Over the past 20 years, Jamal closed multiple $50m deals as an individual contributor enterprise seller, authored the best selling book, Mega Deal Secrets, coached hundreds of ambitious sellers to sell the largest deals of their lives, and founded the Enterprise Sellers Community, a community of practice for individual contributors.

Bad bosses can ruin your health. I know from experience.

Here’s what the worst boss of my life looked like.

He would call me on the weekends to tell me what to do with my deals.

He would brow beat me into chasing the ERP reps in our company who were on my accounts for CRM leads (I sold CRM).

The ERP reps hated me.

I hated doing it.

Once he called me while I was driving three hours to a customer meeting.

He said he needed some names and numbers from my last prospecting campaign.

I told him I’d get them to him later that day, as soon as I could.

He said “Pull over. I need to submit them now.”

As semi trucks almost blew my doors off, I yelled out the names he needed on the shoulder of the four lane highway.

Jeesh.

The pressure on deals got so great that I started having sleep issues.

I’d wake up in the middle of the night DRENCHED in sweat,

Wondering what abuse was waiting for me the next day.

I stuck it out, I didn’t know any better.

I thought I needed to just toughen up to play in the big leagues.

That I was so soft I couldn’t take what must be “standard management” at big tech shops.

As I look back on those years, I see how wrong I was and how pitiful he was.

Let me tell you, if you ever wake up in the middle of the night drenched in sweat over something your manager nailed in your brain,

walk out the next day

let me know

and I’ll help you find your next gig.

LIfe’s too short and you’re too valuable to put up with utter BS.

P.S.

Are you an enterprise seller? Join over 500 ENTs attending my FREE 3-Day Enterprise Sales Secrets Challenge. Learn the skills to close BIG deals.

Register here: https://buff.ly/3IUwKGJ 

Starts April  8.

#sales #enterprisesales

Jamal Reimer

I write, coach and consult about how to find and close mega deals.

The backstory is that have been a career enterprise seller for over twenty years. I learned the art of closing mega deals - uncommonly large and complex enterprise agreements - in 2012 when I closed my first $50,000,000 deal at Oracle. 

I went on to close two more in the following six years and in the process, found my professional passion. 

My Mega Deal Secrets masterclass is the only coaching experience of its kind, attended by ambitious sellers from Salesforce, Oracle, VMware, Outreach, Cisco, Seismic, DocuSign, LucidChart, Dynatrace, Gartner, Teradata, Celonis and many more.

Mega Deal Secrets is my new book which tells the story of my first mega deal journey in detail and is now being read, shared and used as an advanced selling blueprint among tech sales teams from start ups to public companies.

Fast-growing scale ups engage me to upskill their enterprise sellers and to work with management to establish a mega deal selling framework which works with whatever selling methodology they currently adhere to (Command the Message, Corporate Visions, Miller Heiman, Sandler, etc.)

Get the book: megadealsecretsbook.com
Book a masterclass interview: https://calendly.com/megadealsecrets/30min
Discuss consulting or speaking engagements: jamal@megadealsecrets.com

Hey Sales Leaders: it's time to let your sellers sell! 

Over 50% of enterprise sellers I talk to say, “I can’t sell like I want to do at my current company.” 

Why?

Because they were hired to drive larger deals in larger accounts but are being told:

- “We need to show up well on the dashboards”
- “The month is looking light - can you bring in that deal early?”
- “If you could just get on the board with a few small lands…”

This is 180 degrees from how their role was initially positioned.

You need to your enterprise sellers be enterprise sellers.

Don’t push them down to small deals the first quarter in the role.

Building enterprise pipeline will take time.

Telling them to get contacts at 100 accounts on an outbound sequence will kill their time for strategic activity.

Going for a high volume of calls with lower level stakeholders for an un-researched, under-personalized meeting will drive your ENT sellers insane.

DO have them:

- Pick a handful of large accounts with a capacity to buy in large amounts.
- Research the heck out of them (days not hours)
- Craft a customer-specific Point of View for each account
- Rally your own executives and senior players in your ecosystem to help get a warm introduction to senior players within the account.
- If that doesn’t work, invest the time in creative cold outreach (creative items sent through the mail with a relevant message).

All of this to START a compelling business conversation with an Economic Buyer.

All of these activities are strategic, effective and time consuming,

But that is the nature of enterprise sales.

Predictable Revenue, velocity sales plays - they all have their place in the world.

But not when you want to go upmarket.

Let’s celebrate managers who do it right.

P.S.

Want to find and close the biggest deal of your career? Join over 1000 sellers at the Enterprise Sales Secrets  Challenge. Register here: https://buff.ly/43B47YH 

#sales #enterprisesales

Having an AE land a big new logo and then lose the account is madness.

I love Customer Success, but dang it, AE’s need to stay on every account they close.

Customer Success rocks:

- Fulfilling KPI’s
- Increasing likelihood of renewals
- Keeping engagements on the rails
- Teaching customers how to use the solution

Sales is excellent at:

- Engaging executives
- Crafting larger enterprise deals
- Developing relationships with more business units

You need both in an existing engagement to grow an account.

Otherwise you’ll leave big deals undone.

P.S.

I'm unveiling enterprise sales playbook today on the final day of the Enterprise Sales Secrets Challenge today at 2pm ET. Over 1700+ sellers have registered. You can join us here: https://buff.ly/43B47YH 

#sales #enterprisesales

After doing three $50M+ SaaS deals, being top 1% at Oracle and becoming financially independent, here are 5 rules about selling I’ve learned which no one talks about:

1. Email is the absolute worst form of communication.

- Overused in prospecting
- Can’t accurately convey tone
- Too easy for recipients to ignore
- Can’t build relationships through email
- Permanent record of massive faux pas

2. Constantly assess who you are talking to.

- Are they friend or foe
- Do they have influence
- Are they being truthful with you
- Are they invested in the problem you solve
- Do they actually know what’s going on internally
- Deprioritize them if you can’t answer the above affirmatively

3. Break out of common sales plays or you will never land an uncommonly large deal.

- Prospect > discovery > demo > pray = common road to nowhere
- If you haven’t learned to engage executives, that is your glass ceiling
- Learn to get more than you fair share of A-players and other internal resources
- Break rules and get exceptions to internal policies to get your customers unique solutions that hit the nail on the head to address their business realities.

4. When it’s go-time in a big oppty, get serious.

- It will be 24/7.
- There will not be work/life balance.
- You will be making sacrifices.
- It will hurt.
- Sometimes the pursuit of happiness drives you right through stress and pain.

5. Success is short-lived.

- You will/should enjoy it in the moment..
- Reward yourself a little and save the rest of your commissions..
- But come Q1 you’ll be back to zero and management has a short memory.
- Don’t let it rock you. Accept that it's part of the game.

P.S.

Reserve your seat for the Enterprise Sales Secrets Challenge yet? On April 8th, I’m going to teach you things I’ve only shared with my private clients. All for FREE. Join 800+ sellers here:  https://buff.ly/43B47YH 

#sales #enterprisesales

Here is how executives buy software in 2024:

The first thing they do is hop into their private Slack channels (think Pavilion, GTMfund, etc) and have this exact conversation:

Exec: “We’re starting to look at intent data. Who has a view on (xyz supplier)?”

Peer 1: “They’re good at public companies but lack access to data on SMB.”

Peer 2: “We’re using them and are happy so far.”

Peer 3: “Watching - I’m interested too!”

They don't care about your pitch.

They don't want to see a demo.

They want a recommendation from their peers.

If you pass muster there, the next step is often for the exec buyer to seek out an executive at your company for a “higher level” conversation than what they would expect from a rep.

Which leads me to my main question...

How connected is your management team?

Especially with execs in markets/segments you want to sell to?

When selling to the enterprise everyone sells, especially executives.

Reconsider top of funnel strategies to include exec-to-exec interactions.

Host round tables that are only for executives (get the reps involved later)

- Have your executives take on leadership positions in industry groups
- Join or start executive mastermind groups
- Get involved in charities

Bigger deals happen faster when executives (on both sides of the table) are involved.

P.S.

Want to close BIGGER SaaS deals? The Enterprise Sales Challenge starts April 8th. We already have 900 sellers signed up. Register here to join the 3-day sales challenge (100% free): https://buff.ly/43B47YH

The 3 biggest mistakes sellers make trying to sell enterprise deals (and how to avoid them):


In the first decade of my enterprise sales career I hit all three of these mistakes and it slowed my progress big time. 

Here’s what they are and how to avoid them:


1. Batman and Robin selling

Batman and Robin selling is approaching every deal as a two-person team - the seller and the solutions engineer. 

With that dynamic duo, you can go do $50,000 - $100,000 deals all day long. 

But when you're selling to the enterprise, that configuration doesn't work anymore. 

You have to become the field marshal of a Roman legion, and the mindset of Batman vs. the field marshal are totally different. 

Batman and Robin are going to get 1-5 bad guys at a time.

The field marshal of the Roman legion will lead their troops to conquer cities or whole kingdoms in one campaign.


2. Running complex sales cycles over Zoom or Teams.

Two years after COVID many sellers are trying to do everything virtually.

When you start reaching more senior levels of management, that’s madness. 

True relationships are built face to face, especially when 7 and 8 figures are on the line. 

Senior customer stakeholders need to know, like and trust you x100.

The more that you're present with them, the more those relationships of trust can be built. 


3. Premature or overly optimistic forecasting 

Enterprise deals are (almost) require a longer sales cycle. 

There are more stakeholders involved, the deal sizes get bigger, the stakes are higher, and so the decisions both take longer and are more complex decisions to make on the customer's end.

And so it's a lot harder to forecast enterprise deals. 

The right way to forecast enterprise deals is to be in frequent dialogue with your manager, VP or even your CRO in advance of when you need to submit your forecast.

When they not only know what is going on but they are also part of your deal team and you are co-crafting the strategy, you collectively own the forecast and there are no surprises or disagreements about the plan. 

If I submit a forecast on a deal for the first time and it’s a big number (or if there is a big number in place and that number changes and I don't “forecast the forecast”), that will be a surprise and you will unnerve your whole line of management. 

So don't just make changes and commitments in the forecast without having conversations with everybody that needs to know about it in advance, especially at the enterprise level.

P.S. 

T-minus 5 days until the Enterprise Sales Secrets Challenge starts. Over 1200 sellers already registered. Join us here: https://lnkd.in/dTzDduWu

#sales #enterprisesales

Steal my executive talk track template.

Here is the template I use for virtually every exec presentation.

The cool thing is that it doesn't even include the word "software."

1. Crowd Mentality

This is where you tell them things they already know as level-setting. “Ms. Executive, you already know the four biggest trends in your industry, which are 1, 2, 3 and 4."

2. C-level Insight

Here is where you wow them with a revelation about their business which is currently unknown to or under-appreciated by them - but could seriously move the needle if applied…

“We looked deeper into this one business process, and found a huge relationship between x and y and it’s killing your ability to z.”

3. Detail the Pain

This one is best described in the Commercial Teaching section of The Challenger Sale. Describe in detail how the problem impacts the individual living the problem, the business unit, the entire enterprise and the executive who is accountable for the outcome of the process.

4. Desired Future State

Paint a clear picture of the future state the customer can enjoy which is delivered by your offering. This is best put in the context of the business - increases in earnings per share, lower costs, higher output. The more specific the picture is to the customer’s goals, the more compelling.

5. The Path To Paradise

Lay out the journey to go from the customer’s current state to the desired future state. Not only show them the steps and milestones, go into detail about the nature of each, where the risks are, where things are smooth sailing. The more you can describe it, the more the customer will see you as a safe pair of hands able guide them to a better tomorrow.

_

P.S.

If you sell to Enterprise and/or large commercial accounts, then you're invited to a FREE, live virtual event where I (and my friends) will teach you the skills required to close BIGGER deals and make MORE commission. Over 1,300 sellers have already signed up. Register here: https://buff.ly/43B47YH 

#sales #enterprisesales

Many sellers hate this, but personal branding is an important part of becoming an elite seller (especially at the enterprise level). Here's why:
 
As an enterprise seller, you're going to be closing larger deals with larger enterprises. And when that happens, your need to get higher in the account goes up exponentially. 
 
If you want to do a bigger deal in a big, complex organization, you're going to need to learn how to engage with executives.
 
But to get there, you have to bring your own team and you have to go earn the right to get the A players within your own organization and enlist the help of your own executives to co-sell with you. 

Let's look at an example:
 
When it comes to personal branding, one seller is better than most: 

Meet, Chris Bogdan. 
 
Chris is a strategic seller at Mulesoft. 

Once he had to sell a product which was new and did not have a ton of resources, either in terms of assets or a supporting team. 
 
So he went a s Slack and he said, “Hey guys, I'm trying to sell this product. And if there's anybody else out there who's trying to sell this product to an industry that they don't know, and they don't feel that they have the insights to be credible in front of senior stakeholders, let's just work on this together”.
 
And in the beginning, it was just a few people and it was a huge slog. 

They were trying to figure out how to sell the product, understand the value and  the industry. But as he persisted and kept up this internal effort, more and more people started to show up.
 
And then it got the attention of more senior people in product management and strategy and pre-sales.
 
Ultimately, it became an extremely well attended event and Chris's name recognition and branding within Mulesoft shot up.
 
He was able to access A players within his company and it facilitated him creating the best deal teams around so that he could go find and close much larger deals.
 
That's the power of branding.

Cold Plunging is my new answer for everything

Can’t get enough pipeline? Try a cold plunge.

Your main contact won’t let you talk with their boss? A cold plunge should do the trick.

Your contacts go dark after the demo? My go-to strategy is to take a cold plunge.

But if you hate the cold...

You can join 700 sellers at my 3-Day Enterprise Sales Secrets Challenge.

Register here: https://buff.ly/43B47YH 

Starts April 8th.

Save the date!

#sale #enterprisesales

My sales career (summed up in 25 learnings):

I started with the basics.

I felt uncomfortable all the time.

I learned mass prospecting, how to demo.

I failed at being human, closing business.

Next came the jump from commercial to enterprise.

10% excitement, 90% scared out of my wits of screwing up.

I learned how to run a full sales cycle process. PoCs.

I failed at fostering authentic customer relationships.

Then I got fired twice in a row.

I felt worthless.

I learned that you can actually get a job after being fired (twice in a row).

Then cosmic mercy plopped me smack into the biggest opportunity of my career.

The magic happened when mentors showed me the path to massive deals.

We closed a $50,000,000 deal in nine months.

I felt blown away, like I didn’t deserve that kind of success.

I failed my family through neglect due to work.

I learned the power of deep investment in a customer’s success.

Then I did two more eight figure deals.

I felt this was like me now.

I learned it wasn’t about me at all.

I failed at growing because I stayed in the role too long.

Now I’m done with that chapter.

I feel excited again.

I’m learning to help others on their path.

I will not fail them.

#sales #enterprisesales

How to go from $100k SaaS deals to $1M deals

Sell capabilities, not products.

Smart buyers have this internal conversation in every sales scenario:

1. The thing to buy is presented
2. The buyer thinks “for what it is, how much is it worth to me?”
3. They make an instant, back-of-the-envelope judgement of the monetary value of the thing.

Once formed, that judgment is hard to break.

If you present a product, the customer will see a tool:

- A hammer
- A shovel
- A dumbbell

If you present a capability, the customer will see:

- a skill
- a power
- a repeatable achievement

What is more valuable to you - a dumbbell or the ability to bench 200 pounds?

Sell capabilities, not products.

#sales #enterprisesales

Storytelling is a key skill in B2B sales. But most sellers do it wrong. Here's what it typically looks like:

Most sellers' stories goes something like this.. 

“This customer had a problem, then they started to use our solution, then everything got better, and it was happily ever after”. 

Why is this wrong? 

Because it only tells the good part. 

It shows the solution, not the journey that it took to get there. 

Here's the right way to tell a story:

Start by giving context.

You could talk to the customer about a similar client you had and give enough information for them to be able to fully understand their current state, so they can relate to some part of it. 

Then you share five things the customer did to change their situation in a very detailed way. And you're not just talking about your own solution. You're talking about everything that the customer either tried or did that collectively brought them to a new place. 

Bottom line:

Talk about the journey

It’s important to tell the customer about the process. 

Not only the things that they tried, but what the process looked like, giving all the details that you can in order for the customer to trust you and understand the value of what you’re saying. 

Now when you've added these two elements, you shift from becoming a promoter of your product into a trusted advisor. 

You completely change the game in your own branding, in uplifting the value of your solution and differentiating it from all other alternatives.

Mike Fiascone dropping gold during the first session of the Enterprise Sales Secrets Challenge (ESSC). 👇

The Top Down Approach

AKA... How to leverage your executive network for warm intros!

Still time to join us for tomorrow's session.

Register here: https://lnkd.in/dTzDduWu

100% free.

Hey sales leaders, here's the enterprise role you should be hiring for:

I call it the "Mega Dealer Job Description":

High-growth tech company seeks mega dealer to 10x revenue with global accounts:

- The ideal candidate would be able to reach and establish a dialogue with customer executives through creative outreach techniques (because executives rarely respond to cold emails).

- Intensive research skills are required, candidates must be able to analyze quarterly/annual reports and other media to glean insights into c-suite priorities and challenges.

- Executive language fluency is a must-have. Numbers, financial ratios, operational metrics, timelines, outcomes.

- Candidates with a management consulting mindset/background are preferred. As the lead in a complex buying process, the role requires deep problem solving skills as well as the ability to steward a process of analysis and interpretation of the outcomes of process change through implementation of our technology and impact on the customer’s business results in a given line of business or across the enterprise.

- Experience with or willingness to learn project management and delegation skills will increase likelihood of success as strategic sales cycles require multiple work streams with various customer stakeholder types and internal deal team members simultaneously.

Compensation:

- Standard base salary
- 8-15% commission (make it generous for your space)

Expected performance:

At 3x-5x above plan = $600k-$1,200,000/year

Of course, the projections of comp probably would not pass muster with legal, but this is the range of what Mega Dealers make in a single year. 

#sales #enterprisesales

Nate Nasralla shared an absolute masterclass today on How to Craft a Compelling, Exec-Ready Business Case on DAY 2 of the Enterprise Sales Secrets Challenge. Watch this clip:

If you're a seller, join us for the final day of this FREE LIVE event tomorrow!

Over 1,700+ sellers registered!! 

Sign up here: https://lnkd.in/dTzDduWu

I'm PUMPED for today. The Enterprise Sales Secrets Challenge kicks off this afternoon (2pm ET). Not too late to register. Join Mike Fiascone, Nate Nasralla, myself and over 1,600 sellers here: https://buff.ly/43B47YH

Instead of sending another cold email, try sending:

1. An invitation to be a keynote speaker at an industry conference
2. A book on a theme you discussed in your last meeting
3. A piece of artwork you commissioned on Upwork
4. A coffee mug engraved with a quote you learned they love.
5. A cupcake on their birthday

Some of these will take more effort than others.

But, it will show.

If you really let your creativity run wild, you’d come up with killer stuff better than my list.

If you ever needed permission to get super creative - you now have it.

Stop with cold email already.

Get creative.
Get noticed.
Get remembered.
Get the meeting.

__

Over 900 sellers have registered for my FREE 3-day Enterprise Sales Secrets Challenge. 

You can register here: https://buff.ly/43B47YH 

Starts April 8th!

#sales #enterprisesales

If you want to learn how to do really big software deals, you have to learn how to position and lead a business transformation.

For our purposes, a business transformation is changing the way a customer executes a mission-critical business process.

I’m not talking a partial change which delivers an incremental improvement. I'm talking about transformations like:

- Going from analog to digital
- Phone books to web search
- Gas to electric cars

You have to change how your customers do their business in fundamental ways.

Here’s what I've learned is needed to drive business transformations with my customers:

→ New tech that is truly revolutionary

→ A few successful lighthouse customers to prove to your industry that your tool delivers value.

→ A shared vision between your executives and those of your customer as to how your tool helps them achieve their most ambitious goals.

→ Customer executives who are passionate champions of change who are willing to actively participate and enable their teams on the ground to think differently, let go of “this is how we’ve always done it” mentality and give everyone space to try, make mistakes, tweak, try again and succeed.

And here’s the big one...

→ You have the conviction to politely decline customers who want to do an evaluation of your solution without:

- Clear rules of engagement
- Well-defined, measurable success criteria
- Willingness to share as-is metrics
- Willingness to invest time and effort in the evaluation
- Executive sponsorship, availability and commitment to change

This conviction will only help bolster your position as expert in your area in the eyes of your customers. It will also vastly increase your chances of success in closing a huge deal and making the customer wildly successful.

P.S.

Day 2 of the Enterprise Sales Secrets Challenge starts this afternoon. Join over 1600+ sellers here: https://buff.ly/43B47YH 

#sales #enterprisesales

The executive you see:

- Has all the decision-making power
- Covered in gatekeepers
- Won’t take your call
- Has all the budget

The person they are:

- Watches cat videos before falling asleep
- Just got passed over for the COO role
- Snacks too much, gaining weight
- Going through a divorce

We're all just humans.

P.S.

The Enterprise Sales Challenge starts TOMORROW.

Over 1500 sellers have already registered.

Want to learn how to sell to executives?

Sign up here: https://buff.ly/43B47YH 

#sales #enterprisesales

We officially crossed 1,000 signups for the Enterprise Sales Secrets Challenge! If you haven't signed up yet, watch this video...

Then go here to register: https://buff.ly/43B47YH 

#sales #enterprisesales

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