Cedar Collaborative
Cedar Collaborative

Tag: fractional leadership

  • The Sales Problem That Wasn’t

    The Sales Problem That Wasn’t

    Industry: Enterprise AI and search technology
    Project Duration: Seven months
    Engagement Type: Fractional CMO, GTM strategy

    A sales lead brought me in. He’s someone I recommend to other clients now, genuinely talented, the kind of person who can get a message in front of the right person almost on instinct. He’d been hired to build enterprise pipeline in the ANZ market for a company selling AI-layered enterprise search. He was making calls. The calls weren’t turning into anything durable. He didn’t need another salesperson. He needed someone to help him and the founder figure out what they were actually selling and to whom.

    The founder thought like an engineer, which was both the company’s strength and its problem. The product was genuinely good, built for the kind of high-stakes, high-security search that enterprise and government buyers care about. Nobody had done the harder work of deciding which of those buyers to go after first, or how to explain the product in terms a buyer outside engineering would actually respond to.

    What a lead that didn’t close was actually worth

    We moved fast on the first real test. I connected the founder with someone I trusted in the target market, expecting it might turn into business. It didn’t. The conversation gave us something almost as useful: a clear read on what that market actually needed, what competitors were already doing well, and where the real gaps were. That’s the part people underrate about a warm introduction that doesn’t convert. You don’t walk away with nothing. You walk away with data you couldn’t have gotten any other way.

    That data reframed the whole engagement. The question stopped being how to sell the product and became which market it actually belonged in: government, healthcare, higher education, each one wanting something different from the same underlying technology. Going after all of them at once was how a small team drains itself without finding traction anywhere. We spent real time narrowing that down, alongside a parallel track I know well from other work: what an eventual US expansion should look like, separate from what growing ANZ first would require, without assuming either path was obviously right.

    Sales-led AI, without losing the brand

    The part of this engagement I’d point to first is what happened with the sales lead directly. He’d started layering AI into his own process, and he was good at it in the way sales people are good at anything that multiplies their reach. Left alone, that instinct runs toward volume. More messages, faster, to more people. A GTM operator’s whole orientation is acquisition, and acquisition rewards volume. That instinct isn’t a flaw. It’s what makes someone good at the job. It’s also what goes sideways fast without someone paying attention to brand, structure, and who the message is actually landing on. Especially in a market small and specific enough that one badly targeted campaign gets noticed by exactly the people you wanted to reach.

    A good part of this engagement was less about my own campaigns and more about staying close to what he was building. Shaping the messaging and structure underneath his instincts so the reach he was generating didn’t outrun the brand it was supposed to serve.

    What stayed after the engagement ended

    The engagement ended when a major renewal came in smaller than the company had planned for. The founder made the call to protect runway and pause outside engagements while the team regrouped. What we’d built didn’t go away. The founder is still working from the direction we set. The sales lead has the frameworks, messaging, and target-market thinking to keep going without me in the room. Whether the fuller relationship picks back up depends on whether what we rolled out actually pays off. Enterprise sales moves on a longer clock than the six months we had.

    What stayed with me from this one isn’t a tactic. It’s how much better the work gets when sales, marketing, and product are actually talking to each other in real time instead of taking turns. Things heard on sales calls changed how I thought about positioning. What I learned about the market changed what the founder took back to his product roadmap. None of that happens if everyone stays in their own lane. Some of the most useful thing I did on this engagement wasn’t a campaign at all. It was being the person willing to say a market wasn’t ready yet, or that a message needed to slow down before it went out to five thousand people, when the instinct in the room was to keep moving.

  • The Company as Ecosystem: How Work Is Quietly Reorganizing

    The Company as Ecosystem: How Work Is Quietly Reorganizing

    I read a piece in The New York Times recently about professionals who are leaving traditional jobs to run their own businesses. Something clicked.

    What it’s really describing is not a lifestyle trend. It’s a structural shift. A growing group of smart, experienced people choosing work built on ownership, trust, and repeat relationships instead of titles, ladders, or logos. This has been happening quietly for years, but it’s accelerating now, with talented operators, executives, creatives, and strategists choosing independence not as a fallback, but as a deliberate career shape.

    What’s interesting is that this shift is visible from both sides of the table.

    In enterprise environments, consulting is still something you buy from large firms. Deloitte and their peers serve a purpose. Ostensibly, expertise. Realistically, expertise plus insulation. An external recommendation you can point to when the stakes are high and the risk needs to be shared. That model works in certain contexts, especially where scale, governance, and internal politics demand it.

    But startups and the midmarket are doing something different. More and more, they are starting to see the organization less like a machine and more like a biome. An ecosystem. A mix of full-time employees, fractional leaders, independent specialists, and long-term partners who may only work part-time, but are deeply integrated into how the business actually functions.

    That integration is the key part.

    Trust still matters. Context still matters. You cannot outsource understanding. It’s why I always go in person when starting work with a new client, and why I keep showing up in person over time. Not to perform presence, but to understand what’s said out loud and what’s left unsaid. How decisions get made. Where tension lives. What people care about but haven’t named yet.

    Flexibility becomes a superpower only when it is paired with that kind of integration. When it allows a company to afford more experienced people than a single full-time hire ever could. When it brings in judgment, not just capacity.

    From my side, the appeal of this model isn’t flexibility for its own sake. (If anything, job flexibility makes me nervous.) What matters more is being able to work where my energy and values are aligned. Supporting a nonprofit alongside a group of startups and mid-market businesses. Doing long-term, relational work instead of one-off projects. Spreading risk so that if one organization struggles, the whole system doesn’t collapse, and I can invest in fixing what’s broken without becoming a cost burden in the process.

    This is not the gig economy.

    The gig economy stripped trust and protections from work and called it freedom. It treated people as interchangeable labor and platforms as neutral intermediaries. What’s emerging now feels very different. It looks more like a re-forming professional class. Security through networks. Stability through reputation. Teams built on relationships rather than headcount alone.

    In this model, you don’t “hire a team” once and lock it in. You assemble and tend an ecosystem. One that can adapt, contract, expand, and rebalance as the business evolves. One that rewards care, continuity, and mutual dependence rather than constant churn.

    I think we are only at the beginning of this shift. The midmarket is seeing it first because it has to. It doesn’t have the luxury of over-hiring or over-insulating every decision. Enterprise will follow later, once the old models stop working as well as they used to.

    When that happens, the companies that thrive will not be the ones with the biggest org charts or the most software. They will be the ones that understood early that work is not just something you staff. It’s something you cultivate.