Customer Re-engagement Specialist (Work from Home)

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Hiring Remotely in Portland, OR, USA
In-Office or Remote
Edtech • Mobile
The Role

Overview:

The Re-engagement Specialist plays a critical role in Nerdy’s customer retention efforts by reconnecting with former clients and encouraging them to return to our services. By understanding their past experiences and addressing any concerns, this role directly contributes to customer loyalty and business growth.

About Nerdy:

At Nerdy (NYSE: NRDY) -  the company behind Varsity Tutors - we’re redrawing the blueprint of learning. Our Live + AI™ platform fuses real-time human expertise with proprietary generative-AI systems, setting a new bar for measurable academic impact at global scale. 

We recruit the kind of technologists and operators you’d bet on as solo founders - people who turn ambiguous problems into shipping code, iterate faster than markets move, and compound their advantage with every data point. In an era where great employees can deliver 10-times the leverage of the merely good, we back those who play to win.

Fortune favors the bold. Join us.

How we compete:

  • AI-Native at every level
    From the CEO to day-one hires, everyone builds and ships with generative AI. If you’re not wielding AI, you’re not done.
  • Entrepreneurial velocity
    Move at founder speed, prototype in hours, and measure in real user outcomes. Slow teams die.
  • Free-market rigor
    Ideas rise or fall on merit and results - no committees, no politics, no cap on upside.
  • Full-stack ownership
    You design, build, and run what you ship; accountability is a feature, not a bug.
  • Reward for contribution
    Pay rises with impact, not years. Outstanding results earn outsized rewards. We evaluate both what you achieve and how you achieve it: living our leadership principles and using AI effectively are formally measured and rewarded.
  • Relentless exploration
    Push the frontier of generative AI in live learning and - because only the paranoid survive - questioning every legacy assumption along the way.
  • Is Apolitical
    You stay focused on mission-aligned outcomes, not distractions or unrelated causes.

If you’re a technically minded builder who thrives on open competition, personal responsibility, and the chance to redefine how the world learns - while continually stretching the limits of what generative AI can do - come do the most ambitious and rewarding work of your career here. Learn more at nerdy.com.
Nerdy’s shareholder letters below explain our latest products and strategy:

  • Q1-2025 Shareholder Letter
  • Q4-2024 Shareholder Letter
  • Q3-2024 Shareholder Letter

Qualifications:

  • 1-2 years of experience in retention, sales, or a related field, preferably in a high-volume outreach role.
  • Strong communication and interpersonal skills with the ability to build rapport quickly.
  • Persuasive and empathetic approach to customer engagement.
  • Comfort with ambiguity and ability to adapt to changing strategies.
  • Experience using CRM tools and analyzing customer data.
  • A passion for education and the ability to convey the value of Nerdy’s services.
  • Analytical Thinking: Experience in analyzing customer data to identify inactivity patterns and develop targeted re-engagement strategies.
  • Adaptability: Ability to adjust strategies based on customer feedback and changing market conditions to ensure effective re-engagement.

Responsibilities:

  • Proactively reach out to former clients through phone, email, and messaging platforms to re-engage them with Nerdy’s services. This role requires cold calling. 
  • Identify client needs and tailor solutions that align with their learning goals, leveraging Nerdy’s wide range of educational offerings.
  • Utilize persuasive communication and active listening skills to understand and overcome objections.
  • Collaborate with internal teams, including Customer Support and Sales, to ensure a seamless reactivation experience.
  • Track and analyze engagement data to refine outreach strategies and maximize conversion rates.
  • Maintain detailed and accurate records of customer interactions in CRM systems.
  • Understand and appreciate that Nerdy is an apolitical company and that we can have the largest impact if we are united in our focus on helping people learn and not divided or distracted by advancing unrelated causes.

Unleash Your Full Potential at Nerdy:

We offer a competitive compensation package including:

  • $40,000 base salary plus monthly variable compensation target
  • Performance-based advancement opportunities with increased earning potential
  • Comprehensive healthcare benefits
  • 401(k) matching with immediate vesting (no waiting period)
  • Paid training and professional development
  • Company-provided MacBook and equipment
  • Free Varsity Tutors Learning Membership for your household

Location: Fully Remote Position

Upcoming Start Dates/Training: One week paid virtual training will take place Monday - Friday 9am-6pm Central Time

The Bottom Line:

If you're driven by impact, energized by ownership, and excited to help shape what’s next, you’ll thrive here. We move fast, think big, and reward those who deliver. This isn’t a traditional corporate environment - it’s a place to do the most meaningful work of your career

Varsity Tutors Leadership Principles

Relentless Focus on Customers * Comfort with Ambiguity * Ownership * Simplify * Intellectual Curiosity * Build Teams * Think Big * Insist on High Standards * Bias for Action * Build Trust * Go Deep * Have Conviction * Deliver Results * Are Right, a Lot

Varsity Tutors is committed to creating a diverse environment and is proud to be an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or veteran status. (INDHP)

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The Company
St. Louis, MO
4,138 Employees
Year Founded: 2007

What We Do

Varsity Tutors, a Nerdy Company, is the leading direct-to-consumer, curated platform for live online learning benefiting both learners and experts. We have built a comprehensive online learning destination that enables the delivery of scaled high-quality live expertise for learners of all ages across thousands of subjects and multiple learning formats through the application of technology and AI. We've raised $107M million in venture capital from TCV, Learn Capital, and the Chan Zuckerberg Initiative. We also recently announced that Nerdy, the parent company of Varsity Tutors, plans to go public via a SPAC with TPG Pace Tech Opportunities later this year, with a $1.7 billion market valuation.

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