Head of Digital Customer Success – Lead AI‑Powered Customer Success Strategy at arenaflex

About arenaflex

arenaflex is on a mission to transform the way B2B organizations generate revenue by using predictive intelligence to identify the buying teams most likely to convert and by delivering prescriptive actions that accelerate the sales cycle. Our Revenue AI platform is the only solution that combines advanced analytics, AI‑driven insights, and automated engagement to turn anonymous prospects into qualified pipeline and, ultimately, revenue. As a fast‑growing SaaS leader, arenaflex is building the future of revenue operations, and we are looking for visionary leaders who want to shape that future.

Why Join arenaflex?

People are the heart of arenaflex. We live by our core values of Accountability, Growth Mindset, Integrity, Fun, and One Team. Every arenaflexer contributes to defining the next generation of revenue‑focused technology. We foster an environment where bold ideas are encouraged, risk‑taking is rewarded, and success is measured by the tangible value we create for our customers. If you are looking for a place where you can make a lasting impact, grow your career, and work alongside passionate, high‑performing teammates, arenaflex is the next chapter of your professional story.

Position Overview

Title: Head of Digital Customer Success Location: Hybrid (flexible work‑from‑home and office model)

arenaflex is seeking an experienced, innovative, and data‑driven leader to own and scale our digital‑first customer success motion across commercial, velocity, and lower‑touch segments. In this role you will design and execute strategies that drive product adoption, health, renewal, and expansion while leading high‑performing teams that deliver consistent, high‑value experiences at scale.

Key Responsibilities

Digital Strategy & Scale

• Build and execute a digital‑first customer success strategy that drives adoption, health scores, and renewals for lower‑touch accounts.
• Leverage automation, AI, journey orchestration, and self‑service programs to deliver personalized, scalable engagement.
• Partner with Marketing, Product, and Operations to create content, playbooks, and digital channels that accelerate value realization.
• Develop data‑driven health dashboards and predictive models that surface risk and opportunity in real time.

Team Leadership & Development

• Lead, mentor, and grow the Commercial and Velocity Customer Success teams, ensuring they deliver measurable impact across hundreds of accounts.
• Coach managers and individual contributors, fostering a culture of accountability, customer‑centricity, and continuous improvement.
• Design clear career paths, professional development programs, and succession plans for talent across digital and commercial segments.
• Recruit top talent and build a diverse, inclusive team that reflects the global customer base.

Customer Outcomes & Business Impact

• Own retention, expansion, and net‑revenue‑retention (NRR) metrics across all segments.
• Ensure customers achieve measurable business outcomes, reducing churn and driving upsell opportunities.
• Create automated playbooks that react to product telemetry, usage shifts, and emerging customer needs.
• Collaborate with Sales, Support, and Professional Services to deliver a seamless, end‑to‑end customer journey.

Operational Excellence

• Define KPIs, reporting frameworks, and success metrics for both digital and commercial success motions.
• Identify and implement process automation, tooling, and segmentation improvements to scale impact.
• Partner with Customer Success Operations to measure team performance, forecast outcomes, and drive continuous optimization.
• Maintain rigorous data governance and ensure compliance with privacy and security standards.

Qualifications

• 10+ years of experience in Customer Success, Digital Customer Success, or related customer‑facing leadership roles.
• Proven track record of building and scaling digital‑first success programs that leverage automation, AI/ML, in‑app engagement, and community‑driven support.
• Hands‑on experience with Gainsight, Salesforce, Gong, or comparable CRM and Customer Success platforms.
• Demonstrated success managing teams across commercial and mid‑market/velocity segments.
• Exceptional leadership, communication, and stakeholder‑management abilities.
• Data‑driven mindset with the ability to translate insights into actionable strategy and execution.
• Strategic thinker who balances innovative experimentation with operational rigor.
• Ability to harness RevTech tools and advanced analytics to drive customer outcomes.

Preferred Skills & Competencies

• Experience in SaaS or AI‑enabled revenue platforms.
• Deep understanding of customer journey mapping, adoption frameworks, and renewal forecasting.
• Strong project management skills and familiarity with agile methodologies.
• Passion for coaching, mentorship, and building high‑performing, cross‑functional teams.
• Comfort presenting to C‑level executives and influencing senior leadership.
• Fluency in building scalable playbooks that integrate product telemetry, usage analytics, and health scores.

Career Growth & Learning Opportunities

At arenaflex, your growth is a priority. You will have direct visibility to the executive team, enabling you to influence company‑wide strategy. We invest heavily in continuous learning through:

• Access to LinkedIn Learning, Coursera, and industry‑specific certifications.
• Quarterly leadership workshops and mentorship programs.
• Opportunities to lead cross‑functional initiatives that shape product roadmap and go‑to‑market strategy.
• Regular feedback loops, 360‑degree reviews, and personalized development plans.

Work Environment & Culture

arenaflex offers a hybrid work model that blends the flexibility of remote work with the collaborative energy of in‑office days. Our culture is built on:

• Customer‑obsessed mindset – every decision is anchored in delivering value to our clients.
• Inclusive, diverse, and supportive community where every voice matters.
• Fun‑first approach – regular team‑building events, virtual happy hours, and wellness initiatives.
• Transparent communication – open forums with leadership, town‑halls, and an internal knowledge hub.

Compensation, Perks & Benefits

arenaflex offers a competitive total rewards package that includes:

• Base salary range: $159,587 – $234,061 (adjusted for location, experience, and market factors).
• Performance‑based bonus and equity participation to align your success with company growth.
• Comprehensive health, dental, and vision coverage, plus life and disability insurance.
• 401(k) plan with generous employer match.
• Paid parental leave, generous PTO, quarterly self‑care days, and flexible holidays.
• Remote work stipend, ergonomic home office equipment, and access to cutting‑edge collaboration tools.
• Employee Resource Groups (ERGs), wellness programs, and regular mental‑health check‑ins.

How to Apply

If you are ready to lead a high‑impact, digital‑first customer success organization at a market‑defining SaaS company, we want to hear from you. Submit your resume and a brief cover letter outlining your vision for scaling digital customer success at arenaflex.

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 identity or expression, national origin, age, marital status, protected veteran status, or disability status. If you require reasonable accommodation during the application process, please contact us at [email protected].

Join the arenaflex Team

We are excited to meet leaders who are passionate about leveraging technology to drive customer success at scale. At arenaflex, you will shape the future of revenue AI, empower thousands of customers, and grow alongside a world‑class team. Apply today and become a catalyst for transformation.