Five critical lessons for growth from a startup chief executive

When I look back over the past few years since I launched a SaaS startup, the most valuable lessons have come from making mistakes and pushing myself out of my comfort zone.

I’ve learnt many lessons along the way, but I think some were more potent and more business-critical than others.

To help you focus on the critical stuff and avoid some of my mistakes, I’ve put together a list of my top five lessons that will help you to become a more effective chief executive and accelerate your startup.

But first, here’s a quick look at my journey. To cut a long story short, I’m the Aussie chief executive of Simple. I left my day job running marketing and advertising operations at a multi-billion dollar media company in 2008 to start a SaaS business.

My vision was to create a simple solution for marketing teams. It was to be cloud-based with a beautiful interface.

In 2013 we launched our current platform. Over the next few years we validated our market, raised capital, grew our product and engineering teams and expanded into new countries. We worked closely with our patient customers who generously provided feedback on areas where our platform and services needed to improve.

The journey from the start to where we are now has been a winding road complete with setbacks, hiccups, big wins and, of course, countless sleepless nights. We’ve made many mistakes and there have been moments when things just haven’t seemed to click.

Some of the lessons I learned along the way quickly became obvious but as the founder and chief executive, I’ve had to push myself beyond my comfort zone to progress to a new level of discovery.

Here are five of the most critical lessons I believe will accelerate your startup journey.

1. If you’re stuck or struggling, ask for help

It gets lonely at the top. I have had days, weeks and months when it felt like nothing was working out. I quickly learnt that this wasn’t the time to drop my bundle, lose my shit or grill one of my managers.

It was time to reach out and ask for help.

Asking people for advice is the most valuable thing you can do,  so surround yourself with experience that can help.

As chief executive you have to spread yourself thinly across customers, investors, product, marketing, sales, finance and customer success. I admit I am not an expert in every field so I have proactively built a team of advisors who themselves have built multi-billion dollar enterprise SaaS companies before and have specific subject matter experience.

So when I hit a brick wall, I usually know who I’m going to call to tease out a solution.

I recall recently having a very bad week. I was overseas pitching the company’s plan in back-to-back meetings, day in and day out, and I was out of juice. That same week while I was on the road, it felt like the shit was hitting the fan in a number of key areas of the business.

I knew I had to make changes because the way I was working wasn’t sustainable, effective or wise. I wrote down my top three objectives and then called one of my trusted advisors who was always good for some straight talk.

I explained the current situation and how I felt things were going. He then asked me: “What do you think needs to change?”

I explained the three things I had written down. He also then went on to say: “Yep, I think you’re totally right about your top three but there is one thing missing that you know you need to do and fast! Fix your management structure now … that should be your top priority”.

He was totally right. I had left off the fourth point because restructuring involved making some really tough decisions which I had clearly avoided.

That’s the value of asking for help and advice. Experienced people see things differently and can give you a new perspective. It ends the feeling of being overwhelmed in an instant and brings some order to your personal chaos.

2. Know your weaknesses and turn them into strengths 

Before you roll your eyes at another “know your weaknesses” tip, bear with me for a minute.

I’ve learnt in recent years my weaknesses can be turned into strengths with a very simple approach: the right mindset coupled with a proactive plan.

Now I’m not talking just about the power of positive thinking (which I think is a great tool for anything). Rather, it’s about proactively identifying ways in which weaknesses can actually be addressed and worked to become strengths. If you develop the mindset that weaknesses can be overcome, you’ve just broken through your limitations and fears.

When I started my first company, I really sucked at public speaking. It also meant I sucked at sales because selling always involves engaging groups of people. This was not only a weakness, it became a fear and it impacted my life in a dramatic way.

It all came to a head one day when I was pitching to a large executive team from a big prospective client. We had rehearsed the demo and the presentation and all I had to do was deliver it. When I kicked off the presentation, the tech didn’t work and I froze. I fumbled my way through it and two execs left the meeting.

I bombed what was a very important deal.

From that moment I went and consumed every book I could find on public speaking and sales. I practiced and continued to learn from my mistakes. Now, I love doing both and can confidently say I’m pretty good at them too. But it has to be a continuous process.

As chief executive you need to address your shortcomings proactively because your customers, team and shareholders are counting on you.

So ask yourself: What are my weaknesses? Are they holding me or my company back? And how can I turn them into a strength?

3. Define the triage line 

In a startup, time is money and your inaction could be the difference between life and death. If you lose a month or quarter in a startup without progressing your most important priorities, it can mean a big difference to the bottom line and your valuation at the next funding round.

For some, it could spell the end of your startup.

There will always be a lot of competing priorities, but the reality is you can only do a quality job on a few at one time. It’s really important you choose the right ones.

The triage line — a term I heard Reid Hoffman explain at a Stanford lecture on Blitzscaling — is a decision-making tool that I use to determine which actions I need to take to achieve maximum impact for the business.

It really resonated with me because of the feelings of urgency it evokes. In medical terms, hospital teams use the triage system to determine which patients require immediate treatment based on the severity of their condition. I think it works perfectly within the context of a startup.

For me, the critical items are those which create the most value for the business.

Now this isn’t about creating a to-do list, it’s about applying my attention and focus to potentially life-saving issues.

Some examples during the early days of our company were:

• Winning a big brand customer to prove we were the best
• Closing a deal to help meet payroll
• Getting a product release out to keep a key customer
• Organising a bridging loan
• Firing a toxic employee playing politics in the team
• Providing some critical feedback to a team member to get them back on course

These are just a few examples but you get the picture. There are things that are 10 times more important than everything else and quite frankly they are the only ones that count. Get used to being uncomfortable because that’s where the opportunities are that will move the needle.

It’s also really important to understand the lead times on specific initiatives or jobs, for example if you have a major product release that is going to take a quarter to deploy or you have a must-win account or sales you need to make. You need to understand and process that calculation so you prioritise your time correctly.

4. Design the right environment to get the best outcomes 

As chief executive, there is an exhaustive list of items that need your attention. If you do not create the space, time or environment to achieve the best outcomes, you risk everything sitting in the “to do” or “in progress” column without anything ever making it to the “done” column.

This requires a proactive and conscious design to ensure your working environment suits the task at hand. You need to wear different hats for pitching, coaching, counselling, technical solutions, finance, just to name a few. To be effective in each of these, design your day for maximum impact.

Let me give you a few examples:

A product design session is a creative process of collaboration. The session should therefore be given the relevant attention with the right people in the room. It isn’t going to be effective on a conference call, so design the session to get the best outcome you can.

A sales training session won’t be effective if it isn’t inspirational and instructional for your audience and the cohort. Take the time to prepare and give yourself space and balance to get the most out of your team.

Remember, sometimes you have to slow down in order to go fast. Take your time, focus on quality and the business will progress faster as a result.

5. It’s going to take longer than you think – settle in if you want it bad enough

Building a successful and sustainable business takes years. In fact, the average time taken to become a billion-dollar company is six years.

Unicorns or decacorns are rare and, in current markets, sometimes an endangered species. I don’t believe you will find many startups that have been built on cruise mode or overnight. Nothing comes easily or quickly and if it does, it’s pure luck.

Our company has had many iterations over the years. This has slowed us down and we’ve had to move the goalposts many times. Hitting our goals has taken loads of patience and a tonne of perseverance.

So whatever your goal, settle in and manage your own expectations and those of your team; incremental improvements toward a big goal are much better than bullshitting yourself. Base your business on fundamental unit economics that make sense to you and your team.

Be patient and focus on building quality that keeps generating scale.

You’ll have a better chance of survival and then winning if you expect the road to success to be a series of twists and turns. Like a dog with a bone, you have to be tenacious in your approach and never let go.

Following these key lessons will help you avoid some of the pain I’ve experienced growing my startup. They are reference points to keep myself focused on self-improvement and what’s right for the business. I believe they are the foundations for how we will continue to build a really big sustainable business.

James Charlesworth is the co-founder and chief executive of Simple, a SaaS company in marketing performance. 

This article was first published by StartupSmart.