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Learner Success Champion (fully remote)



Silver Spring, MD, USA · Remote
Posted on Tuesday, January 23, 2024

This is a remote-flexible role, and our headquarter is located in Silver Spring, MD. Currently, our employees are based in one of the following states: District of Columbia, Maryland, North Carolina or Virginia. As such, we will prioritize candidates from locations stated above, but we remain open to considering the right candidate from anywhere within the US only.



We are an impact-focused, early-stage startup building a better way for large corporations to reduce the high turnover of their frontline employees. By reducing turnover, we save companies millions of dollars. At the same time, we provide the training and support employees need to both succeed in their current jobs and advance to new jobs where they double their salary.

Leveraging our unique technology, our training and support can be accessed anytime and anywhere. Our product is built to scale, using the learnings from Escalate’s founders decades of experience in workforce development. We’re building a product designed to eliminate user acquisition costs, train hundreds of thousands of employee learners per year, and provide a cost-effective safety net of support to frontline workers across the country.

As a Techstars 2023 portfolio company, we have experienced major traction and are gearing up for growth.


Two problems cost retail companies $40B each year.

The first is turnover of frontline employees. 76% leave their jobs within the first 120 days.

The second is the lack of qualified candidates for middle-skill jobs. 75% of employers say they can’t find people for these jobs. They consider them unfillable.

Escalate leverages these problems in a new way.

70% of those retail employees, who are disproportionately women and people of color, say they would stay with their current employer if they were shown a path to advance.

We create that path. Our mission is to provide frontline workers a clear path to economic self-sufficiency that is not reliant on traditional post-secondary education while engaging employers by impacting their bottom line.


We are now looking for a passionate Learner Success Champion, reporting directly to the Chief Experience Officer (CXO), to build out the instructional experience for our employee learners.

Our program is fully asynchronous (with high support) geared towards incumbent workers who cannot commit to the traditional time commitment of in-person learning or multi-year programs.

You will guide learners through an asynchronous learning experience. Full lessons, course materials, assignments, and assessments are embedded in our online curriculum, and while there is no live instruction, some synchronous workshops may be offered as needed. Your key responsibility is ensuring learner success. This includes making sure employee learners are acquiring the skills they need to advance, promoting retention and completion through community building and support, and connecting learners with the resources they need.

This is a fully remote position. We anticipate a 3-person instructional team to train up to 250 learners per year. We are hiring two Learner Success Champions to accommodate our 32-hour work week schedule, and ensure support 7 days a week to our learners. One Champion will work Wednesday through Saturday from 9am to 5pm ET, and the second Champion from Sunday through Wednesday from 9am to 5pm ET.


Important consideration: As a member of our early-stage start-up team, you won't just be an employee, you'll be a key stakeholder—instrumental to our success. Your role will be dynamic and evolving, and you must be prepared for these to adapt and expand as our company grows. This means wearing multiple hats, taking on tasks that will not be explicitly listed in your responsibilities below, and being willing to roll up your sleeves to build from the ground up.

By joining us early on, you'll have the opportunity to shape your role, develop new skills, and take on leadership responsibilities.

Working in an early-stage startup can be demanding and unpredictable, however, if you're someone who thrives on change and innovation, continue reading!

As Learner Success Champion, you will:

Facilitate 1:1 professional coaching sessions by:

  • Providing personalized career coaching sessions to learners from diverse backgrounds
  • Collaborating with learners to establish short-term and long-term career goals and track progress towards achieving them
  • Offering guidance with challenges that may arise at work (e.g. managing relationships with managers and peers)

Support program design and logistics by:

  • Managing cohorts including daily reminders/updates and weekly program announcements via Slack
  • Cultivating, developing, and discovering pathway-specific experiential learning opportunities for learners
  • Developing reflective activities to promote connection of program content to daily job experience
  • Collaborating and troubleshooting with CXO, Program Director and Product team to identify and address any issues that could prevent learners from completing the program

Foster an inclusive and intentional learning community by:

  • Building relationships with learners, and fostering a supportive and inclusive learning community
  • Conducting professional development 1:1 check-ins with learners
  • Designing and facilitating synchronous cohort community building activities
  • Tracking, planning and celebrating program milestones

Support program management and logistics by:

  • Managing cohorts including daily reminders/updates and weekly program announcements via Slack
  • Building a robust & interactive onboarding experience for new learners
  • Designing program map
  • Providing frequent updates on program status and outcomes; as well as, monitoring learner progress
  • Leading small group synchronous workshops as needed
  • Encouraging learner engagement
  • Designing “how to” videos to improve overall user experience
  • Creating program handbooks / playbooks
  • Tracking knowledge and learnings
  • Effectively utilizing Escalate’s technology platforms
  • Building relationships with learners, and fostering a supportive and inclusive learning community
  • Collaborating and troubleshooting with CXO, Program Director and Head of Product to identify and address any issues that could prevent learners from completing the program
  • Tackling and solving operational and technical challenges as needed

Provide technical assistance by:

  • Responding to technical questions and inquiries via Chatbot within 12 hours
  • Designing interventions at failure points
  • Ensuring all educational training sessions are operating adequately and accessible to learners participating in online sessions
  • Providing technical support, troubleshooting and testing activities as needed
  • Leading ongoing LMS training as needed

Support data collection & analysis by:

  • Assessing and monitoring learner progress weekly
  • Ensuring learners are working towards competencies of program learning outcomes
  • Regularly gathering feedback from learners


You are an educator with experience instructing/teaching. You are excited to join a start-up and build from the ground up. You have an exceptional ability to support learners with different needs. You build strong relationships and a proven record to ensure learners successfully complete asynchronous training programs. You have a knack for ‘getting things done’ and don’t mind rolling up your sleeves. You welcome roles with high levels of ownership.

Specific requirements include, but not limited to:

  • Demonstrated passion for Escalate's mission
  • At least 2 years of digital/e-learning experience
  • Experience education, workforce and/or working with adults
  • Proven experience as a career coach or in a related role, with a demonstrable track record of successful client outcomes.
  • Proficiency in using career assessment tools and resources.
  • Knowledge of various industries and the ability to adapt coaching strategies accordingly.
  • Up-to-date knowledge of job search and professional development best practices.
  • A commitment to continuous learning and professional development.
  • An entrepreneurial spirit that thrives in a fast-paced, dynamic start-up, and ever-changing work environment (i.e. willing to rolling up sleeves)
  • Ability to comfortably navigate new technologies and tools
  • Professional demeanor, excellent organizational and communication skills, and attention to detail
  • Self-reflective and open to frequent feedback from learners and team
  • Positive, solutions-oriented attitude, drive for excellence, and ability to be a team player
  • Creative, strategic, and analytical thinker with the ability to manage multiple projects and balance short and long-term objectives
  • A growth mindset; self-reflective and open to frequent feedback from students and program team


Escalate is a people-first company. We are committed to providing benefits that allow our employees to take care of themselves and their families.

  • Comprehensive and premium medical, dental, vision insurance
  • Flexible paid time off
  • 32-hour work week


We are dedicated to building a team of talented individuals who share our vision. As an early-stage startup, our resources are limited, and our compensation may not match what you might find at larger, more established companies. We firmly believe that the value of joining Escalate extends beyond just financial compensation. By becoming a part of our mission-driven team, you'll have the opportunity to be part of a journey that has the potential for substantial growth and impact.

At this time, the base salary for this role is $60,000. To counter pay inequity and uphold internal parity, salaries are non-negotiable for all employees.


  • We were accepted as a Techstars portfolio company and part of the 2022-2023 Workforce Development Accelerator
  • We oversubscribed our pre-seed funding round, closing at $1.26M on a $7M valuation and backed by top investors, including ECMC Foundation, Gurtin Ventures, Potencia Ventures, Rock Creek Ventures, Techstars, and TEDCO
  • We secured our first contract to train 1,000 employee learners in 2024 at $2M in revenue


Escalate an equal opportunity employer. We provide equal employment opportunities to all employees and applicants for employment and prohibits discrimination and harassment of any type without regard to race, color, religion, age, sex, national origin, disability status, genetics, protected veteran status, sexual orientation, gender identity or expression, or any other characteristic protected by federal, state or local laws. This policy applies to all terms and conditions of employment.