And Many More: Three Lessons from Three Years of Amenable

“The exciting thing about birthdays is that they aren’t just an opportunity to look backward—they are motivation to look forward.”
Anna Montgomery

Happy Birthday to Us

When I filed my LLC paperwork three years ago, it was to establish Amenable (formerly Anna Montgomery & Co) as a side business to fund another idea. For simplicity, I grabbed a domain (annamontgomery.co) with a few friends, and we branded ourselves as Anna Montgomery & Co. Clever, I know.

Fast forward three years and a lot has changed. We turned this side project into a company that now employs myself and twelve other people. We’ve built our own brand, refreshed our brand, and changed our name. We’ve doubled our growth each year and stayed self-funded and debt-free. But most importantly, we’ve had the opportunity to come alongside new and old ventures, legendary creatives, local churches, and ____ nonprofits.

It’s been a blur of decisions, surprises, gut punches, mountaintop wins, and slow faithfulness. Yet, despite this constant breakneck pace of adapting and scaling, the rhythm of most days feels quiet. We’re just, well, working. This humble rhythm reminds us to measure our work not in the websites created or the logos designed, but in the missions we helped move forward and expand.

As I was reflecting on these three years, I began to think about three ideas that continue to shape us:

Good people shape great work.

Sitting at my desk in August 2023, I glanced over to see the notification rolling across my screen.

Intrigued, I left my task and clicked into the message to see an illustration of our team that Jess had created. And immediately the tears came. As a remote team who has never been in the same place at the same time, there was something startling about seeing us actually together. I’m so used to seeing other faces mediated by a computer screen that I hadn’t fully realized how we had built a company of belonging. And it was a place that I love belonging.

With a relatively flat organizational structure, each team member holds a personal responsibility and investment in Amenable and our clients’ work. That means that each staffing change is a change to who we are. Not only are my team members’ genuinely moving our clients’ missions forward, but they are the ones who are building a great place to work. This individual ownership in roles creates opportunities for them to lead in projects where mission and creativity come first.

I’ve had lots of leadership experiences over the years and even have a degree in leadership; yet, when it comes to starting, building, and leading a team while building a business, I’ve realized that I need to rethink leadership. If I center myself as an authority, I can only build something limited by my strengths, skills, and capacity. Or I can create a space where I’m the unseen leader connecting the resources, people, and opportunities for a team. That’s part of the reason why we changed our name; it’s not about Anna and Anna’s creativity anymore. It’s about the Amenable team using their skills and strengths.

My favorite moments are when I see our team leading independently, imagining new possibilities, creating direction, casting vision, pushing themselves to learn, seeking out collaboration, and doing work they’re proud of.

As I wrote in the intro of our new team handbook, if I do one thing with this business, it’s to create a creative space for people to be known and loved, and use their skills and strengths to do their best work. I want them to find a sense of ownership, joy, and freedom in the work they do—to imagine bigger and better futures for our clients’ missions. And that’s ultimately the goal—that the work we do expands the impact of mission-driven individuals and organizations.

Take risks when there is no immediate reward. Make decisions for the long-term.

Strategy is a buzzword. Add it to anything and instantly people think you’re making a better decision. Try it.

In our world of predictability, we simplify strategy in OKRs, data points, five-year plans, and analytics. While those things are part of a strategic process, they aren’t the heart of strategy.

Strategy is imagination at work. It envisions a future yet to be discovered. And it visualizes possibilities and hope.

At Amenable, strategically imagining futures for ourselves and our clients creates the confidence to take risks when we might not see a return for years to come, and it gives us the freedom to make decisions that others don’t understand. This vision also creates a filter for us to evaluate our present decisions, direction, and choices—what are the long-term implications of our immediate solutions?

So while we’re working on social media posts for tomorrow and client projects for next week, we’re also building processes, creating structure, and adding elements that set us up for success in the future. We keep our budgets tight and invest everything back into Amenable. We focus on team member education and client care. We value persistence and patience above present gratification.

This approach spills into the way we see our work. Much like the work many of our nonprofit clients do, the full impact is often unseen for many years. They plant seeds and nurture them for years before the harvest comes. Likewise, we want to measure our work not in the things we check off our list today, but by the long-term impact of the missions we help move forward and expand.

Hold your values tightly, but hold everything else loosely.

With rapid growth comes a constant conversation around goals and values. What should we add? What can be cut? Where can we improve? For our team, we’ve found this state of change forces us to clearly delineate between the values we’ll hold fast and everything else that can be open to adaption. 

This growth has brought great rewards but also big growing pains as we constantly evaluate what is sacred to who we are and what is just a preference. Balancing realistic plans with ambitious ideas requires humility as we are always in a cycle of learning and developing. 

This played out most significantly last year with our rename. One of the themes that began to surface for us in spring of 2023 was the authenticity of our name to who we’d become. I never set out to be the protagonist of Anna Montgomery & Co, but when a business is named after you, it just naturally drifts that way. 

In the past, we’d talked about ourselves as service providers, brand agency, or as many of our clients lovingly call us, “their marketing people.” Even on our team, we had very different ways of describing ourselves. However, as we’d grown as a team together and completed more projects, the reality of our work showed that we do far more vision, strategy, and creative ideation, and organizational health work than a traditional branding or marketing agency. We were finding our niche as a branding and creation firm. 

Whether we’re evaluating a client experience, project failure, software gap, or new possibility, our goal is to see each opportunity for change as a space to find our individuality while growing toward being better client partners. 

And Many More: Thinking About the Future

The exciting thing about birthdays is that they aren’t just an opportunity to look backward—they are motivation to look forward. As I think about Amenable and our work, I’m not sure where we’ll go next. It isn’t from a lack of a plan—it’s just that I’ve been surprised at how often we surpass our plans. 

Regardless of what we do in the next three years, I’m excited to do it with my team, and I’m ready to be surprised again.

Anna Montgomery
Principal & Brand Strategist
Anna is our founder & brand strategist. She’s passionate about connecting with people to sharpen their creative vision and bring it to fruition. In her spare time, she’s often tending to her 87 (and counting!) houseplants.
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