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

The worst advice in sales training is also the most common "People buy from people they like."

This feel-good sound bite has probably cost more deals than any other sales myth.

Modern B2B buyers don't care if they like you.

They care if you can solve their problems.

Buyers are evaluating solutions, not salespeople. Look does it help to be both….10000%

But most will take competence over charisma all day

Here's what actually drives purchase decisions: 
➡️ Understanding their business better than the competition. 
➡️ Demonstrating clear ROI with specific, measurable outcomes. 
➡️ Proving you can implement successfully with minimal risk.
➡️ Providing social proof from similar customers. 
➡️ Making the buying process easier, not harder.

The best sellers I track aren't the most likeable. They're the most helpful.

They don't try to be your friend. They try to be your guide. 
They don't focus on building rapport. They focus on building confidence. 

Stop trying to make buyers like you. Start trying to make them trust you.

Trust comes from competence, not connection.

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

AI training is the new “Sales Kickoff high”

Everyone attends

Everyone nods

Everyone goes back to their desk… and uses it twice.

Then they go right back to the 2018 playbook

That’s the entire game in 2026:

Curiosity + consistency

Not “which AI tool is best”

Not “what prompt should I copy/paste”

The reps (and SEs) who win are the ones who turn AI into an everyday habit… not a one-time experiment.

Here’s the part most sellers miss:

AI’s real power isn’t prospecting

It’s pre-sales

Discovery. Point of view. Tight demo narrative.

Turning a “qualification call” into a validation session.

That’s where teams close 10–30% more (and most orgs have no idea why).

Tomorrow’s episode of AI Powered Seller drops with David Maloof

We get tactical on:
→ How AI-assisted discovery actually works
→ How pre-sales + AEs stop tripping over each other and start attacking deals as a unit
→ How to use transcripts + feedback to rebuild demo stories fast
→ Why “I don’t have time” is officially dead (3 minutes is the new standard)

If your process still starts with:
“What keeps you up at night?”
…you’re already behind.

"We need better leads" is usually code for "our follow-up process is broken" or “I thought my job was to only deal with layups”

I just reviewed lead response data for a company complaining about lead quality.

Marketing was generating 200+ qualified leads per month. Sales was responding to 23% of them within 24 hours.

Speed matters more than script.

The companies with the highest lead-to-opportunity conversion rates respond within 5 minutes.

Not 5 hours. Not end of day. 5 minutes.

But most sales teams treat inbound leads like they're doing them a favor by calling back.

"I'll get to it when I finish these other calls."

Meanwhile, your competitors are already having conversations with those prospects.

The best lead response systems I've seen work like this:
Minute 1: Automated email confirmation 
Minute 2: Text message with calendar link 
Minute 5: Phone call from AE 
Hour 1: Video follow-up if no contact 
Day 1: LinkedIn connection with personal note

Your leads aren't bad. Your response time is.

Marketing can't fix what sales won't follow up on.

New year. Same playbooks.

That gap is about to get expensive.

AI isn’t moving at planning speed. It’s moving at execution speed.

AI isn’t just evolving. It’s outpacing our team’s ability to adapt.

We just dropped a deep-dive on where AI actually stands heading into 2026. What tools are saving reps time, what features are driving revenue, and where the next wave of innovation is going to hit.

Here’s what stood out to me:
⚡ 28% of sellers are already saving 5+ hours per week using GenAI like ChatGPT.

📈 Reps using AI in prospecting are booking 10% more meetings in the first month.

🧠 Adoption isn’t just about automation. It’s about skill development, onboarding, and personalized messaging at scale.

And the gap between prompting and strategy-driven GPTs is widening fast. The winners in 2026 won’t be the teams who use AI.  It’ll be the teams who train it to sell like they do.

If you’re still treating AI like a “nice to have” as you kick off the year, you’re going to get smoked by someone who turned it into a competitive advantage months ago.

Check out the full report below or DM me for the breakdown.

State of AI

Your CRM is making your sales team dumber

Every time a rep updates an opportunity stage without understanding WHY the buyer is moving forward, you're training them to be process followers instead of deal strategists

Guess what MEDDPIC or MEDDICC or whatever Ps and Cs doesn’t actually track if your people ran a good call or now which is the wild part

Most CRMs track what happened.

They don't track why it happened.

Stage: Discovery Complete ✓ 
Why they agreed to move forward… [blank]

Stage: Proposal Sent ✓ 
What convinced them we're the right solution… [blank]

Stage: Negotiation ✓ 
What competing priorities might derail this… [blank]

Your reps are updating stages like they're checking boxes 
They have no idea what's actually driving buyer behavior.

The best sales managers I know have added one custom field that changes everything 
→ Buyer motivation for this stage progression

And then we use AI to summarize and gut check this and call out threats around this as well 💥

This forces reps to document the actual driver 
Instead of "We sent a proposal," they write "CFO confirmed budget approval and wants to see ROI projections."

Instead of "Discovery complete," they write "Security team identified three technical requirements that we uniquely solve."

When reps understand buyer psychology, they can predict next steps.

Your CRM should be building deal intelligence, not just tracking activities.

Generic is officially dead

Not underperforming

Not “less effective”

Dead.

AI can already write a decent email

AI can already personalize at scale

AI can already sound like every other seller in your market

Which is exactly why AI-generated personalization won’t cut through the noise in 2026

The only thing you’ll have left is you

Your judgment

Your point of view

Your ability to make the last 10 percent better than everyone else

That’s the shift

Higher quality work

Done faster

With the human nuance as the differentiator

In my new episode of AI Powered Seller that just dropped, I review the biggest shifts we saw in 2025 and what they actually mean for selling in 2026

Not theory

Real patterns

And what to change now before everyone else catches up

I’ve got opinions on this
Interested to hear what’s working for you 👇

Check out the episode here: https://lnkd.in/gezm4brV

Your team doesn’t need more AI tools

They need AI they’ll actually use when deals are on the line

Back in November, we ran our first AI Sales Certifications for managers and reps
It worked for one simple reason

We removed the intimidation factor

Most people aren’t blocked by AI’s potential

They’re blocked by “this feels too technical for me”

One rep summed it up perfectly

They came in with “zero to little knowledge about AI agents” and still walked out confidently building real tools because complex ideas were broken down into practical, usable steps

That’s the bar

So we’re running it again

🚀 Next session starts in February

What you walk away with in 3 weeks
→ Managers clone their best thinking into AI
→ Reps build a personal AI stack that knows their product, territory, and deals
→ Research, prep, and data entry stop eating selling time
→ Coaching and deal strategy become systematized
→ No code. No technical background. No theory-only slides

This isn’t “try this prompt”

You build Custom GPTs, Gemini Gems, and AI Agents that fit how you sell

Managers close the process vs. production gap
Reps get a digital intern handling the busy work

⏰ Sign up before January 17th and get $150 off
👥 Team pricing available

Check out the links below and DM me with any questions
Managers 👉 https://lnkd.in/gsuQVGCT
Reps 👉 https://lnkd.in/g5vjXdEk

Open article: AI Sales Rep Certification | Sales Agents & Advanced GenAI by bit.ly

AI Sales Rep Certification | Sales Agents & Advanced GenAI

AI fluency won’t get you promoted in 2026

But it will get you passed over

Two VP of Sales candidates

Candidate #1
→ Big-name logos on the resume
→ Ran the “proven” sales playbook
→ Talks about tools, process, and headcount

Then I ask one question

“How are you getting 20% more revenue with the same team?”

No mention of AI

No chance

Candidate #2
→ “Here’s how AI replaces admin work”
→ “Here’s how we personalize without scaling volume”
→ “Here’s how reps perform like 2–3 people”

That’s the hire

This is what I break down on the next AI Powered Seller episode

2026 is the year the gap shows up on the org chart

Who moves up

Who stalls

And why AI fluency decides it

If a candidate doesn’t bring up AI unprompted, do you trust them to lead a team right now?

I want to hear how you’re thinking about this
Drop your take in the comments 👇

Founder @ FDTC → I help startups go from $100K-$15M by improving sales processes, playbooks, & people → Building the #1 SaaS sales coaching program for AEs → Featured in Techstars & Sales Hacker → #helpmedontsellme

It was Monday morning, 11 AM when I went to my boss and said, “I’m sorry, this job, sales...it’s not for me” and I left.

That was 13+ years ago.

At 22 years old I landed my first real job fresh out of college ready to be a “career person.”

I crushed the interview.

But when I came into work for my first day at 10am, I quickly realized that I was scared sh**less of sales, and quit within the first hour.

For the next 3 years, I had PTSD and avoided sales like the plague.

I played it safe and stayed in my comfort zone.

No sales-related stuff whatsoever.

I lost my confidence and ambition. 

I missed career opportunities and wasted away my early 20s.

Fast forward to present day:

I'm a former 2X VP of Sales who took 1 startup from $0 ARR to ≈ $10M ARR in 4 years, and another from $1.5M to ≈ $4.6M ARR in 18 months.

I now teaching SMB AEs and teams how to be top sellers, make higher 6-figures, and get promoted through repeatable systems and playbooks.


Want to learn more? Book a clarity call: https://calendly.com/fdtc/30min 


P.S.⚠️ Grab my top (FREE) 24 discovery questions 6,000+ salespeople are using: https://bit.ly/4d3B2sl


Otherwise, you can find me here:
► YouTube: https://www.youtube.com/@demotoclose
► iTunes: https://apple.co/3Fome9g | Spotify: https://spoti.fi/408V0LS
► Twitter: https://twitter.com/@mistamor

Mor Assouline

A CRO of a Series B company DM’d me this a few days ago:

“Every single AE hit quota this month. 14 for 14. Not only has this never happened before at our company, I’ve never seen this happen at any company I’ve worked at.”

This wasn’t luck.

I’ve been coaching their AEs for the past couple of months.

→ 1:1 sessions.
→ Real call reviews.
→ Deal reviews and planning.
→ Mindset / Belief upgrades.
→ Building better processes and playbooks.
→ Working alongside their talented sales managers every week (who are absolute rock stars)

Here’s what we cleaned up:
1. Rebuilt how they run discovery calls for different segments / personas.
2. Rebuilt how they run demos so they’re selling the problem, not the product.
3. Coached them on how to hold the line when going over pricing.
4. Trained them on how they manage their time and pipeline.
5. Each AE had a personalized skill plan that we reviewed every week and tracked progress.

Every single rep leveled up, and it’s been working.

The sales team set the record for the most new ARR in their company’s history, and this is just the beginning.

You know what's more expensive than coaching?

Replacing reps every six months because they never had a real process to follow.

Missing your number three quarters in a row while you "figure it out."

Watching your best people leave because they're tired ofcarrying the team.

14 for 14 is cheaper.

Founder @ Demo to Close / The #1 Sales trainer & coach for SMB AEs and SaaS companies that want to sell better & close larger deals / 2X VP of Sales / Unseller

I coach an SMB AE who's hit $15K months in commission alone 3 quarters in a row. Within 1 year, he got promoted to MM. Here's something he does that many reps aren't willing to do:

→ He isn’t scared to surface objections on calls.

Most AEs try to avoid objections, but he proactively looks for them.

His thinking: I rather be on the call handling concerns that would come up when we hang up

Some examples I taught him to ask:

→ After showing a feature: “Based on how we [solve problem] what do you feel might not work for you or your team?”

→ At the end of the call: “When you take this back to [stakeholder], what would some things they’d have reservations about that would pause all this?”

→ During call: “What other initiatives is [higher stakeholder] dealing with that would cause this to be pushed to next quarter?”


The top 1% of AEs are masters of asking great / thought provoking discovery questions.



P.S. Here are 24 more discovery questions 6.6K+ AEs are mastering: https://lnkd.in/eR69raD4

High-paid SMB AEs spend their time:

→ Planning their day the night before
→ Recharging so they don’t burn out
→ Disqualifying opps that are not a fit
→ Upgrading their mindset, beliefs and skills
→ Reviewing their metrics weekly like a CFO
→ Calling buyers as soon as they fill out the form
→ Disqualifying fast to protect their time and calendar
→ Consistently blocking out time to prospect and doing it


Low-paid SMB AEs spend their time:

→ Pitching during discovery
→ Letting their calendar run them
→ Waiting for marketing to send them leads
→ Following up with “just checking in” emails
→ Arguing with RevOps about Salesforce stages
→ Complaining about quota instead of raising their skills
→ Talking about features instead of problems on discos/demos
→ Hoping this quarter will be different without changing anything

Same seat.

Different mindset.

Different habits.

Different skills.

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The Battle

Jake Dunlap

Mor Assouline

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Posts

Engagements

Likes

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