Director, Customer Success & Service

About the Role

This is a senior operating and value-creation role focused on transforming customer success, support, and services organizations within high-growth enterprise software businesses. You will work directly with portfolio company executives to identify high-impact opportunities and turn strategic priorities into measurable operational improvements. The role combines AI adoption, workflow automation, organizational design, technology strategy, and cross-functional transformation. You will act as a trusted advisor to C-level leaders while helping teams build scalable, efficient, and next-generation service organizations.

Beyond individual engagements, you will create repeatable playbooks and cross-portfolio programs that accelerate the adoption of proven practices. You will also contribute to investment evaluations, value-creation planning, and technology partnerships that shape future growth opportunities. This is an entrepreneurial, highly collaborative environment suited to a strategic operator who thrives on complex challenges and measurable impact.

Responsibilities

• Embed within portfolio companies to diagnose operational opportunities and define strategic priorities across AI adoption, process automation, workflow optimization, knowledge management, organizational design, and cross-functional operations.
• Serve as a trusted advisor to CEOs, COOs, CCOs, CTOs, and other senior functional leaders, helping them design and execute initiatives tied to measurable performance objectives.
• Lead transformational programs that improve customer support, services, onboarding, and related functions through technology, process redesign, and organizational improvements.
• Develop and codify successful approaches into scalable playbooks, frameworks, and products that can be deployed across multiple portfolio companies.
• Design and lead cross-portfolio initiatives that connect organizations facing similar challenges and accelerate adoption of high-impact operating practices.
• Define strategies for emerging technology adoption, identify priority AI use cases, recommend technology partners, and architect scalable solutions that can deliver measurable business outcomes.
• Build and manage relationships with best-in-class vendors and technology providers, overseeing implementations and ensuring successful integration and adoption.
• Partner with investment professionals on investment thesis development, investment modeling, diligence, and value-creation planning for prospective investments.
• Manage multiple complex initiatives simultaneously, maintaining strong execution discipline, stakeholder alignment, and attention to measurable outcomes.

Requirements

• 10+ years of progressive experience in technology companies, including experience leading teams.
• 3+ years of operational experience within a high-growth enterprise SaaS company with at least $300 million in annual revenue; experience in Customer Support, Services, or Onboarding is strongly preferred.
• 2+ years of experience with a leading consulting firm, investment bank, venture capital firm, or private equity firm, preferably with an enterprise SaaS focus.
• Demonstrated success leading transformational initiatives involving AI adoption, organizational design, workflow automation, or process optimization with significant and quantifiable business impact.
• Genuine curiosity about how AI is reshaping customer support and services, combined with a strong interest in building next-generation operating models.
• Hands-on experience building with AI technologies such as LLM APIs, AI agents, and AI-native workflows, rather than using AI solely as a productivity tool.
• Proven ability to establish credibility quickly and work effectively with C-level executives and senior stakeholders.
• Strong analytical capabilities, including the ability to interpret and work with data at scale to inform strategic decisions.
• Excellent organizational and project management skills, with the ability to manage multiple priorities in a fast-paced and demanding environment.
• Strong influence, communication, and stakeholder management skills across different organizational levels.
• Ability to operate effectively amid ambiguity, develop practical solutions, and consistently deliver superior results.

Benefits

• Annualized base salary range of $200,000-$280,000, depending on experience, expertise, geographic location, and qualifications.
• Potential eligibility for an annual cash bonus.
• Comprehensive benefits package.
• Fully remote position within the United States.
• Opportunity to work directly with C-level executives and senior operating leaders.
• Exposure to a broad portfolio of enterprise SaaS businesses and complex transformation initiatives.
• Opportunity to shape scalable AI, automation, and customer success strategies across multiple organizations.
• Immediate-start opportunity in a high-impact, entrepreneurial environment.
• Professional growth through exposure to technology strategy, operational transformation, investment evaluation, and value creation.