Strategic Change Initiatives

Scaling from 50 to 100 employees almost killed our company. Until we discovered a simple org structure that unlocked $100M+ in annual revenue. In my 10+ years of experience as a founder, one of the biggest challenges I faced in scaling was bridging the organizational gap between startup and enterprise. We hit that wall at around 100~ employees. What worked beautifully with a small team suddenly became our biggest obstacle to growth. The problem was our functional org structure: Engineers reporting to engineering, product to product, business to business. This created a complex dependency web: • Planning took weeks • No clear ownership  • Business threw Jira tickets over the fence and prayed for them to get completed • Engineers didn’t understand priorities and worked on problems that didn’t align with customer needs That was when I studied Amazon's Single-Threaded Owner (STO) model, in which dedicated GMs run independent business units with their own cross-functional teams and manage P&L It looked great for Amazon's scale but felt impossible for growing companies like ours. These 2 critical barriers made it impractical for our scale: 1. Engineering Squad Requirements: True STO demands complete engineering teams (including managers) reporting to a single owner. At our size, we couldn't justify full engineering squads for each business unit. To make it work, we would have to quadruple our engineering headcount. 2. P&L Owner Complexity: STO leaders need unicorn-level skills: deep business acumen and P&L management experience. Not only are these leaders rare and expensive, but requiring all these skills in one person would have limited our talent pool and slowed our ability to launch new initiatives. What we needed was a model that captured STO's focus and accountability but worked for our size and growth needs. That's when we created Mission-Aligned Teams (MATs), a hybrid model that changed our execution (for good) Key principles: • Each team owns a specific mission (e.g., improving customer service, optimizing payment flow) • Teams are cross-functional and self-sufficient,  • Leaders can be anyone (engineer, PM, marketer) who's good at execution • People still report functionally for career development • Leaders focus on execution, not people management The results exceeded our highest expectations: New MAT leads launched new products, each generating $5-10M in revenue within a year with under 10 person teams. Planning became streamlined. Ownership became clear. But it's NOT for everyone (like STO wasn’t for us) If you're under 50 people, the overhead probably isn't worth it. If you're Amazon-scale, pure STO might be better. MAT works best in the messy middle: when you're too big for everyone to be in one room but too small for a full enterprise structure. image courtesy of Manu Cornet ------ If you liked this, follow me Henry Shi as I share insights from my journey of building and scaling a  $1B/year business.

Why does your strategy keeping changing? 1. What you are seeing is not a strategy. You are witnessing tactics masquerading as strategy. The tactics change so often because a) tactics DO change often, and b) there's no strategy grounding those tactics. 2. Premature convergence. The team hastily pulls something together in a rush to have something ready for annual and bi-annual cycles. The new strategy inevitably suffers from recency bias, rushed research, and a lack of real buy-in. You know you're suffering from premature convergence when there is a sense that "the ship has sailed." 3. Recency bias. Recent events (lost deals, won deals, feedback, etc.) overly bias strategic decisions. This phenomenon is especially true for companies that close most of their business at quarter or year's end. 4. Many companies struggle with an "elephant in the room" dilemma (e.g., growth expectations, investor pressure, valuations, sizing the market, pivotal product decisions, etc.). Instead of facing those issues head-on, it is much easier to keep shuffling through interim strategies in the hope that something will magically make the core issue disappear. 5. If you need to shift your strategy often, you're probably not seeing results with your existing strategy. The problem feeds into itself. 6. Layering. A strategy is typically a mix of more stable and less stable/faster-changing components. If everything changes often, you likely lack a "core" that changes less frequently. 7. The strategy is too vague and lacks an actual diagnosis. It isn't actionable. There's nothing wrong with a team tackling a nebulous strategic problem. Still, it doesn't constitute a strategy that can be rolled out across the organization. 8. Watered down strategy. Instead of feedback cycles sharpening the strategy, you end up with a strategy that either a) reinforces the status quo or b) is too vague to mean anything (#7), or c) contains everyone’s pet projects (“oh that, I guess it relates to New Strategy!”) 9. Unsure what is working and why. You tend to see a cycle of reactive strategic shifts when a team has no idea if anything is working (or why it is working). 10. Whiplash. When a team ping-pongs between new strategies, it can take weeks or even months to pivot to the new thing. Before you know it, people are looking for results, and there's nothing much to show for it (yet). The result: "We have to change our strategy!" 11. Difficulty executing. Was the old strategy the wrong strategy? Or did the team have trouble executing the strategy? In many cases, the old strategy never had a fair shot. Instead of addressing that problem, the team keeps making reactive strategic pivots. 12. Lack of continuous learning and research. You'll be all over the place if you need to spin up new research efforts every time you feel a strategy shift is in order. This pitfall is how you end up with strategies containing a "research phase."

A roadmap is not a strategy! Yet, most strategy docs are roadmaps + frameworks. This isn't because teams are dumb. It's because they lack predictable steps to follow. This is where I refer them to Ed Biden's 7-step process: — 1. Objective → What problem are we solving? Your objective sets the foundation. If you can’t define this clearly, nothing else matters. A real strategy starts with: → What challenge are we responding to? → Why does this problem matter? → What happens if we don’t solve it? — 2. Users → Who are we serving? Not all users are created equal. A strong strategy answers: · What do they need most? · Who exactly are we solving for? · What problems are they already solving on their own? A strategy without sharp user focus leads to feature bloat. — 3. Superpowers → What makes us different? If you’re competing on the same playing field as everyone else, you’ve already lost. Your strategy must define: · What can we do 10x better than anyone else? · Where can we persistently win? · What should we not do? This is where strategy meets competitive advantage. — 4. Vision → Where are we going? A roadmap tells you what’s next. A vision tells you why it matters. Most PMs confuse vision with strategy. But a vision is long-term. It’s a north star. Your strategy answers: How do we get there? — 5. Pillars → What are our focus areas? If everything is a priority, nothing really is. In my 15 years of experience, great strategy always come with a trade-offs: → What are our big bets? → What do we need to execute to move towards our vision? → What are we intentionally not doing? — 6. Impact → How do we measure success? Most teams obsess over vanity metrics. A great strategy tracks what actually drives business success. What outcomes matter? → How will we track progress? → What signals tell us we’re on the right path? — 7. Roadmap → How do we execute? A roadmap should never be a list of everything you could do. It should be a focus list of what truly matters. Problems and outcomes are the currency here. Not dates and timelines. — For personal examples of how I do this, check out my post: https://lnkd.in/e5F2J6pB — Hate to break it to you, but you might be operating without a strategy. You might have a nicely formatted strategy doc in front of you, but it’s just a… A roadmap? a feature list? a wishlist? If it doesn’t connect vision to execution, prioritize trade-offs, and define competitive edge… It’s not strategy. It’s just noise.

Most change initiatives don't fail because of the change that's happening, they fail because of how the change is communicated. I've watched brilliant restructurings collapse and transformative acquisitions unravel… Not because the plan was flawed, but because leaders were more focused on explaining the "what" and "why" than on how they were addressing the fears and concerns of the people on their team. People don't resist change because they don't understand it. They resist because they haven't been given a compelling story about their role in it. This is where the Venture Scape framework becomes invaluable. The framework maps your team's journey through five distinct stages of change: The Dream - When you envision something better and need to spark belief The Leap - When you commit to action and need to build confidence The Fight - When you face resistance and need to inspire bravery The Climb - When progress feels slow and you need to fuel endurance The Arrival - When you achieve success and need to honor the journey The key is knowing exactly where your team is in this journey and tailoring your communication accordingly. If you're announcing a merger during the Leap stage, don't deliver a message about endurance. Your team needs a moment of commitment–stories and symbols that anchor them in the decision and clarify the values that remain unchanged. You can’t know where your team is on this spectrum without talking to them. Don’t just guess. Have real conversations. Listen to their specific concerns. Then craft messages that speak directly to those fears while calling on their courage. Your job isn't just to announce change, but to walk beside your team and help your team understand what role they play in the story at each stage. #LeadershipCommunication #Illuminate

companies are terrible at celebrating themselves. like, embarrassingly bad. Most companies put more effort into their intern's birthday than their own company milestone. Think about it: Intern's birthday: Cake, decorations, team gathering, social posts Company birthday: "Thanks for a great year!" + LinkedIn post with stock confetti emoji You just wasted your biggest marketing opportunity of the year. When Creator Match 🧩 turned 1 last month, we didn't just post about it. We engineered it into a content machine. 50+ custom gift boxes shipped to Creators and Brands Hats that said "Pay Creators" Handwritten notes (actual pen and paper) Raw Founder POV with storytelling of how we started What happened? Dozens of organic UGC posts Hundreds of comments and reshares Employees posting because they were genuinely proud One milestone. Weeks of content. Here's what most brands miss: Your audience doesn't care that YOU survived another year. They care about how you made THEM feel during that year. Your birthday isn't about YOU. It's about everyone who helped you get there. The clients who took a chance on you. The team that grinded through the tough months. The community that supported your vision. The partners who believed in your mission. Make THEM the heroes of your story. Give them something worth sharing. Most companies celebrate like this: "We're so grateful for this amazing year!" Smart companies celebrate like this: "Look at what WE built together." Massive difference in shareability. Don't just share the wins... share the losses. When people feel like part of your journey, they don't just like your post. They become your advocates. They save it. They share it. They talk about it in meetings. They remember it when budget decisions come up. Your milestone becomes their proof point. That's how you turn a calendar date into a competitive advantage. The framework is simple: → Anticipate (build the story early) → Activate (surprise and delight) → Amplify (reshare and engage) → Analyze (measure and iterate) Swipe through the carousel for the complete playbook. 👇 Plus a case study from Pretty Little Marketer and Sophie Miller This works whether you're: → A solopreneur hitting year 1 → A startup celebrating Series A → An enterprise marking 10 years The scale changes. The strategy doesn't. 📌 Save this post. Send it to your marketing team on Slack. Use it for your next milestone. Your future self (and your marketing ROI) will thank you. Time to stop being party poopers and start being profit makers (with a community focus)... *** 🔔 Follow me AJ Eckstein 🧩 for more content on entrepreneurship, LinkedIn Creator Marketing, and Brand strategies

Tough Talk Tuesday? If your company says Customer Success is strategic but still treats it like a support function, stop pretending. If your CS team is occupied mainly with “check-in” meetings and renewal prep instead of driving outcomes, stop pretending. If your leaders talk about trust and value but can’t show how CS moves the business forward, stop pretending. Customer Success is not a concierge desk. It is not a feel-good function. It is a growth engine. And it needs to be treated like one. That means: • CSMs who understand the customer’s business better than Sales or Product • Success plans tied to business outcomes, not playbooks • Metrics that reflect value delivered, not just effort made • A culture where CS earns its seat at the revenue table by showing up with data, direction, and urgency We are not here to smooth things over. We are here to move things forward. Five steps to start shifting from support to strategic: 🔢 1. Replace activity metrics with outcome metrics Track customer impact, not just engagement frequency and volume. Stop counting touchpoints and start measuring progress. 🔢 2. Know the customer’s business priorities by heart Treat every EBR and senior executive session like a board meeting. Tie your updates to what your customer’s CEO and CFO care about. 🔢 3. Stop asking “How can I help?” and start saying “Here is what we should do next.” Lead. Recommend. Own the play. 🔢 4. Align CS goals with company goals Revenue, retention, margin, influence - whatever matters to the business should matter to your CS team. 🔢 5. Tell the story of value loudly and often One story, once a week. Share a real example of customer success inside your company until others start doing it for you. The future of Customer Success belongs to those who stop waiting to be seen as strategic and start behaving like it. What is one move your CS team could make this week that shifts how you are seen? #CreatingTheFuture #CustomerSuccess #Leadership #Growth #ClientValue #DISQO

CFO: We're shifting all marketing to DR. Brand building is a luxury we can't afford. CMO: That's exactly what Figs tried in 2023. Want to know how that worked out? CFO: They're a billion-dollar company, so probably great? CMO: Let me walk you through their 18-month brand journey. It's a masterclass in what not to do. CFO: I'm listening, but skeptical. CMO: Phase 1: February 2023. Figs was spending 15% of revenue on a balanced marketing approach—brand building and customer acquisition. CFO: Sounds inefficient. CMO: Phase 2: May 2023. They pivoted to "marketing efficiency" by cutting brand spend and focusing entirely on DR and immediate customer acquisition. CFO: That's exactly what I'm proposing! Smart move. CMO: Phase 3: February 2024. Their earnings call revealed the truth. They admitted they'd gone "too far" from their previous approach. CFO: Wait, what happened? CMO: Their growth stalled. They realized they needed a more balanced strategy with product launches and storytelling campaigns. CFO: But did they actually change course? CMO: Phase 4: Mid-2024. They completely reversed strategy, returning to balancing short-term acquisition with long-term brand equity. CFO: So they went full circle? CMO: Exactly. They're now emphasizing top-of-funnel marketing to enhance emotional connection and community engagement—the very things they cut a year earlier. CFO: But what about their bottom line? CMO: That's the point. When they abandoned brand building, their growth plateaued. The short-term efficiency gains couldn't sustain them. CFO: So you're saying we'd be repeating their exact mistake? CMO: It's the classic pendulum swing. Brands panic, cut brand spend for immediate efficiency, then realize they've damaged their growth engine. CFO: But we need to show results now. CMO: Short-term results at the expense of long-term health is exactly how brands get trapped in the discount-dependency cycle. CFO: So what's the alternative? CMO: Balance. We can optimize DR efficiency while maintaining brand investment. It's not either/or—it's both. CFO: I need to see the numbers. CMO: I've already modeled it. We can improve ROAS on our DR spend by 15% through better targeting, which gives us room to maintain our brand investment. CFO: This Figs case study is uncomfortably familiar. CMO: The best time to learn from someone else's mistake is before you make it yourself. CFO: Fine. Show me the balanced approach. But I'll be watching those numbers like Taylor Swift watches her backup dancers. CMO: And I'll deliver results faster than her ticket sales crash Ticketmaster.

One reason AI initiatives stall? Few execs use AI in their own work. In 3 hours, I take leaders from “I don’t know” to a POV (co-developed with AI!) on how AI can support key strategic initiatives. To crack the code on exec adoption we: >> Focus on Strategic Use Cases that Click with Execs << To get experience with high value use of AI, we dive into cases that directly enhance executive decision-making and strategic thinking. This tends to be a major eye-opener—most leaders don't realize AI can elevate their highest-level work. Once executives experience immediate personal value, they better understand how AI can have immediate impact across the organization. >> Reframe Mental Models << Generative AI operates fundamentally differently from anything we've seen before, so we need to identify why and how digital change playbooks must shift to leverage this moment. I go straight to the heart of the silent organizational barriers that prevent productive adoption, and how to navigate a path forward. >> Start with the Business, Not the Tech << We don’t begin with AI—we begin with your business. We anchor the process with the breakthroughs that will drive real impact—and to get there, we go analog with brainstorming, whiteboards, and post-its, working to envision what advancement could look like. What could be possible if cognitive limits were lifted? What long-standing friction could finally be overcome? This surfaces a library of meaningful, business-driven opportunities. Then, using proven filters and frameworks, we zero in on the highest-impact places to start applying AI. >> Use AI to Develop AI Strategy << We then—on the spot—collaborate with AI to develop executive viewpoints on how AI can accelerate those strategic priorities. This is hands-on work with AI tools to co-create a path forward, often culminating in each group sharing a lightning talk (co-developed with AI) with the broader team. This approach fast tracks execs to: 1️⃣ Build readiness: Gain deep understanding of the new landscape of use cases today’s AI offers, and the organizational structures needed to effectively harness it. 2️⃣ Map use cases: Develop a prioritized library of strategic use cases ready for immediate collaboration with technology and data teams. 3️⃣ Accelerate alignment: Establish common language and jump-start cross-functional alignment on tackling high-impact opportunities. 4️⃣ Hands-on understanding: Acquire hands-on experience with AI tools they can immediately apply to their most challenging strategic work. What do my clients say about this approach? That their teams shift from skepticism to enthusiasm—hungry for more, and from uncertainty to clarity about the next steps. It’s a remarkable change, especially in a few hours. ➡️ Want to learn more? Let’s talk. #AIworkshop

Your company's growth is a tightrope walk between innovation and complacency. Take too few risks? You'll be forgotten. Take the wrong risks? You'll compromise your brand. Plenty of the world’s most innovative companies we work with at Motto have figured it out, and we’ve seen some patterns. They expand boldly *without* compromising who they are. How’s this possible? By aligning innovation with their core values at the foundational level. Here's what that looks like in practice ↓ ⦿ Value-driven decision making Every new initiative should be measured against your company's fundamental beliefs. If it doesn't align, it's not worth pursuing. ⦿ Create a "failure budget." Allocate resources specifically for experimental projects Reward people for trying, not just succeeding. This tells your team it's okay — wonderful, even — to take calculated risks. ⦿ Implement an innovation framework. Set clear guidelines for new ideas. Leaders should ask themselves… → What will keep our company in the leader position? → What is the impact if we play it safe? → How will this innovation align (or not align) with our values? Make sure innovations contribute positively, inside and out. ⦿ Foster cross-pollination Form diverse "skunk works" teams. Give them a specific goal and deadline. Then, watch as fresh perspectives lead to groundbreaking ideas. ⦿ Embed values through education. Your team should breathe your company's values—When they do, even their boldest ideas will align with your core identity. Innovation isn’t about recklessness— It’s about daring to fly while staying true to your roots. When you master this balance true growth happens. Motto® helps tech companies align vision with bold growth. Let's talk about your next big move. → wearemotto.com

Most companies think stakeholder management is about getting buy-in. It's actually about changing predictions.   Years ago, I was helping a technology company with their organizational transformation. They had grown from a startup to several thousand people but were still operating like a startup. No real processes. No decision-making structures. Just running from one urgent need to another.   When I recommended new forms of governance, the resistance was immediate. And here's what made it complicated: each senior leader was resisting against a different, negative outcome as a result of the change.   For example, some believed that structure would slow them down and make them less nimble versus competitors. Others thought it would kill innovation. Some thought it would create bureaucracy by adding layers and layers of approvals to workflows. Many thought it meant they would lose the autonomy to run their business unit.   Here's what was really happening. Each person's brain was making different predictions based on their unique experience. These leaders could only predict problems because unstructured processes and systems were all they'd ever known. Their brains couldn't envision the benefits because they had no (or at least limited) experience with good structure.   Traditional stakeholder management would have grouped them as "senior leaders" and design one strategy for them all. But their concerns were entirely individual.   Changing predictions requires three things. First, understanding that each person's concerns are unique. No two brains make the same predictions. Second, getting people to try new approaches without perfect information. This takes direct, one-on-one conversations. Third, recognizing that predictions don't change overnight. It takes experience and repetition.   If the stakeholders in your company are resisting change understand that their brains are doing what brains do. They're predicting outcomes based on what they know.   The next time you build your stakeholder management approach remember it's not about treating everyone with the same title the same.   It's about engaging everyone, individually, where they are. Michael J Lopez Consulting #change #stakeholdermanagement