Experienced Full Stack Digital Customer Success Leader – Web & Cloud Application Development

At arenaflex, we're revolutionizing the way B2B organizations create revenue by predicting customers most likely to buy and recommending the best course of action to engage anonymous buying teams. Our Revenue AI platform is the only sales and marketing platform to unlock the ability to create, manage, and convert high-quality pipeline to revenue. As a leader in the industry, we're seeking an experienced and innovative Head of Digital Customer Success to join our team.

About the Role

We're looking for a seasoned professional to lead our customer success motion across digital, commercial, and velocity segments. As the Head of Digital Customer Success, you'll design and scale digital-first strategies that drive adoption, retention, and expansion while managing the commercial and velocity CSM teams to deliver consistent, high-value customer experiences at scale. You'll be responsible for building and executing the digital-first customer success strategy to drive adoption, health, and renewals across lower-touch segments.

Key Responsibilities

* Build and execute the digital-first customer success strategy to drive adoption, health, and renewals across lower-touch segments.

• Leverage automation, AI, customer journey orchestration, and digital programs to deliver personalized, scalable customer engagement.
• Partner with Marketing, Product, and Operations to drive proactive engagement and value realization through content, playbooks, and digital channels.
• Lead and develop the Commercial and Velocity Customer Success teams, ensuring they deliver value across hundreds of accounts with efficiency and impact.
• Coach managers and individual contributors, fostering a culture of accountability, customer-centricity, and continuous improvement.
• Build career paths and growth opportunities for talent across digital and commercial/velocity segments.
• Own retention and growth metrics across digital, commercial, and velocity segments.
• Ensure customers realize measurable value through our solutions, reducing churn and driving expansion opportunities.
• Build automated playbooks to respond to customer analytics, such as product telemetry and usage changes.
• Partner with Sales, Support, and Professional Services to deliver a seamless, integrated customer journey.
• Define KPIs, reporting, and success metrics for digital and commercial success motions.
• Identify opportunities for process automation, tooling, and segmentation improvements to scale impact.
• Partner with CS Operations to measure and optimize team performance and customer outcomes.

Qualifications

* 10+ years of experience in Customer Success, Digital CS, or related customer-facing leadership roles.

• Proven experience leading and scaling digital-first success programs (automation, AI/ML, customer communities, in-app engagement, etc.).
• Experience using Gainsight, Salesforce, Gong, or similar CRM and Customer Success tools.
• Strong track record of managing teams across commercial and velocity/mid-market segments.
• Excellent leadership, communication, and stakeholder management skills.
• Data-driven mindset with the ability to translate insights into strategy and execution.
• Strategic thinker who can balance innovation with operational excellence.
• Ability to leverage RevTech tools and data analytics to drive insights and outcomes.

What We Offer

* Opportunity to shape and scale a digital-first customer success organization.

• Leadership role with high visibility and impact on customer outcomes and company growth.
• Collaborative, customer-obsessed culture with strong executive sponsorship for CS.
• Competitive compensation, benefits, and career development opportunities.

Our Benefits

* Full-time employees can take advantage of health coverage, paid parental leave, generous paid time-off and holidays, quarterly self-care days off, and stock options.

• We have a growth mindset culture that is represented in all that we do, from onboarding through to numerous learning and development initiatives including access to our LinkedIn Learning platform.
• Employee well-being is also top of mind for us. We host quarterly wellness education sessions to encourage self-care and personal growth.
• From wellness days to ERG-hosted events, we celebrate and energize all arenaflex employees and their backgrounds.

Equal Opportunity Employer

arenaflex is an Equal Employment Opportunity and Affirmative Action Employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, or disability status. If you require reasonable accommodation in completing this application, interviewing, completing any pre-employment testing, or otherwise participating in the employee selection process, please direct your inquiries to [[email protected]](mailto:[email protected]). Apply for this job