Director of Customer Success

Who is Aiwyn and what do we do?

Aiwyn is transforming the way accounting firms streamline the entire revenue management lifecycle. Backed by top-tier investors (Bessemer, KKR & Revolution), we’re one of the fastest-growing scale-up software companies globally—delivering innovative technology and consistently raising the bar with world-class people, processes, and products.

To learn more, visit our website

This role:

We are seeking a dynamic, results-driven Director of Customer Success to lead and develop a high-performing Customer Success Management (CSM) team. This role is responsible for driving customer retention and engagement through a people-first approach, aligning customer objectives with business goals, and fostering a culture of coaching and growth for the team. You will lead with a focus on creating long-term value for our customers and building strong, lasting relationships.

The ideal candidate will have a proven track record of coaching, motivating, and scaling customer success teams, as well as being an advocate for our customers' needs. In this role, you will directly influence our company's success by aligning customer goals with our product offerings and ensuring that customer success is deeply embedded within our organizational culture.

• Lead and Develop Customer Success Team:
• Manage, mentor, and inspire a team of Customer Success Managers (CSMs), ensuring they are equipped to meet both individual and team objectives
• Provide regular coaching and feedback to enhance team performance and customer outcomes
• Foster a culture of collaboration, professional development, and a people-first mentality that promotes employee satisfaction and engagement

• Set and drive clear metrics for customer retention, engagement, and satisfaction, with a focus on measurable outcomes
• Lead proactive initiatives to ensure customers derive maximum value from the product, reducing churn and increasing lifetime value
• Own customer health monitoring strategies, identifying at-risk customers and collaborating with CSMs to intervene effectively

• Work closely with customers to understand their business goals, challenges, and success criteria, ensuring alignment between customer needs and company offerings
• Advocate for the customer internally, collaborating with product, sales, and marketing teams to deliver tailored solutions that support customer success
• Align customer objectives with measurable business outcomes, ensuring that customer success efforts contribute directly to business growth

• Develop and track KPIs related to customer satisfaction, retention, and engagement, holding the team accountable for achieving targets
• Drive performance-based compensation models focused on retention and customer satisfaction, ensuring alignment with company goals
• Report on team performance, customer success initiatives, and overall program health to senior leadership, providing insights and recommendations for improvement

• Collaborate with the V.P of Customer Success to define the strategic vision for Customer Success, ensuring it is integrated into the broader company objectives
• Lead the continuous improvement of customer success processes, tools, and best practices to maximize efficiency and impact
• Stay informed of industry trends and customer needs, adapting strategies to drive innovation and maintain competitive advantage

• Build strong relationships with Implementation, Support, Sales, Marketing, Product, and other internal teams to ensure alignment on customer objectives and consistent messaging
• Provide feedback to the Product team on customer pain points, feature requests, and opportunities to enhance the product offering based on customer insights

• Bachelor's degree or equivalent work experience; advanced degree preferred.
• 7+ years of experience in Customer Success, with at least 3+ years in a leadership role, managing and scaling teams.
• Proven success in driving customer retention, engagement, and satisfaction in a SaaS or B2B environment.
• Strong leadership and coaching skills, with a demonstrated ability to develop and retain top talent.
• Excellent communication, interpersonal, and relationship-building skills with both internal teams and customers.
• Data-driven mindset with experience using analytics and CRM tools (e.g., Salesforce, Gainsight, etc.) to drive decision-making and performance.
• Ability to prioritize and manage multiple initiatives in a fast-paced, growth-oriented environment.
• Strong strategic thinking and problem-solving capabilities, with a customer-centric approach.

• The big-picture value proposition of this role is simple: join us, and you'll be paid competitively to have freedom in solving worthwhile, challenging problems alongside other A-players at a fast growing SaaS startup led by an experienced and successful co-founding team with industry experience.

• Adventure travel stipend - you receive a $1,000 travel reimbursement on your work anniversary each year. We encourage our team to recharge and explore the world beyond their home office walls.
• Remote, work-from-anywhere culture
• Flexible PTO
• World Class health benefits - we believe in fostering flourishing teams by providing benefits that go beyond the usual standards - Health, vision, dental, HSA/FSA, and mental health support.
• Stock options - every Full Time Employee has ownership in Aiwyn's future and success.
• 401(k) matching

• Trust - We champion transparency, welcome differing perspectives, uphold accountability, and trust that others have good intentions
• Courage - We have the courage to take calculated risks and embrace change, knowing what worked in the past won’t always work in the future
• Impact - Rooted in determination and innovation, we chase extraordinary outcomes and impactful results
• Relentlessness - We approach challenges with an unwavering resolve, never settling for mediocrity, and always striving to surpass expectations

• About us
• Why Aiwyn
• YouTube page

Aiwyn is an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to age, ancestry, color, family or medical care leave, gender identity or expression, genetic information, marital status, medical condition, national origin, physical or mental disability, political affiliation, protected veteran status, race, religion, sex (including pregnancy), sexual orientation, or any other characteristic protected by applicable laws, regulations and ordinances.

Candidate information will be treated in accordance with our CCPA privacy notice which can be found here: https://www.aiwyn.ai/ccpa