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Director of Customer Success

Seattle, WA

Who we are:

Reports to: Esha Joshi, Cofounder and Chief Customer Officer

Yoodli is the AI roleplay simulator redefining how individuals and teams master communication. Think of it as the batting cage before the big game - but for communication. Whether it’s a sales pitch, manager feedback session, or media interview, Yoodli provides private, judgment-free, just-in-time coaching. Leaders at companies like Google, Databricks, Snowflake, RingCentral, Toastmasters, and Dale Carnegie use Yoodli to ramp reps faster, improve message delivery, and reduce coaching burden on frontline managers. The result is stronger performance, greater team readiness, and a more scalable path to impact.

We’re building a new category called Experiential Learning: a new AI-powered category that helps people learn through conversational roleplays. People don’t learn from slides: they learn through dialogue, questions, and iteration. Yoodli makes that process interactive, personalized, and always up to date. It’s learning that feels fun, builds confidence, and finally lets organizations measure the ROI of training.

We’ve raised $40M in Series B funding, doubling our team in 2026, and are headquartered at the beautiful Pier 70 in Seattle.

What you’ll do:

As Director of Customer Success, you'll build and scale the enterprise customer success function at Yoodli - owning the team and systems that drive measurable outcomes for our largest and most strategic customers.

This is a people leader and organizational builder role. You'll hire and develop a high-performing, distributed team of CSMs across time zones and specializations, design the programs and playbooks that make enterprise CS repeatable and scalable, and partner cross-functionally to ensure our biggest customers realize deep, demonstrable value from Yoodli.

Your leverage is your team, your systems, and your ability to elevate how enterprise Customer Success works at Yoodli.

You’ll own team performance across adoption, retention, and renewals, while setting the standard for what “great Customer Success” looks like at Yoodli: proactive, outcome-oriented, and deeply trusted by our customers.

This role is hybrid; we are looking for Seattle-based candidates who will be in the office at least 3 days per week.

People Leader

Build and scale a world-class enterprise CS team.

You'll hire, develop, and retain an exceptional team of CSMs spanning time zones, customer tiers who are accountable not just for activity, but for customer outcomes and value realization.

  • Own hiring, interviewing, onboarding, performance management, and career development for a team of CSMs
  • Build a thoughtful hiring plan based on capacity needs, skill gaps, and customer tiers
  • Make strong hiring decisions, and be accountable for them
  • Set clear performance expectations and address underperformance quickly and directly
  • Establish career ladders, growth plans, and promotion criteria for CSMs
  • Retain and develop top performers, not just manage headcount

Program Builder & Operator

Design the systems and programs that make enterprise CS scalable.

You'll build the operating infrastructure that enables consistent, high-quality customer outcomes as Yoodli grows, not just for individual accounts, but across the entire enterprise portfolio.

  • Define and run the CS operating cadence (team meetings, QBR standards, renewal forecasting, health reviews)
  • Improve, build, and document CS playbooks across onboarding, adoption, renewals, and risk
  • Own CRM hygiene, renewal forecast accuracy, and reporting rigor
  • Partner with RevOps and Product to improve usage tracking, health scoring, NPS/CSAT, and feedback loops
  • Use data to identify risk early and drive proactive interventions

What success looks like

  • Customers achieve the outcomes they bought Yoodli for—and can clearly articulate the value they’re getting
  • Renewals feel earned, predictable, and grounded in trust
  • Expansion happens because customers want to do more with us, not because they’re being pushed
  • CSMs operate as confident customer leaders, not reactive support agents
  • The CS org scales without losing proximity to customer impact

About you:

  • 6+ years in Customer Success or Account Management (SaaS), including 2+ years managing CSMs
  • Proven experience owning renewals, retention, and expansion across enterprise and mid-market customers
  • Strong people leadership instincts: you enjoy coaching, giving direct feedback, and developing talent
  • Comfortable being both the “captain” today and a peer tomorrow - low ego, high ownership
  • Track record of making hard calls (hiring, performance, prioritization) and standing by them
  • Highly organized, detail-oriented, and systems-minded
  • Humble and curious

Extra credit experience:

  • Experience scaling CS teams in high-growth SaaS or AI companies
  • Deep understanding of enterprise customer journeys and change management
  • Strong analytical skills with the ability to translate usage data into action
  • Passion for coaching, enablement, or learning & development

Compensation

  • Total compensation targeted at $180,000 - $220,000 (depending on experience). This includes variable pay tied to team performance
  • Equity at a fast-growing, category-defining company
  • Health, dental, and vision insurance
  • 401(k)
  • Flexible PTO
  • Free lunches/snacks at the office

What’s in it for you?

  • Huge impact opportunity: Build and scale the CS function at a category-creating company
  • Ownership: Shape how Customer Success works at Yoodli
  • Close partnership with the founding team and CRO
  • A humble, ambitious, and mission-driven culture

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