Virtual Success Advisor (Serving Chicago Students)

Posted by
Bottom Line
Chicago, IL
Published 24 days ago

Interested applicants should apply here:

Overview, Job Description & Benefits

Students are at the core of Bottom Line. Every day, we are energized by their drive, potential, and passion. We know that the success of our students will create a ripple effect in our communities.

Bottom Line is bridging the divide of educational inequity by providing a trusted advisor and the social capital necessary for our students to earn their bachelor’s degree, build financial stability, and successfully launch thriving careers. We primarily focus on students of color who will be in the first generation of their family to earn a college degree, are from low-income backgrounds, and are academically prepared for college.

For more than two decades, Bottom Line has been fighting for educational equity by ensuring that the right to a quality college education is accessible to those whose potential and drive exceed their opportunity. For first-generation degree-aspiring students from low-income backgrounds who face systemic barriers, Bottom Line’s advisors are a relentless ally who partner with them to find the right college, persist to a degree, and successfully launch a career.

As one of the first college support organizations to focus on college completion, Bottom Line now produces best-in-class college graduation rates that reduce the significant gap between first-generation students from low-income backgrounds and their wealthier peers. We operate regional programs in Massachusetts, New York City, and Chicago that collectively serve over 7,000 students.

When you join Bottom Line, you will find an organization that lives into its core values. We are committed to building strong, impactful relationships with our students, co-workers, schools, community partners, donors, and other supporters. We are engaging, responsive, caring, direct, honest, solutions-oriented, and we always follow through on our promises. We act with empathy and extend grace to ourselves and each other. We pursue ambitious goals, hold ourselves to high standards, make data-informed decisions, and orient to long-term success for our students and our organization. We operate with curiosity, evolve thoughtfully, take informed risks, and learn from successes, setbacks, and each other. Experts in our field, we are driven by our mission and motivated by the impact we’re achieving. 

At Bottom Line, we have a strong commitment to Diversity, Equity, and Inclusion. We aim to attract diverse candidate pools who hold these same values, and are ready to help us along our journey toward greater equity and inclusion. 

For more information about who we are, please review our Core Values and Careers Page

 Job Description

This position will be responsible for supporting a caseload of 300-400 rising first year college students from Chicago Public Schools in the Bluprint model. This role will primarily report to the Virtual Success Team Manager on the National Program Team with dotted line reporting to the Chicago Regional Managing Director of Programs. The Virtual Success Advisor will spearhead Bottom Line’s first ever hybrid approach to caseload management to serve students via customized content delivered through SMS and supplemented via live, virtual sessions with the advisor as needed for significant issues or that require escalation or more nuanced guidance. Success of this pilot program will propel Bottom Line to both broaden and deepen our service to first-generation college-bound students.  

Bottom Line’s 2030 ambition calls on us to expand our reach to serve 20,000 students while maintaining high-quality programming and outcomes. In order to achieve this vision, our programs need to evolve to improve outcomes, increase efficiency, and drive scale. One of the ways we will do this is by investing in AI powered chat bot  technology (“Blu”) and a new light- touch Success Program model (“Bluprint”), a fully virtual, scaled-down version of Bottom Line’s Success Program model. The program will facilitate personalized, targeted, and automated communication with students via SMS and support students navigating college with a customized virtual assistant, Blu, who will help them stay on track to graduate.  

Blu will communicate with students about routine reminders, frequently asked questions, and additional resources. The chat bot will send out nudges that support key milestones across our College Success Program, supporting student outcomes and satisfaction. Bluprint will allow us to support a population of students we have yet to be able to serve beyond college acceptance, students who are part of our Access program but are not eligible for our Success program because they are not enrolled at one of our target colleges. It will also allow us to serve students who are seeking lighter touch support while in college.

Full list of benefits can be found here:


Primary Responsibilities:

Direct Student Support – 50% 

  • Manage a caseload of 300-400 students with a hybrid approach to our Success Program model that combines technology and live support, adapted from Bottom Line’s core Success Program model 
  • Engage directly with students by answering more complex student questions and engaging in a more meaningful way when chat bot does not sufficiently support a student; “live support” will be provided virtually (phone, video chat, and email) and will be centered around Bottom Line’s DEAL (Degree, Employability, Affordability, Life Skills) model with a focus on students completing key milestones, including but not limited to: 
  • Enroll in classes 
  • Pay balance 
  • Create a professional resume 
  • Complete financial aid applications 
  • Help students resolve general obstacles that come up throughout the school year by coaching them on self-advocacy and resourcefulness skills, and communicating with school offices to advocate for students when necessary 
  • Support with the implementation of a summer melt campaign to ensure students achieve critical milestones that support their enrollment in the fall, including but not limited to: 
  • Finalizing outstanding financial aid issues (verification, institutional forms, etc.) 
  • Pay fall balance or create a payment plan 
  • Complete important forms to support student’s on-campus or commuting plan (housing, meal plans, transportation plan, etc.) 
  • Access work study and other campus resources  

Technology and Design Support- 30% 

  • Support the development of personalized text message content and calendar that contributes to student success in achieving outcomes across Bottom Line’s Degree, Employability, Affordability, Life (DEAL) model  
  • Use an AI-powered chat bot to analyze performance metrics of the platform, adjust as needed and intervene to provide more nuanced support as needed  
  • Test effectiveness of automated messages and share learnings with program teams and organizational leadership to inform ongoing improvements to delivery 
  • Collaborate with Director of Program Design and SMS Design working group to help inform how aspects of this pilot can be incorporated into Bottom Line’s core program 
  • Support training and implementation plans to support scaling-up the intervention upon pilot successes 

Program Support – 15% 

  • Evaluate engagement trends and work with team to identify opportunities to tailor services to effectively meet student needs (online modules, virtual workshops and events, etc.) 
  • Collaborate with the Chicago Managing Director of Programs to recruit initial caseload of students from Chicago Public Schools 
  • Collaborate closely with Chicago Managing Director of Programs and Chicago Public Schools to provide regular cohort updates and share progress 
  • Track student engagements and milestone progress by logging case notes and updating appropriate database fields 

Secondary Responsibilities:

Organizational Support – 5%

  • Represent the Bottom Line brand in a positive light, and take actions to increase brand awareness throughout the community 
  • Follow trends and best practices in the field of college success and technology to support persistence efforts to inform evolving program design  
  • Participate in facilitation of strategy and design sessions to inform evolving program strategy

Duties, responsibilities and activities may change at any time with or without advanced notice.



  • Bachelor's degree and work authorization required
  • Demonstrated commitment to Bottom Line’s Mission, Vision, and Core Values
  • Demonstrated proficiency and/or growth potential in Bottom Line's seven core competencies: Relationships, Results, Communication, Inclusiveness, Talent Development, Agility, and Planning
  • Experience developing trusting relationships with students, and coaching them toward goals
  • Demonstrated ability to craft and customize messages that inspire action among first-generation college students
  • Demonstrated ability to effectively prioritize and respond to student questions and needs
  • Comfort with ambiguity and an entrepreneurial mindset as we work to design the road map for the pilot and future iterations of this program model 


  • Fluency in a language other than English a plus 
  • Familiarity with Chicago Public Schools and the higher education landscape in Illinois


All employees are expected to demonstrate continued growth within our seven core competencies.

  • Relationships: Identifies opportunities and takes action to build and maintain meaningful and collaborative connections with various stakeholders
  • Results: Produces quality outcomes; compiles and analyzes data to drive future plans; uses creative solutions
  • Communication: Effectively articulates information in a clear, concise, and timely manner to a wide range of stakeholders
  • Inclusiveness: Helps to create an environment that respects and values the identities and cultures of all colleagues and students we serve
  • Talent Development: Effectively assesses one’s own, and others’, strengths and areas for improvement
  • Agility: Demonstrates adaptability and openness to shifting priorities, needs of stakeholders, and organizational changes
  • Planning: Effectively and efficiently uses resources (time, materials, technology) in order to create, meet, and assess goals

Interested applicants should apply here:

Overview, Job Description & Benefits

Students are at the core of Bottom Line…

Details at a Glance

  • Time Commitment
    Full Time Schedule
  • Start Date
    July 12, 2021
  • Application Deadline
    May 31, 2021
  • Education
    4-Year Degree Required


$40,000 - $40,000Completion bonuses available in June 2022


Medical, Dental, Employer Matched Retirement

A full list of benefits can be found here:

Medical, Dental, Employer Matched Retirement

A full list of benefits can be found here:

Level of Language Proficiency

Fluency in multiple languages a plus

Fluency in multiple languages a plus


Work may be performed anywhere in United States
Associated Location
65 E Wacker Dr, Chicago, IL 60601, USA

How to Apply

Please apply through our website:

Please apply through our website:

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