HeadAhead | 22 followers on LinkedIn. HeadAhead is Canada’s newest tutoring marketplace that offers students and parents the opportunity to make better choices to best fit their learning needs. HeadAhead merges the best of existing technologies to provide instant scheduling and payment options. HeadAhead uses unique learning-style analysis to match students with tutors that can teach in the way they learn best, creating a truly one-on-one student-centered learning experience.