Director, Customer Success - Scaled Programs

Affinity is a leading relationship intelligence platform that transforms how businesses manage and leverage their professional networks. Our innovative CRM solution empowers investment firms, consulting companies, and other relationship-driven organizations to unlock the full potential of their connections through AI-powered insights and automated relationship mapping. At Affinity, we're passionate about helping our clients build stronger relationships and drive better business outcomes through data-driven relationship intelligence.

The Customer Success team at Affinity are the trusted private capital advisors who ensure every Affinity customer maximizes the value of their network and relationships. We deliver this by combining deep industry expertise with proactive guidance, helping customers adopt best practices that drive measurable business outcomes.

The Role

As Director of Customer Success, Scaled Programs you'll architect and execute a sophisticated digital-first customer success strategy that drives exceptional outcomes for our 1,500+ scaled customer segment while establishing this portfolio as the strategic testing ground for programs that benefit Growth, Mid-Market, and Strategic tiers. Reporting to the VP of Customer Success, you will lead a team of scaled Customer Success Managers while working cross-functionally with Marketing, Product, Revenue Operations, and Finance teams to create AI-forward customer journeys. You will be accountable for adoption leading indicators that directly influence user and account retention, establishing unified measurement frameworks that transform digital initiatives from foundational programs into strategic, revenue-correlated business drivers.

What will I be doing?

Strategic Digital CS Leadership and Framework Development:

• Establish and own unified measurement frameworks with revenue-correlated "North Star" metrics to evaluate digital initiative effectiveness across all customer programs. 
• Develop adoption leading indicators that directly influence user and account retention across the scaled customer segment. 
• Create comprehensive AI-forward scaled models for predictive engagement, risk detection, and personalized customer experiences that move beyond traditional support models while serving as an innovation laboratory for methodologies that benefit Growth, Mid-Market, and Strategic segments.

Cross-Functional Process Design and Leadership:

• Create clear ownership frameworks and swimlanes to eliminate ambiguity in digital program execution across Customer Success, Marketing, Product, Revenue Operations, and Finance Teams
• Lead customer journey mapping initiatives identifying key moments for automated intervention across the entire user lifecycle, partnering with Marketing and Product to deliver integrated experiences.
• Collaborate with Finance to optimize billing and licensing models based on customer usage patterns and feedback from the scaled segment.

Technology and Knowledge Systems Optimization:

• Optimize and fully leverage existing tech stack capabilities (Gainsight, Pardot, Service Cloud, Amplitude, Segment) to create cohesive data ecosystems for behavior-driven engagement.
• Architect automated journey orchestration frameworks for scaled customer engagement. 
• Lead knowledge center strategy, systematizing and formalizing current resources into cohesive, just-in-time customer support systems that serve as strategic customer enablement platform. 
• Partner with Revenue Operations and CS Operations to evaluate and test new AI tools and technologies that enhance scaled customer engagement and operational efficiency.

Team Leadership and Scaled Program Execution:

• Recruit, mentor, and develop a high-performing team of scaled Customer Success Managers who manage 300+ customers  through sophisticated digital engagement strategies. 
• Build and optimize scaled CSM operating models including territory design, customer segmentation, and customer management frameworks. 
• Foster a data-driven culture focused on automation, efficiency, and measurable customer outcomes.

Digital Engagement Channel Expansion:

• Design and execute digital-first customer success programs that provide optionality across channels (self-serve when possible, human contact when needed). 
• Expand digital engagement capabilities including in-app guidance, email campaigns, webinar programming, and integrated Marketing partnerships.
• Implement sophisticated customer segmentation by ARR/usage to optimize program delivery and resource allocation while developing proven methodologies that can be adapted for other customer segments.

Metrics and Strategic Accountability:

• Build sophisticated reporting frameworks and dashboards to track health metrics and attribute lift from digital CS programs. 
• Establish robust data hygiene frameworks and consent management to prevent customer communication overlap. 
• Drive experimentation culture through A/B testing of customer engagement strategies, implementing risk mitigation throughout the customer journey.

Qualifications

Don’t meet every single requirement? Studies have shown that women and people of color are less likely to apply to jobs unless they meet every qualification. At Affinity, we are dedicated to building a diverse, inclusive, and authentic workplace, so if you’re excited about this role but your past experience doesn’t perfectly align with the qualifications above, we encourage you to apply anyways. You may be just the right candidate for this or other roles.

Required:

• Proven experience as a Director or Senior Manager in digital customer success, growth marketing, or scaled customer engagement at a successful B2B SaaS company ($50M+ ARR).
• 7+ years of customer success or growth startup experience, with 3+ years leading scaled customer success teams managing 300+ accounts per CSM.
• Demonstrated track record establishing unified measurement frameworks and North Star metrics for digital customer programs with measurable impact on user and account retention.
• Expertise in customer success platforms and analytics tools (Amplitude, Segment) for behavior-driven campaign design, with experience evaluating and implementing modern customer journey orchestration solutions.
• Strong background in AI integration for customer success including predictive modeling and personalized engagement strategies.
• Experience architecting cross-functional processes and RACI frameworks between Customer Success, Marketing, Product, Revenue Operations, and Finance teams.
• Exceptional communication and facilitation skills with proven ability to work effectively in matrixed organizational structures.
• Strong people leader with experience building and scaling high-performing customer success teams focused on digital engagement.
• Knowledge center and content strategy development experience with information architecture expertise.
• Experience with SaaS companies managing 1,000+ customers in scaled segments is preferred.

Location: Austin, Chicago, New York or San Francisco

For those located in SF or NY, for this role we're embracing a hub-hybrid model, designed to balance flexibility with meaningful in-person collaboration. Team members within commuting distance are expected in-office 2–3 days per week, typically Tuesday through Thursday. We believe great things happen when people come together intentionally to connect, create, and build momentum as a team.

What you'll enjoy at Affinity: 

• We live our values: As owners, we take pride in everything we do. We embrace a growth mindset, engage in respectful candor, act as playmakers, and "taste the soup" by diving deep into experiences to create the best outcomes for our colleagues and clients.
• Health Benefits: We cover your medical, dental, and vision insurance premiums with comprehensive PPO, HDHP and HMO options (in CA), and offer flexible personal & sick days to support your well-being.
• Retirement Planning: We offer a 401(k) plan to help you plan for your future.
• Learning & Development: We provide an annual education budget and a comprehensive L&D program.
• Wellness Support: We reimburse monthly for things like home internet, meals, and wellness memberships/equipment to support your overall health and happiness.
• Team Connection: Virtual team-building activities and socials to keep our team connected, because building strong relationships is key to success.

A reasonable estimate of the current range is $150,000 to $200,000 USD. In addition, this position is also eligible to receive Commission based on departmental KPIs.  Within the range, individual pay depends on various factors including geographical location and review of experience, knowledge, skills, abilities of the applicant.