What I Learned From Closing a Multi-Million Dollar Deal in 11 Days

Highlights: How to position yourself and company to land large deals quickly. Here are five lessons to consider and incorporate into your strategic selling process:

• Be ready for the challenge by creating the capacity to sprint hard
• Sprinting hard in short bursts on large deals requires building up your professional stamina, or “opportunity capacity”
• Opportunity capacity is built over time with deliberate focus and is a holistic approach to work/life integration
• Dedicate time to go deep into thinking creatively and collaborating effectively within a small team to deliver a compelling proposal
• Don’t forget the bigger picture and to remain grateful and humble after the win

Start with the Intent

I debated on writing this article considering the macro events occurring in our world and that so many people have been suffering - from frontline healthcare and essential workers risking their lives every day, to friends and family losing loved ones, to small business owners and employees experiencing economic pain, to social injustice continuing to divide us. I did not want this article to be perceived as another person with privilege bragging about their gains when so many don’t have access to the same opportunity.

However, what reminded me to forge ahead was my past.

It wasn’t too long ago when I was in my mid-20s, deep in debt, working two jobs to just pay rent (which was often late), and struggling to make it in NYC. I was reminded of that version of me who knew things would get better, but it just wasn’t quite crystal clear on how.

I am writing this article to that person, knowing there are several others out there who want to do good and achieve big things in their careers and lives.

My hope is that this article will provide some helpful guidance and considerations you can make in your own sales career right now in order to make things better for yourself and those around you.

Being ready for when opportunity knocks on the door

This is not something that is harnessed overnight. Whether you are leading the charge to open a door within a big account or your leaders are relying on you for help to bring something over the line in the last month of the quarter and year, you need to build a reputation that you’re not afraid to ask for the ball so you can sink the winning shot before the buzzer sounds.

How do you do that?

“Think of trust like a bank account. You need to make frequent deposits and ensure you don’t over withdraw.”

First, you have to prove you can deliver results. Results are ultimately the fastest path to earning the respect of your peers, leaders, and company’s key stakeholders.

But of course, results alone are not enough. Different people can achieve the big numbers in different ways.

Some will plow ahead on big deals, not respecting the efforts of their teammates in helping them with the win or thinking through the long-term consequences by over-promising capabilities that don’t exist just to get the deal done quickly, passing the buck to others to have to figure out how to manage expectations once the client is live.

Both approaches may deliver fast results, but they erode long-term confidence internally and externally, putting the individual under pressure eventually. This is why so many sellers have to jump ship once their pipeline runs thin or things get challenging, oh you know, like a global pandemic!

Don’t be too short-sighted. Your personal reputation lasts much longer than any deal. We all know nobody’s talking about that big whale you snagged at the end of last year right now, but they will remember how you helped prop up a teammate or how you dropped personal things to step in and get something important done for the company.

Think of trust like a bank account. You need to make frequent deposits and ensure you don’t over withdraw.

Secondly, you have to be mentally, emotionally, and even physically ready for the challenge.

I haven’t been shy on social media talking often about the direct correlation between world-class athletes and professional sellers, and how we need to operate in a similar way to ensure our sleep, nutrition, and energy levels are optimal to ensure we reach peak performance.

This takes a consistent routine, all built on good habits. That system you build for yourself requires actually monitoring these things so that you create a space to thrive in life beyond just following the limiting sales activity numbers from your CRM.

You need to actually build self-awareness in tying all of the pieces of your daily work and life together and the how, when, and what that actually contributes to success and satisfaction.

Watch this space for more on how I achieve this, the tools I use, and even some exciting surprises I’m developing for the sales community next year.

I think about it this way as it relates to this quick 11 day sprint to get a large opportunity over the line...

If I had been operating in the “old world,” aka pre-pandemic - on a plane every week, exhausted because of high sleep debt and poor nutrition, I may not have had the energy or even the time capacity to effectively work on this opportunity.

My prospect would have suffered, my company would have suffered, and ultimately I too would have suffered by missing out.

However, because 2020 forced me to rethink how to operate in a whole new way, I actually benefited from the remote-first work approach.

Being a 100% remote seller was actually an asset in this situation, helping to debunk the myth that large, strategic deals can only happen with a handshake (or fist bump) in person.

Equally important, was that leading up to this opportunity, my sleep debt was down to zero, my exercise regime was on point, I was eating well and avoiding alcohol, and I was strategically pruning my calendar to focus only on the big stuff.

All of that strategic work put me in a position to run really fast and really hard so that I could break barriers and records.

Now I can go back into a bit of recovery mode because I know specific data points like that my sleep debt is above 10 hours which causes my energy potential to only be 50 - 60%, or that my physical capabilities are dipping into the red zone due to low HRV scores.

Deep work is necessary to bring big things to life

It’s often a misconception that operating fast in business means things have to get broken or a pitch deck can’t be perfect.

If you don’t strive for delivering the best product possible (and your most important product is you), you’ll constantly be relegated to the bench when champions are knocking down those critical winning shots season after season.

That’s because the champions work extra hard on the important things when nobody’s watching, as they don’t work to please others, they work to maintain their own high standards, which are, and always will be, much higher than anyone else’s.

Even when things get stressful and are moving 100 MPH, they can still maintain control of the car, avoid danger, and for the top 1%, even actually do it with a smile on their face and a calmness that bewilders others.

Remember, it still needs to be fun and enjoyable - all of it!

So how do you work deeply in a sprint and constant barrage of modern distractions?

You have to be adaptable to change and not too rigid to routine, something I call “flexipline” - the combination of flexibility and discipline.

In these high-stakes situations, you need both. When you can rely on discipline, as outlined above, and balance that with flexibility, you’ll create the “opportunity capacity” to deliver high quality work at a fast pace when called upon.

Our proposal was lauded by the prospect, now partner, as extremely powerful and right on target with what they are trying to achieve long-term. That ultimately helped them to make a decision quickly with confidence.

I treated each interaction with care, and ensured I was ready to perform. That required being prepared, but also required me to be hyper-focused in doing the things I normally would do over a longer period of time, and instead, condense it into short 15, 30, and 45 minute planning sprints when my calendar permitted.

That actually kept me and my small team focused on delivering impactful content and keeping the proposal concise, which is exactly what we needed to win the deal. I’ve noticed the bigger the opportunity and the higher the level of stakeholders involved, the shorter you need to keep your content.

Don’t forget to show gratitude and respect the bigger picture

Believing in a higher power, to me, is not so much about religion, but is more about a way of operating as a human being.

In the grander picture of life, this deal is a tiny spec in the universe.

However, this particular initiative will certainly lead to building something we’ll be excited to announce to the world soon that will have a major impact on people’s health and safety, while shifting commerce to a much better place than the sometimes toxic space with which it exists today (think bargaining our personal data and privacy for ad dollars that funds a digital marketplace that is fundamentally broken).

That is certainly a noble cause and much bigger than the big dollars it produces, so watch out for more on this soon!

Ultimately, whether you believe the higher power is a God or deity, an elaborate alignment of the cosmos, raw matter constantly colliding, karma, or just the belief that your hard work and positive attitude will pay off - just remember to always keep your mind and heart focused on something higher than the here and now.

It’s not always about the material benefit. Big things in your life will arise when you constantly work to create the capacity for it.

In short, stay focused on the long-term, take care of yourself and others, and when the time comes, be ready to move fast without sacrificing your core principles.

That to me is the true definition of success.

Let’s thrive!

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