Growing a company presents unique challenges for founders. This article shares valuable insights from experienced entrepreneurs who have successfully scaled their businesses. Learn from their hard-earned wisdom on topics ranging from hiring strategies to leadership evolution.
- Slow Down to Hire the Right People
- Empower Your Team Through Delegation
- Navigate Complexity with Clarity and Resilience
- Trust Others with Your Vision
- Expand Your Expertise Beyond Original Scope
- Evolve from Driver to Empowering Leader
- Build Systems to Scale Decision-Making
- Embrace Team Ownership and Accountability
- Facilitate Growth Through Humility and Listening
- Enable Others by Letting Go
- Focus on High-Impact Leadership Tasks
- Adapt Leadership Style for Team Growth
- Overcome Doubt Through Successful Scaling
- Learn to Be a People Person
Slow Down to Hire the Right People
Hiring the wrong people is the fastest way to slow your company down.
In the early scaling phase of my startup, I was in constant motion, building systems, chasing growth, and generating attention. I applied that same speed-driven mindset to hiring, thinking I could spot talent on instinct and fill seats as quickly as I needed them. I was wrong.
I brought on people who looked great on paper but weren’t aligned with the way we worked. Skill alone didn’t cut it. Culture matters. Attitude matters. And hiring the wrong person, even one, can stall momentum, create internal friction, and cost more than just time.
After rushing the process a few too many times, I forced myself to slow down and get methodical. I started treating recruiting like product development. That meant structured interviews, real assessments, and most importantly, asking myself if this was someone I’d still want to work with at 2 a.m. when everything’s on fire.
That mindset shift changed everything. I stopped hiring for speed and started hiring for impact. I built teams that could not only do the job but elevate the work, support each other, and thrive under pressure.
That philosophy runs through every team decision we make. We don’t just look for resumes with fancy titles. We look for people who move with purpose, punch above their weight, and care about what we’re building. Onboarding is expensive. Energy is expensive. We measure twice and hire once.
Because when you get the right people in the room, everything else moves faster. And this time, for the right reasons.
Bryce North
Founder, Don’t Be A Little Pitch
Empower Your Team Through Delegation
My biggest personal growth moment during our scaling phase? I can still feel my back pain from those sleepless months getting things out ASAP to adapt to the pandemic!
But seriously, learning to let go of trying to do everything myself was my biggest challenge and growth opportunity.
In the early days, I was involved in every decision, every feature, and every customer interaction. As we grew, this became impossible, and honestly, it was becoming a bottleneck for the team.
The turning point came when we needed to rapidly pivot during the pandemic. We had to recreate the whole app again to adapt to newer technologies available. The workload was massive, and I realized I couldn’t micromanage everything anymore.
Learning to trust my team, to delegate responsibilities, and to accept that sometimes things wouldn’t be done exactly the way I would do them—that was tough! But it was also liberating. Our teams are working hard behind the scenes, around the clock on enhancements to existing features, all the while keeping services up and running.
This experience shaped me into a leader who focuses more on empowering others rather than controlling everything. The platforms you see today aren’t just my vision anymore – they’re the collective expertise of an entire team who often have infinitely better ideas than I do!
The funny thing is, once I learned to let go a bit, we actually moved faster and built better features. That’s been a valuable lesson that continues to shape how we grow.
Dennis Seymour
Head of Growth, NowServing
Navigate Complexity with Clarity and Resilience
One of my biggest growth moments as a leader came when we hit a point where scaling wasn’t just about doing more of the same—it required us to do things entirely differently. Up until that moment, I was very hands-on, involved in almost every detail, thinking I could juggle it all. But as our team and client base grew, that approach became completely unsustainable. I remember one late night when I realized I was the bottleneck, holding things back because I wasn’t delegating enough. Handing over control was tough—I’ll admit, there were moments where I double-checked too much or micromanaged without meaning to—but trusting my team to take ownership became a turning point.
One specific instance stands out: we had a critical project for a client with a tight deadline, and instead of overseeing every part of it, I assigned one of my team members to lead the charge. Not only did they deliver, but they went above and beyond in ways I wouldn’t have even thought of. That experience taught me the power of building and empowering a team, leaning into their skills while stepping back when necessary. It also shaped how we approach leadership; we actively create opportunities for our team to run with projects, knowing it helps them and the company grow. Leading during scaling isn’t just about driving growth—it’s about growing yourself to enable others to thrive. Looking back, letting go wasn’t losing control; it was creating space for something better.
Niclas Schlopsna
Managing Consultant and CEO, spectup
Trust Others with Your Vision
One of the biggest turning points for me came when we pivoted to serve enterprise clients like the U.S. Air Force.
That move brought a whole new level of complexity: strict security protocols, government-grade compliance, and a completely different sales motion than we’d ever navigated before.
It was more than just a technical shift. The change pushed me to grow rapidly as a leader. I had to communicate more clearly under pressure, get the team aligned quickly, and make decisions with long-term impact in mind. There wasn’t room for hesitation.
That experience shaped me in ways I hadn’t anticipated. It taught me what agility really means in a high-stakes environment and how to lead with clarity even when the path is unclear.
More than anything, it built resilience. I emerged from it with a stronger team, a sharper sense of focus, and the confidence to lead through the next unknown—whatever that might be.
Alexander De Ridder
Co-Founder & CTO, SmythOS(dot)com
Expand Your Expertise Beyond Original Scope
When I reflect on scaling from a solo consultancy into a five-person, tech-forward creative agency, the moment that stands out is when I first learned to trust my proprietary PRISM Ascend™ framework in the hands of others. Initially, I was the sole architect of every pitch, every client conversation, and every late-night strategy adjustment.
However, as the demand for our work grew—coinciding with my navigation through the emotional whirlwinds of welcoming my son and overseeing a major home renovation—I realized that insisting on doing everything myself was both unsustainable and a bottleneck for the very impact I wanted to create. Entrusting key elements of our analytics-driven media outreach to my team wasn’t just about delegation; it was about deepening my ability to mentor, listen, and allow our group’s collective strengths to elevate my vision. That leap of faith paid off: campaigns ran more smoothly, our client relationships grew richer, and I gained the bandwidth to refine our AI-enhanced tools and expand FemFounder’s digital template library.
This shift transformed me from a task-oriented founder into a purpose-driven leader who thrives on amplification over control. Embracing vulnerability—sharing the challenges of scaling, the sleepless nights, and the moments of self-doubt—became one of my greatest assets. It taught me that true leadership is about creating an environment where innovative ideas can surface, failure is reframed as feedback, and every team member feels ownership of our collective success. Today, that lesson underpins how I design our Dual Catalyst Visibility™ sessions and how I approach both motherhood and business with curiosity, compassion, and a conviction that growth happens most powerfully when we lift each other up.
Kristin Marquet
Founder & Creative Director, Marquet Media
Evolve from Driver to Empowering Leader
One of my biggest growth moments remains the realization that all of your skills and experience can be reimagined and applied across a much broader part of the business. As we scale, I’ve had the opportunity to step beyond my original scope of expertise and fully embrace being a true generalist—wearing multiple hats, jumping into new functions, and solving new puzzles.
A great example of this has been expanding my long-time focus on employee experience to include customer experience. Throughout my career, I’ve been responsible for shaping internal culture and driving employee engagement—and it felt both natural and deeply strategic to extend that lens externally. At the core, both disciplines are about cultivating meaningful experiences, building trust, and driving sustained engagement. By bringing that expertise forward, I am able to help shape our customer journey with the same intentionality. The parallels are powerful. Just as employee experience fuels retention and performance, customer experience directly impacts satisfaction, advocacy, and ultimately our growth.
There’s nothing more energizing than that stage of growth where you can expand your scope, try new things, and stretch your capabilities in unexpected ways. It’s a rare chance to rethink what you bring to the table and apply it in ways that create meaningful impact across the business.
This shift reminds me that leadership isn’t about staying in your lane—it’s about showing up wherever you’re needed, trusting your ability to learn fast, and adapting with purpose. It inspires me, empowers me, and fuels my drive to grow. That mindset—of expansion, adaptability, and strategic impact—continues to define how I lead.
Heidi Hauver
VP, Customer & People Experience, LearnExperts
Build Systems to Scale Decision-Making
My biggest personal growth moment came when I realized I couldn’t do everything myself. In the early days, I wore every hat—sales, marketing, operations. But as we began to scale, I had to shift from being the driver of everything to being a leader who empowers others. Learning to trust my team, delegate with clarity, and step back so others could step up was a humbling but powerful turning point. It taught me that growth isn’t just about expanding the business; it’s about evolving as a leader. That mindset shift shaped how I build culture, hire talent, and make long-term decisions today.
Robin Cherian
CEO, The Canadian Home
Embrace Team Ownership and Accountability
My most significant growth moment occurred when we rapidly scaled our third-party logistics (3PL) partner network while maintaining our quality standards. Initially, I was hands-on with every partnership, personally vetting warehouses and building relationships. However, as demand surged, I struggled to relinquish that control.
The turning point came when we missed onboarding an ideal logistics partner for a high-growth direct-to-consumer (DTC) brand because my approval was bottlenecking the process. That failure had a profound impact—we had let down both the 3PL and the brand due to my inability to delegate.
I realized then that my role wasn’t to personally validate every decision but to build systems and empower my team to make those decisions without me. This meant creating standardized vetting processes, developing clear success metrics for partnerships, and—most importantly—trusting my team’s judgment.
This shift was genuinely terrifying. The relationships with our 3PL partners and eCommerce clients are the lifeblood of our business. Stepping back meant accepting that mistakes might occur without my oversight, but it also opened possibilities for scaling beyond what I could personally manage.
The experience transformed my leadership approach from controller to enabler. I learned that growth-stage companies don’t just need founders who work harder—they need leaders who systematize their expertise and distribute decision-making.
Today, our team onboards new 3PL partners with a thoroughness I couldn’t maintain alone, and we’ve expanded our matching capabilities far beyond what was possible when I was the bottleneck. Our warehouse partners often comment on how seamless our processes are compared to other platforms.
This lesson—learning to let go while maintaining standards—wasn’t just about business growth. It fundamentally changed how I approach leadership and has become the foundation for how we continue scaling while preserving what makes our marketplace valuable to both 3PLs and the brands we serve.
Joe Spisak
CEO, Fulfill(dot)com
Facilitate Growth Through Humility and Listening
A huge factor in my own personal growth when we were scaling up was letting go of micromanagement, and it was by far one of the biggest growing pains for myself. I lived and breathed every aspect of the business, from product creation to marketing tactics. But as the team expanded and our work became more complicated, I began to stretch myself too thin. There was just no way to be really, truly watching everything without either doing shoddy work or killing myself.
One of the earliest memories I have is when we released a new feature in the wrong way. I was managing every move and, in that process, overlooked crucial input from the team on any roadblocks. I got a wake-up call when the launch didn’t work. I learnt that if I wanted to grow, I needed to believe in my team and allow them to take ownership of their roles.
This change in personality type of leadership was hard at first, but it ended up being a game changer. I started putting more effort towards building a good company culture and ensuring more transparent communication, getting the team aligned with end-to-end company goals rather than being lost in the details of everything. I needed to relinquish control and let my team be free to create and solve problems on their own. It was this moment that helped define me as a leader, and it taught me that scaling a business was not just about managing operations; it was about creating a climate in which everyone felt ownership and accountability.
Dennis Shirshikov
Head of Growth and Engineering, Growthlimit(dot)com
Enable Others by Letting Go
My growth came from redefining what leadership means. I used to believe it was only about providing answers. However, during the scaling process, I found myself having more questions daily. I learned that leadership meant constantly listening without defensiveness. That shift opened up new ideas and stronger alignment quickly. Letting others shape the direction made everything better.
Now, I intentionally facilitate more than I command. I create space instead of filling it hastily. Scaling forced me to evolve both emotionally and structurally. And that evolution gave others permission to lead too. Real growth as a leader comes through daily humility. That’s what makes scale feel sustainable and human.
Ivan Rodimushkin
Founder, CEO, XS Supply
Focus on High-Impact Leadership Tasks
One of the biggest personal growth moments for me came when I realized I couldn’t be involved in every decision. In the early days, I was across everything, from product design to customer support to hiring. But as we started scaling, that approach became a bottleneck. I was burning out, and more importantly, I was holding others back by not giving them space to lead.
Letting go wasn’t easy, but it forced me to shift from doing to enabling. I had to trust the team, create clear frameworks, and focus on building a culture where people could take ownership and move fast without constant oversight. That change shaped me into a more deliberate and supportive leader. I became less reactive and more strategic. I started thinking in terms of systems, not just tasks.
Jamie Frew
CEO, Carepatron
Adapt Leadership Style for Team Growth
One of the biggest moments of personal growth for me during scaling was learning to prioritize and focus on high-impact tasks. In the early stages, I was involved in everything, but as we scaled, I realized that I needed to focus on the most critical areas like strategy and vision. This required letting go of the small stuff and trusting my team to handle the day-to-day tasks. This shift in mindset allowed me to lead more effectively, driving growth without getting lost in operational details.
C. Lee Smith
Founder and CEO, SalesFuel
Overcome Doubt Through Successful Scaling
One of the biggest pitfalls and challenges is finding the first employees and especially co-founders who are willing to put in the same effort as you. It might be an impossible search as you will always love your “child” more, and many people will tell you a lot in the beginning, but you end up being a babysitter. Unfortunately, I was naive with many of my hires and choices of people.
Now, after 13 startups and startup projects that I have started, I can definitely say that I have had a steep learning curve. It also goes a little bit against my own intuition because I am someone who is more focused on the issue and the task and not the “big people person,” but obviously that had to change. I had to put a lot more effort and time into selecting people, motivating people, interacting with them, following up, etc., and it was hard. It was hard for me because I felt like I was losing momentum in my own work and losing time because I wasn’t as productive as I used to be, but I had to deal with that in order to grow.
It shaped me a lot because it went against my nature, and I had to learn faster than I wanted to in a subject that I never liked. But I still had to do it in order to become the leader that allowed my startup to thrive and not be the blocker in the process. That took a lot of time and courage to do because at the beginning, you have to be the lone wolf kicking ass alone without interference from others.
You know how fast you can do things, but suddenly you hit a wall. You need more hands on deck, and you feel that everyone else should become “like you.” You feel that losing 10% of your time is already more than someone bringing in 50% of their time, and you struggle with the trade-off until you realize that you have to do a better job to lose 20% but gain 80% on the other side. But you have to do it differently, and the lone wolf strategy no longer works.
Benjamin Talin
CEO, MoreThanDigital
Learn to Be a People Person
Honestly, I think the first time we did a significant scale-up shaped me in terms of really helping me to see that I was, in fact, succeeding. As an entrepreneur, as excited and passionate as you may be, you are also usually dealing with so much doubt. For me, in those early days, even though things were going well, I still had a lot of doubt in the back of my mind about longevity. So, when we had our first big scale-up, that was essentially proof to me that I was doing well and that I had what it took to succeed entrepreneurially.
Edward Tian
CEO, GPTZero