;
  • a strong and warm relationship builder and communicator with a keen ability to engage a diverse cross-section of stakeholders and to socialize new ideas across teams;
  • adept at managing highly complex projects with precision and without ever losing clear connection to the purpose (which means being ready to adjust and rethink at every turn);
  • an exceptional strategic thinker with strong planning, organization, and detail-driven implementation skills;
  • a creative thinker;
  • sensitive to different personality types and processing styles;
  • comfortable doing high-level, high-stakes work in a fast-paced environment (with thought partnership and collaboration, but...) without always having a flawless blueprint;
  • a seasoned communicator who can cultivate strong, enduring relationships;
  • the type of person who thrives in ambiguity and complexity, and is a consummate self-starter.

You will:

  • Engage in a rapid, learn-by-doing onboarding process, which will include conversations across internal teams, shadowing the COO in virtually all external meetings, and tackling small initial projects in tandem;
  • Work w COO to refine and focus your role across the 6 teams (focusing on a tactical subset), based on your interests and aptitudes as well as the company’s most pressing needs;
  • Co-design potential solutions to determined challenges;
  • Concretize high-level blueprints created in quick conversations into more substantive plans, bringing them back for feedback before socializing them with other stakeholders across teams, refining them, and ultimately supporting any implementation of new systems or processes;
  • (Once more practiced...) Lead the diagnosis of specific areas of opportunity and challenge;
  • Design experiments to test hypothesis for ways to level-up strategy and processes;
  • Support the sales team -- and upgrading of sales processes -- as we scale;
  • Serve as a thought partner and sounding board, providing useful checks and challenges;
  • Consistently analyze various data sets in order to surface trends and insights that will lead to increasing both impact and growth with our partners;
  • Collaborate cross-functionally to establish and continuously evolve best practices across go-to-market strategy;

You have:

  • A minimum of 6-8 years of professional experience (or 5 yrs + MBA), preferably within k-12;
  • Mid-level leadership experience, within a high-growth environment;
  • Equal parts confidence and humility; well, maybe 60/40 ;)
  • Excellent judgment;
  • Strong auditory processing;
  • A believable, impossible-to-miss passion for equity through education, and teacher support as a promising vehicle for that equity;
  • been successful at simultaneously managing multiple highly complex projects across multiple teams;
  • shown excellent organization, detail-orientation and project management skills;
  • an ability to communicate complex trends and outcomes simply and effectively;
  • strong verbal and written communication skills;
  • A sense of adventure (See above!);
  • Lovely additions: If you have experience with school districts as a teacher or administrator, that’s fantastic. And if you’ve spent time marketing, selling, or doing customer success work within k-12, that’s terrific too.

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 Porter Square in Boston (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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C Level Executive Leadership

Experience Level

Senior Level


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

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