Head of Sales


Founded in 2015, we are the only organization that focuses exclusively on helping universities engage and re-enroll the more than 40% of US students who have “stopped out” and support them until graduation, through our technology-enabled service. To date, we have re-enrolled over 7,500 students and recaptured over $18 million in tuition for our university partners.


We are looking for our first Head of Sales to join the ReUp Education team! The Head of Sales will oversee the operation and development of ReUp’s world-class sales organization. You will work directly with the CEO and COO to establish your client and revenue targets, and then set out to successfully achieve these sales targets with your team of three Individual Contributors and a Business Development Representative. You will implement our sales playbook, employing a consultative sales process to secure long-term Higher Ed partnerships that expand ReUp’s scope of student impact and revenue results. As you achieve critical sales milestones, you will add to your team of passionate sellers while enhancing your sales organization to sustain ReUp’s success.

Our ideal candidate is excited to commit their strong sales leadership and drive to help ReUp build and deliver transformative experiences that guide students back to school and a degree. Top candidates have demonstrated consultative sales success, preferably in both enterprise and Higher Ed markets. Deep experience building, managing and coaching a sales team to high-levels of performance is a must, as is strict adherence to a defined sales process. You must possess ability to operate nimbly in a fast-paced, entrepreneurial environment. This position can be based anywhere in the US and reports directly to our CEO.


  • You will recruit, train, and manage a high performing sales team.

  • You will set sales and revenue targets and then personally execute and lead all aspects of our sales process to hit and exceed both sales and revenue targets.

  • You will continually analyze sales forecasts and pipelines to monitor progress and adapt sales activities to achieve goals.

  • You will immediately take over and advance several active prospects and partners with the goal of deepening relationships with key decision makers.

  • You will ensure new lead generation and pipeline growth that will sustain your defined revenue targets.

  • You will oversee and execute our consultative / solutions based sales playbook to engage Higher Education prospects with a clear value proposition of ReUp’s tech enabled service.

  • You will collaborate with leadership to continually evolve our sales and marketing strategy. This includes improving our go-to market narrative and developing sales materials to help enrich our business.

  • You will inform our product and marketing team about specific client needs, market trends, competition, changes in the higher ed environment, and other factors impacting sales.

  • You will act as a role model and leader by promoting a growth-mindset culture and positive can-do environment, and advise our team on taking our key partnerships relationships to more strategic levels.


  • You’ll be successful if:

    • You have a Bachelor’s degree in Business or a related field.

    • You have 6+ years of enterprise and Higher Ed technology sales and sales team management experience.

    • You have significant experience running the complete sales cycle, from prospecting to managing and closing deals.

    • You have a clear track record of consistently meeting or exceeding revenue targets.

    • You have deep experience in using the consultative / solutions based sales approach.

    • You have experience working in the launch and growth phases of a start-up.

    • You have convinced sales prospects of the complete value proposition of conceptual product offerings, and have helped identify funding sources.

    • You have closed long-term deals by aligning multiple decision-makers in a complex or tiered organization

    • You have varied experiences validating product fit with teams and clients.

    • You are a disciplined user of Salesforce or similar CRM to manage, track, and report on pipeline.

    • You are comfortable with some travel (~25%).

    We’ll be a great match if:

    • You’re mission oriented; you’re passionate about making an impact in education.

    • You understand that adhering to a great sales process leads to great sales results.

    • You are eager to support our sales team in the successful attainment of their quotas.

    • You always have a plan – you’re organized, highly resourceful and take initiative to execute on multiple priorities and tasks to meet individual and company outcomes.

    • You excel at verbal and written communication and can express complex topics clearly.

    • You easily develop strong relationships with colleagues and team leads, with an ability to align a wide range of perspectives on sales and marketing strategies.

    • You’re naturally curious and a quick learner, picking up on new topics quickly and easily.

    • You thrive in fast-paced, entrepreneurial environments with changing expectations and responsibilities.

    • You are persistent and tenacious — you are accountable for your own activity and success

    • You appreciate a challenge and like to grow and tackle new things each day


ReUp is a distributed company. You may join us in our San Francisco, CA office, or work remotely.


ReUp employees share a passion for supporting students as they embark on finishing what they started. We believe in the power of human potential and feel that in our bones and our culture. We really mean it when we say we care about hiring people from diverse backgrounds and building an equitable company.

We strive to create a safe and supportive environment where trust, communication, creativity, and humility are valued as highly as technical skills. We believe shared ownership builds a more resilient company, and we tackle hard problems, together. If that sounds like your dream work environment, we look forward to hearing from you.


  • Medical, dental, and vision insurance for employees; we pay 100% of the employee’s premium and 50% of any dependents’ premiums

  • Flexible time off and work from home policies

  • 401(k) plan

  • A diverse team that fosters a high level of collaboration despite being highly distributed

  • We will supply the tools you need to set your workspace up for success, including a Mac or PC laptop

ReUp Education is an equal opportunity employer. Our company values diversity and believes diverse teams make innovation possible. We encourage all qualified applicants from any race, color, religion, sex, gender identity, sexual orientation, national origin, disability status, protected veteran status, or other characteristics to apply.

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