Senior Director of Customer Success | B2B Customer Growth, Revenue Leadership & Strategic Account Management

Join arenaflex: Shape the Future of Customer Success

Are you ready to lead a transformative customer experience function at a company that's revolutionizing how businesses connect with their clients? At arenaflex, we're not just building products—we're crafting meaningful relationships that drive mutual growth and lasting value. We're seeking a visionary Senior Director of Customer Success to spearhead our B2B customer success initiatives and help us achieve ambitious growth targets while delivering exceptional value to our clients.

This is a unique opportunity to build something extraordinary. As arenaflex's first Senior Director of Customer Success for our B2B division, you'll have the chance to architect and scale a world-class customer success organization from the ground up. You'll report directly to the Head of Customer Success and lead a team of talented customer success managers who are passionate about driving client outcomes. If you're energized by the challenge of building high-performing teams, driving revenue growth through customer advocacy, and creating transformative client experiences, this role is perfect for you.

Why arenaflex?

At arenaflex, we believe that great products are born from great partnerships. Our cutting-edge solutions help businesses across industries streamline operations, enhance productivity, and achieve their strategic objectives. We're proud to foster a culture built on our core values: ethical conduct, adaptability, boldness, empathy, and excellence. These aren't just words on a wall—they guide every interaction we have with colleagues, customers, and partners.

Our remote-first hybrid model enables collaboration across geographic boundaries while maintaining the flexibility our team members need to thrive. We invest heavily in professional development, wellness, and creating an inclusive environment where every voice matters. When you join arenaflex, you're not just accepting a job—you're becoming part of a community that's committed to making a meaningful impact.

About the Role

As the Senior Director of Customer Success, you'll be the driving force behind customer satisfaction, retention, and expansion for our B2B client base. You'll own revenue-related targets including pipeline generation, growth metrics, and Net Dollar Retention (NDR). This role requires a strategic thinker who can balance hands-on leadership with big-picture vision.

You'll collaborate cross-functionally with Sales, Product Management, Revenue Operations, and Product Marketing teams to ensure a seamless customer journey from onboarding through renewal and expansion. Your leadership will be instrumental in scaling our customer success capability to support our aggressive growth objectives for 2023 and beyond.

What You'll Do

• Strategic Leadership: Develop and execute comprehensive customer success strategies that align with business objectives and drive measurable outcomes


• Team Management: Lead, mentor, and grow a high-performing team of customer success managers, fostering a culture of excellence and continuous improvement


• Revenue Ownership: Own and drive pipeline generation, growth, and Net Dollar Retention targets while identifying expansion opportunities within existing accounts


• Cross-Functional Collaboration: Work closely with Sales, Product, Marketing, and Operations teams to ensure aligned customer engagement strategies and seamless handoffs


• Process Optimization: Design and implement playbooks, best practices, and performance metrics that scale efficiently as our customer base grows


• Customer Insights: Translate customer feedback and data into actionable insights that inform product development and service improvements


• Executive Presence: Serve as a trusted advisor to C-suite clients and represent arenaflex as a leader in customer success excellence

Your Impact Journey

First 30 Days: You'll immerse yourself in learning our business inside and out. This includes understanding our customers, product capabilities, value proposition, sales processes, technology stack, and value-based selling methodology. You'll meet key stakeholders across departments and begin building relationships with your team.

By Month 3: You'll have onboarded new team members, developed and tested new playbooks, established performance measurement frameworks, and created a strategic roadmap for the year ahead. Your team will be consistently meeting pipeline generation, quantity, and NDR expectations.

By Month 6: You'll have established a highly effective operating rhythm, realized performance improvements, and built a predictable, repeatable enterprise customer success motion. You'll be confidently driving expansion conversations and deepening client relationships.

By Year One: You'll have built a tier-one Customer Success capability that's ready to efficiently and effectively support a rapidly growing and globally diverse client base. Your organization will be a key driver of arenaflex's continued success and market leadership.

What We're Looking For

We're seeking a leader who embodies our core values and brings a proven track record of building and scaling customer success organizations in B2B environments. The ideal candidate will be located on the West Coast of the US or Canada and can collaborate in-person one week per quarter, traveling as needed to the hub where the team is based.

Essential Qualifications

• Bachelor's degree in Business, Marketing, or a related field


• 7+ years of experience in Customer Success, Account Management, or Sales in B2B SaaS environments


• 3+ years of leadership experience managing high-performing customer success or sales teams


• Demonstrated success in driving revenue growth, improving customer retention, and expanding existing accounts


• Strong analytical skills with the ability to synthesize quantitative and qualitative data to inform strategy


• Excellent communication and presentation skills, with the ability to inspire and influence stakeholders at all levels


• Deep understanding of subscription business models including freemium, free trials, account expansion, and upsells


• Proven ability to build and maintain relationships with executive-level clients

Preferred Qualifications

• Experience building customer success functions from the ground up


• Background in fast-growing SaaS companies with $50M+ ARR


• Knowledge of customer success platforms like Gainsight, ChurnZero, or Totango


• Experience in enterprise software, productivity tools, or communication platforms


• MBA or advanced degree in a related field

Core Competencies

• Strategic Vision: You set aggressive short and long-term goals and have a strong drive to achieve them


• Relationship Building: You build and grow connections with people, understand their needs and objectives, and own solutions


• Data-Driven Decision Making: You look for reasons and can blend quantitative and qualitative data to make informed decisions, using available data to identify gaps and opportunities


• Storytelling: You bring stories to life, make them exciting and clear, and transform dry ideas into compelling narratives with examples and analogies


• Value-Based Selling: You understand how to communicate business value and expand client relationships through a deep understanding of client needs, rather than feature lists


• Adaptability: You thrive in dynamic environments and can pivot strategies as business needs evolve

What arenaflex Offers You

Professional Development

We believe that autonomy and trust are essential to empowering our team members to do their best, most innovative work in a way that aligns with their interests, gifts, and well-being. We support professional development and advancement through comprehensive training, mentorship, and regular feedback. You'll have access to learning opportunities that help you grow both professionally and personally.

A Connected Team

arenaflex builds products that help people connect, and we apply this mindset to our own team. Our remote-first hybrid model enables a highly collaborative culture supported by our Energetic values. We work to foster belonging among team members in various ways, including our employee resource groups, arenaflex Circles, which promote connection among those with shared identities such as BIPOC and LGBTQIA+ colleagues, women, and parents. We also celebrate our colleagues' achievements with global, local, and team-specific programs.

Compensation and Benefits

arenaflex offers all team members competitive compensation along with a comprehensive benefits package including:

• Excellent healthcare coverage (including comprehensive 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 each year, eleven days of paid holidays each year, and unlimited flexible time off


• Home office allowances


• Pet care and child care support


• Wellness stipends


• Certification reimbursement


• Extensive learning and development opportunities

Join Us

If you're passionate about customer success, driven by results, and excited about the opportunity to build something transformative at arenaflex, we want to hear from you. This is your chance to make a lasting impact, grow your career, and be part of a team that's redefining what's possible in customer experience.

Apply today and take the first step toward an incredible journey with arenaflex. Together, we'll create meaningful connections and drive mutual success.