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Director of Customer Success

ActiveCampaign
Chicago
ActiveCampaign supports over 185,000 customers globally—from small businesses to scaling mid-market companies. As we evolve how we serve and scale with them, we’re seeking a forward-thinking Director of Customer Success to lead and grow our Customer Success team. This is a pivotal leadership role focused on guiding our organization into the future—blending strategic account leadership with the power of AI, digital engagement, and scalable models to drive adoption, retention, and customer-led growth across our entire customer base.

What your day could consist of:

    • AI-Enabled Engagement: Champion the adoption of AI tools that surface actionable insights, automate workflows, and enable teams to proactively drive customer value at scale.
    • Shape the AI Strategy: Co-develop the long-term vision for how AI is embedded across the customer lifecycle—including segmentation, engagement models, team workflows, and customer insights. Partner with AI and operations teams to pilot, test, and refine new models of customer engagement.
    • Design for Scale: Own the evolution of scalable success models—combining human, digital, and AI-led approaches to support customers efficiently across segments, including unmanaged accounts.
    • Customer-Led Segmentation: Redefine customer segmentation strategies using AI-informed behaviors, product usage, and lifecycle needs—moving beyond traditional ARR tiers to enable personalized, data-driven engagement.
    • Retention & Growth: Define and execute strategies that deliver measurable outcomes across value realization, product adoption, and Net Revenue Retention (NRR), using product usage, health scores, and growth signals to identify both risk and opportunity.
    • Cross-Functional Collaboration: Partner with Product, Marketing, and Sales to deliver customer feedback, influence roadmap and go-to-market strategies, and align on success metrics and expansion motions.
    • Operational Design: Help shape the future-state Customer Success operating model—defining team structures, processes, and tools that support a digital-first, insight-driven approach to customer engagement.
    • Continuous Improvement: Drive operational rigor through forecasting, enablement, performance measurement, and iterative process improvements that scale impact and innovation.

What is needed:

    • 8+ years of progressive leadership experience in Customer Success, including direct management of managers and oversight of cross-regional or multi-functional teams within a SaaS or tech-driven environment.
    • Proven track record of scaling Customer Success programs across diverse customer segments (SMB, mid-market, enterprise), with measurable impact on adoption, retention, and expansion outcomes.
    • Demonstrated success implementing AI and automation capabilities within customer-facing workflows—ideally including tools like predictive health scoring, AI-driven segmentation, or co-pilot-style enablement for customer-facing teams.
    • Expertise in customer journey design and lifecycle strategy, with a data-driven approach to personalization, onboarding, engagement, and long-term value realization.
    • Strong analytical and strategic mindset, with the ability to translate data and insights into scalable plays, prioritization frameworks, and customer-centric actions.
    • Deep experience in operational excellence, including team structure design, process optimization, playbook development, KPI tracking, and performance management.
    • Ability to lead and influence cross-functional initiatives—partnering closely with Product, Marketing, Sales, and Operations to advocate for customer needs, drive alignment, and support company-wide growth initiatives.
    • Fluency in scalable engagement models, including tech-touch, digital CS, and hybrid models that blend automation with human expertise.
    • Exceptional communication and leadership skills, with the ability to inspire and develop talent, foster accountability, and drive a high-performing, customer-obsessed culture.
    • Experience with customer success and data tools such as Totango and Looker is a strong plus, particularly in building health models, tracking performance, and delivering actionable insights.
    • Bachelor’s degree in Business, Marketing, or a related field is preferred, but not required. Advanced degrees (e.g., MBA) are a plus.
$160,000 - $220,000 a year
Compensation details listed in this posting reflect the base rate only and do not include bonus, equity, sales incentives or other role specific compensation that the role may be eligible for. ActiveCampaign believes in and is committed to equitable compensation practices. The salary range provided above is a good faith estimate of the pay range determined by the location associated with the job posting. The actual salary depends on a candidate’s skills, experience, and work location.
About ActiveCampaign:
ActiveCampaign is an AI-first, end-to-end marketing platform for people at the heart of the action. It empowers teams to automate their campaigns with AI agents that imagine, activate, and validate–freeing them from step-by-step workflows and unlocking limitless ways to orchestrate their marketing.

With AI, goal-based automation, and 950+ app integrations, agencies, marketers, and owners can build cross-channel campaigns in minutes–fine-tuned with billions of data points to drive real results for their unique business.

ActiveCampaign is the trusted choice to help businesses unlock a new world of boundless opportunities–where ideas become impact and potential turns into real results.

As a global multicultural company, we are proud of our inclusive culture which embraces diverse voices, backgrounds, and perspectives. We don’t just celebrate our differences, we believe our diversity is what empowers our innovation and success. You can find out more about our DEI initiatives here. 

Perks and benefits:
ActiveCampaign is an employee-first culture. We take care of our employees at work and outside of work. You can see more of the details here, but some of our most popular benefits include:

-Comprehensive health and wellness benefits that includes a High Deductible Health Plan (HDHP) fully covered by ActiveCampaign, complimentary access to telehealth and tele-mental health resources, and a complimentary membership to Calm
-Open paid time off
-Generous 401(k) matching program with immediate vesting
-Quarterly Path Perks with options for commuter and lunch benefits (for those reporting to a Hub), or a remote home office stipend
-Access to professional development resources through LinkedIn Learning
-After five years of service, you’ll be eligible for a four-week paid sabbatical leave and a sabbatical leave bonus

ActiveCampaign is an equal opportunity employer. We recruit, hire, pay, grow and promote no matter of gender, race, color, sexual orientation, religion, age, protected veteran status, physical and mental abilities, or any other identities protected by law.

Our Employee Resource Groups (ERGs) strive to foster a diverse inclusive environment by supporting each other, building a strong sense of belonging, and creating opportunities for mentorship and professional growth for their members.
Apply Now

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