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Experienced Senior Director of Customer Success - Driving Business Growth through Strategic Client Relationships and Team Leadership

Remote, USA Full-time Posted 2025-11-03

Introduction to Grammarly and Our Mission

Grammarly is a cutting-edge technology company that is revolutionizing the way people communicate. Our innovative AI-powered writing tool is used by millions of people around the world to improve their writing skills and achieve their goals. We are a dynamic and fast-growing company with a strong focus on customer success, and we are seeking an experienced Senior Director of Customer Success to join our team.

Job Overview

We are looking for a highly skilled and motivated Senior Director of Customer Success to lead our customer success team and drive business growth through strategic client relationships and team leadership. The successful candidate will have a strong track record of success in customer success management, with a proven ability to build and maintain strong relationships with clients, identify new business opportunities, and lead high-performing teams.

Key Responsibilities

  • Develop and execute strategic plans to drive customer success and business growth, including pipeline generation, expansion, and net dollar retention
  • Lead a team of senior customer success managers and provide coaching, guidance, and support to help them achieve their goals
  • Build and maintain strong relationships with key clients, including regular communication, quarterly business reviews, and strategic planning sessions
  • Collaborate cross-functionally with sales, product management, revenue operations, and product marketing teams to drive business outcomes and align with company goals
  • Develop and manage customer success metrics, including customer health scores, net promoter scores, and customer retention rates
  • Identify and prioritize new business opportunities, including upsells, cross-sells, and new logo acquisitions
  • Stay up-to-date with industry trends, best practices, and emerging technologies, and apply this knowledge to drive innovation and growth

Essential Qualifications

  • Bachelor's degree in a related field, such as business, marketing, or communications
  • Minimum 5 years of experience in customer success management, with a proven track record of success in driving business growth and leading high-performing teams
  • Strong understanding of customer success principles, including customer journey mapping, customer segmentation, and customer health scoring
  • Excellent communication, interpersonal, and leadership skills, with the ability to build strong relationships with clients, colleagues, and stakeholders
  • Strong analytical and problem-solving skills, with the ability to analyze data, identify trends, and develop strategic plans
  • Experience with customer success platforms, such as Gainsight, Salesforce, or Medallia

Preferred Qualifications

  • Master's degree in a related field, such as business, marketing, or communications
  • Minimum 8 years of experience in customer success management, with a proven track record of success in driving business growth and leading high-performing teams
  • Experience with AI-powered writing tools, such as Grammarly, and a strong understanding of the technology and its applications
  • Strong understanding of sales and marketing principles, including sales strategy, account planning, and demand generation
  • Experience with data analysis and visualization tools, such as Tableau, Power BI, or D3.js

Skills and Competencies

  • Strong leadership and management skills, with the ability to motivate and inspire teams
  • Excellent communication and interpersonal skills, with the ability to build strong relationships with clients, colleagues, and stakeholders
  • Strong analytical and problem-solving skills, with the ability to analyze data, identify trends, and develop strategic plans
  • Ability to work in a fast-paced, dynamic environment, with a strong focus on innovation and growth
  • Strong understanding of customer success principles, including customer journey mapping, customer segmentation, and customer health scoring

Career Growth Opportunities and Learning Benefits

At Grammarly, we are committed to the growth and development of our employees. We offer a range of training and development programs, including leadership development, customer success training, and technical skills training. We also provide opportunities for career advancement, including promotions, lateral moves, and new role creation.

Work Environment and Company Culture

Grammarly is a remote-first company, with a strong focus on collaboration, innovation, and growth. We have a dynamic and diverse team, with employees from all over the world. We are committed to creating a positive and inclusive work environment, with a strong focus on employee well-being, diversity, and inclusion.

Compensation, Perks, and Benefits

We offer a competitive salary and benefits package, including:

  • Great healthcare, including medical, dental, vision, mental health, and fertility benefits
  • Disability and life insurance options
  • 401(k) and RRSP matching
  • Paid parental leave
  • Twenty days of paid time off per year, eleven paid holidays per year, and unlimited sick leave
  • Workspace allowances
  • Parent and pet care stipends
  • Wellness stipends
  • Education discounts

Conclusion

If you are a motivated and experienced customer success professional, with a strong track record of success in driving business growth and leading high-performing teams, we encourage you to apply for this exciting opportunity. At Grammarly, we are committed to creating a positive and inclusive work environment, with a strong focus on employee well-being, diversity, and inclusion. We offer a range of training and development programs, including leadership development, customer success training, and technical skills training. We also provide opportunities for career advancement, including promotions, lateral moves, and new role creation.

Apply now to join our team and help us drive business growth and customer success.

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