Go To Market Planning

I recently spoke with an early-stage AI app founder who was desperate to hire sales reps because he dreaded founder-led sales. This is one of the most common failure modes I see with technical founders—and it significantly impedes the path to product-market fit. Here's how to think about the right order of operations in early sales motions: Phase 1: Prototype & Validation In the earliest stage, the feedback loop between customer conversations and product roadmap must be extraordinarily tight—making founder-led sales absolutely non-negotiable. This phase is critical because you're identifying your true ideal customer profile (ICP) and learning how to effectively communicate your product story and address common objections. As you accumulate hundreds of demo repetitions (while refining your product based on feedback), you gradually assemble a winning process. Phase 2: Founder-led Sales Scale-Up Your mission here is to create the sales playbook that will guide future reps. You need sufficient pattern recognition to understand which messages resonate with which personas. I recall meeting Desmond Lim, CEO of Workstream, several years ago (not an Emergence portfolio company, but I deeply admire what they've built). He showed me the remarkable 60-page playbook he crafted documenting their entire sales process—before hiring a single AE. Every nuance. Every objection. Everything a new rep would need to succeed. While perhaps extreme, this perfectly illustrates the principle: scaling go-to-market requires mastering your ideal sales motion before delegating it. Phase 3: Hiring Initial Sales Reps Most founders default to sequential hiring—start with one rep, evaluate results, then proceed. However, we recommend hiring 2-3 sales reps with diverse backgrounds simultaneously, enabling you to effectively A/B test different profiles. Regardless of approach, ensure these early hires are "renaissance reps" with rapid iteration capabilities rather than purely "coin-operated" sellers. Mark Leslie has a great foundational article on the Sales Learning Curve provides excellent guidance. I'll link it below. So embrace the early sales work, even when it feels uncomfortable. It's fundamental to building a foundation for lasting success.

We closed enterprise customers like Airbnb, DocuSign, and the NBA without a sales team. Instead, we used one unconventional strategy: founder-led content. Here's why storytelling beats selling every time - and how any B2B founder can use it. If you haven’t noticed, the old growth channels don’t work anymore: - Paid ads are saturated and expensive - Hiring a sales team with AEs and SDRs doesn't work if they don't have a playbook to follow - Cold email open rates are down 25% With minimal funding early on, we had to find creative ways to get in front of our customers for Chezie. Eventually, we figured out that webinars + LinkedIn was the best setup: 1. We hosted webinars that our ICP (ERG owners at 1000+ person companies) cared about and got 250-500 registrations 2. We shared every webinar on our personal LinkedIns 3. We started every webinar with our founder story and why we cared so much about ERGs (Dumebi Egbuna and I used to lead ERGs when we worked in corporate) The result? 60% of our early pipeline is INBOUND; they came to us. Most founders overcomplicate content. Creating content doesn’t have to be creating a newsletter and posting 5x/week on LinkedIn and launching a customer community and replying to messages in relevant Reddit communities and publishing case studies and writing blog articles to get a presence on SEO and… You get it. My advice? Pick ONE channel: - LinkedIn (my personal recommendation) - Webinars - An email newsletter - SEO-optimized articles/blogs/case studies/templates - TIkTok/YouTube videos Go with the channel where the largest percentage of your customers spend their time. Use their interactions as fuel for future content. Lead with your personality and why you felt compelled to start your company. In the age of AI, there is only ONE thing that your competition can't copy: you, the founder. Everything else (product, design, team experience, etc.) can be replicated in a month. Every day you wait, another founder in your space is building an audience. Pick your channel. Share your story. Do it today. Your future customers are already scrolling. Will they find you or your competitor?

I recently redesigned the marketing operating model for a $350 Millon B2B software company — and it reminded me just how context-specific org design really is. One of the most strategic (and overlooked) decisions a CMO makes is how to design the marketing organization. It’s tempting to replicate what worked in your last company. But in B2B software, there’s no one-size-fits-all. What worked for a $20M PLG business may not suit a $100M enterprise SaaS platform. 1. Design for business outcomes, not headcount. Start with goals: new segments, enterprise expansion, category leadership. Org design should mirror business intent — not legacy structures. 2. Build capabilities before filling roles. Ask: Do we have strong demand gen, lifecycle, product marketing, content, partner marketing, ops, and analytics? Capabilities come first — roles come second. 3. Structure around your go-to-market motion. If your growth lever is partners, embed partner marketing early. If it’s PLG, prioritize lifecycle and in-product activation. For enterprise, double down on ABM, field marketing, and enablement. 4. Where should Product Marketing sit? There’s no single right answer: In product-led orgs, it makes sense to sit within product to shape narrative from the roadmap. In sales-led orgs, it’s more effective aligned to revenue to sharpen messaging and enablement- drive pipeline velocity. What matters more is the evolution toward GTM solution marketing — cross-functional teams that bridge product, sales, and marketing to tell customer-centric value stories. 5. Build for agility, not bureaucracy. Your org should flex across geos, customer types, and growth motions — without needing to reorganize every time strategy shifts. 6. Invest early in Marketing Ops, Data & Analytics. This is your engine room. From attribution modeling and lead routing to campaign performance, experimentation, and forecasting — high-performing orgs are built on strong ops and data infrastructure. Ops is not a support function. It's a strategic growth capability. 7. Culture, collaboration, and clarity are non-negotiables. No structure works without trust across sales, product, and marketing. Shared KPIs, aligned planning, and a performance mindset are critical. Bottom line: Design for outcomes. Build capabilities. Leverage data. Stay context-aware. Your next marketing org shouldn't look like your last one — it should reflect the business you're building. #B2BMarketing #MarketingLeadership #CMOInsights #MarketingOps #MarketingAnalytics #ProductMarketing #GTMStrategy #MarketingOrgDesign #SaaSGrowth #B2BSoftware #GrowthLeadership #ModernMarketing

Founder-led sales is the only way to find PMF. You can't delegate customer discovery. Most founders hate sales - it's hard so I can understand. It's uncomfortable and feels like it's taking you away from building. But it's the most important thing you can do. At Scriptbee, I personally did our first 50 interview calls. and now over 100+ sales calls after that. Because each call taught me something critical. What I learned: Call 1-10: Our messaging was confusing. Call 11-20: We were targeting the wrong persona. Marketing Managers didn't care. CEO and CMOs cared. Call 21-30: Our pricing was too high. Call 31-40: One specific use case resonated 10x more than others. If we'd hired a salesperson at call 10, we would have scaled the wrong message to the wrong people with the wrong price and use case. You need to do 30-50 calls minimum before you really understand your market. There's no shortcut. After 50, you're a machine. Sales feels like a distraction from building. It's actually the most efficient way to figure out what to build. #BuildInPublic #FounderLedSales #GoToMarket

Over the years, I've discovered the truth: Game-changing products won't succeed unless they have a unified vision across sales, marketing, and product teams. When these key functions pull in different directions, it's a death knell for go-to-market execution. Without alignment on positioning and buyer messaging, we fail to communicate value and create disjointed experiences. So, how do I foster collaboration across these functions? 1) Set shared goals and incentivize unity towards that North Star metric, be it revenue, activations, or retention. 2) Encourage team members to work closely together, building empathy rather than skepticism of other groups' intentions and contributions. 3) Regularly conduct cross-functional roadmapping sessions to cascade priorities across departments and highlight dependencies. 4) Create an environment where teams can constructively debate assumptions and strategies without politics or blame. 5) Provide clarity for sales on target personas and value propositions to equip them for deal conversations. 6) Involve all functions early in establishing positioning and messaging frameworks. Co-create when possible. By rallying together around customers’ needs, we block and tackle as one team towards product-market fit. The magic truly happens when teams unite towards a shared mission to delight users!

$6M in forecasted revenue. 11 months of chasing “maybe.” Two founders. 11 buying influencers. No decision. If your go-to-market process includes enterprise selling, you know this pain. You meet a “champion.” They’re smart. Interested, and they love your solution. You spend weeks demoing, customizing decks, and answering follow-up questions. They say there’s interest in moving forward. “We’ll loop in leadership,” they say. Then more meetings. Then, silence Over the past year, I’ve worked with multiple founders who are selling software, services, and products into enterprise healthcare. When onboarding new clients, I see a pattern. Drag and lack of clarity kill deals. We don’t have a marketing or sales problem. We have a stall problem. The stall happens between “this looks promising” and “let me see if I get you on my VP’s calendar.” The deal begins to drag, and this is the start of the death cycle. It's not that drag kills deals; drag is only a sign of a bigger problem. Deals die because customers have become tolerant to pain and don't have a nagging need to address a problem. What are the early signs of a deal stall? ➡️ Your champion is the only point of contact. ➡️ The champion does not have a mandate. ➡️ There is no urgency at the account. ➡️ There is no problem identified. ➡️ There is no budget. Here's the advice I share with my clients: ➡️ Define the problem you're trying to solve: Where do deals stall? ➡️ Analyze the root cause: What's causing the stall? How do you know? ➡️ Validate your hypothesis: Talk with customers and stakeholders. ➡️ Fix problems in the customer buying journey: Test...measure...improve. I'm focusing on accelerating buying velocity and reducing customer time to value this week. Each day, I'll share something I've learned, and I invite you to share your insights as well. What's something you've learned from enterprise selling that's changed how you go-to-market? Comment below. ⤵️ #complexselling #enterpriseselling #GTM #businessgrowth

Every startup has a product roadmap. But what about a go-to-market roadmap? Paul Williamson built one that scaled Plaid from $3M to $300M ARR 🚀 In this episode, he breaks down how to build a forward-compatible go-to-market roadmap that evolves intentionally from scrappy v0.1 experiments to multi-year strategy. Key takeaways from the conversation: 1️⃣ Build GTM like product. Plaid iterated through 9-10 GTM versions in year one (they treated GTM as a roadmap, not a static plan). 2️⃣ Make your GTM roadmap “forward-compatible.” Each version should extend the last, not force you to rebuild from scratch. 3️⃣ Not all inbound is good inbound (writing this while at INBOUND!). Plaid filtered for value (not volume), routing low-value use cases to PLG instead of sales. 4️⃣ Pattern recognition beats volume. The team learned to spot ICPs vs. anti-patterns by manually reviewing deals daily. 5️⃣ Run daily standups (twice). In early days, Plaid used AM/PM GTM standups to refine qualification and learn fast. 6️⃣ Sales-led ≠ better. Some customers were better served via PLG. The team used human routing to steer deals appropriately. 7️⃣ Go-to-market must match product readiness. Moving upmarket required SLAs, uptime, SSO. Roadmap GTM and product together. 8️⃣ Avoid overbuilding too early. The best GTM orgs feel slightly behind…just enough to stay lean, focused, and adaptable. 9️⃣ Your comp plan shapes sales behavior. SMB-style comp delayed enterprise deals. Fixing this reduced cycle time and risk. 🔟 Write it down. Documenting the GTM roadmap helped align the org and communicate clearly with technical founders. -- 🎧 Tune in and subscribe on YouTube, Apple, Spotify or wherever you like to listen by searching "The GTMnow Podcast." 💡 GTMnow is the media brand of GTMfund. Build, scale and invest with the best minds in tech.

>>>My 9 go-to-market commandments that get you off to the right start. I've noticed that folks like to discuss methods when describing their going-to-market. My approach Principles > Methods. If you grasp principles, you will successfully select your own methods. Here's why a killer go-to-market always wins over a great product: 1. Your market segmentation defines your business model, routes to market, traction channels, sales engagement, etc. ↳ You can start with a minimum viable segment and iterate it with your minimum viable product. 2. Products are built for channels, not vice versa! ↳ There are more fits than just product-market fit (model/market fit, channel model/fit, product/channel fit). 3. You will bleed to death using the wrong business model/segmentation. ↳ CAC - Customer Acquisition Cost is the #1 startup killer. 4. Your job is to find the green space, which will be the starting point for your GTM. ↳ Why you, compared to others, vs. why you at all for new solutions, determine how you will enter the market. 5. Businesses that scale consistently from one stage to the next are stronger and more likely to succeed. ↳ It is vital to have a clear checklist for what it means to go from idea to proof of problem to proof of market to proof of scale. 6. Not all GTM advice is created equal. Flex your critical thinking muscle. ↳ Going to market is a system; the founder's job is understanding all the moving parts. Getting the right help matters, but your understanding of positioning, sales, and marketing can't be outsourced. 7. Before PMF, you need someone who understands the system and interactions of all parts. ↳ Think of somebody like Enola or Sherlock Holmes - bringing a different point of view to your bubble. Beware if they start with the business canvas and not how you gather customer insights. 8. Following a playbook is NOT a strategy. ↳ There is a tiny chance you will build leverage by copying somebody else's playbook. 9. Your personal brand as a business leader or founder matters greatly! >People buy from people. That matters for clients and raising cash for your startup - the most followed CEOs raise 20% more cash. TL;DR: Killer go-to-market strategies are designed, not copied. === Technology Park Ljubljana created a fantastic program called BALI. The founders pitched a demo pitch to VCs, who gave them feedback. They are now improving their pitch decks for the second pitch. This Wednesday, I had a three-hour intensive with the founders. We focused on improving the pitch deck, especially the most critical slide on going to market. Because GTM depends on the market dynamics, not the product. === HI, I'm Jasna! I accelerate sales in B2B tech companies with go-to-network, LinkedIn, trade shows, events, and a tailored marketing and sales toolkit. I help business leaders and founders design a strategy that you can execute. DM me to find out more!

Every revenue leader talks about sales and marketing alignment—but most still struggle to make it work. Here’s why. Sales and marketing should operate as a single, high-performing revenue engine. But in most organizations, they function more like disconnected teams, leading to missed revenue, wasted budget, and deals slipping through the cracks. If you’re a revenue leader facing these challenges, here are the three biggest roadblocks getting in your way—and how to fix them. 1. 𝗗𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁 𝗗𝗲𝗳𝗶𝗻𝗶𝘁𝗶𝗼𝗻𝘀 𝗼𝗳 𝗦𝘂𝗰𝗰𝗲𝘀𝘀 Marketing focuses on MQLs, brand awareness, and content engagement. Sales focuses on closed deals, quota attainment, and speed to revenue. If these goals aren’t aligned, it creates tension. Fix it: • Set shared KPIs that both teams are accountable for—like pipeline velocity, win rates, and customer retention. • Regularly sync on revenue impact metrics, not just lead volume. 2. 𝗣𝗼𝗼𝗿 𝗖𝗼𝗺𝗺𝘂𝗻𝗶𝗰𝗮𝘁𝗶𝗼𝗻 & 𝗟𝗮𝗰𝗸 𝗼𝗳 𝗖𝗼𝗹𝗹𝗮𝗯𝗼𝗿𝗮𝘁𝗶𝗼𝗻 Too often, marketing hands off leads without sales understanding the strategy behind them. Sales dismisses marketing’s efforts as “not helpful.” The disconnect creates frustration and lost opportunities. Fix it: • Implement structured feedback loops so sales can report back on lead quality. • Create joint working sessions where both teams contribute to messaging, targeting, and go-to-market execution. 3. 𝗠𝗶𝘀𝗮𝗹𝗶𝗴𝗻𝗲𝗱 𝗣𝗿𝗼𝗰𝗲𝘀𝘀𝗲𝘀 & 𝗜𝗻𝗰𝗲𝗻𝘁𝗶𝘃𝗲𝘀 If sales and marketing aren’t rewarded for the same outcomes, they’ll never truly work together. A sales team compensated only on closed deals won’t care about lead nurturing. A marketing team judged on MQLs won’t focus on sales enablement. Fix it: • Align compensation and incentives around revenue impact. • Ensure marketing KPIs include pipeline and sales contribution—not just lead gen metrics. 𝗕𝗼𝘁𝘁𝗼𝗺 𝗟𝗶𝗻𝗲:The companies that will win in 2025 and beyond aren’t just the ones generating more leads—they’re the ones ensuring their sales and marketing teams operate as a single, high-performing revenue engine. If you’re seeing any of these roadblocks, you’re not alone. The companies solving them now will have a real competitive edge in the years ahead.

Your biggest revenue leak isn’t lack of leads — it’s the silent war between Sales and Marketing. When two teams share the same target but operate in isolation, growth stalls. Marketing produces campaigns. Sales handles customers. But without shared intelligence, both sides miss the mark. Where things break down • Marketing builds personas based on assumptions • Sales uncovers real objections and buying triggers • Marketing crafts messaging from theory • Sales hears the unfiltered truth daily • Insights stay locked within teams • Collaboration becomes optional • Growth becomes accidental The real issue Marketing plans content and strategy using reports and trends. Sales gets live feedback straight from the people who buy. Yet the most important insights rarely make their way back into the marketing engine. It’s like watching a climber scale a wall: one person creates the base, the other uses it to rise. That’s exactly how Sales and Marketing should function — one unified system. The alignment model 1. Shared Reality • Weekly joint reviews • Marketing participates in sales calls • Sales audits messaging and content • Customer language captured and shared 2. Common Targets • Pipeline, not vanity metrics • Revenue, not activities • Quality over volume • Customer success as a shared outcome 3. Continuous Feedback Loop • Sales validates personas • Marketing refines messaging based on real objections • Results reviewed together • Adjustments made consistently Your alignment action plan 1. Set a weekly Sales–Marketing sync 2. Build one shared “Voice of Customer” document 3. Bring Marketing into live sales calls 4. Create a unified performance dashboard Because just like the wall climbers — one can’t reach the top without the other. Aligned teams don’t just grow… they scale. #SalesAndMarketing #RevenueGrowth #GoToMarket #CustomerInsights #B2BMarketing #SalesStrategy #MarketingLeadership #BusinessAlignment #GrowthStrategy