Trajektory - Director of Customer Success
Chicago, IL | Hybrid (three days in Chicago office HQ)
About Trajektory
Trajektory is a Chicago-based sponsorship intelligence and valuation platform built by former execs from the NFL, NBA, MLB, NHL, NCAA, WNBA, AFL, and esports. We help the sports, media, and entertainment ecosystem understand the value of partnership exposure through contextualized, multi-channel data.
Our culture is centered around curiosity, collaboration, good humans, and a nerdy sense of humor. We believe in transparency, ownership, personal and professional growth, and building an environment where people actually enjoy showing up to work.
We work hard, we have fun, and we’re building something genuinely new in the market. If you want to be part of a highly analytical team solving problems the industry has never solved before, we’d love to talk to you.
Role Overview
We are seeking a Director of Customer Success to lead our Customer Success (CS) function and ensure customers achieve maximum value from our platform. This role is both strategic and hands-on: you’ll serve as a player-coach, managing a small book of high-value accounts while leading and developing a team of CS Managers.
The Director of Customer Success will drive customer retention, satisfaction, and account expansion, both building and implementing scalable processes that directly impact ARR growth year-over-year. And expanding on the success of the team over the past few years.
Key Responsibilities
- Lead and mentor a team of four Customer Success Managers, fostering professional development and performance accountability.
- Manage a small portfolio of key customers, serving as their trusted advisor and ensuring successful adoption, retention, and growth.
- Support a diverse customer portfolio, including major sports properties, brands, and agencies, tailoring success strategies to different data and activation use cases.
- Own renewal and expansion strategy across the customer lifecycle, partnering with Sales and BI to drive measurable ARR growth and prevent churn through predictive analytics and proactive engagement.
- Design and implement scalable processes, playbooks, and best practices that improve retention, upsell opportunities, and customer health.
- Lead operational excellence within CS by developing processes for onboarding, QBRs, NPS tracking, and value documentation at scale.
- Partner cross-functionally with Sales, Marketing, BI, Product, and Engineering to ensure alignment on customer needs and value delivery. Collaborate closely with Product and BI teams to translate customer needs into actionable roadmap priorities and performance insights.
- Analyze customer trends, usage data, and feedback to inform strategy and identify opportunities for improvement.
- Leverage data insights and platform analytics to identify value realization trends, surface risk signals, and create structured success reporting frameworks.
- Own Customer Success KPIs, including retention, ARR growth, and expansion metrics.
- Act as the voice of the customer internally, ensuring insights flow back into product development and company strategy.
Qualifications
- 8+ years of experience in B2B SaaS customer success or account management, ideally in data, analytics, or marketing technology platforms, including 3+ years in a leadership capacity, directly managing high-performing teams.
- Have built CS functions from Series A/ B to $20M+ ARR.
- Must understand SaaS metrics (ARR, churn, NRR, gross retention, etc.), customer health scoring, lifecycle management, and renewals/ expansion motions.
- Exceptional customer-facing skills with executive presence and the ability to influence at all levels.
- Experience balancing hands-on account management with team leadership responsibilities.
- Strategic thinker with the ability to build processes and structure in a growth-stage environment.
- Excellent communication, presentation, and problem-solving skills.
Reporting & Growth
- Reports to the VP of Operations.
- Expected to play a pivotal role in scaling Customer Success as Trajektory grows ARR and global customer footprint.
Compensation
- The compensation package will be commensurate with experience and includes a base salary, with the potential for an annual bonus tied to personal, team, and company success metrics.
- Compensation includes health benefits and potential company options.
- Total compensation range: $100,000 - $145,000, inclusive of bonus, options, and full benefits package.
