Head of Customer Success – Transforming Customer Experiences at arenaflex

At arenaflex, we're revolutionizing the way organizations capture, analyze, and optimize their most valuable resource: time. As the leading AI Time platform for professional services firms, we're transforming the industry with our proprietary machine learning technology that automates work time capture and connects time data to business outcomes. Our mission is to empower workers to deliver twice the value in half the time, giving people more time to be creative and impactful. We're seeking an exceptional leader to join our team as the Head of Customer Success. This is a unique opportunity to shape the future of customer success at arenaflex, driving product adoption, accelerating onboarding, and enhancing customer value. If you're passionate about building, passionate about helping customers realize real business outcomes, and excited to influence both internal strategy and external experience, we'd love to meet you.

About arenaflex

arenaflex is a cutting-edge AI Time platform that's transforming the professional services industry. Our team comprises top talent in AI, product development, and engineering – innovative, humble, and forward-thinking professionals committed to redefining productivity in the knowledge economy. We're building solutions that empower workers to deliver twice the value in half the time, giving people more time to be creative and impactful.

About the Role

As the Head of Customer Success, you will be responsible for developing and scaling the strategy, programs, and team that drive product adoption, deepen user engagement, and deliver measurable value for our customers. You will serve as a key partner to our Product team, bringing structured, insight-rich customer feedback to the table and helping shape the roadmap based on real-world usage and outcomes. You'll be expected to bring a strategic lens to how our customers experience the product, acting not just as a service leader but as an expert on product behavior, friction points, and value realization patterns.

Key Responsibilities:

* Build and lead the Customer Success team, including hiring, coaching, and developing Customer Success Managers (CSMs)

• Define and execute the Customer Success strategy with a strong focus on driving product adoption, accelerating onboarding, and enhancing customer value
• Own value realization outcomes, proactively driving usage, uncovering barriers to success, and ensuring customers achieve meaningful results through arenaflex
• Serve as a strategic partner to the Product team, identifying patterns in usage, surfacing insights from the field, and helping inform roadmap priorities and UX enhancements
• Develop, uplevel, and scale Customer Success programs and playbooks across onboarding, product education, lifecycle management, and value realization
• Design and continuously improve the customer journey, ensuring consistent, high-quality experiences that drive measurable outcomes at every stage of the lifecycle
• Partner cross-functionally with Implementation, Account Management, Product, Sales, and Support to deliver a seamless and impactful customer experience
• Develop and report on key success metrics such as product usage rates, onboarding effectiveness, realized ROI, etc
• Advocate for the voice of the customer internally, surfacing insights to influence product strategy and customer experience improvements

Essential Qualifications:

* 7+ years of experience in Customer Success or other customer-facing post-sales roles in B2B SaaS, including 3+ years of experience managing and scaling customer-facing teams

• Experience supporting complex, enterprise customers with large ASPs and multi-faceted internal teams
• Strong operational skillset with experience developing playbooks, processes, and adoption-driving initiatives
• Data-driven mindset with the ability to leverage usage metrics and customer insights to inform strategy
• Exceptional collaboration skills; ability to work cross-functionally with Sales, Product, Support, Implementation, and Account Management
• Strong communication skills with an ability to build trust with both customer stakeholders and internal executives

Nice to Haves:

* Experience scaling Customer Success teams in high-growth SaaS environments

• Familiarity with Customer Success platforms (e.g., Gainsight, ChurnZero, Catalyst) and CRM systems (e.g., Salesforce)
• Background working with professional services or legal industry customers
• Experience operating within a functionalized post-sales model across CS, AM, and Implementation

Flexibility and Logistics:

* Location: This role will be based in our company office in New York and hybrid at least 3 days per week.

• Visa Sponsorship: Unfortunately, we are unable to sponsor visas at this time.

Why join arenaflex:

* To date, we've secured significant funding from renowned venture capitalists (Google Ventures, IVP, Anthos, Upfront Ventures), as well as notable individuals like Marc Benioff, Gokul Rajaram, Kevin Weil, and Alexis Ohanian

• A smart, fun, collaborative, and inclusive team
• Great employee benefits, including equity and 401K
• Bi-annual, in-person company off-sites, in unique locations, to grow and share time with the team
• An opportunity to perform at your best while growing, making a meaningful impact on the company's trajectory, and embodying our core values: understanding your "why," dancing in the rain, being your whole self, and sanctifying time

We encourage diverse perspectives and rigorous thinkers who aren't afraid to challenge the status quo. arenaflex is an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status. We are not able to support visa sponsorship or relocation assistance. If you think you'd be a good fit for this role, we encourage you to apply, even if you don’t perfectly match all the bullet points in the job description. At arenaflex, we strive to create an inclusive culture that encourages people from all walks of life to bring their unique, diverse perspectives to work. Every day, we aim to build an environment that empowers us all to do the best work of our careers, and we can't wait to show you what we have to offer! Apply for this job