Selected Work & Reflections

Finding the Entry Point 
SaaS Startup: Higher Ed Vertical

A software company I worked with was stagnating. Growth had plateaued, and we needed to find a new path forward or risk becoming irrelevant.

I noticed that one of our existing customers had a strong relationship with a local university. Both were dealing with the same challenge our software addressed. It seemed like a natural connection worth exploring.

Rather than trying to pitch the entire university system at once, I focused on one department—the place where our municipal customer could make an introduction. Just one potential champion who might see value in what we were building.

That first department took a chance on us. Once they had success, other departments started paying attention. Not because we pushed hard, but because they saw real results. When about 20% of our target departments were engaged, something shifted—they started opening doors to their networks, and opportunities expanded from there.

What began as a survival strategy became an entry point into a market we hadn't originally considered.

What I learned: Decision makers wrestle with a paradox: they want change but are risk-averse. It's safer to take their cues from sources they trust. Sometimes the best approach is finding the one person  downstream who's willing to take a chance—wow them, and  let the results speak upstream. 

De-Risking GTM: Solving the Bigger Problem
Early Stage Modular Housing ($15M ARR): Expansion Woes

Our company was being courted by a region eager for economic development. They wanted us to bring jobs and investment. On paper, it looked like a win-win.

But as I dug deeper, I saw a problem. The area's largest employers were already struggling with workforce shortages and limited housing. If we moved in at scale, we'd inherit those same challenges—and likely make them worse for everyone already there.

I realized we needed a solution that worked for the whole ecosystem, not just our company. So I started mapping out partnerships that could address the underlying issues—workforce development, housing, infrastructure. The resulting structure was complex: federal programs, state incentives, municipal support, private investment, and regional lenders all working together.

It took significant time and resources to coordinate, which felt risky when we were eager to move quickly. But it reduced our long-term risk and helped us build a sustainable position in the market.

What I learned: Moving fast can sometimes mean moving fragile. Taking time to stabilize the foundation can feel slow, but it hedges against unforeseen turbulence that could stall momentum.

Asking Better Questions
Startup GTM

We had our business model mapped out and were ready to launch a B2B venture. We just needed some validation first. We knew where to find potential customers, and several agreed to talk through our MVP.

The early conversations seemed to confirm what we thought. Things were going according to plan.

Then, about thirty minutes into one conversation, I watched the person across from me lean forward, their expression change. They started telling me what was really keeping them up at night—and it wasn't what we'd been addressing at all. It was a completely different problem we hadn't considered.

That moment stuck with me. I wondered if we'd been asking leading questions, hearing what we wanted to hear. We built a new MVP to test this different problem. The response was notably different. I realized our original framing had been reinforcing our assumptions rather than uncovering real needs.

That one conversation led us to pivot the entire value proposition before launch.

What I learned: I'm naturally drawn to validation—it feels good to be right. But real learning comes from being contradicted. I need to stay open to hearing things that challenge my assumptions and ask questions that invite those challenges. The best insights often come from being willing to be wrong.

Making More from What We Had
Optimized for Revenue

I was working with a mission-driven organization that was struggling financially. Even though they were running lean, revenue wasn't keeping pace with expenses. There was no excess to cut, and they had no appetite for taking on debt or diluting ownership. The only path forward was increasing sales—but in their sector, that doesn't happen overnight.

As I looked around, I noticed they had assets that weren't being fully utilized. I started exploring whether those assets could generate new offerings. The initial feedback was encouraging.

There was a trade-off, though: the new revenue streams weren't directly tied to their core mission. But the additional income doubled their monthly recurring revenue each quarter. Once they had built up enough reserves, they were able to shift focus back to balancing their mission with financial sustainability.

What I learned: Sometimes growth isn't about doing more—it's about using what's already there differently. The resources we need might already be in front of us, just waiting to be seen from a new angle.

 Making the Investment Make Sense
Seattle Startup

I co-founded a startup that quickly found itself competing on thin margins. We needed funding to survive, but we were struggling to find the right fit.

Angels would listen politely and express interest, but checks weren't coming. I eventually realized the issue: our revenue-based buyback model didn't offer the risk-adjusted returns they were looking for. The risk was too high relative to what we could promise.

We needed to lower the risk profile. So we explored adjacent opportunities—real estate, equities—sectors that complemented our core product. By building a portfolio approach rather than betting everything on one product, we created diversification that made the overall investment less risky.

That's when the funding started to materialize.

What I learned: Capital follows confidence, and confidence comes from structure. De-risking feels like it slows things down, and it does require resources. But I've learned that getting to the finish line matters more than getting there first.

When Things Go Wrong
25 Employees/ 3 Countries/ $15M ARR

We landed our first major B2B sale—an $8 million account. Then the product arrived damaged. It was our quality control oversight.

Leadership was anxious. We didn't have the reserves to easily absorb the cost. Legal conversations were starting to happen, and the situation felt like it was heading toward litigation.

Before things escalated further, the CFO and I worked through our financial model to understand what an emergency capital injection could look like. We took our analysis to our capital partner and reframed the situation—not as a crisis to survive, but as an opportunity to demonstrate our commitment and secure the relationship long-term.

They approved a bridge loan, which gave us the resources to make things right.

The client noticed how we handled it. They not only moved forward with the next phase of the project, but later became a reference when prospective customers reached out.

What I learned: People remember how we respond when things go wrong more than they remember the mistake itself. The stumble is just the setup—the response is what people talk about later. Being remarkable means owning the problem and doing what it takes to make it right.

Translating Expertise into Connection
I joined a project with complicated technical requirements and multiple stakeholders. The product was complex, and our team had deep expertise.

During an all-hands meeting with the client, I watched our technical experts respond to questions with detailed, precise explanations. They knew their stuff. But I noticed the conversation losing energy—the client seemed to disengage.

Afterward, I followed up with the client. I admitted I didn't fully understand all the technical details and kept asking "why"—why this mattered, why now, why this approach. The conversation shifted. We started talking about their values, what they were really trying to achieve, and what success would mean for them personally.

Keeping that connection between their values and our solutions kept them engaged throughout the project. Later, I was asked to help our technical team learn how to bridge that gap—how to translate what they're passionate about into what resonates with clients.

What I learned: Expertise alone doesn't create engagement. People connect with meaning, not specifications. I need to remember that clients aren't buying technical solutions—they're buying what those solutions represent: their goals, their values, their vision of a better outcome.

Where the Experience Actually Happens
Institutional Client (+1,000 employees)

I was asked to address a pattern of customer dissatisfaction at a company that positioned itself as a white-glove service—the kind of place where clients could hand off their problems and trust everything would be handled.

I mapped out the customer journey to see where things were breaking down. The mismatch became clear: the intake process was impersonal. The back-office team was relying heavily on CRM automation, asking prospects to fill out detailed forms about their situation with a promise that someone would call them back soon.

I remembered something from business school—Steve Blank's advice to "get out of the building." Stop assuming and actually talk to customers.

When I visualized the journey, it turned out that just a few touchpoints were driving most of the dissatisfaction—the Pareto principle at work.

We simplified the intake to make initial contact easy and quick, removing that friction. Then we added a personalized follow-up to have a real conversation about their needs. This small shift aligned with the white-glove promise, and customer satisfaction scores improved.

What I learned: The gap between what we promise and what we deliver often lives in small, overlooked moments. Mapping the journey helps me see where those gaps are, so I can close them instead of guessing.

When I Was the Wrong Fit
Startup: 25 Employees/ 3 Countries/ $15M Sales

The team was struggling. Weekly meetings had no agendas. Issues lingered unresolved. Each department used different tools, and communication happened reactively. Trust had eroded. Frustration was building, and people were worried about burnout.

We accepted these outcomes as the reality of working across three countries and four time zones. But what if we could create more consistency and predictability? Could we rebuild trust?

I pulled from frameworks I'd seen work elsewhere: EOS for structure and accountability, OKRs and KPIs to track what mattered. I customized an operating system for the organization.

It should have worked. But I failed.

I didn't properly set expectations with leadership about how long real change takes. Leadership expected quick results, and when they didn't see them immediately, frustration grew instead of decreasing. These frameworks require a shift in mindset, and mindset development often is patient work. I didn't communicate that upfront. 

I was the wrong person in the right seat.

What I learned: Even well-designed systems are no match for failed expectations. A framework is only as good as the alignment behind it. Anticipate misalignment—get ahead of it before I start implementing, not after.

Rebuilding Trust Through Transparency
Chief of Staff

The Board was frustrated. Communication with management had deteriorated. Decisions were slow. Progress felt stuck.

After talking with Board members individually, I realized their frustration wasn't really about results—it was about surprises. Missed expectations had eroded trust over time.

I thought a single source of truth might help—a dashboard where everyone could see the same information, agree on what mattered, and have aligned conversations.

There was no BI team—this was a startup. I figured the dev team could build something. The CEO agreed and assigned the task to product development.

The dev team did what dev teams do: they emailed the Board a form asking what they wanted to see. I should have anticipated that.

I stepped in and sat down with everyone—Board members and the dev team—individually first, then together, back and forth until we had something that actually worked. Board meetings became structured around the dashboard.

The surprises stopped. Over time, trust started to return.

What I learned: Alignment isn't just about having the same goals—it's about seeing the same picture and speaking the same language. When everyone is looking at the same information, uncertainty becomes consistency, and consistency rebuilds trust.

When the Answer Included Me 

I was brought into the leadership team. In my first private conversation with the CFO, I learned our burn rate was unsustainable. We'd been surviving on rolling bridge financing, and we were running out of runway. We needed to reduce burn by 40%, and we needed to do it fast.

I used EOS principles to map accountability across the organization: What outcomes were necessary? What tasks and KPIs drove them? Who owned what? The exercise revealed redundancies and also exposed critical gaps we'd been missing.

But even after identifying inefficiencies, the numbers still didn't add up. When I finished the restructuring plan, I added my own name to the list.

What I learned: Real efficiency requires clarity about what truly drives outcomes and the discipline to let go of everything else.