Wryver Founder Lena McDearmid on Building Culture That Drives Business Performance

Lena McDearmid has spent more than two decades working inside scaling organizations, and she kept seeing the same pattern. Smart teams. Sound strategies. But execution slowed, decisions stalled, and alignment quietly eroded as the business grew.

That experience across Fortune 500 companies and high-growth fintech startups eventually led her to launch Wryver, a culture architecture and leadership advisory firm that treats culture as a core business operating system rather than an HR initiative.

In this interview, she shares what she learned building and scaling organizations from the inside, why she believes most performance problems trace back to execution rather than strategy, and what it looks like to intentionally design an environment where clarity, accountability, and trust drive real outcomes.

Tell us about yourself and your business.

I’m the founder of Wryver, a culture architecture and leadership advisory firm that helps companies improve performance by strengthening how their organizations actually operate. My background covers more than 20 years of operations, product, technology, finance, and organizational leadership in both Fortune 500 companies and high-growth fintech startups, including GreenSky and later Momnt, where I served as Co-founder, Chief Culture Officer, and COO and scaled the business through rapid growth.

Throughout my career, I’ve worked inside organizations during periods of expansion, pressure, and transformation. I’ve seen firsthand that most performance problems are not strategy issues. They’re execution issues, driven by how decisions move, how information flows, and whether teams are aligned and accountable. That experience shaped the foundation of Wryver.

Wryver partners directly with founders and leadership teams to treat culture as a business operating system, not an HR initiative. The work focuses on decision speed, alignment, leadership behavior, and execution clarity so organizations can grow without the drag that often appears as companies scale. Our clients range from early-stage founders to growth-stage companies and leadership teams navigating change or realignment.

How does your business make money?

Wryver generates revenue through advisory and execution engagements with founders and leadership teams. Our work involves culture architecture, organizational operating models, and the technology and product systems that enable execution. Engagements are structured based on the company’s needs and may include project-based work, fractional leadership support, or embedded partnership within the organization.

In practice, this ranges from building or guiding technology platforms and product development to advising on technical architecture, delivery models, and scaling infrastructure. In other cases, we operate as strategic partners across the business, supporting go-to-market strategy, operating design, leadership alignment, and customer experience. Many executives also engage Wryver directly as an independent thought partner, providing experienced outside perspective on complex decisions, growth challenges, and organizational inflection points.

The common thread across all engagements is helping leadership teams strengthen the systems, technology, and organizational structures that drive execution and long-term performance.

What was your inspiration for starting the business?

The foundation of Wryver comes from a pattern I saw repeatedly across my career. Data consistently shows that clarity, speed, accountability, and trust drive performance and long-term value. In my operating roles, I saw what happened when an organization’s culture wasn’t aligned with the level of growth, pressure, or change the business was asking people to carry. Strategy was sound, talent was strong, but execution slowed because the environment wasn’t built for the reality of the work.

After working across multiple startups and large organizations, the signals became consistent. Regardless of size or industry, the same friction points appeared. Decision speed slowed, accountability blurred, and alignment weakened. Even in successful companies, there were predictable pressure points where growth made execution harder. What was often missing wasn’t effort or capability. It was missing a shared language and structure to address what was actually happening inside the system.

Wryver was created to bridge that gap. We are at a point in the evolution of work where leaders understand that performance is shaped by how their organization operates, not just the strategy they choose. The purpose of Wryver is to help leadership teams recognize what’s happening inside their own organizations, strengthen the systems that drive execution, and build environments where clarity, accountability, and trust translate into better outcomes.

How and when did you launch the business?

Wryver officially launched in 2025, but the work behind it began years earlier. Over the past decade, alongside my operating roles, I was increasingly brought into organizations to help leaders navigate growth, alignment, and execution challenges. Much of that work focused on the intersection of performance, culture, operations, and product delivery, where consistent patterns began to emerge across companies.

After nearly six years as a founder and COO in fintech, and more than 15 years in the industry overall, I chose to step outside a single sector and focus more directly on helping other organizations apply the lessons I had learned, both successes and mistakes. Before Wryver was formally established, I was already working closely with founders and leadership teams in a hands-on capacity, often inside their operating environments, reviewing data, supporting product and delivery decisions, and helping teams improve how work actually moved through the organization.

The early growth was entirely relationship-driven. Leaders began reaching out through introductions, industry conversations, speaking engagements, and professional networks. During a sabbatical in 2024, I reflected on the common thread across my career. The consistent theme was that founders and executives sought me out to help them think through growth, leadership decisions, and organizational complexity. Wryver was built around that demand.

As the work expanded, something else happened that has been equally meaningful. Experienced leaders I’ve worked with over the years began joining me on client engagements. Today, Wryver operates as a network of senior operators  and leaders across technology, product, operations,  risk, and go-to-market. Individuals who build and lead the same way I do and share the same standards for how organizations should function. Depending on the scope, we bring the right expertise to the work. What began as individual advisory has grown into a team effort, and I’m incredibly proud of the caliber of leaders and the impact we’re able to deliver together.

Tell us about your team.

Wryver operates as a lean, flexible network of senior operators rather than a traditional full-time team. Depending on the scope of the work, we assemble experienced leaders across product, technology, operations, go-to-market, risk, and strategy, all of whom have built and scaled organizations themselves.

Many of these leaders, I’ve worked alongside over the years, in operating roles, on leadership teams, and in growth environments. Several have served as founders, C-suite executives, or functional leaders responsible for scaling companies through periods of rapid growth and change.

The model is intentionally designed so clients work directly with experienced operators, not layers of junior staff. We bring in the right expertise for the problem at hand, and the work remains hands-on, practical, and execution-focused.

What makes the team effective is not just functional depth, but a shared approach to building organizations, one grounded in clarity, accountability, and performance.

How are you funded? 

Wryver is bootstrapped and self-funded. The business has grown through client revenue and personal investment rather than outside capital.

This approach allows Wryver to build deliberately and stay focused on long-term value rather than short-term growth targets. Our work sits closely with founders and leadership teams, it was important to establish the model around trust, outcomes, and sustainability.

Over time, the goal is to continue growing through earned demand, strategic partnerships, and scalable services.

How did you acquire your first customers?

Our first clients came through existing relationships and professional networks built over years of operating in high-growth environments. Many founders and executives were facing familiar challenges around scaling, alignment, and execution, and those conversations naturally turned into advisory engagements.

Even before Wryver was formally established, leaders were already reaching out for perspective on growth decisions, organizational challenges, and leadership questions. The early work was entirely relationship-driven, often starting with a conversation, a referral, or an introduction through a mutual connection.

Speaking engagements, industry events, and informal conversations also played a role. As more leaders became aware of the work, referrals became the primary source of new opportunities. Because the work is closely tied to business outcomes and leadership decisions, trust and credibility have been the most important drivers of early growth.

Tell us about your primary driver(s) for growth. What worked for you in the beginning? What’s working now?

I consider Wryver still in our early stage, and growth is driven almost entirely by credibility and trust built through operating experience. Founders and leadership teams tend to seek advisors who have worked inside the complexity of scaling a business, not just studied it, and that background created strong early demand.

Today, the primary drivers of growth are referrals, thought leadership, and strategic visibility. When the work leads to measurable improvements in alignment, decision speed, or execution clarity, clients naturally recommend us to peers, investor networks, and other leadership teams.

Thought leadership has also become an important growth channel. Writing and speaking about culture as a performance system, rather than a people initiative, has helped position Wryver within a conversation that resonates with founders, operators, and investors.

What has been your biggest challenge so far, and what did you learn from it? How are you dealing with this issue today?

The biggest challenge has been category clarity. Wryver sits at the intersection of culture, performance, technology, and operating strategy, which doesn’t fit neatly into traditional boxes like consulting, HR, or product development. Early on, I realized that while leaders understood the problems they were experiencing, they didn’t always have language for the type of solution we provide.

The lesson was that building the business meant building the narrative at the same time. It’s not enough to do the work well, leaders need to quickly understand what you do, why it matters, and how it connects to business outcomes. Today, we are very intentional about our messaging, positioning culture as a performance system and staying focused on clarity in how we describe the work and the results it drives.

Can you tell us about any upcoming developments we can look forward to?

The most meaningful development has been the continued expansion of the types of work we’re able to support as experienced operators have joined Wryver. Today our engagements range from focused strategic projects to longer-term embedded support and executive advisory, allowing us to meet organizations at different stages of growth and complexity.

While my background spans finance, technology, and fintech, the work is now extending across a broader set of environments, including platform and marketplace businesses, software development organizations, and technology solutions operating in regulated industries. What’s been especially rewarding is seeing how consistent the underlying performance patterns are, even as the industry context changes.

Staying connected to founders and early-stage builders will remain an important part of the work. I continue to spend time mentoring within startup ecosystems and development communities, often working with companies before they are ready for a formal engagement. Not every conversation becomes client work, but those relationships often grow into a strong network of founders and operators who support, refer, and learn from one another.

Our focus right now is depth rather than expansion. We are concentrating on continuing to strengthen the core work, building experience across industries, and creating measurable value for the organizations we support. Workshops and executive sessions are available when clients request them, but we are not building standardized product lines. Growth is being guided by demand, experience, and the opportunity to stay close to the real challenges leaders are navigating.

You’ll also see increased visibility through media, speaking, and industry conversations as we continue to contribute to the broader dialogue around leadership, performance, and how work is evolving in a more complex and fast-moving environment.

How do you see your business evolving in the next 5 years?

Over the next five years, I believe Wryver will grow alongside a larger shift that is already underway. We’re part of a broader movement where leaders are beginning to recognize culture not as a soft concept, but as a strategic business asset, something that directly impacts decision speed, execution, retention, and long-term value.

What’s changed recently is the level of awareness. Leaders are starting to see the connection between how their organization operates and the performance outcomes they’re getting. They’re asking better questions. They’re looking for language, structure, and support to intentionally shape their environment rather than reacting to problems after they show up. That shift in demand is what I expect to accelerate over the next several years.

For Wryver, that means continuing to grow as a network of experienced operators who don’t just talk about culture, but work alongside leadership teams to build it into their systems, operations, and decision processes. Our role is not only to help leaders understand the concept, but to help them implement it in a way that fits their business and evolves with them over time.

Success, five years from now, won’t just be measured by the size of the firm. It will be measured by the number of organizations that treat culture as a core operating discipline, a standard expectation rather than an afterthought. If leaders begin to proactively recognize organizational friction, ask for help earlier, and build environments intentionally, that will be the real sign that the work is moving from idea to norm.

We’ll continue to contribute to that shift through our client work, through media and industry conversations, and by staying close to the real challenges leaders are facing as the pace and complexity of work continues to increase.

What are some trends in your industry that you’re excited about?

One of the most encouraging shifts is how the definition of leadership itself is changing. More organizations are recognizing that the future leader isn’t just someone with technical expertise or a strong résumé. They’re expected to navigate complexity, manage tension, communicate with clarity, and lead with emotional intelligence. Research from organizations like the World Economic Forum and McKinsey consistently shows that skills such as empathy, resilience, adaptability, and the ability to lead through uncertainty are now among the most critical capabilities for senior leaders.

What’s exciting about this shift is what it signals. Companies are beginning to understand that leadership behavior directly shapes organizational performance. Decision speed, trust, alignment, and psychological safety don’t happen by accident, they’re outcomes of how leaders operate day to day.

Another trend I’m encouraged by is the growing recognition of organizational friction as a business risk. As companies navigate rapid change driven by technology, AI, and economic pressure, strategy alone isn’t enough. The organizations that can move quickly, stay aligned, and adapt without burning out their people are gaining a meaningful advantage.

Overall, the mindset is moving in a healthier direction. Culture is no longer being treated as a soft initiative. It’s increasingly viewed as part of the operating discipline of the business, something leaders manage intentionally because of its direct impact on execution and long-term value.