Head of Finance & Strategy 


40% OF COLLEGE STUDENTS IN THE UNITED STATES DROP OUT. That’s more than 37 million Americans who were on the path to a degree but couldn’t finish. Many dropouts are the first in their family to go to college, with a myriad of financial, social, and academic challenges that keep them from finishing. To help combat this, ReUp Education partners with universities to find students who have dropped out and are eager to get back to college. We come in to give them the support they need to re-enroll and graduate.

Founded in 2015, we are the only organization that focuses exclusively on helping universities engage and re-enroll students who have “stopped out.” To date, we have re-enrolled over 6,500 students and recaptured over $16 million in tuition.

The Role

Do you enjoy simplifying complex business questions and providing strategic input using financial models? How about analyzing key performance metrics to discover crucial insights that will supercharge growth? ReUp Education is looking for a Head of Finance & Strategy to join our growing team and help the 37 million Americans who have taken a break from college to return to school, complete their remaining credits, and graduate.

Reporting directly to our COO, you will own all aspects of the Finance function at ReUp Education, including financial planning & analysis, financial reporting, A/P, A/R, and business model forecasting. You will play a key role in helping the ReUp executive team achieve its performance goals by conducting analyses to inform pivotal operational and business decisions. This will also be a highly collaborative opportunity, in which you’ll partner with our data, product, and coaching operations teams to measure relevant KPIs against company goals. As we approach our Series A round, expand our student services, and look to double in size over the next year, your financial and business acumen will be critical at every step.

The ideal candidate has a strong track record of success at growth-stage companies, is comfortable working across a variety of teams, and geeks out on data analysis that will help further an important social mission. If this sounds like you, we’d love to hear from you!


  • Budget management including leadership of the annual budget planning process and regular budget variance analyses for review by the executive team

  • Maintenance of ReUp’s long-term business financial model, updating as needed to suit evolving needs

  • Regular financial reporting and analyses for the ReUp Board and external stakeholders, including investors, partners and clients

  • Oversee accounts payable and accounts receivable processes

  • Determine the ROI of new partnership deals and corporate initiatives

  • Support the executive team in defining company level performance goals and creating plans to achieve them

  • Work across departments to design, implement and track KPIs to measure performance against company goals

  • Provide recommendations to improve business performance based on regular analyses of operational and financial data

  • Material/content creation for investors, our sales team, and other ad hoc purposes

  • Regular usage of Excel, Tableau, and other analytical tools

  • Occasional board presentations and pitching to potential investors

  • Limited travel (bi-annual retreats; investor meetings)



  • Bachelor’s degree in Business, Finance, Economics, or a related field. Master’s Degree a plus.

  • 8+ years experience in corporate planning, business finance, investment banking, management consulting, private equity, or related fields

  • Higher ed, ed tech, and startup experience a big plus

  • Mastery of MS Excel and Google Sheets

  • Experience producing business insights from data

  • Experience with analytical tools and techniques a plus (SQL, statistics, data visualization and predictive modeling)

  • Experience building and maintaining financial models

  • Excellent interpersonal and written/verbal communication skills

  • You care about ReUp’s mission and are committed to helping us open new opportunities to students

What does success look like?

  • You will have thought critically about and updated our long-term business model to reflect changing priorities, partnerships, and services since our beginnings in 2015

  • You will have successfully helped guide us through a Series A funding round and played a key role in winning investments

  • You will have made sure we’re regularly establishing and hitting goals through close monitoring of KPIs

  • You have worked to implement the financial infrastructure needed to ensure we keep a close pulse on our financials and can quickly respond to market changes as needed 


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


  • Competitive salary and equity stake

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

  • Unlimited time off and remote work opportunity

  • 401(k) plan

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

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



ReUp employees share a passion for second chances. We fight hard to support students as they embark on finishing what they started. We believe in the power of human potential and you can feel that in our bones and our culture. We really mean it when we say we care about hiring people from diverse backgrounds. Take a look at our team tab on our website to read about our staff’s stories. 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.


Submit your resume and cover letter to careers@reupeducation.com

ReUp Education, Inc. ("ReUp") provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, or genetics. In addition to federal law requirements, ReUp complies with applicable state and local laws governing nondiscrimination in employment in every location in which the company has facilities. This policy applies to all terms and conditions of employment, including recruiting, hiring, placement, promotion, termination, layoff, recall, transfer, leaves of absence, compensation and training. ReUp expressly prohibits any form of workplace harassment based on race, color, religion, gender, sexual orientation, gender identity or expression, national origin, age, genetic information, disability, or veteran status. Improper interference with the ability of ReUp’s employees to perform their job duties may result in discipline up to and including discharge.