Senior Customer Success Manager - U.S. Remote

Job Title: Senior Customer Success Manager

Location: U.S. Remote – preferred US-based time zones, CST or EST

Company Description:

CYPHER Learning is leading the necessary disruption of learning platforms to unleash human potential with modern learning experiences. We exist to ignite lifelong learning passions through personalized, engaging, and limitless learning experiences for all, giving L&D pros and educators more time to teach and train, building human connection into everything we do, and delivering tailored learning experiences that are meaningful and measurable. We are a fast-growing company with a passion for education and technology.

Position Overview:

As a Senior Customer Success Manager at CYPHER Learning, you will serve as the strategic owner of a portfolio of our most important customers, including complex, multi-regional accounts, acting as a trusted advisor to senior stakeholders. You will drive retention, expansion, and measurable business outcomes by aligning customer objectives to adoption and value realization. This role blends strategic ownership with hands-on execution. You will lead complex customer engagements, proactively manage risk, and ensure strong renewal performance, while identifying and driving growth opportunities in partnership with Sales. You will work closely with cross-functional teams to align priorities, influence outcomes, and elevate the customer experience, ensuring our customers realize long-term value and continue to grow with CYPHER.

What You Will Do:

• Own a portfolio of strategic and enterprise customers, with accountability for retention, renewal outcomes, and expansion.
• Lead end-to-end renewal strategy, including executive alignment, commercial negotiations, and order execution.
• Build and maintain executive-level relationships, positioning yourself as a trusted advisor to key stakeholders.
• Develop and execute account success plans aligned to customer goals, business outcomes, and measurable value.
• Drive adoption and value realization across customer organizations to support long-term success and renewal strength.
• Lead Executive Business Reviews (EBRs) and strategic planning sessions that reinforce value and uncover growth opportunities.
• Proactively identify risks and implement mitigation strategies to protect renewals and customer health.
• Identify and drive expansion opportunities, including upsell and cross-sell, in close partnership with Sales.
• Partner cross-functionally with Product, Support, and other teams to align on priorities and deliver customer outcomes.
• Serve as the voice of the customer, translating insights into actionable feedback that informs product and experience improvements.
• Track and manage key performance indicators, including customer health, adoption, retention, and growth.
• Act as a senior escalation point for complex customer situations, driving resolution and preserving customer trust.
• All other duties as assigned.
  
  

Skills & Experience:

• Bachelor’s degree in Business, Communications, Technology, or a related field, or equivalent practical experience required.
• 7–10+ years of experience in Customer Success, Account Management, or similar client-facing roles, with a focus on enterprise or strategic accounts across multiple regions required.
• Proven track record of driving retention, renewals, and expansion across existing customer portfolios required.
• Experience owning end-to-end renewal cycles, including commercial strategy, pricing, negotiation, and closing expansion opportunities required.
• Demonstrated ability to engage and influence executive stakeholders (VP to C-level) across complex organizations.
• Strong strategic thinking and problem-solving capabilities, with the ability to navigate ambiguity and drive outcomes.
• Ability to translate customer goals into measurable outcomes and structured success plans.
• Commercial acumen with a consistent ability to identify and convert growth opportunities.
• Excellent communication and presentation skills, with the ability to manage complex stakeholder environments.
• Experience in SaaS environments required; experience in LMS or HR technology is a strong plus.

  
  

Our Values:

Curiosity: Continues learning to stay agile and innovative.

Connection: Embracing and celebrating our differences.

Empowerment: Rewarding positive people-centric behaviors and decisions.

Potential: Challenging the status quo and pushing for what is possible.

Impact: Making a positive impact for our clients and communities around the world.

Equal Employment Opportunity

At CYPHER Learning, we believe diversity is essential to innovation and progress. We are committed to creating a workplace where individuals of all backgrounds, identities, and experiences are respected, included, and empowered to thrive. Our culture is built on connection, curiosity, empowerment, potential, and impact—and we know that these values are only fully realized when everyone has a seat at the table.

CYPHER Learning is proud to be an Equal Opportunity Employer. We make all employment decisions based on merit, qualifications, and business needs—without regard to race, color, religion, sex, sexual orientation, gender identity or expression, age, national origin, disability, veteran status, genetic information, or any other protected status under applicable law.  As a global, remote-first company, we embrace flexibility and accessibility in every aspect of how we work. If you require a reasonable accommodation during the application or interview process, please contact our People team at [email protected]. We are committed to providing an inclusive and equitable experience for every candidate.