Job Title: VP of Leave Operations & Customer Success @ Tilt

Tilt (check us out here) is looking for a VP of Leave Operations & Customer Success to join our team, build a world-class customer experience capability, and lead our team of Leave Success Managers and Customer Success Managers! This position will work with Tilt leaders to lead this function for the business with a focus on quality of service, operating model scale, financial outcomes, continuity from sales to customer experience, customer delight, and then customer retention. Tilt is revolutionizing leave by intelligently applying technology to the complexities of leave while ensuring the human elements of leave continue to be human. To be successful in this role, this leader needs to be adept at balancing technology-driven product scale and human experience architecture. This position is a full-time role reporting to the Chief Operating Officer. We want you to be successful here at Tilt! Below is a description of your role and responsibilities, including the things you will be held accountable for and the virtues, behaviors and competencies that are expected for this role.

Responsibilities will include:

Setting and & Executing the Strategic Direction for Customer Success

• Define the future of Customer Experience (CX) at Tilt by building a strategy that scales intelligently and sustainably.
• Drive a transition from high-touch service to a technology-enabled, data-informed function.
• Ensure CX goals align with company-wide objectives including revenue growth, customer value realization, and long-term profitability.
• Collaborate across functions to build and manage a customer success roadmap that reflects business and customer priorities.

Drive Scalable & Efficient Customer Experience

• Implement a service-to-tech default model—preserving empathy while automating routine engagement.
• Redesign core CS processes with embedded KPIs to track onboarding, support, renewals, escalations, and overall satisfaction.
• Identify opportunities for automation and operational streamlining through internal tooling and third-party integrations.
• Create a framework for continuous process improvement based on data and user feedback.

Own Customer Retention & Success Metrics

• Maintain customer retention above 95% and drive Net Revenue Retention (NRR) to 100%+.
• Reduce time-per-leave management by doubling team productivity while enhancing engagement quality.
• Design proactive risk mitigation strategies to drive customer health and long-term success.
• Develop and operationalize customer success metrics (Value Sentiment, usage, health scoring) that feed real-time insights into executive decision-making.

Build & Lead a High-Performing CS Team

• Design a scalable team structure optimized for lifecycle stages, customer segments, and tech-driven workflows.
• Foster a high-trust, growth-oriented team culture with clear roles, progression paths, and leadership development.
• Ensure CS team engagement scores exceed benchmark expectations.
• Develop accountability systems and coaching frameworks to empower the team to perform at their highest level.

Deliver Customer Insights to Drive Company Strategy

• Create a consistent process to translate customer insights into actionable strategy for Product, GTM, and Operations teams.
• Lead quarterly Customer Health & Insights Reviews for executive alignment.
• Build accessible dashboards and reporting systems that centralize CS performance and customer intelligence.

You’re a great fit if 🤩

• You have held customer experience, operations, and customer success management roles with at least 8 years of leadership experience.
• You have successfully led change management and customer experience transformation efforts.
• You have led customer experience, operations, and customer success teams of 100 to 200+ people.
• You have a proven track record in an operational leadership role, with a strong ability to drive business outcomes.
• You bring experience in operations, with expertise in report creation, process optimization and project management.
• You possess strong business acumen with an ability to make sound business decisions leveraging data analysis and business intelligence for customer experience innovation.
• You can grasp high-level strategies, translate them into system and process requirements and ensure successful local execution with measurable business impact
• You have advanced proficiency with a broad set of operations, customer success, and support tools enabling technology and tool leadership for the department and collaboration with the Tilt product and engineering teams.
• You excel in problem-solving, with a knack for crafting efficient and scalable processes.
• You demonstrate strong project management skills, capable of driving projects to completion while effectively communicating and collaborating with stakeholders.
• You are a strategic thinker, skilled at integrating diverse inputs, encouraging innovation, and challenging the status quo, all while managing multiple tasks under tight deadlines.\
• You have outstanding interpersonal and communication skills with proven experience in cultivating collaborative relationships across an organization.
• You thrive in dynamic environments, showing comfort to multiple demands, shifting priorities, ambiguity, and rapid change.
• You have high levels of empathy and can connect deeply with Tilt’s mission
• You have experience working with a startup and/or with a B2B SaaS business, bonus point if you have an understanding of SAAS metrics.

Virtues/Competencies 🔐

1. Health & Family First

You balance work and personal life effectively

You get things done at a pace consistent with the business needs

You show up and are reliable

You encourage others to put their health and family first

2. Autonomy + Team. Always

You are highly organized and can manage multiple priorities and deadlines at once

You are focused on scale and building - you understand that pace is equally as important as quality

3. Be Curious

When you don’t have all of the answers, you dig in and ask questions

You don’t let negative assumptions drive your actions and instead assume positive intent and find truth

You are intentional in discovering the paths of self development Tilt has to offer and seek out opportunities to engage in professional growth

4. Love Our Customers

You show empathy and compassion; you strive to meet people where they are to offer maximum support

5. Fearlessly Flexible

You go with the flow and deal with (lots) of ambiguity

You’re not afraid to work without clear direction

Total Compensation 💰

The projected annual salary range is $210-240K USD plus stock options (ISOs), because we believe everyone should have some stake in our business.

Additional benefits include:

Comprehensive medical, dental, and vision benefits paid at 100% for all employees and 50% for dependents.

401k + match (100% match on the first 3%, 50% match on the next 2%)

$100 monthly to spend on “What Matters Most”

Responsible Time Off - take what you need, when you need it!

More about our amazing Perks and Benefits can be found here!

More about Tilt

Tilt’s mission is big: make leave not suck. We are building a product that makes it easy for people to switch between work and life. If you join us, you’ll be part of a fearless band of humans helping employers balance empathy with economics. We’re changing the status quo and it’s hard. You should know that now. You should also know that joining Tilt means the opportunity to be a change-maker. We’re thinkers, doers, revolutionaries, dreamers, get shit done-ers, and bold enough to tackle a really complex space.

Remote Work & Flexibility 🌸

We are a fully remote company. We are committed to being fearlessly flexible and ensuring that all employees are set up and have the autonomy to do their best work, as well as have the balance to care for their health, family and life outside of work. Overall, we trust our team and are focused on outcomes not outputs.

Equal Opportunity Employer 🌎

We celebrate and support our differences. We believe in the power of equality which is why we are an equal opportunity employer. Employment at Tilt is based solely on a person’s merit and qualifications related to their professional competence. Tilt does not discriminate against any employee or applicant because of race, color, creed, religion, sexual orientation, gender identity/expression, national origin, disability, age, genetic information, veteran status, marital status, pregnancy, or any other basis protected by law. We comply with all applicable national, state, and local laws pertaining to nondiscrimination and equal opportunity.

You must be authorized to work in the US.

So what do you say? Do you want to join our team?