Customer Success Operations Strategy Lead

Summary

Join Freshpaint, a rapidly growing, venture-backed SaaS company, as our Customer Success Operations Strategy Lead. You will play a critical role in optimizing and scaling the performance of our Customer Success Engineering, Account Management, and Support Engineering teams. This high-impact role requires strategic thinking, process optimization, and data-driven insights to ensure Freshpaint delivers exceptional value to customers. You will own key operational aspects, including compensation plans, headcount models, and NPS programs. You will collaborate extensively with cross-functional teams and leverage data to inform strategic decisions. Freshpaint offers a fully remote work environment with numerous benefits.

Requirements

• Experience: 5+ years in customer success operations, revenue operations, or a related strategic role in a B2B SaaS environment, with a proven track record of scaling operations in a high-growth setting
• Strategic Thinking: Ability to think critically and strategically, connecting the dots between data, processes, and business outcomes
• Operational Expertise: Strong experience with tools like HubSpot, Zendesk, Monday.com, and data visualization platforms (e.g., Looker, Tableau). Proven ability to design and manage NPS programs and customer health scoring end-to-end. Familiarity with forecasting and ARR modeling is a plus
• Data-Driven: Exceptional analytical skills to model operational questions end-to-end (from assumptions to outputs), interpret data, and translate insights into actionable strategies
• Communication & Collaboration: High EQ with the ability to influence and build relationships across teams and at all levels of the organization. Senior presence to convey complex information clearly and concisely to executives
• Problem Solving & Ownership: Hands-on builder with a problem-solving mindset, demonstrated lateral thinking, and a first-principles approach. History of leading projects from concept to execution over 2-5+ month timelines with an ownership mentality to work independently and drive impact in ambiguous situations
• Passion for Customer Success: A deep commitment to ensuring customers achieve their desired outcomes, coupled with a proactive mindset for solving challenges

Responsibilities

• Partner with the VP of Customer Success to define and execute strategies that align with Freshpaint’s growth goals
• Build and maintain a Customer Success operational roadmap to drive customer retention, expansion, and satisfaction
• Own and design compensation plans for Account Managers, including setting quarterly targets in partnership with Finance
• Create headcount models for Customer Success Engineering and Support teams, optimizing for hiring and time tracking
• Establish metrics, KPIs, and reporting frameworks to track team performance and customer outcomes, ensuring alignment with company objectives
• Design and implement scalable processes across Account Management, Customer Success Engineering, and Support Engineering teams
• Optimize workflows in tools like Delighted, Monday.com, HubSpot, and Zendesk to ensure seamless transitions across the customer lifecycle
• Drive adoption of automation and best practices to improve efficiency and reduce friction for both internal teams and customers
• Enable customer-facing teams to focus on their work by minimizing operational distractions
• Design, implement, and manage the NPS program end-to-end, including data analysis and reporting
• Build and maintain customer health scoring models to identify at-risk accounts and expansion opportunities
• Use insights from NPS and health scores to inform customer success strategies and improve retention
• Build dashboards and reporting mechanisms to provide visibility into key performance indicators for the Customer Success organization
• Leverage data to identify trends, opportunities, and risks across the customer base, informing strategic decisions
• Develop predictive models for churn risk and customer health, incorporating insights from usage data, account history, and support metrics
• Serve as the key liaison between Customer Success and other teams, including Sales, Product, Engineering, Marketing, Finance, and Sales Operations, ensuring seamless handoffs and alignment
• Provide actionable feedback to Product and Engineering teams based on customer insights to improve the platform and enhance customer satisfaction
• Create and maintain resources, playbooks, and training materials to enable the success of Customer Success Engineering, Account Management, and Support Engineering teams
• Lead initiatives to onboard new tools and processes, ensuring smooth adoption and measurable impact
• Act as a mentor and thought partner to team leads, helping them solve complex challenges and scale their functions effectively

Preferred Qualifications

• Experience in healthcare or regulated industries
• Familiarity with product analytics tools
• Background in supporting or managing Customer Success, Account Management, or Support teams

Benefits

• Joining a high-growth venture-backed startup as part of the early crew. You will be employee #70-80ish
• Competitive compensation with generous, employee-friendly equity. We have a 10-year exercise window
• Freshpaint Fridays: Half-day Fridays. Every week
• Unlimited PTO, with a minimum requirement of 2 weeks per year. Plus various observed holidays
• 100% remote
• Flex in-office if you want with $150 WeWork credits each month
• 401k
• Health, dental, and vision insurance 100% covered by the company (some states it’s 99% because laws)
• Mental health benefits - therapy appointments and more covered by the company
• 2 Treat Yourself Days per year: We'll pay you $100 to take a day off and do whatever makes you happy. The only catch is you have to share what you did with the rest of the team
• Generous parental leave
• Paid Spotify
• Health & Wellness benefit – gym membership or similar covered
• Regular team offsites 2-4 times per year. We’ve been to Greece, Jackson Hole, Cabo, Santa Fe, California wine country, and Mexico City in the recent past. Ask us about the legendary Jackson offsites!
• Ownership of your work, collaboration with a close team, and direct access to founders and what it’s like to build a startup. If you leave to start your own company, we'd love to be your first angel investors