GOOD TROUBLE
Strategic Advisors
Collaborating with good, smart people to build organizations the world needs
Jeff Liberty is Good Trouble’s Founding President and CEO. Over a distinguished career spanning four decades, Jeff has developed extensive expertise in supporting the launch and maturation of mission-driven organizations.
An educational entrepreneur with over 20 years of experience as a teacher, district administrator, literacy coach, and the founder of a new green-themed secondary school in Boston, Jeff joined the BetterLesson team in 2014 and played a critical role in the growth of the company over ten years where he served as BetterLesson’s Senior Vice President of Innovation and most recently as its National Vice President of Urban and Strategic Partnerships.
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As BetterLesson's 12th employee, Jeff worked closely with the company’s founders to help pivot the organization from a scrappy, small-scale educational resources provider to an internationally respected professional learning company with a team of 300+ full- and part-time employees.
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Jeff was responsible for developing, sustaining, and growing a diverse $20m+ portfolio of partners on three continents in public and private schools, districts, national foundations, and state departments of education.
​Being an executive in an early or mid-stage company or nonprofit that has its sights set on growth and social impact can be a thrilling experience. It can also be very demanding and, at times, overwhelming. Good Trouble can supplement the talent and experience of CEOs, Executive Directors, and their senior leadership teams in all of the following areas:
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Executive coaching
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Support with culture building and team retreats
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Business model and business development consulting
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Strategic planning, networking, and partnership facilitation
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Product development
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Marketing, finance, customer success, sales, and go-to-market strategy
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Recruitment/candidate screening for new and existing leadership roles
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Management of mission-critical projects
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Governance and Board Development
Testimonials
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Tikvah Wiener, CEO, Kadima Coaching
With clarity and care, Jeff is mentoring me and my partner (and sister!) Smadar Goldstein as we launch our educational coaching company, Kadima. Jeff is guiding us with wisdom, humility and humor, helping us make pivotal strategic decisions as we build and grow our organization. His many years of experience in both education and in the business of providing educational services to schools make him the perfect partner for us, but anyone seeking coaching, support, and guidance as they start and develop a venture will benefit from Jeff's talents, insights, and expertise. You are in good hands with Jeff as you find ways to get into Good Trouble!​
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Guivens Andre, CEO, Amie
Jeff possesses a rare ability to distill complex strategic challenges into clear, actionable insights. He's been instrumental in refining my tech venture's positioning, demonstrating a keen understanding of market dynamics and a talent for innovative problem-solving. Jeff's guidance is both practical and visionary, making him an invaluable asset to any business seeking growth. His thoughtful approach and genuine dedication shine through in every interaction. I wholeheartedly recommend Jeff to anyone looking for a strategic consultant who delivers real results and will help you better position the problem you look to solve.
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Over my many years of working with him as an advisor, Jeff Liberty has imparted invaluable information that has supported me as a leader in the non-profit and social good sectors. As a former Founder and Executive Director, I always knew that I count on Jeff for mentorship and guidance, given his years of experience in the non-profit sector. While he has a long history in non-profit governance, program development, and fundraising, he was especially valuable to me as an advisor, because of his own experience in starting something from scratch and from the ground up.
What also makes Jeff stand out as an advisor is that he has never hesitated to provide guidance around the ethical challenges that frequently come up in the field. While many can advise around constructing a non-profit board or one can read books about cultivating funds and development, Jeff provides insight around how to maintain one's integrity and how to strengthen one's own moral courage and sense of ethics in a complex field. That is something that comes with years of knowledge and a willingness to mentor the next generation of social change leaders, which Jeff is especially gifted at.
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Jeff Liberty is a seasoned leader who played a pivotal role in the development and launch of our core professional development business. His leadership was instrumental in refining our business model, and he successfully closed several critical deals that not only validated our initial concept but also gave us much-needed credibility in the market. These achievements directly contributed to us securing a vital round of funding, allowing the company to scale.
Jeff consistently provided my co-founder and me with sage counsel. His unique blend of optimism, creativity, and innovation was key to pushing boundaries and exploring new opportunities for growth. Jeff’s ability to balance big-picture thinking with practical execution made a huge and lasting impact on the trajectory of our business.
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Jeff stepped in to support TeachUNITED during a pivotal moment of scaling, where we had strong outcomes but were feeling short on capacity. With such an important mission ahead of us serving teachers and schools, Jeff was recommended as a strategic advisor but quickly became an integral part of the team on several key projects. From project management to leadership staffing to KPIs, Jeff's experience in all aspects of the business was instrumental in helping TeachUNITED with both strategy and execution. I consider Jeff an investment in the core business to help meet our goals and prepare for the next stage of growth.
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I've known Jeff professionally for some time, and I've always admired his approach to achieving goals through empowering others and building strong relationships. I met with him recently to discuss the challenges of growing a company with co-founders. I knew we were facing some challenges, but they were hard to pinpoint. Jeff's questions and experienced perspective uncovered gaps and opportunities in how our team thinks about this phase of our business, and he provided practical strategies that we're excited to try to see how we can communicate better and learn more intentionally as a team.
I can't recommend working with Jeff enough to unlock your organization's potential so you can make the impact you hoped to make by getting into business in the first place!
