5 Mins Read

Before You Can Sell Mega Deals, It’s Helpful to Sell to Mega Brands

Brandon Fluharty |

Brandon Fluharty |

⚡️ Today’s level up ⚡️

Not all environments are suited for closing mega deals, but they can be ideal for getting mega brand experience. Today’s edition focuses on helping you think about building your mega growth strategy.

Let’s go!

Read time: <5 minutes


It takes time to get into mega deal territory

Image Source: Go Limitless

Yesterday, I had a productive strategy session with Gordon.

Gordon is an Enterprise AE with a PLG (Product Led Growth) SaaS company that is widely used in the consumer space. He’s on a small enterprise team with major, well-known brands on his account list.

He approached me on fine-tuning his personal operating system so that he could set himself up for optimal success.

I loved that he came to the call with a mature observation about his current situation, which was he “aspires to close his first mega deal,” but realizes at this stage, he may first “need to get comfortable with selling to mega brands.”

I also liked that Gordon used “mega deal” terminology. If you are unfamiliar with mega deals, I highly recommend my friend Jamal Reimer’s book, Mega Deal Secrets. That book is a masterclass and his Enterprise Sellers Community is the vehicle on how to effectively close the biggest deal in your career.

But what if it’s clear you’re not quite in a mega deal environment.

Here’s the checklist and overall strategy that we discussed that may be helpful if you find yourself in a similar situation.


A mental checklist for “mega dealing”

Image Source: Progressive Culture

I shared my story on how I got into a mega deal environment, which I’ll share here with you.

It started back in the spring of 2014 when I left a large, public SaaS company that focused on digital marketing solutions for SMBs and joined a private, regional IT consulting firm.

Looking back, it was the most pivotal year in my sales career, even though I took a $30K pay cut. It was like an apprenticeship, because I worked closely with the CEO learning how to craft large strategic transformation deals within a specific industry (mid-market, multi-unit restaurant chains).

It gave me a glimpse into how to work directly at the top to help organizations operate in a better way. I learned the ins and outs of how multi-unit restaurants should scale.

I then parlayed that experience into approaching the major SaaS companies in the enterprise space for the restaurant and retail industries.

A late stage startup out of San Francisco snapped me up to join a small Enterprise team.

I went on to have a great 3-year run at that startup before leveling up to strategic accounts and entering the most prolific period in my sales career with a public conversational AI company where I started closing mega deals (for fun).

Similar to Gordon, when I was at the late stage startup, I was on a very small enterprise team. The company had grabbed significant marketshare with emerging brands and SMBs, but aspired to go upstream into the true enterprise space.

However, that takes significant company resources (like legal and security), product customization and stability, deep integrations, enhanced service delivery and support, and a slew of other key assets. At the time, the company had more aspirations than capabilities in the enterprise space – but nonetheless, it was still an enjoyable ride.

When I closed Estée Lauder at the startup, it was clear the company lacked the full resources to be able to earn the confidence to win mega deals out of the gates, and instead required a steady land and expand approach. Established logos of that size simply couldn’t take on the risk of handling key operations (point of sale and backend commerce and labor operations).

However, I still landed big deals (for the company) and got exposure into how mega brands operated to evaluate and bring in new, key technology aimed at displacing their legacy incumbents.

The consulting experience gave me a double-whammy, because I didn’t just talk about point-of-sale technology, I broadened the scope on how to modernize operations and infrastructure.

It wasn’t until I got to LivePerson, which is an enterprise-first company, could I bring together all of the key skills and assets I had developed over my career, albeit in a different space (Conversational AI).

Some of the key things I’d look for and questions to ask when it comes to selling mega deals at a startup or a PLG company include:

→ Are there any enterprise logos with scaled deployments?

→ Does the legal team have experience negotiating large contracts?

→ What does the enterprise service delivery and support team look like?

→ What does the product roadmap look like for supporting large deployments?

→ Is there a formal process for conducting InfoSec audits and security reviews?

→ Is there a revenue (and customer success) leader in place that has true enterprise experience?

And of course, you need to leverage a maturity model to gain the confidence of key enterprise stakeholders if you ever want to prove you have the chops to transform their business.

Speaking of designing effective maturity models, I am going to have a special guest on our upcoming Make More Hustle Less Monday session on February 13th – the person who introduced me to using maturity models to close 7 and 8-figure transformation deals.

If you’re already a 7 Steps to 7 Figures student, you can join here, or if not, you can click on the button below:

A system for harmonizing activity and impact in pursuit of mega deals

Just because there may not be an existing mega deal closing blueprint at your company, it doesn’t mean the green space is off limits.

If you have the personality and chutzpah for it, this is where Diamond Account hunting can be a lot of fun.

But a good personal operating system will be key. You’ll need to come across as savvy and sophisticated as a McKinsey consultant, but bring the sex appeal of a cool SaaS startup. That’s the winning combination and it takes designing your approach with strategic thinking.

Here’s what I recommended for Gordon. Feel free to steal it for yourself:


Step 1: Leverage the 80/20 rule

As outlined in detail in 7 Steps to 7 Figures, identify your Diamond Accounts by using criteria that is meaningful to you.

– Do you have specific knowledge?

– Does the company need a certain headcount?

– Are they in an industry where you can move fast?

Spend 20% of your time with these Diamond Accounts. They will be your “strategic bets” while you continue to focus 80% of your time on other steady state opportunities. You’ll want a diverse portfolio to pursue and ensure you can harness gains from multiple motions.

→ Need help? Check out: Ditch The Activity Game and Graduate to the Impact Game


Step 2: Define your “category of one”

Gordon had a great hypothesis, which was to focus his Diamond Account pursuits on BPOs (Business Process Outsourcers) who could be a low-entry, big headcount opportunity for his AI software.

We talked about the “Wall Street Journal test,” which is to imagine the WSJ comes to you and asks you to write an article about how to transform a business (using your specific knowledge and capabilities of your company).

Work backwards to clarify what that article would say and then use it as a blueprint for guiding your strategy with the Diamond Accounts. It will grow and iterate as you get experience, but 9, 12, or 18 months down the road, once these deals land, everyone in your organization will be asking you how you did it.

You’ll now have it documented. Then it becomes rinse and repeat.

→ Need help? Check out: Become a Category of One Seller Through Effective Writing


Step 3: Design your days for maximum impact (while avoiding burnout)

You’re a performance-based professional, and you need to treat yourself with care.

And as a knowledge professional, you also need to work with purpose (working in a way that has meaning, while also very purposeful in generating specific outcomes).

To do that, it requires deep work as your default mode and removing the noise and distractions in your life. Gordon, based on the east coast, and his company on the west coast, gives him ample time to carve out specific deep work blocks in the morning before things get too hectic.

We identified 90 minutes after waking up at 6am as his peak energy state and a good time to put in undistracted efforts towards progressing his Diamond Accounts. Soon enough the 20% will start to bleed into his 80% as he progresses the mega deals.

He’ll go from mega brand experience to mega deal specialist.

→ Need help? Check out: Design A Great Day Using the 2-4-8 Framework

That’s a wrap – see you next time!



When you’re ready, here are 3 ways I can help you:

1 | Unlock the 7 Figure Seller Bundle

This combines the 7 Steps to 7 Figures system along with a lifetime membership to our Make More Hustle Less Club where we put the system in action as a community (big changes coming and prices will increase soon!).

2 | Book a 1:1 advisory session

You can book a 60 minute session with me here.

3 | Apply to my Category of One 1:1 coaching program

All Q1 slots are filled, but I will be selecting Q2 spots in about 4 weeks.

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