Customer Success Operations Strategy Lead
Freshpaint
About Freshpaint
Customer data is the fuel that drives all modern businesses. From product analytics, to marketing, to support, to advertising, advanced data analysis in the warehouse, and even sales – customer data is the raw material for each function at a modern business.
For highly regulated businesses in healthcare, it’s always been a challenge to harness that customer data and get it to the marketing and analytics tools that require it while following patient privacy laws….until now.
Something as simple as running ads to get more users is simple for an e-commerce of software company to do. But common web analytics and advertising tools collect sensitive user identifiers and healthcare information automatically. Those same tools are not HIPAA compliant.
We provide a layer of data governance to make current web analytics tools HIPAA-compliant. For analytics, our customers can continue getting the insights they need to improve the patient experience. For marketing, Freshpaint safeguards health information while helping our customers promote access to care through popular advertising platforms like Facebook, Google, and others.
In short, we help healthcare marketers promote access to care and safeguard patient privacy at the same time. This is an important, complex problem in a massive market (healthcare is 20% of the US GDP).
Our customers manage their customer data with:
Privacy Platform. We help healthcare providers automate their website’s + app’s HIPAA compliance, and safeguard patient data. This is our core product today
Future additional product lines! Our core product provides a platform that we're building marketing applications on top of.
We’re fully remote. If you strongly value in-person work, Freshpaint is likely not the best fit for you. Even though we don’t care where you’re located, we need employees to be based in the US. Many of our team is concentrated in various metro areas like SF or NYC.
To balance out our remote-ness, we gather the team 2-4 times per year for offsites. We’ve been to Greece, Jackson Hole, Cabo, Santa Fe, and California wine country in the recent past.
We’re backed by leading investors including Y-Combinator, Intel Capital, and angel investors like the Head of Data from Slack, Head of Data at LinkedIn, and more.
Who we are:
Freshpaint was founded by web analytics veterans who realized how hard it was for highly regulated companies to collect and use customer data in a compliant way. We started as part of Y Combinator’s S19 cohort and have been focused on enabling healthcare companies collect, safeguard, and activate patient data since.
In 2022 the government issued updated guidance around HIPAA, basically making our software a requirement to use for healthcare companies. As a result, we're one of the fastest growing software companies on earth right now.
Our team has deep analytics and growth experience, with all of us coming from high-growth companies like Heap, Pendo, Iterable, Quantum Metric, and Retool.
If you value lots of freedom and ownership in your work, interfacing with customers, and working on a product with high customer impact, then Freshpaint is your home.
The Role
Our success is defined by the success of our customers – we’re looking to bring on a Customer Success Operations Strategy Lead to help optimize and scale the performance of our Customer Success Engineering, Account Management, and Support Engineering teams during a period of rapid growth. Reporting directly to the VP of Customer Success, this high-impact role blends strategic thinking, process optimization, and data-driven insights to ensure Freshpaint delivers exceptional value to customers while scaling efficiently.
The Customer Success team at Freshpaint empowers customers to deliver on their goals while prioritizing privacy and data quality. We focus on delivery excellence, industry expertise, efficiency, and dedication to customer outcomes. As the Customer Success Operations Strategy Lead, you will play a critical role in helping Freshpaint’s Customer Success organization achieve its goals.
You will own, maintain, and improve our capacity and forecast models, manage our NPS program and customer health scoring, create compensation plans for Account Managers, set quarterly targets and lead analyses that uncover the “why” behind performance. You will also innovate on operating procedures to ensure a predictable and precise business cadence. Ultimately, your work will help Freshpaint run smoothly today and make the right big bets for tomorrow.
We are looking for someone who is a first-principles thinker, has strong analytical skills, and is effective at building cross-functional partnerships. This person should be excited to dive into analyses, modeling and process improvement — as well as have a high sense of ownership, track record of building from scratch and ability to communicate across levels and audiences to get things done.
What You’ll Do
Strategic Planning & Execution
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.
Operational Excellence
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.
NPS Program & Health Scoring
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.
Data-Driven Insights & Reporting
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.
Cross-Functional Collaboration
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.
Team Enablement
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.
What You’ll Bring
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.
Nice to Have
Experience in healthcare or regulated industries.
Familiarity with product analytics tools.
Background in supporting or managing Customer Success, Account Management, or Support teams.
Benefits - what we offer in return:
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.
If you are interested in reading more about our team and our values, check out our team page.
Interested? How to apply
Please reach out even if you don’t meet all criteria! If you’re smart and driven, we’d love to hear from you.
What happens after you apply
If you apply online, you will hear back if you're a fit within a week or two. You will not hear back if you're not a fit (or the position gets filled before we have a chance to chat). We look at everything, we promise.
