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Matt Wallaert
Matt Wallaert
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Associate Director of Product

Upright Education

Upright Education

New York, NY, USA
Posted on Monday, November 20, 2023

Company Overview

Upright Education provides a turnkey platform for community colleges and regional universities to easily launch and monetize specialized bootcamps in fields like software engineering, data analytics, tech sales, and digital marketing. Our part-time, hybrid programs are specifically designed to serve underserved schools and overlooked communities. In addition to technical skills, we offer career services to help learners transition successfully into their new careers.

Role Overview

The Associate Director of Product at Upright Education plays a pivotal role in shaping the direction and enhancing the effectiveness of our digital learning products. As a thought leader in the product space, you will work closely with a cross-functional team to ensure that our bootcamps meet the evolving needs of our learners, instructors, and other stakeholders, all while aligning with our company's strategic objectives.


Product Strategy & Vision:

  • Collaborate with senior leadership to align product direction with the company's overarching strategy.
  • Develop a multi-year product vision that anticipates market shifts and learner needs, ensuring the company remains at the forefront of online training bootcamp innovation.
  • Lead brainstorming sessions and workshops to generate new product ideas and features including new revenue generating courses.
  • Regularly research market trends and competitor activities in the bootcamp sector to maintain alignment with the evolving landscape and ensure Upright remains the leader in innovative online training bootcamps.
  • Collaborate with Marketing team to drive product marketing and messaging including unique value proposition and feature & benefit promotion.

Stakeholder Collaboration:

  • Engage regularly with the curriculum team to understand evolving educational objectives and translate them into product requirements.
  • Work in tandem with Learner Success team to ensure a seamless and learner-centric approach that drives forward exemplary learner satisfaction and experience.
  • Regularly communicate with sales, marketing, and learner support teams to understand the market landscape and learner feedback as well as provide regular product training on Upright bootcamps to sales and marketing to ensure product expertise across front-line efforts.

Product Development:

  • Oversee the entire product development lifecycle, from ideation and design to testing and launch of all new courses and bootcamps.
  • Prioritize iterations and initiatives based on company goals, learner needs, and ROI.
  • Ensure rigorous quality assurance testing and learner acceptance testing processes are in place before any public release of new or iterative curriculum and content.

Data-Driven Decision Making:

  • Implement metrics-driven strategies, ensuring every product decision is backed by data and analysis of market fit, learner expectations, and revenue generating viability.
  • Regularly review product performance against KPIs and set clear benchmarks for success.
  • Lead retrospectives on product launches to identify areas of improvement and lessons learned to improve launch processes across product, marketing, and sales.

Learner Research:

  • Design and implement comprehensive learner research studies, including surveys, interviews, and usability testing to gauge learner satisfaction with the overall product experience, curriculum, and delivery platform.
  • Analyze research findings to derive actionable insights that inform curriculum and product design and strategy.
  • Establish a continuous feedback loop with learners and instructional staff to ensure the product remains relevant and user-friendly as well as satisfies the learner outcomes goals.

Mentorship & Leadership:

  • Foster a culture of innovation, collaboration, and continuous learning within the product team.
  • Provide regular coaching and feedback to team members, guiding their professional development.
  • Lead by example, setting high standards for work ethic, creativity, and dedication.

Stakeholder Communication:

  • Develop and maintain a communication calendar to regularly update different stakeholders on product initiatives and iterations.
  • Lead product update meetings and quarterly reviews, ensuring all relevant parties are informed and aligned.
  • Manage and address concerns or feedback from internal teams and external partners relating to the products and curriculum.

Budget Management:

  • Oversee the product department's budget, ensuring optimal allocation of resources.
  • Collaborate with the finance team to track expenditures, forecast future financial needs, and ensure ROI on product initiatives.

Continuous Improvement:

  • Keep abreast of industry trends, competitor products, and technological advancements.
  • Champion a culture of continuous iteration, encouraging the team to regularly refine and improve product features based on real-world feedback and changing market conditions.


  • Minimum of 5 years of experience in product management, in the ed-tech, online learning domain, or the bootcamp space.
  • Proven track record of successfully launching and scaling digital products.
  • Strong analytical skills, with experience in using analytics tools.
  • Strong financial acumen, including P&L and budget management.
  • Excellent communication, leadership, and project management skills.
  • Ability to work in a dynamic, fast-paced environment.
  • Familiarity with Agile methodologies and tools.
  • Learner-centric mindset.


Hybrid Work Environment: Tuesday-Thursday in LES Manhattan office; Monday and Friday remote, work from home.