Senior Director, Customer Success

Swooped is a Talent Platform (not a staffing agency). We are not the employer for this role and do not make hiring decisions. Clicking "Apply" takes you to Swooped to review the role and hiring company details.

About the Opportunity

A leading platform used by over 7,500 companies, from startups to global brands, powers automated communication that people actually want to receive. This platform helps teams send smarter, more relevant messages using real-time behavioral data.

The organization is seeking a Senior Director, Customer Success to lead its Customer Success organization. Reporting to the Chief Revenue Officer, this role will be responsible for driving adoption, delivering value, and ensuring customer retention through a combination of scaled digital programs, high-touch enterprise engagement, and AI-powered systems.

This is not a purely operational role. The individual will be expected to build and run the Customer Success function from the inside out, designing systems, coaching managers, and owning executive relationships with the most strategic customers. This role will also serve as a key voice in the Chief Revenue Officer's leadership team, contributing to decisions that shape the company's growth.

Key Responsibilities

• Own Net Revenue Retention (NRR), retention, and onboarding outcomes across the Customer Success organization, setting metrics, managing to them, and holding the team accountable.
• Build and scale Customer Success through AI, automation, and systems thinking, designing programs that serve more customers efficiently without simply adding headcount.
• Own relationships with the largest, most strategic accounts, leading executive QBRs, onsite meetings, and C-level conversations that connect product capabilities to clear business outcomes.
• Step in directly when needed to stabilize or expand key accounts, navigating complex organizations and aligning multiple stakeholders.
• Design and evolve engagement models across customer segments, from one-to-many digital programs for SMB and mid-market to high-touch enterprise partnerships.
• Hire, coach, and develop Customer Success managers and individual contributors into a high-performing, customer-obsessed team.
• Partner with Sales, Product, Engineering, and Marketing to close feedback loops and ensure customers are getting continuous value from the platform.

Required Qualifications

• 10+ years in Customer Success or related customer-facing roles, with at least 5 years in senior leadership (Director/Senior Director).
• Proven track record driving NRR, retention, and adoption outcomes at a B2B SaaS company, ideally supporting both mid-market and enterprise customers.
• Hands-on experience with AI and automation in a Customer Success context, with a builder's instinct for how to apply them.
• Strong executive presence; equally comfortable in internal strategy conversations with the Chief Revenue Officer and in C-level customer meetings.
• Demonstrated ability to scale Customer Success programs, from digital, one-to-many engagement to tailored executive business reviews.
• Experience managing and expanding strategic customer accounts, including driving adoption, deepening executive relationships, identifying growth opportunities, and delivering measurable business outcomes.
• Strong operational acumen, able to bring structure, metrics, and process without sacrificing agility.
• A collaborative leader who welcomes debate, challenges assumptions, and thrives in a fast-moving environment.

Why You'll Love This Role

• AI-First Opportunity: Build the next generation of Customer Success from the ground up, with AI and automation as core inputs.

• Enterprise Impact: Own and deepen relationships with the most strategic customers, influencing outcomes at the highest levels.

• Strategic Scope: Shape how Customer Success operates and evolves at a company scaling toward significant revenue milestones.

• Leadership Platform: Join the Chief Revenue Officer's leadership team and contribute to company-wide priorities.

Compensation & Benefits

The salary range for this role is $200,000 - $220,000 (or equivalent in local currency) depending on experience and subject to market rate adjustment. In addition, there will be a variable compensation target.

The organization offers an inclusive benefits package supporting well-being and growth, including 100% coverage of medical, dental, vision, mental health, and supplemental insurance premiums for employees and their families. Additional benefits include 16 weeks paid parental leave, unlimited paid time off, stipends for remote work and wellness, and a professional development budget.

Our Process

The hiring process is designed to be clear and human, facilitating informed decision-making for all parties.

• 30-minute video call with Recruiter
• 45-minute video call with Hiring Manager
• 3 x 45-minute interviews with potential team members
• 60-minute Case Study + Review Call

All final candidates will be asked to complete a background check and employment verifications as part of the pre-employment process.

The organization recognizes the impact of systemic injustice on diverse communities and commits to using its influence to increase inclusion and equity within the tech industry. The company strives to build an inclusive team culture, implement bias-free hiring practices, and develop community partnerships to expand its global impact.

Virtual interviews will be conducted using video conferencing capabilities. Offers will be extended in writing on official company letterhead.

Join Us!

For more information about why you should join the team, please visit the careers page. The organization believes in empathy, transparency, responsibility, and a collaborative spirit. If you are excited by this opportunity, apply now.