Jake Dunlap

2025 will be the year EVERY company must implement Generative AI in their revenue org. I personally am seeing time savings for SDRs, AEs, and AMs of 20-30% per role and predict that we will see quality of sales conversations go up by 40% or more.

We have developed a new category of consulting designed to help your company see these results in just weeks/months: AI-enabled Revenue Transformation

My deep passion for the science and art of sales has fueled my journey over the past 12 years as the founder and CEO of Skaled, a globally recognized sales consulting firm. According to G2, we have outperformed industry giants like McKinsey in Management Consulting and Accenture in Sales Consulting due to our mix of strategic foresight and tactical follow through.

We’ve consistently driven a 10-20% increase in qualified opportunities, reduced sales cycles by 8%, and enhanced overall team productivity by 20% within the first 60 days of engagement. Our approach is methodical and data-driven, ensuring that every strategy we implement translates into tangible business results.

With a team of over 30 elite professionals and access to a vast network of industry experts, we specialize in aligning sales and marketing to create scalable, replicable processes. We leverage cutting-edge generative AI technology to automate critical functions like follow-up, data entry, and task management, freeing your teams to focus on what truly matters—closing deals and driving growth.

As the USA Today bestselling author of Innovative Seller, I’ve helped to shape the future of sales, offering insights and strategies that resonate with both seasoned executives and the next generation of sales leaders. My work has been recognized in the New York Times, Forbes, Inc., and HuffPost. 

Check out my YouTube: Jake Dunlap to discover over 500 sales, revenue and AI for Sales videos: bit.ly/2Qu3niE

Highlights:

	• USA Today Bestselling Author of Innovative Seller - #21 in all books
	• First VP of Sales at Glassdoor (acquired for $1.2 billion - May 2018)

Chief Executive Officer

Everyday we help companies operationalize key aspects of their sales and marketing organization.  As CEOs, Senior Execs, and Sales people, our world is changing so rapidly and keeping pace is extremely hard.  We help with both strategic and tactical support through various phases of scaling and when larger organizations are looking to re-invent or stay relevant with their current marketing and sales strategies.

Here are a few of our clients in key verticals:

Enterprise Technology and Services:
Microsoft / GLG

Hospitality/Customer Service Tech:
Duetto / NoWait (acquired by Yelp) / Stella Service

HR Tech:
LinkedIn / ADP / The Muse / Grovo / ConveyIQ / Wayup / Vettery / Paypro

Education/Legal Tech:
Newsela / Bodhala / Hire an Esquire / Allovue / Codio / Busylamp

Real Estate/Financial Services Tech:
Breather / Nestio / Honest Buildings / Hightower / Everplans / CredSimple / Captalys / ReThinkCRM

Sales Technology:
Outreach / SalesLoft / Everstring / Lead Genius / Terminus / Discoverorg / Emissary.io / Redbooks / Speek / 15Five / Honey

Advertising and PR tech:
BounceExchange / SaleMove

Services:
Dom & Tom / Betts Recruiting / Moxie / Palantir

Two Sundays ago, a VP of Sales I know was on his laptop at his kid’s soccer game. Not because he wanted to be. Because it was “forecast week.”

He wasn’t coaching.

He wasn’t thinking about strategy.

He was chasing grown adults for CRM updates, cleaning up pipeline, and rebuilding the same forecast slides everyone pretends to trust.

That’s the job now. And it’s insane.

60% of Sales Manager time is getting burned.

Not on revenue.
Not on coaching.

On admin, pipeline clean-up, and babysitting updates.

Most managers are spending 15–20 hours a week doing stuff that shouldn’t exist:

Manually reviewing deals like a detective

Writing recap emails no one reads

Building forecast decks that go stale in 24 hours

Guessing which reps actually need coaching
Sitting through 1:1s with vibes… not data

That’s 800+ hours a year per manager.

At a $150K salary, that’s roughly $72K of leadership time lit on fire.
And the worst part?

We’ve all just accepted it as “part of the job.”

It’s not. It’s a broken system we normalized.

Here’s what’s changed: AI can remove 40–60% of that load in 30 days—without a massive “transformation project.”

What it looks like in the real world

1) Pipeline Reviews (no more deal detective work) - we have an AI Agent that reviews 100% of deals the EXACT way you would

AI flags deals that are fake or drifting:

-No real number / no quantified pain
-No access to buying committee
-Timeline slipping (but not reflected)
-Stage aging that doesn’t match activity
-Managers stop interrogating reps and start making decisions.

2) Coaching Prep (real coaching, not “how’s it going?”)
Instead of showing up blind, AI shows up with receipts:

-Conversion rates by stage
-Talk-to-listen ratios
-Stalled deal patterns
-Deal risk drivers by rep
-Now coaching is 30 minutes of impact, not 90 minutes of wandering.

3) Forecasting (data, not rep emotion)
AI analyzes:

-historical close rates
-velocity + stage aging
-activity quality
-prior slippage patterns

No more optimism. No more “I feel good about this one.”

Just reality.

One client freed up 12 hours per manager per week in 6 weeks.

They didn’t hire more reps.

They increased coaching capacity.

Revenue followed.

So if your managers are still spending Sundays updating Salesforce…

You don’t have a talent problem.

You have a systems problem.

I partner with forward thinking B2B CEOs/CROs/CMOs to transform their business with AI-driven revenue strategies | USA Today Bestselling Author of Innovative Seller

I started my last software evaluation exactly like this

“Before we start…here’s how you compare to your top 3 competitors, what we think fair pricing is based on public comps, and the ROI model we’ll use internally. Tell me where we’re wrong.”

I wasn’t being arrogant. I was doing what 30-40% of buyers are doing today already and just not telling reps.

I built it in 10 minutes with JourneyAI

Meanwhile, the rep was probably toggling between LinkedIn and Salesforce like it’s 2018… five minutes before the meeting. Then had prepped a bunch of MEDDPICCDPICAPECIPC qualification questions and was completely unpreapred.

Here’s the uncomfortable truth:

Your buyer often knows more about your product than your rep does.

Gen AI made that possible.

B2B buyers aren’t “learning from sales” anymore—they’re arriving pre-educated:

70%+ prefer self-serve research before talking to sales
80%+ have mostly defined requirements before the first call

They’re showing up with:

→ competitive comparisons
→ pricing benchmarks
→ ROI models
→ negotiation strategies

And it’s not because they’re brilliant.

It’s because they have a tireless analyst in their pocket now.

The old advantage in sales was information asymmetry.

That’s dead.

So what’s the new edge?

Judgment.
Diagnosis.
Reframing.

Quantifying impact in CFO language.

If your seller can’t:
quantify the cost of inaction
tie value to a CFO-level metric (cash flow, margin, payback period, risk)
reframe the problem beyond the buyer’s initial “requirements”

…then they’re not leading.

They’re just confirming what the buyer already researched.

AI is upgrading average buyers every day.

Is it upgrading your reps… or exposing them?

Your hiring process is about to get disrupted

Not by recruiters

By AI

This week on The AI Powered Seller, I sat down with Krissy Manzano, CEO & Founder of Blueprint Expansion, to break down how AI is completely reshaping recruiting and hiring.

And most sales leaders aren’t ready.

We talked about:
→ AI screening candidates before a human ever looks at a resume
→ How candidates are using AI to game your interview process
→ Why traditional hiring signals are becoming useless
→ The risk of building teams that look great on paper… but can’t actually sell

Here’s what actually happens in most companies:

A candidate interviews.

Then 4–6 execs sit in a room and say:
“Yeah, they were solid.”
 “I liked them.”
 “I don’t know… something felt off.”

That’s not a hiring process.

That’s vibes.

Krissy breaks down how AI, when used inside a GOOD, structured interview process, eliminates that ambiguity.

→ Standardized scoring based on competencies
→ Pattern recognition across top performers
→ Real data instead of memory-based opinions
→ Clear signals on adaptability and AI fluency

AI shouldn’t replace human judgment.

It should sharpen it.

Because in an AI-first sales world, hiring “pretty good” reps won’t cut it.

This episode drops TOMORROW, link in comments

Leading International @Personio | Building community @Pavilion | Architecting Growth @Winning By Design | Showing revenue teams what’s next @GTM OS

Over the past 12 years in SaaS, I’ve seen firsthand where most Founders and Revenue leaders fail: 

- No structured Go-To-Market strategy → Running multiple GTM motions at once. Growth stalls, especially beyond the home market.
- No consistent sales process → Relying on individual performance instead of repeatable systems. No scalable growth engine.
- No clear revenue insights → Looking at blended metrics instead of pinpointing what drives conversions. Low rep productivity, declining ARR per FTE.

I get it. Day-to-day operations take over, and revenue inefficiencies stack up.

The bad news? You’re responsible for fixing it.

The good news? I can help you and your SaaS business.

How I help B2B SaaS teams ($5M-$25M ARR) scale faster:

- GTM & Sales Strategy – Structuring inbound, outbound, and partner strategies across SMB, Mid-Market, and Enterprise.
- Sales Process Optimization – Improving conversion rates and reducing reliance on top performers.
- Playbooks & Execution – Building structured systems, coaching frameworks, and checklists for consistent revenue growth.
- High-Performing Teams – Hiring, developing, and structuring commercial teams with clear accountability.

Results I’ve helped drive:

→ Increased sales team efficiency by 2X through scalable sales team structuring and skill development frameworks.

→ Improved win rates to 25% by implementing structured tactical and operational Go-To-Market tactics.

→ Built GTM playbooks that accelerated ARR growth for early-stage and scaling SaaS companies to $10M ARR.

How we can work together: 

1. Coaching & Advisory – Hands-on support to build a scalable sales engine.
2. On-Demand Sessions – Solving your biggest sales execution challenges.
3. GTM Playbooks & Frameworks – Proven templates for predictable growth.

Scaling isn’t about luck. It’s about building the right systems.

What’s blocking your revenue growth today? Let’s fix it.

DM me and let’s chat.

Koen Stam

Anita has made President's Club 3 years straight. Last year she hit 183% of target while spending Q1 as interim sales leader. Earlier this month, she told 500 colleagues exactly how she does it.
 
It disappointed half the room.
 
If it were up to her, she would keep it quiet. She even called me out on stage. 
"Koen is going to put this on LinkedIn."
 
She was right.
 
Half the room wanted a template. A single tactic. A checklist they could copy.
 
Anita gave them something harder. Pure execution rigor.
 
Here are five things she does consistently that most reps skip.
 
1. She qualifies out early. And she never stops running discovery, even deep into a deal.
 
2. She maps every internal stakeholder. The blockers, the influencers, the people who show up late and kill deals.
 
3. She brings peers and leaders into deal reviews to pressure test risk. Not to show off. To find what she is missing.
 
4. She pulls in partners and customers to validate quality. Social proof from people who are not on her payroll.
 
5. And the thing that ties it all together. She runs every deal through trumpet 🎺, builds a Mutual Action Plan, and uses video to stay present when she is not in the room.
 
No shortcut. No magic script.
 
Just a rep who refuses to wing it on a single deal.
 
That is what 183% looks like up close.

3 years ago I bet on async selling. This week my face was on a Times Square billboard.
 
Let me rewind.
 
In 2022 we started using Digital Sales Rooms. The belief was simple. We needed to digitalize how we collaborate with buyers.
 
Mutual Action Plans became the core of every deal. One shared workspace. One URL. Every resource, every next step, every stakeholder aligned in one place.
 
We chose trumpet 🎺 as our platform. 12 months ago I became a Brand Ambassador. And across 1,000+ LinkedIn posts over the last 36 months, async selling has become the concept I return to more than any other.
 
Because I see what it does to pipeline every single week.
 
The numbers tell the story. Win rates across all deals were 67% higher when trumpet was used. Average deal value increased by 57% (amazing enablement work done here by Aaron and the wider enablement team led by the amazing Gesine.
 
Those are not industry benchmarks. Those are ours.
 
What Nick and Rory have built at trumpet goes beyond a Digital Sales Room tool. They are building a category. And the speed of their progress has been remarkable.
 
This week they put my face on a Times Square billboard alongside Brian LaManna, Hailey Linz, and Aoife Coburn from Gong, HubSpot, and Stripe.
 
Proud product user. 
Proud ambassador. 
Proud band player.
 
3 years of betting on async. The data did the talking. The billboard was just the receipt.

I’m happy to share that I’m starting a new position as Co-chapter Lead the Netherlands 🇳🇱 at Winning by Design Growth Institute!

In 2017 I implemented Winning by Design at Teamleader and something clicked.
 
Bowtie. 
Data model. 
RRR emails. 
Compelling event. 
Emotional vs Rational impact. 
Critical event. 
First impact. 
SPICED. 
SP3V.
 
Every framework made sense. Not because it was trendy. Because it was grounded in how buyers actually buy.
 
I walked out thinking: this is how it should work everywhere.
 
Eight years later, I still think that. Every company I have touched got better when I applied these fundamentals. Every single one.
 
And I have watched enough companies do the opposite. More tools. More headcount. More complexity. Still wondering why growth feels broken.
 
The ones that win have better systems underneath their growth. Better process design. Better architecture across the entire revenue engine.
 
That is what Winning by Design called Revenue Architecture. Now it has evolved into Growth Architecture.
 
Together with André, my partner in crime for over five years and a true operator who lives this work every day, we are launching the Dutch community for the Winning by Design Growth Institute.
 
15+ founding members are already in.
 
On Thursday March 26th we are hosting our first informal introduction here in the Netherlands.
 
This is for founders who are done guessing. 
For GTM operators who want proven systems. 
For fractional leaders who want real frameworks behind their work. 
For investors who want their portfolio companies to scale with structure.
 
If any of that sounds like you, DM me "Growth Institute" and I will send you the details.

3 years of ChatGPT. Thousands of prompts.
 
And I still had to explain who I am every single time.
 
That was the moment I knew it was over.
 
Here is what broke it for me.
 
I write LinkedIn posts, a Substack newsletter, and GTM playbooks every week. Content is how I build trust with founders and GTM operators.
 
And for 3 years, every time I opened ChatGPT, I started from scratch.
 
Pasting my tone of voice. Explaining my audience. Describing what I do and do not write.
 
And still the output read like it could have come from anyone.
 
I tried Claude on a random Wednesday. Built my first project.
 
Uploaded my writing instructions. What to write. How to structure. What to avoid.
 
Then I uploaded 20 previous LinkedIn posts, a few newsletters, and two GTM playbooks I had already written.
 
Something shifted.
 
I recorded a voice note on a walk. Raw thoughts, unfiltered. Pasted it into Claude.
 
And what came back read like me. My words. My rhythm. My edge. No cleanup needed.
 
That never happened with ChatGPT. Not once in 3 years.
 
Here is why it works:
 
1. The instructions tell Claude how I write. My rules, my formatting, my voice.
2. The uploaded content shows Claude what my writing actually looks like in practice.
3. Memory compounds. Every conversation makes the next one sharper.
4. My voice input is always the starting point. The raw thinking stays mine. Claude shapes it, it does not replace it.
5. It pushes back. Questions my structure. Challenges a weak hook. ChatGPT just said yes to everything.
 
The workflow is simple. I think out loud. Claude builds with me.
 
The output sounds like a human who has done the work. Because the input came from one.
 
If you want to try this, start here.
 
Create a project. Upload your best previous work. Write clear instructions on who you are, who you help, and how you talk.
 
Then give it a voice note and see what comes back.
 
Most GTM operators are still using AI the same way they did 12 months ago.
 
Are you?

Saturday morning. 45 minute walk. No music. Just me and something my CRO told me in January that I keep coming back to.

“How you start Q1 defines how your full year gets shaped.”

We had a rough start. Pipeline was slow. Energy was off. The kind of January where you tell yourself there is still time.

Fast forward to today. Halfway through Q1. Almost at 100% year to date. Last week was one of our best weeks for new business all year.

What changed?

Not a new playbook. Not a new hire. We stopped drifting and started correcting. Early.

Here is the thing most operators miss in Q1. You get pulled into execution fast. Day to day takes over. Deals move. Fires start. You feel productive.

But the big programs that define your year need to get shaped in Q1. Delay those and you delay pipeline. Delayed pipeline means delayed conversion. Delayed conversion means your new customer cohort shows up late. And late adoption compounds into a weak H2.

A strong Q1 sets up a strong H1. A strong H1 carries momentum into H2. The math is simple. The discipline is not.

This morning I went out with the dog (she is lovely to babysit André 🐶) and the kids first. Then I kept walking. Alone. 45 minutes, maybe 60. No agenda. Just letting my brain process the week, the last 7 weeks, and the 6 weeks we have left in Q1.

What do I need to keep doing. What do I need to stop. Where do I need to course correct.

You do not have to do this weekly. You do not even have to do it monthly. But some cadence of structured reflection is the difference between operating with clarity and just being busy.

I have started using Claude as my reflection partner. Not for answers. For structure. Every reflection compounds on the last one because it remembers context. It turned scattered thinking into a system.

Busy calendars will always win if you let them. Reflection is how you take back control.

No alternative text description for this image

I scaled a SaaS company from 2M to 10M in under 3 years.
 
The playbook that worked was the opposite of what most teams attempt.
 
We narrowed instead of expanded.
 
Netherlands first.
 
Belgium could wait. The book of business was not large enough and I did not care.
 
We trimmed our ICP from "50 to 500 employees" to something so specific it included industry, desk vs non-desk ratio, and tech stack attributes.
 
We gave our CSM veto power over new pipeline.
 
If we could not make a customer happy, we did not accept the deal.
 
Pipeline went down.
 
Win rates hit 34%. ACV went up. Cost of acquisition dropped.
 
Every growth ceiling I have hit in the last decade taught me the same thing.
 
The answer was never more channels, more headcount, more spend.
 
The answer was better execution, better focus, better discipline on what actually moves pipeline.
 
I spent the last months turning that lesson into a system.
 
The GTM Channel Reset Playbook.
 
12 steps across 3 phases. Built on 10+ years of GTM leadership and backed by 100,000+ signals from operators and founders.
 
It includes a self-assessment, a full workbook, an implementation timeline, and a cadence pack to keep the system running.
 
I am publishing it in 3 parts this week on my Substack.
 
Part 1 and 2 are free. Monday and Wednesday.
 
Both designed so you can take what you read and apply it in your day to day immediately.
 
Part 3 drops Friday exclusively for paid subscribers, including the full workbook, implementation timeline, and cadence pack.
 
Part 1 drops today.
 
This playbook is also the foundation of my first GTM OS Cohort.
 
12 weeks. Weekly office hours. All the learnings from 10+ years of scaling SaaS companies, packaged into one program.
 
Starting April.
 
Keep an eye on my posts in the coming weeks.
 
Link in the comments.

We have run 100+ deal reviews over three years.
 
The ones that actually moved deals forward all share one thing. 15 minutes per deal. Here is the system.
 
45 minutes. Three deals. 15 minutes each. Hard stop.
 
Before the session, nobody prepares a narrative. Gong already captured the calls. MEDDICCC (yes 3 C's) fields are populated. The data is there before anyone walks in.
 
We don't ask "how is the deal going." We open with the qualification score and go straight to the weakest field.
 
One field. One gap. One action.
 
The AE doesn't defend the deal. The AE owns the takeaway. They close the loop before the next review. If the gap is still open, we know exactly where the deal stands.
 
No storytelling. No 30 minute walkthroughs. No manager rescuing deals on Friday because nobody caught the weakness on Tuesday.
 
This changed how our team closes.
 
In 2026, pipeline is shrinking. Win rates are dropping. Buying committees are growing. You cannot afford deal reviews that hide structural gaps behind narratives.
 
Deal reviews are one piece of a bigger system.
 
I spent the past weeks building a full Deal Progress and Closing playbook. Structured discovery. Weighted qualification scoring. Stage gates built on evidence. Multithreading protocols. Momentum tracking. Forecast governance.
 
Every component comes with an implementation timeline and the infographics to run it.
 
The full playbook is on my Substack.

taplio

The Battle

Jake Dunlap

Koen Stam

Followers

Posts

Engagements

Likes

Performance ScoreJake Dunlap's LinkedIn Performance

Performance ScoreKoen Stam's LinkedIn Performance

Ready to grow your LinkedIn presence?

taplio

The Battle

Jake Dunlap

Koen Stam

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Jake Dunlap's LinkedIn Performance

Performance ScoreKoen Stam's LinkedIn Performance

Ready to grow your LinkedIn presence?

Performance ScoreJake Dunlap's LinkedIn Performance