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LATEST POSTS 📚

If you’re new, not yet a subscriber, or just plain missed it, here are some of our recent editions.

🦠 The Black Death & How It Birthed Today's Prosperity. How one little flea, on one little rat, changed the course of history.
🏃🏻‍♂️ DoorDash & How A Growth Mindset Fueled 10B Lifetime Orders. An interview with Brian Hale, Chief Growth Officer at DoorDash.
🦙 How Vanta Went From 1 To 100. A deep look into how product and growth works at one of the great companies.

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HOUSEKEEPING 📨

Most founders, myself included, have a special place in their heart for Brian Chesky. From the cereal box escapades, to ‘doing things that do not scale,’ to their awesome product release communications. And for that matter, their product in general. Airbnb is awesome. But this tweet by Eucalyptus’ Tim Doyle, sums up how I think of Airbnb’s latest announcement. Airbnb … the … everything … app?

Why do I need to book a training session on Airbnb? Or get my nails done? I feel like this is a little bit of shiny object syndrome. Taking your eye off the ball. As the post highlighted, Airbnb’s market cap hasn’t moved since it listed half a decade a ago. The core product is incredible, the rest of the company seems to be a fever dream to me right now. Anyway, that’s just my two cents. I wish Brian and the team the best of luck. Onto today’s piece!

ZERO TO ONE 🌱

Unfiltered: Vanta’s Product & Growth Leaders

Recently we took a closer look at how Vanta became a category-defining company in the trust management space. Now, you get to peek behind the scenes. In this edition of Unfiltered, we hear directly from two of the company’s driving forces—CPO Jeremy Epling and CRO Stevie Case. From reimagining how businesses approach security to building a global revenue engine, they share the bold bets, unexpected hurdles, and gritty execution that powered Vanta’s rise from startup to $100M+ in ARR. Let’s get into it.

Jeremy Epling - CPO at Vanta

Jeremy Epling is the Chief Product Officer at Vanta, the leading trust management platform helping businesses simplify security and compliance with AI and automation. At Vanta, he oversees engineering, product, and design, driving innovation across features like Vanta AI and guiding the company’s expansion into global markets. With a background in scaling complex enterprise tools, Jeremy brings a product mindset deeply rooted in customer empathy and technical rigor.

Before joining Vanta, Jeremy was VP of Product at GitHub, where he led teams behind GitHub Actions, Codespaces, npm, and Packages—platforms now used by millions of developers worldwide. He also spent over 16 years at Microsoft, including leading product for Azure DevOps. Across roles, Jeremy has built a reputation for growing high-impact teams and launching tools that make developers’ lives easier.

What does your day-to-day look like at Vanta?

I believe that to build a great product, you need to be actively using it. So, I dedicate time each day to use our product, assessing areas for improvement and new features we've recently implemented. I often test upcoming features in our staging environment to provide feedback to our team, considering both minor details like copy and visuals, and larger workflow elements.

A significant portion of my day involves interactions with our customers, especially as we move upmarket. Bigger customers often expect to discuss the product roadmap with me, which I really enjoy as it allows me to gather their feedback directly. We also have design partnerships with some of our larger customers, and I spend additional time ensuring our product aligns with their strategic directions and deeper needs.

Execution is another critical aspect of my role. While strategy is essential, the ability to execute consistently is what really determines whether a company or a team succeeds. Many people can have good ideas, but delivering on these ideas consistently is key.

Lastly, I like to explore other products in our space or even in different fields, particularly those involving AI, to understand current trends and innovations. This not only helps me keep our product competitive but also ensures it integrates well with the tools and technologies our engineers and customers are using.

What do the design partnerships look like?

Our approach to design partnerships typically involves multi-year commitments, especially with larger enterprise customers. This long-term commitment is crucial because it often takes time for the partnership to fully develop and for the product adoption to mature. I prefer not to rush into renewal discussions only a few months in. We usually meet with our design partners monthly or even more frequently if needed. These meetings are a collaborative effort to refine and evolve our product offerings in areas like GRC (governance, risk, and compliance), and cloud security. During these sessions, I encourage partners to demonstrate how they currently use our tools and discuss any gaps they find. This isn't just about fixing immediate problems; it's about envisioning a transformative experience that redefines how they think about these areas.

The real advantage for our partners is their significant influence on our product roadmap. While we may not implement every request, we prioritize their needs highly and may accelerate certain features that benefit them directly, even if they aren't immediately necessary for other customers. This proactive approach ensures they receive the enhancements they need sooner rather than later.

Having previously focused on developer tools and security, compliance is a relatively new area for me. Spending time with these customers, understanding their daily operations, and seeing the decisions they face helps me grasp how we can improve our products to better align with their security programs. This deep dive into their everyday challenges enriches our partnership and guides our product development direction.

How many design partners do you have at any given time?

Right now, we have about four or five deep design partnerships where we're engaging frequently. Beyond these, we have top customers we meet with often, though I wouldn't classify them strictly as design partners. When selecting a design partner, it's crucial for us that they provide valuable feedback and engage actively, even with products that are still in development. This engagement goes beyond just having influence over our roadmap; it's about a reciprocal relationship where both sides contribute meaningfully.

Commercially, design partnerships are not just standard transactions. We maintain a closer relationship with these top customers, allowing them influence over our product roadmap and frequent interactions. Typically, these partnerships involve long-term commitments, especially for products that are not immediate launches but are planned for future development. We offer favorable terms, like better pricing, recognizing the collaborative effort over several years. It's important to set these expectations from the beginning to ensure all parties are aligned and enthusiastic about the partnership.

Who are your direct and indirect reports?

So I have a few direct reports. I have a Head of Engineering, Iccha Sethi, who's fantastic and leads all the engineers at the company. Then there's Deb Kawamoto, who's the Head of Design. Additionally, I oversee a Product Operations team managed by Jimmy Singer. We keep that team relatively small, focusing on automating processes rather than employing numerous project managers. This team is unique because they consider our internal teams as their customers, aiming to make them more efficient and automate our internal systems as much as possible.

What are the job titles of the two product leads that you have? How do they differ?

The job titles of the two product leads I have are VP of Product, GRC and VP of Product, New Business. Boris focuses on our core Governance, Risk, and Compliance products, managing everything from automated compliance for smaller customers to enterprise-level services. On the other hand, Chase is responsible for incubating and leading the development of new product initiatives, helping to expand and diversify our product offerings.

What key metrics or OKRs do you track to measure product success?

We track a variety of metrics and OKRs to measure product success at Vanta, focusing on both commercial outcomes and product satisfaction. Key commercial metrics include ARR (Annual Recurring Revenue), NRR (Net Revenue Retention), and GRR (Gross Revenue Retention). These metrics help us gauge financial performance and customer retention.

Additionally, we pay close attention to 'product love,' a more qualitative metric that assesses user satisfaction with our core experiences. For instance, we monitor the effectiveness of our remediation processes—how well our product identifies issues, explains them to users, and facilitates quick resolutions, ideally through automated solutions like one-click fixes. This involves leveraging AI to generate code that users can directly implement to resolve detected issues.

Another crucial aspect is our security reviews, where we use templates and AI to automate the assessment process based on documents provided by the user, aligning it with their specific risks and controls.

Overall, our goal is to ensure that the product not only meets commercial targets, but also resonates well with users, making their daily tasks more efficient and enjoyable.

How do you think about what to build, partner on, and what to buy?

When deciding what to build, partner on, or buy, we consider several factors. We did make an acquisition about six months before I joined—Trustpage—which has been instrumental in expanding our offerings into trust centers and customer trust management. This acquisition was driven by the need for technology and talent that could accelerate our entry into new markets and enhance our existing capabilities.

The decision to build internally versus acquire depends on a few key things. First, if there’s a company whose technology and team align well with our culture and strategic goals, and if they have expertise in areas we want to grow into, acquisition can be a much faster path than building something from scratch. Second, we always weigh the integration costs—both from an engineering standpoint and in terms of how well the new tech fits into our existing stack. Finally, if a product is on our roadmap but still a ways out, a partnership or acquisition can give us quicker market access and valuable customer insights we’d otherwise need more time to develop internally.

Overall, our strategy is to ensure that any acquisition or partnership aligns with our long-term goals and adds tangible value to our platform, enhancing our end-to-end trust management capabilities while maintaining a cohesive and integrated user experience.

How do you balance shipping new features vs protecting the core?

Our philosophy revolves around a few key principles. First and foremost, we continually invest in our core product. It’s essential to never lose sight of the foundation upon which our business is built. I've seen other products lose their way, and we strive to maintain a clear focus, particularly for startups, ensuring they have an excellent automated compliance experience for obtaining SOC 2 or ISO certifications. We aim to keep this process simple, focused, and effective.

Strategically, we think about investments across different time horizons. In the short term, we focus on features and investments that will yield returns this year, aligning with our revenue goals and product vision. Looking further ahead, we plan investments for the next few years, segmenting them into stages: Horizon 1, Horizon 2, and Horizon 3. This method ensures we are continuously seeding new products and innovations, some of which may not fully materialize but provide a buffer in our strategic planning.

Moreover, the mindset of our teams is crucial. We differentiate between those who thrive in creating and exploring new concepts and those who excel in scaling and optimizing existing offerings. While some individuals can adapt to both roles, most tend to specialize, preferring either the dynamic environment of innovation or the structured world of growth and optimization. This specialization allows us to tailor roles and responsibilities to match the strengths of our team, ensuring both innovation and operational excellence across our product lines.

What was the result of hiring the first design team at Vanta?

Hiring our first design team at Vanta had a transformative impact on our product. Initially, Vanta focused on making complex compliance processes simple and automated. While this approach effectively addressed the functional needs, the user experience wasn't as engaging or delightful as it could be. With the introduction of the design team, led by our first VP of Design, we began to elevate the user experience significantly.

The design team's influence extended beyond aesthetics, deeply integrating with how features were conceptualized and implemented. They brought a new level of clarity and intuitiveness to the interface, which made the product not only functional but also enjoyable to use. This shift was crucial as it helped differentiate our product in a market where functional parity was high.

They also played a pivotal role in making sure the product could scale gracefully while serving both smaller companies and larger enterprises. This balance is critical in maintaining the product's simplicity for new users while offering the depth required by more sophisticated customers.

Overall, the introduction of the design team enhanced our product's usability and appeal, which in turn improved customer satisfaction and engagement. This strategic move has been integral in shaping Vanta's product into a more user-centric and market-competitive offering.

How do you stay ahead of market and/or regulatory changes?

Vanta stays ahead of market and regulatory changes by maintaining a proactive approach to industry trends and government regulations. We have a dedicated head of government affairs who monitors potential legislative changes in the U.S. and internationally, helping us anticipate and respond to new compliance requirements. This foresight allowed us to be among the first automated compliance providers to offer built-in frameworks for emerging standards like the EU AI Act and ISO 42001.

We also leverage AI to enhance our responsiveness to market and regulatory changes. AI tools help us analyze large volumes of data and documents, which is crucial for maintaining compliance in a dynamically changing environment. This capability enables us to quickly adapt our offerings to meet new regulatory demands and to provide our customers with the most current and effective compliance solutions.

Additionally, we engage with our customer advisory boards regularly. These boards consist of high-level security officers and other key stakeholders who provide insights into industry trends and challenges. Their feedback helps us refine our strategic direction and ensure that our product development aligns with the evolving needs of the market.

By combining technology, expert oversight, and customer feedback, Vanta effectively navigates the complexities of the regulatory landscape, ensuring that both our product and our customers remain compliant and competitive.

What are the biggest product decisions coming up for Vanta in 2025 and beyond?

Looking ahead to 2025 and beyond, some of the biggest product decisions for Vanta revolve around scaling to meet the needs of larger, more sophisticated customers while maintaining the simplicity and effectiveness that our smaller users value. This involves a strategy of progressive disclosure, where advanced features are made available in a way that does not overwhelm new users but is accessible to those who need them.

We're also focusing on deeper integration of AI technologies to enhance our product's capabilities. With advancements in AI, particularly in document and data analysis, we see significant opportunities to automate more complex compliance processes. This will allow us to handle large volumes of data more efficiently, offering our customers faster and more accurate compliance solutions.

Another major area of focus is the expansion of our trust management platform to include more comprehensive coverage across different compliance domains. We're looking to integrate with the best-in-class tools for each domain, ensuring that Vanta not only excels in its core compliance capabilities but also offers extensive support across various security and compliance needs. This broad approach aims to provide a more holistic view of our customers' security postures, enabling them to prioritize and address vulnerabilities more effectively.

These decisions are guided by our commitment to staying at the forefront of compliance technology, continuously enhancing our platform to meet the evolving needs of our customers and the regulatory landscape.

Stevie Case, CRO at Vanta

Stevie Case is the Chief Revenue Officer at Vanta, where she has led the company’s go-to-market transformation since joining in 2022. Under her leadership, Vanta crossed $100M ARR (and in just 5 years to market!). She oversees sales, revenue operations, customer success, partnerships, and more, driving Vanta’s expansion into international markets and enterprise segments—all while maintaining a remote-forward culture.

Stevie’s path to revenue leadership is as unconventional as it is inspiring. She made history in the late 1990s as ‘KillCreek,’ the world’s first female professional gamer, before transitioning into game development and later into tech sales and business development. Her career includes leadership roles at Twilio, Visa, and Layer, where she built and scaled high-performing teams. At Vanta, she’s known for creating a ‘learning machine’ culture—emphasizing execution, clarity of ownership, and continuous improvement.

What does your day-to-day look like at Vanta?

At the start of the fiscal year, much of my daily work is centered on the annual changeover. We reassess our business segmentation, reconsider our Ideal Customer Profile (ICP), different buyer personas, and how we can better tailor our teams than we did the previous year.

My current daily activities involve almost entirely reestablishing how we run the business from the ground up. This includes rebuilding teams and extensively hiring, especially for our strategic move upmarket, such as hiring a global leader for our solutions engineers. Central to my go-to-market strategy is my operational cadence—how I manage weekly forecasts and inspections.

We've completely overhauled our operational calendar. A significant portion of my work now involves ensuring we are analyzing the business correctly, inspecting the right data, and identifying the correct trends. Once we've settled into these new routines, I turn my focus to maintaining a steady state and resolving any ongoing issues.

Can you tell me what inspection looks like?

Inspection is really my primary responsibility. I think of my job as inspecting and then debugging. I've built an operational cadence that drives inspection on a weekly basis. We have forums for longer-term inspections, but each week I run a forecast that combines reviewing trends, KPIs, how we work, opportunities, what's working, what isn't, and a big deal review. This is done segment by segment. I expect my leaders and all the way down to our individual contributors to maintain the same kind of cadence, which all ladders up to me. I'm involved in looking at top-level data and also spot checking individual deals to ensure we are selling on value and following the playbook, ensuring things operate in the field as I intend.

We've also established what we call our operational meetings. For every segment, we have a forecast meeting early in the week that's very deal-centric and revenue outcome-centric. The operating meeting is focused on KPIs and operational metrics, broken down into three sections. We examine the general operating metrics for that segment, then look at go-to-market specific metrics like efficiency and win rates, and finally, we assess our APD team and their metrics to ensure we're shipping features on time for this buyer, receiving and acting on feedback in a timely manner. It's designed to be an operational cadence that inspects the entire funnel, the entire business end to end. It's important to note how we run forecasts: it's a full funnel forecast, looking at everything from the top of the funnel all the way through the post-sales customer experience and all the metrics and forecasts in between.

Who's your team? Who reports directly to you?

I have a few key partners who report directly to me. One of my closest operating partner is my SVP of Sales and Partnerships, Elliott Goldwater, who oversees sales for all of North America and manages our global partnerships. He commands a large team, essentially half of my world, and is my most senior sales leader.

Next is my VP of GTM Operations & Strategy, Mark Lail, who manages a broad team covering traditional operations to analytics. His team is responsible for revenue strategy and analytics, our reporting infrastructure, IT systems, and enablement—taking all our messaging and materials and training the team.

Kelly Bray is my VP of Customer Success and Account Management. She handles the entire post-sales world, which includes customer success—focusing on adoption, onboarding, and customer health—and account management, which is really a sales function where we sell new products to our existing customer base.

I also work with a head of sales in EMEA, who manages all our sales in that region, and a general manager in Asia Pacific, who oversees go-to-market in that area. Additionally, Eric Martin, Vanta’s original head of sales, now runs what we call specialty sales. He takes on new initiatives or new teams to stand up, helping to build those businesses for me. He’s like my zero to one guy. These are my main direct reports, along with a few others handling specific roles within the organization.

How do you set revenue goals in the organization?

Setting revenue goals in our organization is a multifaceted process. We start from the top down, beginning with our three-to-five-year vision for the company, considering what top-line growth and secondary metrics we need to hit to achieve this vision. Based on our long-term goals, we set a top-line revenue target for the year, reflecting the growth rate we want to achieve. Once the overarching goals are defined, we identify a short list of secondary metrics that are crucial, such as net retention, and set targets for these for the coming year. This gives us a basic framework for where we need to go.

Next, I sit down with my team early in the process, and we often whiteboard out what natural growth looks like from our current position. We assess which segments we sell into and where we see outsized opportunities. We discuss if we were to double down on certain segments and grow our teams there, what that would look like and how it could help us close the gap to our top-line goal.

The third stage involves collaboration with our CPO Jeremy and our EPD team to align on product strategy and the roadmap. This discussion typically leads to investment decisions in areas that might not show immediate revenue impact but are crucial for strategic, long-term growth. For example, this year we are building a specialty sales team focused on selling new, standalone products that are part of our platform, but require dedicated efforts to gain traction in the market.

What has changed in the go-to-market from when you joined until now?

In the last three years, a lot has changed in our go-to-market strategies and channels at Vanta. If I had to highlight one major change, it would be our evolution from primarily serving startups to taking on the legacy GRC market. Initially, Vanta was a platform for startups—an automated compliance platform for founders tackling compliance for the first time. Since then, we've expanded significantly.

Today, while we continue to lead in automated compliance for startups, we're also displacing legacy, manual platforms for governance, risk, and compliance at scale. This shift was something I couldn't have predicted when I first joined. We've moved from serving founders needing basic compliance certifications to addressing complex, long-term security and compliance needs for larger enterprises. This involves a much more technical sale, requiring deep customization and integration to accommodate existing programs on our platform.

Our sales strategies have had to evolve significantly to match these changes. Selling an automated compliance tool to a startup founder is vastly different from engaging with a CSO at a large enterprise to manage comprehensive GRC programs. The skills, messaging, and sales processes needed are entirely different. Over these three years, we've built and adapted our capabilities to successfully engage these varied customer segments, transforming our go-to-market approach to a more sophisticated, enterprise-focused model.

What is the career path for a sales hire in your organization?

Today, we're really focusing on career paths because we want Vanta to be a place where a salesperson can spend over a decade of their career. The typical starting point is often our Sales Development Representative (SDR) team. This team performs cold calling and sets appointments, and we've established what we call SDR University, a program specifically designed for top-performing SDRs to learn how to become closers and then promote to account executives.

This progression allows salespeople to gradually move up to selling to larger and larger companies throughout their career at Vanta.

What has been the biggest challenge that you've had in your three years?

The biggest challenge in the early days, which is now behind us, was dealing with the influx of copycat competitors. When Vanta introduced automated compliance, it led to an explosion of competition, with dozens of copycats emerging, some of which even replicated typos from our website, indicating they had simply copied and pasted our content. These competitors would market their platforms as identical to ours but cheaper, creating a noisy environment that confused potential clients.

To combat this, we didn't just rely on having the strongest product; we also transformed our go-to-market approach by adopting a value-based selling methodology. This approach shifted our sales focus from features and functionality to deeply understanding and addressing the pain points in our prospects' businesses. We trained our entire go-to-market team to sell based on the ROI of solving a customer’s problems, emphasizing how we address these better than anyone else.

This method required a significant shift in how we trained our team and presented our product, but it has unified our approach to overcoming challenges and now serves us well as we move upmarket, facing legacy players. It remains a powerful tool in differentiating Vanta in a crowded market.

What is the biggest go-to-market bet you're currently making?

The biggest go-to-market bet we're currently making is on the enterprise segment. We are investing ahead of this opportunity, which involves everything from accelerating our roadmap to hiring enterprise sellers experienced in this area, to doubling down on account executives (AEs) who have enterprise sales experience, and building out a solutions engineering (SE) team. We are also bringing on GRC (Governance, Risk, and Compliance) subject matter experts to fully staff this initiative.

We expect this investment to be a material revenue contributor this year. It's structured around dedicated teams with substantial resourcing aimed at capturing enterprise-level business. This bet is about expanding our reach into larger, more complex organizations, where the sales cycles are longer and the deals are bigger, requiring a more nuanced approach to how we sell and integrate our platform.

How do you think about experimentation?

Experimentation in our go-to-market strategy varies depending on the revenue horizon we expect from each bet. For immediate revenue-generating projects, like our current push into the enterprise segment, we allocate significant resources. This includes hiring specialized staff such as enterprise sellers, solutions engineers, and GRC experts, and accelerating relevant parts of our product roadmap. We invest heavily here because we anticipate these areas to contribute materially to our revenue this year.

For longer-term bets, such as new market segments or innovative product lines, our approach is different. We create dedicated teams tasked exclusively with those initiatives. These teams are not put on traditional sales quotas; instead, they have specific objectives like securing a small number of high-value deals with significant logos. Their success isn't measured by immediate revenue generation, but by strategic achievements that lay the groundwork for future growth.

This strategy ensures that we don't dilute our efforts across too many objectives, allowing us to focus resources effectively and measure success in a way that aligns with our long-term growth strategies. We structure incentives and goals to encourage dedicated focus on these long-term initiatives, even if they don't contribute significantly to revenue right away. This approach helps us manage risk while fostering innovation within the company.

Extra reading

• Building a More Trustworthy Internet - June, 2022

• Cybersecured: Vanta’s Zero To One - March, 2025

• Unfiltered: The Details Behind Vanta's Meteoric Rise - March, 2025

• How Vanta Went From 1 To 100 - May, 2025

And that’s it! You can keep up with Jeremy, and Stevie, on LinkedIn or check out Vanta on their website.

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