We're Hiring a Director of Training!

About Ask Big Questions

We know today, more than ever before, that the future of our democracy depends on our ability to listen to, understand, and trust people different than ourselves. That’s why Ask Big Questions seeks to build the future leaders of our communities by teaching young adults how to have conversations about vital questions across lines of difference. We partner with colleges and universities to engage young adults in reflective community conversations about purpose, identity, and responsibility. These conversations build trust, strengthen community, and deepen understanding within diversity.


Ask Big Questions was developed, launched, and scaled by Hillel International. Since 2011, Ask Big Questions has trained over 1,000 student leaders, faculty, and staff on 109 campuses in our method of community conversation, engaging over 25,000 students. Ask Big Questions® is a registered trademark of Hillel International.


About the Role

Reporting to the Senior Director for Partnerships, the Director of Training plays a critical role in designing, delivering, and continuously evolving Ask Big Questions’ programs. You lead the collaborative development of training plans and related program materials to effectively prepare postsecondary students and their advisors to convene meaningful civil conversations with their peers. You recruit and manage a team of skilled facilitators, train them in the Ask Big Questions model, and use their feedback for continuous program improvement. Guided by the Director of Assessment, you integrate outcomes measurement throughout Ask Big Questions training and implementation, and ensure quality data collection. You are an active contributor to the Partnerships team’s efforts to expand and enhance Ask Big Questions’ relationships and programming with postsecondary education groups.




  • In collaboration with the Senior Director for Partnerships and Director of Assessment, continuously refine program offerings in anticipation of upcoming partner commitments
  • Establish, implement, and assess train-the-trainer certification program for university faculty and staff. Pilot and actively train at least eight participants within first six months on the job, and according to defined goals thereafter
  • Craft syllabus for trainer certification, including learning outcomes, culturally mindful resources and activities, and rubrics to assess mastery.
  • Develop implementation plans for student and professional trainings, from recruitment through event schedule and activities, data compilation, and partner debrief sessions
  • Oversee execution of training events (for a total of 33 campuses in FY17, and 45 campuses in FY18, and a growing number beyond those years) including ongoing development of culturally effective training materials in collaboration with trainers, and communications and marketing staff
  • Hire, coordinate and manage trainers who work remotely; regularly solicit feedback from them and use it in continuous program development; evaluate their individual performance and coach on ongoing professional development
  • Contribute to partnership proposals, program reports, conference presentations, and other administrative projects
  • Stay current on literature, practices and networks in relevant fields including training and professional development, student learning and development, diversity programming, and higher education trends
  • Actively participate in staff meetings, communications and project management. Represent Ask Big Questions at conferences or other events, when called upon to do so
  • Other duties as assigned


What to expect from the role:


  • You will help thousands of college students learn to lead more reflective conversations, and grow through constructive conflict, across lines of difference
  • You will enhance the professional development of dozens of talented university faculty and staff through skills training in the methodology of Ask Big Questions
  • You will cultivate a community of talented trainers committed to culturally competent, engaging, productive campus conversations
  • Your work will result in measurable positive effects on students and campus outcomes
  • You will hone your ability to design and execute a multi-level curriculum
  • You will deepen your understanding of assessment tools, how to integrate them effectively into program work, how to learn from them, and how to adjust program models in response
  • You will further develop skills in recruiting, training, and managing a diverse team of talented educators
  • You will receive generous benefits including, but not limited to, health insurance, retirement plan with employer contribution, and a robust list of holidays, vacation, and leave
  • You will be empowered and expected to bring your best ideas to work, and to offer feedback and constructive critique
  • You will have clear objectives, with flexibility in designing approaches to achieve them
  • You will join a dynamic and collaborative team of exceptional educators and professionals


We're looking for someone who is:

  • Passionate, talented, and skilled in training and facilitation with large and small groups, and who has a strong and inviting presence in a room
  • Fluent with higher education contexts (i.e. academic, student affairs, civic engagement and service learning, residence life, , orientation programs)
  • Experienced in designing curricula for diverse stakeholders
  • Adept at managing a dispersed team of colleagues
  • A strong written and oral communicator
  • A strategic thinker who is also able to prioritize among competing needs
  • An experienced team leader and respectful, engaged contributor to a dynamic, multi-faceted team
  • Committed to our mission to change the world through better conversation


You will thrive in this role if:

  • You have a sense of humor, a willingness to learn from and collaborate with colleagues, and the ability to not take yourself too seriously as you do transformative work
  • You take responsibility for your work, are ready to be held accountable for it, and are open to giving and receiving honest feedback
  • You are creative and willing to try new strategies that serve our mission and key objectives
  • You’re a person who gets the job done
Other key information:
  • Masters Degree and minimum 5 years relevant experience preferred
  • This job will require significant travel
  • The position must be based out of our Evanston headquarters or San Francisco office
  • Review of applications will begin by July 25
  • This search is being managed by Hillel International



About Hillel International:

Hillel International is the largest Jewish campus and community-based organization in the world serving the college-age population. Working with hundreds of thousands of students globally to help Jewish students make an enduring commitment to Jewish life, learning and Israel, Hillel serves students at more than 500 colleges, universities and communities. In addition to its presence on more than 450 North American campuses, Hillel works in more than 55 cities in Israel, the Former Soviet Union, Latin America, Australia, and the United Kingdom. Hillel meets all of these students during this most formative time of their lives and engages, educates and inspires these future leaders to make an enduring commitment to Jewish life, learning and Israel.



Ask Big Questions is an equal opportunity employer. We are interested in receiving candidates from a broad spectrum of people, including women and people of diverse racial and ethnic backgrounds.


To apply, click here.