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.

How to build a Deal Map

“I showed this deal map during my QBR and my management team’s jaws dropped - ‘Where did you get THAT?’ - my SVP of Sales said. It completely changed the discussion of the account and my plan. It was a game changer.” This is what a beta user of Whyzer.ai said weeks before the official launch a few months ago. 

A deal map is a strategic tool that quickly highlights the hot spots within an account. Addressing key issues for a POV from their financial health to executive priorities for the fiscal, deal maps are becoming the new go-to canvas for enterprise sellers.

Here’s how to build a deal map:

Step 1: Identify the top 3-5 Executive Priorities for the fiscal year

• Review the most recent 3 earnings calls, investor presentations and annual reports
• Example: Margin expansion, AI-driven innovation, or global expansion

Step 2: Analyze Financial Performance Metrics

• Look at publicly available financials or industry data:
→ Revenue growth trends
→ Profit margins (GAAP/non-GAAP)
→ Operating income
• Identify any financial hot spots or areas of investment (e.g., rising R&D spend, declining margins, etc)
• Mark financial pain points and momentum areas with color codes (e.g., red for risk, green for opportunity)

Step 3: Map Challenges and Market Trends

• Identify external pressures:
→ Competitive threats
→ Cybersecurity risks
→ Regulatory changes
• Consider how these trends might influence buying behavior or urgency
• This is your tension layer — what’s at stake if they don’t act?

Step 4: Outline Strategic Initiatives

• What big moves are they making? What outcomes are being mandated by their board?
→ AI adoption
→ Cloud migration
→ Operational cost optimization
• List key programs, tech rollouts or org-wide changes that support the executive priorities
• Tie your product to one of these initiatives to stay relevant and timely

Step 5: Define Desired Business Outcomes

• Identify the “why” behind their decisions:
→ Investor confidence
→ Enhanced security
→ Competitive differentiation
• These are the results that matter most to the C-suite
• Match your offer to outcomes, not just features

Step 6: Mark Solution Fit

• Where does your product intersect with their world?
→ Does it reduce cost? Improve compliance? Accelerate adoption?
• Draw lines between your offer and key initiatives or outcomes.
• Make your value story visually obvious

Step 7: Highlight Next Moves

• Identify gaps:
→ Missing champions? Incomplete insight on an initiative?
• Define your next actions:
→ New discovery calls
→ Exec alignment meeting
→ Custom demo based on initiative X

Doing a deal map right takes hours, even with your favorite LLM.

Or you can have Whyzer do it for you with a click of a button (Whyzer has 6400 deal maps ready to go for public companies on US exchanges).

{EDIT} Register here: https://lnkd.in/drwJUVqg

Jamal Reimer

Talks about #saas, #sales, and #enterprisesales

I help enterprise sellers find and close the biggest deals of their career through coaching and a community of ambitious sellers | Hit the 🔔 to be notified of my latest posts

Here are 10 SaaS sales lessons I learned at Oracle that hold true in 2025:

1. Multi-threading is like having backup wifi.
Your home internet goes down? 
You switch to your phone. 
Your main contact ghosts you? 
You keep talking to the 2-5 others you've engaged.
You can't run a business without redundant systems. 
Same goes for your deals.

2. Email is the absolute worst form of communication.
Can't convey tone. 
Too easy to ignore. 
Yours is 1 of 500 unsolicited sales emails in their inbox.
Pick up the phone.
Meet people face to face. 
Expand your channels = expand your chances. 

3. Everyone in the room has their own motivations.
Constantly assess who you're talking to. 
Are they friend or foe? 
Do they have real influence? 
Are they being truthful? 
What will make them look good?
If you can't answer yes to most of these, 
you're wasting time on someone who can't help you win.

4. Challenge yourself to NOT mention the name of your company or product.
The moment you say "Oracle can..." you've stopped thinking.
Customers don't buy brands. 
They buy exits from pain.
Force yourself to explain value without ever naming what you sell.
If you can't, you don't understand it well enough to close anything that matters.

5. Every stakeholder lives in a different movie.
IT is watching a thriller about security breaches.
Finance is watching a drama about missed targets.
Operations is watching a comedy about "simple implementations" that aren't.
Walk into each room speaking their genre.
Or watch them all vote no for completely different reasons.

6. Healthy paranoia keeps you sharp. Unhealthy anxiety burns you out.
Look at every angle a deal could go south. 
Then handle the top 4 risks. 
The other 6? 
Odds are so low it's not worth the cycles. 
As my MD Steve Rosenberg used to say: 
"No one ever died over software." 
Remember that when you're spiraling at 11pm.

7. You have to slow down to speed up.
Enterprise sales is a winding path. 
Sometimes you hit a dead end and have to turn around and find another route. 
Sellers are wired to go fast. 
But speed without direction is just chaos with better activity metrics.

8. Bias for action beats perfect planning.
Thoughts don't close deals. 
Action does. 
Think some, do more. 
Try it. 
Reflect. 
Adjust. 
Try again. 
Don't spend three weeks perfecting a plan you'll execute once. 
It's go time. Move.

9. When you have a big opportunity, get serious.
It will be 24/7. 
There will not be work/life balance. 
You will make sacrifices. 
It will hurt. 
This is nothing but the truth.
And honestly? 
Nobody closes $50M deals working 9 to 5. 
You know this. But you still need to hear it.

10. Success is short-lived. Really short.
You'll enjoy it in the moment. 
Give yourself a small reward…
…Then save the rest. 
But come Q1 you're back to zero and management has the memory of a goldfish. 
Don’t be bitter.
It's part of the game. 
The scoreboard resets every quarter for all of us.

-
What's your biggest lesson?

The best executive meeting I ever ran lasted 18 minutes. No demo. No discovery. No deck. Just one insight that made the CFO say "when can we start?" Here's the framework.

Most sellers typically create value stories around the operational benefits of their solution: 

"Sales tech consolidation is important. We can help you reduce tool sprawl with our platform. We're the best at consolidating your stack. We've helped companies cut costs by 25%. Now, tell me about your current setup..."
But the VP of Sales Ops isn't sitting there thinking, "I really need to consolidate our sales tech today."

They're thinking about:

- The Q4 pipeline gap their CEO is asking about
- The rep onboarding that's taking too long
- The CRM migration project that's behind schedule
- The forecast accuracy problem their CFO keeps mentioning

Tool consolidation is on the list. But it's not THE priority. 

The bullseye is the specific metric they have to report to the board (that is not on track).

Everything else is peripheral…

…unless it helps them reach that metric. 

Tool consolidation will become relevant ONLY when it ties the problem and solution together. 

Here's how that sounds (30-sec opener):

"I was reading through your Q2 earnings call and noticed you're sitting at 18% operating margin. Your CEO mentioned operational efficiency three times in that call. That usually means the board's putting real pressure on margin improvement.

What I've been seeing lately with companies in similar situations is interesting. The board sets a 25% margin target. CFO starts doing the math on cost per rep. And suddenly sales ops is in the hot seat because you're managing somewhere between 12 and 15 tools that all made sense when you bought them, but nobody's ever looked at the total cost.

Some of the teams I've worked with have been able to hit those margin targets without touching headcount. They consolidated down to 4 or 5 core tools, dropped cost per rep by about 25%, and bought themselves another year before having to talk about layoffs.

The teams that waited ended up in a different conversation - where HR is involved and morale takes a hit.

Is that what you're navigating right now?"

Now what just happened?

You didn't pitch your product.

You connected their public financial pressure (18% margins, efficiency mandate) to a specific action (tool consolidation) that solves it.

You named the change (board pressure for margin improvement).

You made the stakes clear without mentioning a feature.

You’ve asked them to validate the pain and build the case WITH you.

Now the VP is leaning in.

Not because you have a better consolidation platform.

But because you just connected their CEO's #1 priority to something they can actually control.

That's when you introduce your solution.

Sellers pitch.

Advisors provoke. 

-

{EDIT} Take the quiz here: https://lnkd.in/dCZ--x5g

The right way

If you’re selling into mid-to-late-stage SaaS and you’re not framing your POV around the Rule of 40, you’re already behind.

Every CEO, CFO, and COO is being judged on this metric - and 99% of sellers have no idea how to use it to win deals. 

Here’s how to catch up.


This shorthand metric tells you how efficiently a company balances growth and profitability. It's used by investors and boards to evaluate software or subscription business performance. 

Think of it like your blood pressure: one reading that tells you instantly whether things are balanced or out of whack.

The formula is simple:

Rule of 40 = Revenue Growth Rate (%) + Profit Margin (%)

A healthy SaaS company should hit 40% or higher.

Based on which "side" of 40 the company is on, the Rule of 40 creates two different but predictable buying environments:

1. Prioritize Growth

2. Prioritize Margin

Let’s do both roleplays: 

Scenario A: Company at 20 points below the benchmark (10% growth + 10% margin)

What most sellers do: "Our tool drives 25% productivity improvement"

What the CFO hears: "Another vendor asking for budget when I'm under pressure to cut costs”

What elite sellers do: "You need to add 20 percentage points to hit the 40% benchmark. Based on your recent earnings call, you mentioned 'operational efficiency', which signals you're prioritizing margin expansion over growth.

Our solution helps companies reduce operating expenses by 5-7% by consolidating 3 expensive tools you're currently paying for. That's 5-7 percentage points added to your profit margin. Which means your Rule of 40 score moves from 20 to 25-27 without having to accelerate growth"

What the CFO hears: "They’re talking about moving a number I'm being measured on by the board. NOW I’m listening"


Scenario B: Company at 55 above the benchmark (45% growth + 10% margin)

What most sellers do: "We improve efficiency and save costs"

What the CFO thinks: "Things are working. Why would I add friction to a machine that's already humming?"

What elite sellers do: "Your Rule of 40 score is 55, which is excellent. But sustaining that depends on 2 things: maintaining CAC efficiency as you scale, and keeping net retention high. We've seen companies at your stage lose 15 percentage points on their Rule of 40 score when unit economics deteriorate. Our solution protects your growth rate by ensuring every dollar you spend on sales actually converts efficiently"

What the CFO hears: "This person understands we're optimizing to sustain our performance"

-

If you don't connect your solution to how it moves their Rule of 40 number, you're forcing the CFO to do that translation work themselves.

And they won't.

They'll approve deals that clearly connect to their mandate. 

-

In this week's Financial Fluency Session I'm teaching how to find these metrics, understand what they mean for budget decisions, and speak the language that gets deals approved. Comment INVITE and I'll send you the link.

I snuck away with my family to Rome last week. Slow mornings and long dinners where work simply didn’t exist.

Silas discovered the best pizza spot.
Nuria hunted down the best tiramisu in the city.
And we walked over 20 miles taking in every corner of history.

So much pasta, so little time.

Now- outside of Thanksgiving- it's go time.

As tough as this year has been for many, 

there’s $100M+ in live deals across my coaching students and members of Enterprise Sellers

And hundreds more across the greater B2B sales community.

This is your moment.

Pull out all the stops.
Do the unscalable.
Give your champions everything they need to win.

You are in the arena.
The crowd is watching.
Finish strong. 💪

Most deals don’t die in the demo. They die five minutes into the CFO conversation. That’s when your champion gets hit with questions they can’t answer like:

 “How does this hit our margin targets?”
 “What’s the breakeven?”
 “Why now?”
If you haven’t armed them with financial logic and business framing, their credibility - and your deal - gone in minutes.

Here's the strategic shift:

You need to make your champion bulletproof from 4 perspectives:

1. Financially credible

Vague statements like "this tool will save us time and make us more efficient" will be met with executive frustration from lack of detail.

Specific narrative stories get attention: "We committed to 25% operating margins by Q2. We're at 18%. The board is expecting a plan. This approach gets us 2 points closer without touching headcount, which means we avoid the morale hit and the rehiring costs 6 months from now when we realize we cut too deep"

Cover: total cost, breakeven point, ROI, risk to capital (likelihood of success)

2. Technically viable

When IT asks "how does this fit our architecture".

They say: "This plugs into our existing Salesforce instance via API. No rip-and-replace. Implementation runs parallel to the Q1 ERP upgrade, so we're not competing for the same IT resources. We've already validated compatibility with our security protocols"

Cover: how it fits into current technical architecture, roadmap alignment, implementation risk

3. Measurable business value

The CFO doesn't care about "cost savings" in the abstract. They care about hitting the specific number the board is tracking.

Your champion says: "The board wants 25% margins. We're at 18%. We've identified $5M in obvious cuts. That gets us to 20%. We're still 4 points short. This solution closes 2 of those 4 points"

Cover: does it support an existing executive priority? What specific KPIs will it improve? How does it improve the business approach?

4. Negotiation-ready

When procurement says "we'll do this for half the price," most champions come back to you panicking.

Your champion says: "We can reduce scope to $X, but at that price point, you're only closing 1 point of the margin gap instead of 2. If getting to 25% matters, we need the full solution. If 24% is acceptable and you're willing to explain that delta to the board, we can talk about the reduced scope"

The CFO has to decide: is saving money on the vendor more important than hitting the number I committed to the board?

-
Your champion has no power in the CFO's office. If you don't give them the language, the logic, and the financial framing, they walk in armed with a water gun.

I'm teaching these 4 points in this week’s Financial Fluency Webinar. 

{EDIT} Register here: https://lnkd.in/da_zhNWg

We didn’t plan to build an AI company. 

We just wanted to make enterprise selling easier for us and sellers like us.

We’re not founders.
We’re sellers.
We’re not product managers.
We are sales practitioners.
We’re not VC-backed operators.
We are bootstrappers.
We are experts in enterprise sales, doing big deals,
not building technology.

But here we are:

146 days later, Whyzer.ai hit $10K MRR.

It wasn’t built by startup guys in a garage. It was built by sellers for sellers who want to work smarter not just harder.

Whyzer would not have come into this world without the support and input from hundreds of ambitious sellers, cutting their own paths to success.

To the hundreds of reps who tested, gave feedback, and told us where to aim next - THANK YOU!

For the thousands of sellers who are ready to leave transactional selling behind - join the journey: https://lnkd.in/dBEea5EY

Pulling back the curtain on what happens to reps who have carried 30% - 80% of their entire company's annual number. One rep. Bringing in most of the entire company’s revenue. It sounds heroic. It often is. But it also comes at a cost.

These sellers tend to:

- THINK differently than all other reps on the team
- BELIEVE huge value is on the table and LEAD others to see it
- They become their champion’s champion - giving them support, external -validation, ammo for the internal budget fight, political coverage, confidence
- Eat up a ton of internal resources
- Ask for exceptions in business model and contracting terms to get mega deals done
- They break a lot of eggs internally on behalf of their customer, challenging the status quo

They often bring a whole new (internal) meaning to Challenger Sale.

Despite being extremely focused and time-constrained stewarding these huge deals, many of them still do the insane, senseless over-reporting and one-off updates every flavor or management asks of them despite having logged everything in detail in their CRM. 

Because they’re asked to.

Some also faithfully run high-volume, low-impact outreach… because they’re asked to.

…but some don’t. 

And whether they do or don’t, the below increasingly happens:

- They've had their commissions capped just before the deal closes
- Been fired just before or within 12 mos of doing one of the company’s biggest deals 
- Been sidelined during important deal negotiations 
- Been told that if their big deal doesn't close others will be fired for lack of budget
- Had accounts shifted out of their named list just when they get hot

Even with all the peril and intrigue, I still maintain that being an enterprise seller is the most glorious, impactful, adventurous and even heroic role in all of tech sales.

When companies say they want to do more with less, they’re talking about you.
You don’t carry quotas, you carry companies.

Respect.

-

If you want to learn not only how to become one of these sellers but how to protect yourself from the politics that come with it… 

{EDIT} Register here: https://lnkd.in/dk_2nej9

The worst advice I ever followed in enterprise selling came from my first manager at Oracle.

Year one. I'm 39. Just a few grey hairs coming in.

I'm selling CRM in a company that just acquired three other CRM companies. Which means I'm competing with my own colleagues for the same deals. Larry Ellison's version of natural selection.

My manager pulls me aside one Monday morning.

"You need pipeline. Jean's been selling ERP into your accounts for six years. She knows everyone. Go get her to introduce you."

Sounds reasonable, right?

So I walk over to Jean's desk.

"Hey Jean, I know you have deep relationships at [Account Name]. Any chance you could introduce me to the VP of Sales?"

She looks up from her screen.

"Sure, Jamal. What do you have for me?"

I freeze.

"What do you mean?"

"I mean, what accounts are you going to help me with? You want an intro, I need an intro."

I had nothing.

No relationships. No leverage. No reciprocity.

She smiled. Went back to her email.

I walked away.

But my manager kept pushing.

"Did you talk to Jean? What about Tom? He's got three executives over at [Other Account]. Go ask him."

So I did.

Tom. Then Kirk. Then Brad.

Every time, same result.

Polite smiles. Vague promises. Nothing.

And then something worse happened.

Jean would see me coming and suddenly need to take a call.

Tom stopped responding to my Slack messages.

Sarah literally turned around and walked the other direction.

Because I was doing exactly what my manager told me to do: take, take, take.

It took me six months to realize the advice was poison.

And another six months to repair those relationships.

Here's what I learned:

Internal relationships aren't about asking. They're about trading.

Find an account where you have a relationship and they don't. 

Proactively bring them on a call.

Share intel from a deal you just closed that might help them in theirs.

Build the bank account before you try to make a withdrawal.

Because here's the thing:

If you're at a big company like Oracle, this dynamic is everywhere. Multiple products. Overlapping territories. Sellers competing for the same budget.

And if you're at a small company? It's even more critical.

You have fewer colleagues. Fewer second chances. Fewer opportunities to rebuild burned bridges.

The relationships you have internally are the difference between selling alone or selling with an army.

Here’s an important caveat:

Be the generous one - but maintain control.

Some reps will unfortunately be inclined to take more than what’s been given and try to redirect the conversation rather than add to it.

This is a long-standing reality in competitive environments.

You don’t need to play that game but you do need to defend against it.

-

{EDIT} Register here: https://lnkd.in/dFbusN9M

“I’m just a salesperson, how could I ever go toe to toe with a senior customer executive who’s been in the industry for 20/30 years?” - That’s the question that lived in my mind every time I was about to have an exec conversation. Turns out it wasn’t voodoo or rocket science. You CAN have a boardroom-level conversation. You CAN close megadeals. You just need to stop waiting for permission to learn how:

If you've been around for the past couple of months, you know I've been hosting sessions on financial fluency.

The big elephant in the room that feels like learning Mandarin from scratch.

As I did these sessions, it became clearer that 100% of sellers have everything they need to master this skill, and only 5% of them know where to start. To become financially fluent, you need: 

1. Access to public documents of the companies you are selling to.

Any seller with a computer can download this. 

2. Basic acumen on what financial terms like margin pressure, cash depletion, or cap-ex spike mean. 

These aren't secret executive language. Any seller with a computer can Google this. 

3. To find these financial triggers in those public documents. 

They will reveal executive priorities and current efforts. Any seller with eyes can do this. 

4. Deep knowledge of your solution. So you can build a point of view that connects what you sell to the specific priority the executive is being measured on.

Any seller who takes the time to think strategically instead of pitching features can articulate this. 

I’m not saying it’s easy. I’m saying it’s DOABLE. But no company is teaching it. So most sellers live with that "how do I bring value?" question rattling around in their heads forever.

I had the privilege of joining Jody Geiger and James Kaikis on The Shift Sessions to talk about how Whyzer.ai fills that gap.

We covered:
- Why Whyzer isn't just ChatGPT with a sales wrapper
- How Whyzer surfaces executive priorities so you don't have to dig for three hours
- How the podcast function turns dense financial filings into 6-8 minute summaries you can digest on your commute
- How the POV builder gives you strategic angles you can tailor to your solution, like having a partner who just saved you two weeks of work

I invite you to watch the full session and try Whyzer.ai to see the results for yourself. 

Thank you, Jody and James, for having me. 

{EDIT} Register here: https://lnkd.in/d4Xyb8Gj

Everyone’s getting on the financial fluency bandwagon but most are parroting stats, not challenging the comfort zone of the C-suite.

That’s not financial fluency (yet). The next step is building the story.

Building the story means connecting the numbers to narrative.

It’s where you move from “I read your 10-K” to “I found a way to hit your board’s goal.”

Anyone can spot a trigger.

Few can turn it into a reason to act.

That’s the real skill gap in financial fluency.

The CFO wasn't impressed that you noticed the margin compression. They've been in four board meetings and had seventeen internal conversations about it. 

You telling them their margins compressed is like a doctor walking into the ER and saying "I noticed you're bleeding."

No kidding.

What the CFO was actually evaluating was whether you understood what they're being asked to do about the problem. And whether you could help them do it smarter.

Because here's what you haven't learned yet:

The board didn't just say "fix the margins." They said "get us to 25% by Q2 next year."

The CFO went back and ran the numbers. To hit 25%, they need to cut $18M in operating costs. 

So they started with the obvious moves: freeze hiring, cut travel, renegotiate vendor contracts, look at sales tool consolidation.

Those moves will get them maybe $4M-$5M if they're lucky.

They're still $13M short.

And now they're looking at layoffs. Which the board will hate because it signals the company is struggling. 

That's the decision-making context you walked into.

And you opened with "I noticed your margins compressed."

You just proved you can read a 10-K.

Now imagine you'd walked in and said this instead:

"I was looking at your Q2 results. 18% operating margin, down from 22%. Your CEO mentioned 'operational efficiency' three times in the call, which usually means the board set a specific target. My guess is somewhere around 25% margins by next fiscal year. Is that close?"

CFO: "Close. We're targeting Q2."

You: "So you're looking at roughly $15-18M in cost cuts to get there. And I'd bet you've already identified the obvious moves. Those usually get you about a third of the way. Which means you're probably staring at the gap right now and trying to figure out how to close it without touching headcount."

CFO leans forward.

Because you just described their last three weeks.

You: "Here's what I've seen with companies in similar situations. The real margin leak is usually tool sprawl - that's invisible because it's spread across departments, or process inefficiency that's costing you 15-20% in productivity. The teams that figure that out hit the target without layoffs."

Now what just happened?

You went from "I can read" to "I understand your world."

-

Most sellers stop at the trigger because that's where the training stops. 

{EDIT} Register here: https://lnkd.in/dqDebXdX

It’s Q4. And it’s all about closing. Executive-to-executive conversations can cut your close time by 50%. Right now, that's the difference between a December close and a Q1 maybe.

Most sellers are trying to close their biggest deals alone right now.

Your champion is supportive but can't get traction internally. You're sending a lieutenant to answer the CFO's financial questions only a general can address at this stage. So the decision keeps getting pushed.

Meanwhile, your competitor just got their CEO on a call with the prospect's CEO. General to general.

And suddenly they are miles ahead of you. 

Here are the 2 barriers that stop sellers from mobilizing their own executives:

1. You think you need to grovel or justify why you deserve their time

You don't. But you do need to show them why it's worth theirs.

Any executive worth their salt will engage when they see it’s a good use of time:

- Building relationships with executives at strategic accounts (this call opens a door they want open)
- Hitting metrics they report to their board (strategic account wins, competitive win rate, pipeline in key segments)
- Maintaining competitive positioning (if your competitor's CEO is engaging with the prospect's CEO and yours isn't, they're losing ground in that relationship)

So the ask isn't "hey, can you help me close this deal?"

The ask is: '[Executive name], I've got [Company] at [$X] - one of our target accounts. Their CFO has concerns about vendor stability that would carry more weight coming from you peer-to-peer. This call positions us competitively and opens the door to a strategic relationship. I’d really like to get you on a 20-minute call if you’re up for it’

2. Prep your executive

“The will to win is not nearly as important as the will to prepare to win” – Vince Lombardi

Your executive will not show up to a call unprepared. They also will not spend an hour figuring out who they're talking to.

That's your job.

Send them a one-pager:

- Who the company is, what stage the deal is in, why this account matters
- Who their executive is, what pressure they're under, what they actually care about
- And this is the part most sellers miss: you need to give them a point of view

Not "here's what our product does."

Like this: 'Their CFO has vendor stability concerns because they're consolidating from 15 vendors to 8 as part of a board mandate to improve margins. The concern isn't whether our solution works. It's whether we'll be around long enough to matter as a consolidated, long-term partner. The message is: we've been profitable for six years, we're not dependent on VC funding, and we've supported customers through 5-7 year contracts without acquisition risk.'

That's a point of view. Not a pitch.

Then you give them three key messages, a simple call structure, and you're done.

-

{EDIT} Register here: https://lnkd.in/df7UzDEW

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