On Product-Led Growth (PLG) and Go-to-Market Strategy

  1. Have a "theory of your business." This means holistically understanding where your customers will come from, how you will make them successful, and how you will ultimately build a profitable business. [1]
  2. PLG is not just a distribution channel; it's a holistic way of architecting your product, business, and organization. It requires deep intentionality and can't be simply "added on." [1]
  3. Good PLG businesses have a specialized, non-paid customer acquisition channel. If you're relying on paid acquisition early on (under $100M in revenue), you might not be a true PLG company. [1]
  4. The "1-2-3 Framework" for go-to-market: First, nail the free, single-user product. Second, perfect the self-serve team-level product. Finally, build out the outbound enterprise motion. [2]
  5. Don't rush into enterprise sales too soon. You should generally focus on one motion (PLG or enterprise) until you reach at least $10 million in revenue. [1]
  6. Free is a crucial component of PLG. If you monetize too aggressively and don't have genuine engagement, you'll pay for it later in retention and quality. [2]
  7. PLG is hard because it demands a high level of cross-organizational collaboration. The free, self-serve, and enterprise motions are often in conflict, and aligning them is a significant challenge.
  8. The journey from a free user to a high-value enterprise customer is a series of phase transitions. You need to architect your business to guide customers through this journey. [1]
  9. Beware of the "enterprise mirage." Early enterprise traction from unnatural or unrepeatable sources is different from building a scalable, enduring enterprise business. [3]
  10. Going enterprise is not just about hiring a sales team. It impacts every function, including marketing, product, engineering, and customer success. [4]

On Leadership and Company Building

  1. Navigate your company on two dimensions: be emotive and be strategic. You need to create a product that people connect with emotionally, but you also need a clear strategy for business impact. [1]
  2. The power of alignment is immense. A well-aligned organization, where everyone understands the goals, is the most powerful state a company can be in. [1]
  3. Your ability to get an organization's time, attention, and focus is the most precious resource you have. Don't waste it with bureaucratic planning processes. [1]
  4. Don't get too religious about your own culture. What made you successful in the past might not be what gets you to the next level. Be willing to challenge your core beliefs. [1]
  5. A growth mindset means being so religiously customer-focused that you're willing to challenge the core values you believe contributed to your success. [1]
  6. Salesforce's success was built "brick by brick" through the pure energy and intentionality of its team. It wasn't just luck or being in the right place at the right time. [1]
  7. The most important decision you'll make next year is how you invest your resources across the three motions of free, team, and enterprise. [4]
  8. Think about organizational planning as a practice, like yoga or exercise. The point is to do it with a regular cadence to drive narrative clarity and alignment.
  9. To get alignment, tell stories. Your strategic plan should be as satisfying as watching a great movie with three clear acts.
  10. Avoid OKRs if they feel like a tax or an administrative burden. If the planning process isn't creating clarity and alignment, something is wrong.

On Product and Customer Experience

  1. You need "Enterprise Empathy" to be successful. This means deeply understanding how your product fits into the full context of your customer's world. [1]
  2. The responsibility of a product manager is the "whole product" and the ultimate success of the customer using it. This can even include writing documentation to build deep user empathy. [5]
  3. To get individual users, you have to be empathetic and care about the experience. This is why many great products come from PLG companies. [1]
  4. At Heroku, we would have debates in the management team about minor switches in the command line. That's the level of care required to build a great developer experience. [1]
  5. The hard thing for a PM to do is to measure less. Find the few key, simple, shared metrics that everyone in the organization can keep in their head. [5]
  6. User experience is the differentiator in successful AI products. [2]
  7. Don't over-monetize a brand that people have a high affinity for. It's a tragedy of SaaS in recent times that companies have damaged their brands by over-monetizing when growth slowed. [2]
  8. We made a very explicit strategy... to reemphasize and reinvest in free. This is a way to build a higher quality, more sustainable business in the long run. [2]
  9. If the only problem you solve is video hosting, that is an entree to solving any number of more strategic problems. Always look to climb the ladder of customer problems. [2]
  10. The answers don't lie in the data; they lie with the customers. When he started at Vimeo, one of the first things he did was remove 80% of the metrics to focus the team. [2]

On Enterprise and Sales

  1. The enterprise decision will touch everybody in your company. It's a profound decision that affects product, engineering, marketing, and sales. [4]
  2. The core value proposition of an enterprise product is often compliance and security. This is a distinct product you need to build, not just a deployment model. [4]
  3. Tenancy is the core expression of the enterprise value proposition. How you architect your product for different deployment models is a fundamental decision. [4]
  4. You will always have to manage security and compliance as part of your business. Treat it as a distinct value proposition to build for, not an objection to circumvent. [4]
  5. The "indecent proposal" of a large on-premise deal will happen to every successful cloud company. Be prepared to say no if it doesn't align with your strategy. [4]
  6. Deal size is a really good proxy for everything else associated with a sale. It determines the complexity and the capabilities you need to build as a company. [3]
  7. A majority of our enterprise business is being fed by our self-serve business. This highlights the power of a strong PLG motion to fuel enterprise sales.
  8. You have to be good at cross-organizational collaboration in three go-to-market modes: free, self-serve, and enterprise. This is what makes building a comprehensive GTM strategy so challenging.
  9. In the old days, engineering would create a product, put it on a CD, and throw it over a wall. That's not how modern products work, where engagement is a key part of the customer journey.
  10. Who owns free? Their KPI is monthly active users (MAUs). You need to have clear ownership and metrics for the top of your funnel.

On Career and Personal Philosophy

  1. Heroku was where I was finally able to see PLG in full IMAX 3D Glory. It proved that you could have a deeply emotive, individual product and also build a great enterprise business. [1]
  2. At Salesforce, I learned the genuine power of a growth mindset. It's about forging your own success through intentionality every single day. [1]
  3. You can have your cake and eat it too. It is possible to synthesize a high-quality, empathetic individual product with great enterprise features. [1]
  4. PLG is hard because it requires a much higher level of cross organizational collaboration and alignment than previous models.
  5. The way to drive alignment is through very thoughtful and intentional planning processes.
  6. If you're viewing [planning] as a tax or administrative, something's wrong. The goal is narrative clarity.

Learn more:

  1. Adam Gross: Why Startups Doing Paid Under $100M ARR are not PLG | E1145 - YouTube
  2. How to sell to developers (tldr: you don't, sell to their boss) - Developer Markepear
  3. Navigating the Leap into Enterprise w/ Adam Gross of Heroku, Salesforce, and Dropbox
  4. Navigating the Leap into Enterprise with Adam Gross - Heavybit
  5. Adam Gross - The New York Restaurant Show
  6. Welcome Adam Gross, former Heroku CEO, to the Cypress.io Family