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Head of Revenue Operations

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:

  1. Privacy Platform. We help healthcare providers automate their website’s + app’s HIPAA compliance, and safeguard patient data. This is our core product today

  2. 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.

About the Role

We are looking for a Founding member of our Revenue Operations team who is energized by a challenge to support a high-functioning team through a hyper-growth stage. You will be a thought partner for our collaborate closely with our CEO, Finance, Marketing, Sales and Customer Success teams and define what great looks like, eventually scaling it.

Your responsibilities will include:

Strategic Leadership:

  • Drive alignment between Sales, Marketing, Customer Success, and Finance on operational strategy and execution

  • Partner with the executive team on annual planning, P&L management, and strategic growth initiatives

  • Partner with the GTM leadership to support selling/upsell/renewal motions combining your thought leadership, insights derived from data, and business priorities. 

Process & Systems:

  • Own forecasting, territory design, headcount planning, quota planning, and sales compensation across GTM teams

  • Design and implement revenue reporting dashboards and KPIs

  • Own operational cadence including lead routing, book assignments, QBRs.

Analytics & Insights:

  • Develop sales performance reporting to track productivity and identify areas of opportunity

  • Drive deep-dive root cause analysis on any growth challenges

  • Ensure data accuracy and hygiene 

Requirements - what you'll bring:

(If you don't meet all of these requirements, you should still apply. We're big on high-slope individuals, so if you can quickly grow into some requirements we'd love to hear from you)

  • 8+ years of experience in revenue operations, ideally working with Enterprise customers  

  • Proven experience in driving revenue growth and operational efficiency in a high-growth SaaS business

  • Proven experience in annual planning, territory management, compensation and quota design for both new sales and renewals

  • Excellence working with HubSpot and Excel. We are a lean team and move fast. If you need to run an analysis - you should be able to pull/setup the data in HubSpot and run an analysis in Excel by yourself 

  • Analytical mindset with deep expertise in data analysis, performance metrics, and financial reporting

  • You are proactive and will build the function without step-by-step instructions

  • High degree of adaptability and comfort working in a fast-paced, dynamic environment with minimal supervision

  • You are empathetic and will enjoy collaborating with other departments 

  • No job is too big or too small for you. You take ownership and solve problems when you see them

  • Based in the US.

Nice To Have

  • You thrive in ambiguity. You’ve been an early employee at a similarly early stage startup and you know what it’s like (you’ll be employee #75ish at Freshpaint)

  • Early career experience as an Account Executive or Account Manager.

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.

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Average salary estimate

$135000 / YEARLY (est.)
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$120000K
$150000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Head of Revenue Operations, Freshpaint

At Freshpaint, we're on the hunt for a dynamic Head of Revenue Operations who thrives in fast-paced environments and is ready to help us navigate our hyper-growth stage. As a key founding member of our Revenue Operations team, you'll work closely with our CEO and collaborate across various departments including Finance, Marketing, Sales, and Customer Success to drive alignment and operational strategy. Your primary responsibilities will include managing the P&L, designing effective sales compensation plans, and owning forecasting and territory planning. With your analytical mindset, you'll develop insightful sales performance reports to track productivity and uncover growth opportunities. This role is perfect for someone with a strong background in revenue operations, especially if you have experience with enterprise customers in a SaaS environment. At Freshpaint, we're dedicated to safety and privacy in the healthcare space while ensuring our team enjoys the flexibility of remote work. Join us and become a part of a talented team that values collaboration and ownership while solving complex challenges in customer data management. If you're looking for a role where you can make a significant impact while having a blast working with passionate professionals, Freshpaint may just be your next home!

Frequently Asked Questions (FAQs) for Head of Revenue Operations Role at Freshpaint
What are the main responsibilities of the Head of Revenue Operations at Freshpaint?

The Head of Revenue Operations at Freshpaint will lead the alignment between Sales, Marketing, Customer Success, and Finance, ensuring operational strategies are executed effectively. Key responsibilities include managing annual planning, overseeing P&L management, designing sales compensation plans, and developing insightful sales performance reports to drive growth.

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What qualifications does Freshpaint require for the Head of Revenue Operations position?

Freshpaint seeks candidates with 8+ years of experience in revenue operations, particularly in high-growth SaaS businesses. Ideal candidates should have experience in driving revenue growth, managing territory and quota designs, and proficiency in using HubSpot and Excel for analytics and reporting.

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Is remote work an option for the Head of Revenue Operations position at Freshpaint?

Yes, Freshpaint primarily operates remotely, allowing employees the flexibility to work from anywhere in the U.S. While the company holds occasional offsite gatherings, the role itself does not require in-person attendance, making it suitable for those who prefer a remote work environment.

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What benefits can a Head of Revenue Operations expect while working at Freshpaint?

Freshpaint offers a competitive compensation package with generous employee-friendly equity, unlimited PTO, 100% company-covered health insurance, and unique perks such as Freshpaint Fridays and Treat Yourself Days. The culture encourages ownership, collaboration, and fun team offsites.

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How does Freshpaint support personal and professional growth for the Head of Revenue Operations?

Freshpaint fosters personal and professional growth by encouraging autonomy, providing opportunities to collaborate closely with founders and other teams, and supporting continuous learning through attendance at relevant seminars and conferences. The dynamic startup environment ensures that employees can rapidly develop their skills and careers.

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Common Interview Questions for Head of Revenue Operations
How do you prioritize your tasks as a Head of Revenue Operations?

In answering this question, highlight your ability to balance immediate operational needs with long-term strategic goals. Discuss specific tools or frameworks you use to prioritize tasks while outlining how you can pivot when unexpected challenges arise.

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Can you give an example of how you've driven revenue growth in your previous roles?

Be prepared to share a specific instance where your actions directly led to revenue growth. Focus on the strategies you implemented, the data you analyzed, and the results achieved to demonstrate your impact.

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What experience do you have with compensation plan design?

Discuss your previous experience designing sales compensation plans, focusing on how these plans motivated the sales team. Provide specific metrics or outcomes that demonstrate the effectiveness of your designs.

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How would you ensure alignment among cross-functional teams within Freshpaint?

Talk about your approach to fostering collaboration and communication among different teams. Recommend utilizing regular meetings and dashboards to track progress and address any misalignments promptly.

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What key performance indicators (KPIs) do you consider essential in revenue operations?

Identify important KPIs such as customer acquisition cost, customer lifetime value, and sales funnel efficiency. Explain why they matter and how you’ve used them to monitor performance in past roles.

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How do you approach forecasting in a rapidly changing environment?

Explain your methodology for adjusting forecasts based on market conditions, historical data, and sales team input. Emphasize your flexibility and the importance of regular reviews.

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Describe a time you resolved a significant operational challenge.

Provide a concise story that details the challenge you faced, the steps you took to resolve it, and the results achieved. Focus on how your proactive approach made a difference.

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How do you measure sales team performance?

Discuss specific metrics that you track for sales team performance, including activity levels, conversion rates, and overall contribution to revenue. Stress the importance of not only evaluating results but also providing ongoing feedback.

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What software tools do you rely on for revenue operations?

Mention your preferred tools such as HubSpot, Salesforce, or Excel. Elaborate on how each tool has been instrumental in managing operations and enhancing productivity.

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What is your leadership style, and how does it benefit your team?

Articulate your leadership approach, whether it’s collaborative, data-driven, or hands-off. Stress how your style fosters team growth, encourages innovation, and aligns team objectives with the company’s vision.

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Full-time, remote
DATE POSTED
January 7, 2025

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