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Swooped · United States

Director of Customer Success

Remotedirectorfull time$160,000 – $194,000 / yearPosted yesterday
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iottime-seriesdata-analysismachine-learning

About the Opportunity

The Director of Customer Success is a strategic leadership role responsible for building, scaling, and directing the customer success organization to drive sustainable revenue growth, customer retention, and expansion. This position plays a critical role in shaping post-sale strategy and market position, with direct accountability for customer outcomes, team performance, and enterprise-wide customer-centric initiatives. The Director will lead a team of up to 20 or more Customer Success Managers and Leads across multiple levels, ensuring consistent delivery of high-quality service, driving product adoption, and embedding AI-powered solutions and best practices throughout the organization.

Key Responsibilities

- Develop and execute customer success strategy aligned with revenue targets and product roadmap, focusing on NRR, GRR, retention, and expansion revenue.

- Own key performance indicators with direct accountability: NRR (110%+ minimum), retention (95%+), churn (under 5% annually), expansion revenue growth (20%+ year over year), NPS (45+ minimum), and customer health scores.

- Define customer segmentation and lifecycle models that optimize value realization and maximize ROI for customers and the organization.

- Lead the post-sale organization to drive product adoption, customer experience excellence, and measurable business outcomes.

- Recruit and develop talent, establishing a culture of excellence and accountability while targeting turnover under 15% annually and a 40%+ internal promotion rate for leadership roles.

- Build organizational infrastructure to support scaling across multiple regions, with an emphasis on Mexico and Latin America operations.

- Develop a strong leadership bench with clear career pathways, maintaining two to three identified successors for key roles.

- Foster a continuous learning culture, targeting 10+ training hours per CSM annually.

- Hold the team accountable to performance standards while maintaining psychological safety, collaboration, and mutual support.

- Implement standards that elevate team capabilities, methodologies, and customer outcomes.

- Lead strategic integration of AI capabilities into customer success operations, targeting 100% adoption across CS tools and a 20%+ improvement in CSM productivity within 18 months.

- Champion AI adoption for predictive analytics, health scoring, churn prevention, and personalized engagement.

- Evaluate and implement AI-powered CS tools, including AI health platforms, conversational AI integration, and automated insights engines.

- Partner with Product and Engineering to ensure customer feedback informs the AI roadmap and platform integration.

- Own gross and net revenue retention targets and churn reduction initiatives, targeting 10–15% annual churn reduction and 20% expansion revenue growth year over year.

- Develop and operationalize CS lifecycle frameworks across onboarding, adoption, value realization, renewal, and expansion, targeting a time-to-value of 30 days or less and first-year GRR of 90%+.

- Manage strategic account relationships and escalations for high-value accounts, maintaining direct visibility into at-risk accounts and driving proactive intervention.

- Lead initiatives to maximize adoption and ROI of condition monitoring solutions across customer manufacturing operations.

- Establish and monitor CS programs including business reviews, executive sponsor relationships, and customer advisory boards, targeting quarterly executive reviews for 100% of top 20 accounts.

- Partner with Sales, Product, Marketing, Engineering, and Operations to ensure seamless handoffs and customer-centric decision-making.

- Serve as the voice of the customer to executive leadership, presenting quarterly customer health and success metrics along with market trend insights and recommendations.

- Collaborate on feature prioritization and product roadmaps informed by customer feedback, securing input from a minimum of 50% of the customer base quarterly.

- Work with Sales on renewal forecasting and expansion opportunities, participating in monthly pipeline reviews with plus or minus 10% forecast accuracy.

- Partner with Marketing on retention campaigns, case studies, and reference programs, targeting 20+ case studies and 30+ customer references annually.

- Design and optimize CS processes, playbooks, and SOPs that scale with growth, implementing 4–6 process improvements annually with documented impact.

- Lead the evolution of the CS technology stack and CDP to ensure data integrity, actionable insights, and seamless integration with sales, marketing, and product systems.

- Establish metrics dashboards with real-time visibility into customer health and team performance, ensuring 95%+ data accuracy and weekly metric availability.

- Identify and eliminate operational bottlenecks through continuous improvement, retrospectives, and feedback loops.

- Develop training and enablement programs, targeting new CSM onboarding completion within 30 days with 80%+ competency scores.

- Lead customer success strategy for international expansion in Mexico and Latin America with cultural competency and localized approaches, scaling regional operations to support 20%+ annual revenue growth.

- Build and manage remote, distributed teams across time zones and geographies with strong processes and communication cadences.

- Navigate diverse regulatory and contractual environments, maintaining 100% compliance with local labor and data privacy regulations.

Required Qualifications

- 8+ years in customer success, account management, or related roles in B2B SaaS.

- 4+ years in director-level leadership managing 15+ people with multiple supervisory levels.

- 2+ years managing CSM teams.

- 2+ years with revenue accountability or expansion metrics ownership.

- Minimum 3+ years of experience in SaaS, HaaS, IoT, predictive maintenance, manufacturing, or similar B2B sectors.

- Deep understanding of customer lifecycle management, SaaS metrics, and renewal and expansion economics.

- Proven track record of recruiting talent, developing leaders, creating accountability, and managing 15+ direct and indirect reports with demonstrated success elevating team performance.

- Demonstrated ability to develop and execute strategies that drive measurable improvements in retention (90%+), NRR (110%+), NPS (45+), and expansion revenue (20%+ growth).

- Minimum 2+ years of experience managing remote, geographically distributed teams.

- Technical and AI fluency, including comfort with technology, data analytics, and AI/machine learning applications, with the ability to quickly learn and champion tools that enhance customer outcomes.

- Strong customer-centric orientation with a proven ability to balance customer needs with business objectives using data-informed decisions.

- English language fluency.

Preferred Qualifications

- Experience in SaaS, HaaS, IoT, predictive maintenance, manufacturing, or similar B2B sectors is strongly preferred.

- International experience in Mexico or Latin America, or comfort living or working in Mexico or other international markets.

- Spanish or other additional language skills.

- Manufacturing acumen, including familiarity with manufacturing operations, predictive maintenance, IoT, condition monitoring, and asset-intensive industries.

Compensation and Benefits

- Base salary range: $160,000—$194,000 USD. Individual pay is determined by work location and additional factors, including job-related skills, experience, and relevant education or training.

- Stock options and equity package.

- Variable pay, bonuses, and other cash compensation to be discussed during the interview process.

- Comprehensive benefits package, including health coverage and a retirement plan with organizational match.

- Unlimited paid time off (PTO).

- Flexible work schedule.

Work Environment

- Full-time, remote position based in the United States.

- The hiring organization operates a distributed team working remotely across locations in the United States and Ontario, Canada.

- Active collaboration within core working hours is required.

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