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GTM Systems teams CANNOT be order-takers in the AI era. Innovation won’t come from requirements - it will come from experiments. And these teams must evolve into true Product orgs. I see this as the most overlooked challenge with adopting AI in GTM Systems. A successful strategy means you need to move FAST. Experiment. Prototype. Iterate. This is the default standard in Product culture. The Problem: this approach runs counter to Biz Tech culture. Salesforce & Internal Tools experts will hear this and say I’m crazy. “You need strict governance & careful planning to scale systems infrastructure.” And previously, I would completely agree. But the AI era is a different beast for a few reasons. 1) Teams don’t know what’s possible or what they want from AI. • Success is judged by behavior change, not completion of a backlog item. • The value of AI will emerges through usage and iteration • New features will not result from traditional requirements gathering. 2) AI has completely shifted the delivery timetable. • Historically, the goal is to craft a long-term GTM Systems roadmap. • Then, you break key initiatives into months long implementation cycles. • But AI innovation is moving too fast to only ship 1x in 3 months. • Companies need to adopt a rapid experimentation mindset. 3) You CAN move fast by investing in composability. • An API-first approach allows you to ship outside core infrastructure. • Previously, all new feature build happened in tools like Salesforce. • You’re constrained by technical debt, dependencies, and more. • Now, you can deploy AI solutions in isolation. • An app that communicates to other systems via API is relatively low risk. Realistically, this approach will make most Biz Tech teams uncomfortable. Rapid experimentation historically led directly to scalability issues. But this is the default way of operating for core Product teams. A few ways they get it right without leaving a wake of technical debt: 1) Use MVPs with clear scope • Ship measurable slices of value to learn, not solve a whole problem up front. 2) Invest in composability • Every test is built with future modularity in mind - winning ideas can scale. 3) Leverage Users for Research • Stakeholders & Users are a source of insights, not requests. • It’s the old Henry Ford quote: “If I asked people what they wanted, they would have said faster horses.” 4) Document Assumptions • Experiments have clear hypotheses - learn from every test, even if it fails. GTM Systems teams have the opportunity to lead innovation like never before. AI is delivering the much-needed attention and investment in this function. And for the first time, they are less constrained by stakeholder requests. These teams can finally DRIVE strategy, not just support it. But success will depend on their ability to embrace this new approach. __ #AI #GTM #CRM

We are seeing the future of GTM Systems at Vanta and Notion. And it will NOT be Salesforce. Takeaway: Embrace API-first development NOW 👇 Successfully adopting AI means decoupling from existing Internal Tools. I firmly believe that building apps directly on the data source is the future. Current State = Hub & Spoke Model • Salesforce or Hubspot is the central nervous system • All data and systems integrations lead here • Automations are built directly into these platforms Future State = Modular or Composable Architecture • Each tool or applications is just a building block • APIs create a new orchestration layer with data flowing laterally • Stitch together the right blocks for each individual use case • Automation happens at the intersection of systems, not within one Hiring efforts at two companies highlight this future state perfectly. 1. Vanta’s "Founder in Residence, GTM Innovation” 2. Notion’s CX Automation Engineer Both roles focus on “re-imagining” and “transforming” GTM motions. Companies aren’t adopting AI for incremental improvements. Instead, it’s viewed as an opportunity to re-build from the ground up. Key Takeaways from the Positions: • Emphasis on an API-first approach to systems design • Prioritization of complex integration engineering knowledge • Focus on rapid prototyping and experimentation • Collaboration with Product Engineers outside traditional Biz Tech teams GTM Systems roles are slowly becoming core Engineering roles. Soon, hiring “just a Salesforce Admin or Developer” won’t be enough. Companies will require significantly deeper technical expertise. And a breadth of experience beyond just a single application. It’s a shift from building for humans to building for AI. We aren’t building UI-driven workflows for Reps to click through anymore. We are designing backends for AI agents to take action autonomously. And traditional Salesforce teams will need to evolve dramatically. Capabilities need to center around: • Fluency in APIs and event-driven architectures • Proficiency with middleware platforms such as Workato and Tray • Ability to design data models supporting real-time decision-making • Expertise in tool-agnostic orchestration vs. platform-specific (i.e. flows) • Skills designing systems for machine-to-machine interaction, not UI Transformation will be driven by true Product & Eng innovation. Slowly, GTM Ops is becoming a legitimate Engineering function. We can't merely optimize existing systems for AI compatibility. It's a complete re-imagination of business processes and customer journeys. This requires real product thinking to envision what's possible. No longer constrained by a CRM, the sky is truly the limit. __ #AI #GTM #CRM

We eagerly await seeing who takes this role at OpenAI 👀

Rev Ops teams in hypergrowth startups share a UNIVERSAL problem. Inbound drives early growth, so GTM Systems are built to support it. But you won’t win on Product. You win on Distribution. Startups with early Product Market Fit are flooded with inbound. As a result, they build infrastructure around that specific motion. Often, this means relying on external Consultants. It works because you’re just laying a repeatable foundation. Operationalizing workflows that surround inbound. ✅ Relatively easy ✅ Highly repeatable ✅ Not entirely unique per org The challenge comes as your GTM Strategy begins to mature. At this stage, the tactics become unique to your business. • ICP, segmentation, and lead scoring becomes more defined • GTM Org becomes layered (AE, SDR, AM etc) • Outbound scales quickly as you go up-market • Multi-Product and Multi-Region complexity is introduced • Expansion and CX Strategy comes into focus • Insights required become more advanced and complex • Complexity of GTM Systems infrastructure explodes Now, the approach to GTM Systems is critical. And this is where most companies get themselves in trouble. You have 1 of 4 paths forward: 1. Continued reliance on external Consulting Firms 2. Expect the lean Rev Ops team to build GTM Systems 3. Underinvest in GTM Systems and wait for things to break 4. Make the GTM Systems investment from the start Option 1 will yield more generic solutions. Consulting Firms will never have the full context like an internal team. You will get playbooks from other clients retrofit to your org. Option 2 simply won't scale. Your GTM Systems will constantly be trailing the needs of the business. Option 3 results in disaster every time. Technical Debt. Tool Sprawl. Lack of Documentation. Quick Fixes Breaking. Option 4 is the only path enabling you to win on distribution. It's expensive and requires time from everyone in the organization. Regardless of how you start, all paths lead to the same outcome. You WILL invest in GTM Systems. • Proactively with a sound strategy in place. • Or reactively out of necessity as things break. The longer you wait, the harder it becomes. Your rocketship growth won't last forever as competitors enter your market. And assuming that you will forever win on Product is a losing strategy. __ #RevOps #GTM #Salesforce

There is a HUGE disconnect in how companies invest in Rev Ops vs Systems. Exhibit A: $200m ARR, 45 in Rev Ops… and 6 on GTM Systems 🤔 This mistake happens for 1 of 2 reasons. For starters, this is an actual company we’re researching. • 2,000+ total headcount • 600+ Reps in Sales • $200m ARR (2x Growth in 2 Years) • $650m Series F in mid-2024 They have built a powerhouse Rev Ops & GTM Strategy team. • 3 at the VP Level • 6 at the Director Level • 15 at the Manager Level • 21 Individual Contributors And they correctly have a high degree of specialization in the group. 1. A heavy emphasis on Sales Enablement 2. Strong Insights & Analytics capabilities 3. A focus on CX Operations & Strategy 4. An emerging Program Manager discipline to work cross-functionally This is how you set the foundation for GTM Strategy. It’s what allows you to add $100m ARR in just 2 years. But the cracks start to show when your systems infrastructure can’t scale. 6 people working on GTM Systems is simply unsustainable. There are only 2 conclusions to draw from this data. Scenario 1: They don’t understand the importance of GTM Systems • Highly unlikely in this particular situation. • You don’t get to $200m ARR without smart people that get it. Scenario 2: They outsource virtually all GTM Systems to a vendor  • Based on what we see in the market, this is almost certainly the case. • Expecting the same result you get from internal teams, they rely on “experts”. It’s a fundamentally misguided approach. And I saw this as someone that helps companies build project-based teams. Even IF you partner with the absolute best Salesforce Partner. (A big “if” in a field crowded with mediocrity these days.) You simply cannot outsource GTM Systems strategy in its entirety. • There is far too much business context required to get it right. • You lose organic knowledge-transfer-by-osmosis with external teams. • The relationships & trust you build with stakeholders is invaluable. Most importantly, you need alignment on the vision. An internal team is building toward the future of your company. A Consulting Firm is approaching this as just another project. The Consultants working for you didn’t even CHOOSE the project. It matters. This scenario is the case at companies of all sizes. Startups that outsource to Partners, only hiring a couple Admins in-house. Established companies with minimal roles in-house, vendors for the rest. It’s amazing that we’ve finally woken up to the value of Revenue Operations. (That didn’t happen overnight.) But too many companies are missing a critical piece of the investment. You can’t spend millions on the tools themselves and expect it to work out. Build a GTM Systems team to innovate and drive maximum value. __ #RevOps #CRM #Salesforce

Every Rev Ops team should study OpenAI’s Head of GTM Innovation role. GTM Strategy is being redefined for the first time in 25 years. And this is the only effective way to harness AI. The last real innovation we saw in Go-to-Market was in the early 2000s. It all started with Salesforce (and the modern CRMs to follow). Pre-Salesforce, we lacked the visibility needed for Rev Ops to truly exist. Salesforce made real-time sales analytics possible. This leap made way for a data-driven, analytical Sales strategy. It was the birth of modern Rev Ops. Artificial Intelligence WILL fuel the next leap in GTM Innovation. The most sophisticated Rev Ops teams today will look archaic. But you need to adopt it at a foundational level to drive lasting change. AI isn’t a silver bullet you switch on to solve everything. Look no further than OpenAI to be at the forefront of it. While, they have an obvious advantage, we should all take note. They are hiring a Head of GTM Innovation to lead an “internal incubator”. • Aligned closely with internal stakeholders, they conduct deep research. (This isn’t the work of a Business Analyst - but they could learn.) • It’s behavioral research, qualitative and quantitative analysis. • The research methods that go into core Product Development. • Then, rapid prototyping tests assumptions and iterates on solutions. • Validate, synthesize, and formalize before shipping scalable solutions. This is the mindset every Go-to-Market team needs today. In theory, this is the role of GTM Systems - Internal Product Innovation. In reality, these teams are almost never set up for success. • Resource constrained • Directed by stakeholders • Rushed to address today’s priorities This approach leaves little room for true innovation. And that type of shortsighted prioritization won’t work with AI. Adopting AI at a foundational level requires unwavering buy-in. Budget. Resources. Time. (All Non-Negotiable) It’s more than just having the right techno-functional strategist place. Your team needs the freedom of time! To properly conduct user research. To experiment with prototypes and POCs. And permission to fail. GTM Systems teams almost never experiment. POCs are mostly used when the decision has already been made. We're too afraid for our ideas to fail when it comes to GTM Systems. But that can't be the mindset with AI. You need to embrace curiosity and experimentation. Companies thinking this way will gain a material edge from AI. Everyone else will wait on a product to hit the market that solves it all. It’s not going to play out that way. The most sophisticated application of AI will be company specific. A more customized experience than anything we’ve ever seen. __ #RevOps #AI #GTM

It’s INSANE how often GTM Systems teams are underfunded. Spend millions on Sales & Marketing - pinch pennies on core infrastructure 🤔 Fortunately, AI is shifting this entire dynamic. Execs can’t wait to start adopting AI. (They don’t know what to do with it but they want it.) Because they see AI as an opportunity for Internal Product innovation. A way to increase productivity and drive operational efficiency. Hmm, sounds a lot like your GTM Systems team. The only thing holding them back has been a lack of proper investment. • Not hiring the resources needed to function like a true Product org • Below market salary bands that won’t attract the right level of experience • Offshoring roles that can’t perform well with a 12+ hour time zone gap Companies willingly invest in the areas they understand. And quickly fall behind when overlooking the wrong things. This was very much the dynamic in Rev Ops just 6-7 years ago. It was a relatively new function, particularly in earlier stage startups. A role hired later and in far fewer numbers than what we see today. Because it was a new approach. Now, it’s accepted that data-driven Go-to-Market is the only way. These Ops & Strategy teams are incredibly well resourced today. And it makes sense. You’re spending millions on AEs and incentive structures. Millions more on Marketing programs. So investing in the underlying strategy that powers these groups? Seems like a reasonable way to maximize ROI. Interestingly, companies also willingly spend on the tools used by these teams. 6-figure and 7-figure license agreements with Salesforce, Gong, and others. But the actual team behind those mission-critical tools … The tools you’re spending millions per year on. The tools directly supporting the teams you spend millions more on. Well, that "IT team" is an afterthought. Underresourced. No clear reporting structure. Forced to be scrappy. The only logical conclusion is that Execs don’t understand GTM Systems. In theory, they know what these applications do. In reality, they have no idea how to extract real value. They completely overlook the OPPORTUNITY for continuous innovation. Buying into a false narrative that once you implement, the work is done. Fortunately, AI is shifting this entire conversation. There is blind optimism and buy-in to the potential value it offers. AI budgets being earmarked with no idea how it will be spent. At the end of the day, AI is just the new flavor of Internal Tools. It won’t be some catch-all solution to your problems. And adopting it is going to be MESSY. But it’s already shifting how Internal Tools teams are perceived. It’s putting them at the center of the conversation. Finally, an opportunity to be viewed as INNOVATORS. __ #AI #GTM #CRM

Last year, Klarna scrapped Salesforce to build their own AI-powered stack. Their CEO just outlined the immense challenges with that decision. And it’s what every company will face in adopting AI. In September 2024, Klarna announced plans to build over buy. The Goal: adopt AI & LLMs in place of traditional SaaS. Their CEO just posted the biggest learnings & challenges that followed. And it pretty much all comes down to DATA QUALITY. “Feeding an LLM fragmented data will result in a very confused LLM.” The first question Klarna asked themselves: What data is actually valuable and where does it live? • Why Klarna exists (Docs) • What does it try to accomplish (Slides, Tickets, Kanban boards) • How it is doing (Sheets, Analytics) • Who is it dealing with (CRM, Supplier Management) • Who works here (ERP, HR) And the result was learning the degree to which their data was fragmented. Living across dozens of SaaS tools. Leading to “an unnavigable web of knowledge…” “Requiring a tremendous amount of Klarna specific expertise to utilize.” So, they moved to start consolidating data and breaking down siloes. The end goal being to unify and standardize their knowledge. Once centralized, they started building directly on top of the data source. Leveraging tools like Cursor to quickly deploy new interfaces. Klarna says the end result was massive gains in productivity and data visibility. But their CEO doesn’t believe everyone will follow this path. Instead, he suspects many will consolidate into traditional SaaS like Salesforce. Not because it will lead to the best outcome. Because most companies don’t have the appetite to take on the challenge. I firmly believe the future of Internal Tools is building directly on the data source. • Custom applications with very specific use cases • Deployed in a fraction of the time using tools like Cursor • Significantly lighter weight and easier to maintain It’s a long road ahead for companies that want to truly adopt this approach. Much of the work to be done is not glamorous. It’s the messy behind-the-scenes stuff. Data quality. Governance. Integration architecture. Adding AI on existing systems infrastructure will be a mess for 99.9% of you. For those that plan to adopt it, learn from the Klarna scenario. The preparation needs to start well before experimenting with the fun stuff. __ #SaaS #AI #Salesforce

GTM Systems teams can be a powerhouse of innovation. But most companies get this one decision wrong — and it holds them back. Apollo and Amplitude demonstrate the right way. One of the MOST overlooked aspects of scaling GTM Systems: Reporting Structure It seems like an afterthought for so many companies today. But it’s one of the most important decisions you need to make. In general, there are 4 Org Structures commonly adopted. Centralized • Full Team reports into CIO or Technology Leader Siloed • Business Analysts & Product Managers >> Rev Ops • Admins, Engineers, and Architects >> Technology Shared Services • Business Analysts and Product Managers >> PMO • Admins, Engineers, and Architects >> Technology Other • Full Team reports into Revenue Operations, CFO etc. ❗The Problem with Business Systems Living in Multiple Places Bigger companies have a lot of options when it comes to reporting structure. And it turns out this is part of the problem. They have PMOs and Shared Services teams. By definition, these groups are centralized to support the entire business. But they're designed to operate in a way that’s inconsistent with the end goal. You want your Business Systems team to PROACTIVELY push strategy forward. Shared Services are designed to be REACTIVE, responding as needs arise. It's a huge mistakes to put ANY Business Systems functions in this group. (Or within Revenue Operations, where they likely reported in the early days.) And it’s usually the Business Analysts and Product Managers reporting this way. Arguably the most critical functions in your Salesforce org. This move completely detaches them from the broader Salesforce team. • You lose the knowledge-sharing-by-osmosis benefit • The Technology team loses control over how these resources are allocated Both of this make it near impossible to execute a long-term product strategy. 👉 2 Way to Centralize Orgs with a CIO or Head of IT If you have a single Technology Leader, Business Systems lives under them. Period. It's the easiest scenario to get right and Amplitude adopts the model perfectly: • Chief Digital & Information Officer owns Corporate Engineering • Business Systems rolls up there • Distinct Leaders for each workstream: º Head of GTM Process & Applications º Director, Enterprise Technology º Sr. Director, GTM Systems º Sr. Manager, Business Systems º Manager, Business Systems (Integrations) Orgs without a CIO or Head of IT This is where companies often stumble. There's no obvious place to put Business Systems, so its broken up. Apollo adopted a model highlighting the value of Internal Tools. • VP of Business Systems† reports directly to the CEO. • The mandate: “be the architect of Apollo’s next-generation infrastructure”. This decision makes a clear statement to the organization. Internal Tools are AS IMPORTANT as core Product & everything else. The team is given the visibility required to make a true business impact.

The best GTM Systems teams don’t just sustain growth - they accelerate it. Since 2020, Udemy hit $450m in Enterprise ARR (9x). Canva grew to $2B (16x). But cracks might be showing in one of their approaches. Over the last 5 years, we’ve seen a complete GTM transformation in these orgs. In 2019, Udemy's B2B revenue was ~$51m. By 2024, B2B revenue was over $450m - 62% of total. Meanwhile, Canva was around $125m ARR in 2020 - almost entirely PLG. By 2024, they surpassed $2B ARR - 300+ Sales Reps, heavy Enterprise focus. In both scenarios, we see a complete Go-to-Market transformation AT SCALE. If you think scaling GTM Systems is hard in a high-growth startup… Imagine an org that's new to Enterprise Sales AND supporting millions of users. Today, the GTM Systems teams at Canva & Udemy are close in size. But the composition of the teams couldn’t be more different. Canva has very much evolved with a “build first” approach. And the hiring timeline for that team shows it every step of the way. In late 2021, Canva’s Salesforce team was 5 people: • Head of Sales Systems • 3 Salesforce Developers • 2 Salesforce Administrators By mid-2023, they added 8 more people but almost all were builders. As they continued to focus on execution, the strategy capability lagged. Out of 20 GTM Systems team members today, 50% are Salesforce Admins. • 2 Sales Systems Leaders • 10 Salesforce Administrators • 5 Salesforce Developers • 2 Business Analysts • 1 GTM Systems Product Owner 20 people on Go-to-Market Systems for that Sales org is a decent investment. And looking at the overall size doesn’t raise any flags. It’s the lack of Business Analysts and Product Owners causing problems. • It creates a build-first mentality of one-off requests and siloed feature build • Stakeholders get what they want because you have the capacity to deliver • And you DON’T have the resources to think about strategic roadmap planning Especially when you factor in that Canva is still rapidly growing on all fronts. In 2024, they added 17 people in Rev Ops - and they all need things built. In contrast, look at the structure of Udemy’s GTM Systems team. At ~28 people, it’s larger than Canva but also supporting a bigger Sales org. And it has BALANCE. • 4 GTM Systems & Enterprise Applications Leaders • 6 Salesforce Administrators • 6 Salesforce Developers • 5 Business Analysts • 7 Salesforce Product Owners • 1 Salesforce Architect Udemy has slightly less delivery capacity in-house than Canva. But a massive layer focused on driving strategy & aligning stakeholders. Canva’s story is one of the most common challenges we see in the space. The foundation of your Salesforce team will shape its long-term identity. It will establish an expectation for how the team functions in the business. This is why building the right team structure from the start is mission critical. __ #Salesforce #RevOps #GTM