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From startup to market maturity, there’s much to learn about scaling a business and your career. The harsh reality is that over 90% of startups don’t make it, and nearly 20% fail within the first year. So, if you happen to be among the minority of those who survived the gauntlet of challenges in the early years, first of all, congratulations. Second, you might be at a point where you need to scale in order to grow.
As CEO of a leading SaaS company, I get a lot of questions about what it takes to grow a company while also learning to scale as a leader. I joined Pushpay in 2016 when the company was experiencing triple-digit growth year-over-year, with about 3,500 customers and less than 200 employees. Fast forward to today — the company is wildly profitable, has more than 15,000 customers, and has 500 proud employees around the globe. On paper, I certainly did advance from a senior manager to CEO in a matter of just six years. Yet the reality is that I had been preparing for a C-suite role for years. From owning my own consulting practice to leading a growing nonprofit organization, I have been investing in professional learning and leadership at every stop, paving the way to my role as CEO.
Along the way, I’ve learned a few things about what it takes to reach the top — and spoiler alert, they’re all things you can do, too.
1. Invest in mentorship and coaching
A mentor recognizes your potential and encourages you to reach that potential. Reaching the top is difficult, but it’s even more difficult on your own. Find a mentor who will champion your interests and can act as a good sounding board as you continue to evolve in your career. A good mentor supports and guides you through the ups, downs and everything in between and gives you the nudge you need to accomplish things you didn’t think were possible. Establishing a relationship with a coach is also immensely valuable. A coach can help you develop skills in specialized areas, offer valuable feedback and challenge you to consider different perspectives. There have been times in my career when I was meeting with a mentor or coach weekly — or even daily — depending on the challenge at hand. From a corporate perspective, seek coaches and mentors who understand the challenges of your industry.
I have received a lot of valuable advice and guidance over the years from these individuals who have influenced my leadership approach. Some tactical examples include:
Creating a safe place to battle out hardpoints
In preparation for challenging meetings or discussions, it’s important to practice and refine your talking points in advance. Create a group of trusted people to help you debate topics and use them to help you refine your talking points in advance of a presentation or discussion (think quarterly earnings announcements, investor calls or a business pitch). The entire intent of this group, and these sessions, is to challenge the status quo and to call out the hard points so you have practice in how to respond well.
Never present a new idea in the boardroom for the first time
Thoughts and pitches should be circulated and socialized in advance. This allows for an initial temp check and early buy-in so that at the Board meeting, the answer is a quick ‘yes.’ On the contrary, socialization also allows you to understand if there’s a debate to be had and allows people to be prepared to have that debate.
Involve mentors and advisors in the talent acquisition process
For most of our VP and above hires, and certainly all of our C-suite hires, I now invite mentors into the candidate review process. They are a critical part of helping build the scorecard and ensure accountability, which has been extremely helpful for me throughout my career. Involving a mentor or advisor also helps ensure you are hiring without bias.
I attribute much of my success to the many mentors and coaches who have invested in me over the years. As you advance in your career, consider paying this forward by mentoring other aspiring leaders.
2. Fail fast
Taking risks can be terrifying, but to elevate your career, it is necessary to learn how to take calculated risks and embrace failure. Get comfortable with being uncomfortable. Taking risks challenges you and helps you strive for growth — and if you’re not pushing the envelope, you’re not innovating and evolving. Outweighing the risk versus reward is where the balance comes in. Does the potential failure have a significant negative impact on the business, or would it just be uncomfortable? If (and when) you do fail, the important thing is to be able to pick yourself back up, learn from the failure, move forward fast and improve for next time. When you truly embrace this approach as a leader and support it as a part of your culture, you’ll be amazed by the creativity and innovation that follow from your team.
In fact, at Pushpay, we embrace, what we call a Blameless Culture approach, which actually originated from the healthcare industry. Moving from blame to promoting a culture of accountability creates trust and psychological safety within your organization and supports growth. At Pushpay, this approach has not only shaped our product and engineer development culture but has benefited our entire company as we work together to achieve our mission. One of the earliest examples I can remember of our team modeling a “Blameless Culture” approach was when a senior leader within our engineering team at the time (in our early startup days) accidentally deleted and lost a mountain of code. It was erased and lost forever, which in turn had some downstream impacts. While it felt like a devastating loss at the time, the team immediately shifted to a solution-focused mindset rather than lingering on the action of the individual. The blameless concept, at its core, is really about learning from failures, implementing those learnings to mitigate for the future, and coming together as a team to celebrate the failures as much as the wins.
Related: Take the Risk or Lose the Chance
3. Invest in tools that can help you scale
Operating with a constrained budget is not fun in the early years and often dictates what investments you can make — especially when it comes to corporate tooling. However, one of the best investments you can make is in software and technology that will have a long-term impact on your business and customers. For example, Salesforce was an early investment for us at Pushpay and one that’s paid dividends as we’ve continued to grow and scale. At the time, it felt like the investment was more than we could justify as a company in its infancy. However, our leadership team understood how important it was to set a solid foundation to ensure we had the right tools in place to support customer relations, sales, marketing and more. From a customer and data management perspective, investing in the right tools helped set us up for success against our competitors in the years to come.
4. Have a continuous improvement mindset
No one ever has all the answers – not even the CEO. The path to successful leadership is filled with curiosity and continuous learning. There is a big difference between managing a team of five and leading a team of 500. Ask questions, don’t be afraid to admit you don’t know something, and relentlessly pursue knowledge and truth.
As leaders, it’s also imperative that we maintain an edge for innovation and personal learning, as we’re responsible for inspiring creativity and innovation among our teams. I think it is critical that leaders are intentional about continuing to learn, improve and advance their skills. This is especially true for middle and upper managers, who often need to activate new skills and capabilities to scale departments. Having a continuous improvement mindset leads to small incremental changes that lead to significant improvement over time. What’s one thing you can learn or do today that will help you be a better leader?
Be proactive in learning about the industry you are in and expanding both your hard and soft skills. Hard skills that are needed and necessary in advancing in most careers are things like data analysis, decision-making frameworks and performance management methodology. Soft skills include executive communication, cross-functional collaboration, networking and building effective business relationships.
You can broaden your technology skills by achieving certifications and participating in training, conferences and other continuing education programs. Don’t wait for someone to raise their hand to inform you of industry innovations — take the initiative on your own.
5. Do the work
It sounds cliche and almost crass, but there is no substitute for doing the work. In a world where AI is at our fingertips, and outsourcing is normalized — there is no replacement for digging in and problem-solving in an authentic way. Leadership is hard, getting a promotion is hard, and, as I mentioned above — growing and evolving in your career can be challenging. Simply put, successful leaders aren’t successful because of luck. They are successful because they have put in the time and energy and have prioritized hard work and professional growth. I’m not saying the hustle culture is the way to go here. In fact, as a society, I think we have shifted our mindset to better support a more harmonious balance of careers and home life. However, I firmly believe that success comes to those who put in the work, and oftentimes, that means outside of the standard “work day.”
What are you doing outside the standard nine-to-five to help you grow as a leader? Are you spending some of your nights and weekends on passion projects that are helping propel you forward in your career? Are you initiating time with leaders or influencers in your industry? Much of my growth as a leader has come from a commitment to myself to maximize those moments and be intentional about what and who I am investing time with beyond the standard workday.
The last piece of advice I would give to anyone climbing the ladder of success is to love what you do. A large part of success comes from finding clear purpose and meaning in your work. When your mind and heart are connected to what you do, this fuels you to come to work each day to do great things.