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Experienced Full Stack Director, Strategic Customer Success – AI Writing Solutions

Remote, USA Full-time Posted 2026-06-17

At arenaflex, we're revolutionizing the way businesses communicate with their customers through cutting-edge AI writing solutions. As a leader in the industry, we're seeking an exceptional Director, Strategic Customer Success to join our team. This is a unique opportunity to shape the future of customer success and drive growth for our strategic customers.

About this role

As our Director, Strategic Customer Success, you'll be responsible for leading a high-performing customer success team that works with CIOs and Business leaders at Fortune 500/Global 2000 companies. You'll lead a team of 6-8 Strategic CSMs focused on adoption, retention, expansion, and ROI measurement. Your primary goal will be to deliver on revenue targets, be active in the field with your team, improve existing processes, and help arenaflex improve how we work with Strategic customers. A critical part of the role is providing guidance, coaching, and support to your team to enable individual and collective success. Your positivity, sense of curiosity, winning mindset, and ability to create champions from early adopters in the AI writing space will help shape our entire culture. If you have a builder mentality, this is the role for you.

Your responsibilities

As our Director, Strategic Customer Success, you'll be responsible for:

  • Delivering against aggressive but attainable NRR/GRR targets to continue building and developing arenaflex's success with strategic customers
  • Driving CSMs to effectively lead customers through a defined success delivery methodology
  • Hiring and developing CSM talent aligned with our connect/challenge/own company values, creating personal development plans for each individual contributor to grow
  • Collaborating with cross-functional teams including Sales, Marketing, Solutions architecture, and Product to align solutions that drive meaningful business value for our customers
  • Providing regular GRR/NRR forecasts, performance reports, and insights to senior leadership, highlighting key metrics and areas for improvement
  • Fostering a culture of high-performance, collaboration, and continuous learning within the CSM team. Model the integrity, attitude, and sense of urgency that you’ll expect from your team
  • Establishing and personally maintaining strong relationships with key customer executives, acting as a trusted advisor and advocate

Is this you?

To succeed in this role, you'll need:

  • 10+ years in SaaS with engaging Fortune 500/Global 2000
  • 5+ years in Success leadership or similar leadership role
  • Highly strategic with deep experience in consultative, complex delivery methodology
  • Proven experience building and leading a team from an early stage
  • Proven ability to work across the GTM organization to strategize, plan and execute a cross-functional approach
  • Hands-on success leader, energized by the transformative potential of generative AI and working with talented CSMs
  • Commuting distance to a arenaflex Hub: New York City, San Francisco, Austin, Chicago

Benefits & perks (arenaflex Full-time employees)

At arenaflex, we offer a comprehensive benefits package to support your well-being and career growth. As a Full-time employee, you'll enjoy:

  • Generous PTO, plus company holidays
  • Medical, dental, and vision coverage for you and your family
  • Paid parental leave for all parents (12 weeks)
  • Fertility and family planning support
  • Early-detection cancer testing through Galleri
  • Flexible spending account and dependent FSA options
  • Health savings account for eligible plans with company contribution
  • Annual work-life stipends for:

+ Home office setup, cell phone, internet + Wellness stipend for gym, massage/chiropractor, personal training, etc. + Learning and development stipend

  • Company-wide off-sites and team off-sites
  • Competitive compensation, company stock options, and 401k

Why join arenaflex?

At arenaflex, we're committed to diversity and inclusion. We believe that a diverse and inclusive workplace is essential to driving innovation and success. We're an equal-opportunity employer and welcome applications from qualified candidates from all backgrounds.

How to apply

If you're a motivated and experienced leader with a passion for customer success, we'd love to hear from you. Please submit your application on our website, and don't forget to review our Global Candidate Privacy Notice. Apply to this Job Apply for this job

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