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

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

I used to say I have no time to work out.

A 30–45 min workout isn’t just 30–45 min.

Between commuting + showering it’s at least 1–2 hours.

But what if it didn’t have to be?

3 of the best purchases I made over the last 6 months:
	1.	A pull up/dip bar for my office
	2.	A stand up desk
	3.	An in office treadmill

All are in office.

Requires 0 commute.

Integrated in my work.

I made it too easy for myself to say yes.

Founder @ Demo to Close | “Success feels like luck. I don’t have a repeatable process.” → I coach SMB & MM AEs on the system for predictable performance | 2X VP of Sales

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SMB sales is overwhelming.

Unlike ENT, it feels like you don’t have time to breathe.

I’ve been there.

- Running 5-6 sales calls every day.
- No time to prep for next meeting.
- Forgetting to follow your call structure.

It’s a lot.

So here’s how I'd reset my focus before the next call:

I’d have a pre call ritual.

Before every call, I’d take a walk around the office, and mentally rehearse what’s about to happen.

It worked for me.

What’s yours?

I audited 47 discovery calls. Inbound close rate = 45%. Outbound close rate =17%. Same MM AE, same approach, but completely different results.

They forgot the most important part of discovery:

You should not treat inbound and outbound leads the same way.

Inbound prospects:
- Raised their hand
- Have a problem they're trying to solve
- Expect to be challenged and questioned

You can be direct: "What's broken that made you reach out?"

Outbound prospects:
- Didn't ask to talk to you
- You're coming to them
- Need context before they'll engage
- You have to earn the right to ask questions

The principle: Your approach should match their entry point.

Inbound = Permission granted They gave you permission by raising their hand. Use it.

Outbound = Permission required You need to earn the right to dig deeper.

Example:
Wrong way with outbound: 
→ "What challenges are you facing with your current system?" (They're thinking: "Who is this person and why should I tell them anything?")

Right way with outbound: 
→ "When I speak with [personas], they tell me they're dealing with [problem A], [problem B] or [Problem C]. So when I did some research, I noticed [relevant trigger] and was wondering if any of that is also something you're experiencing too?"

The lesson: Stop using the same playbook for different situations.

Read the room and map your approach to where the buyer lives.


P.S. Here are 24 of the top discovery questions 7,000+ AEs have been using: https://lnkd.in/eR69raD4

A mid-market AE I just started coaching told me his problem is "inconsistent prospecting." I asked him to screen share and show me his process. 

I found the real problem within 5 minutes.

Me: What does inconsistent mean?

Him: prospects once or twice a month instead of weekly.

Me: Why?

Him: It takes 3-4 hours and it's exhausting.

Me: Okay. But why does it take 3-4 hours? What are you actually doing 
during those 3-4 hours?

Him: He logs into database directory, searches a specific vertical and adds 
some criteria, opens 50+ websites. Decides if each one is a fit.

Me: How does you decide which is worth going after?

Him: Gut feel. I just know when I see it.

Me: What IS gut feel?

Him: don't know. It's like... I can't explain it. I just know based on certain 
things I’m noticing.

Me: sounds like its a mix of certain criteria and intuition?

Him: Yes

Me: "So your brain has seen hundreds of companies. Some closed. Some 
didn't. Your brain learned patterns. What "good" looks like. But you never made those patterns conscious. So you can't fully articulate them."

Him: Yeah, exactly. That's the problem. It only works when I do it.

That's the actual bottleneck.

His knowledge is trapped in his subconscious and he’s working off of intuition.

So here's what we're doing:

Step 1: Figure out what his brain is actually looking for.

Pull every deal he closed won → Feed it into Claude → See what's consistent.

The goal: find the patterns of what good looks like.


Step 2: Write it down.

Once we know what "good" looks like, we make it a checklist.

Now it's not in his head (step 1 and 2 will be tedious at first).


Step 3: Let Claude do the work.

Export companies from the data base results that match the initial criteria and upload to Claudecowork.

Claude checks each website against the checklist and returns the good ones.

20 minutes instead of 3-4 hours.

He’ll be able to build more pipeline, faster.

His "intuition" won't be stuck in his head anymore.

It's in a system.

Which means he can repeat it and scale it



P.S. I’ve been spending 3-4 hours a day vibe coding. All this AI can be overwhelming if you don't know where to point it to. The easiest place to start, at least for me, is looking at what tasks are draining my time that I'm doing manually that I can automate.

Every week I run a group coaching call for AEs at companies like LinkedIn, Hubspot, Klaviyo, Nooks, etc.

Every week after the call, I'd spend 30+ minutes doing the same thing:
→ Pull up the Fathom recording
→ Read through the transcript
→ Summarize the key topics
→ Format everything into a lesson
→ Publish it to our learning portal
→ Copy the topics into Slack for the community

It's not hard work.

But it's tedious as hell and eats at my calendar.

So I automated the entire thing with AI (via Claude Cowork).

Now, every Friday at 1:00 PM, a Claude task kicks off automatically.

It opens Fathom, extracts the full transcript, identifies the coaching topics, generates a formatted title and "How to..." summary for each topic, creates and publishes the lesson in Kajabi, moves it to the top of the course, and posts a recap to our Slack channel.

The whole workflow runs itself. I just show up, coach, and it's done.

Fathom uses encrypted video streaming that blocks automated downloads. Kajabi's drag-and-drop needed custom browser scripting to reorder lessons. The "simple" automation required real problem-solving at every point.

Some lessons I'm learning:
1. "Automate everything" is the wrong goal.
2. Recurring tasks are the highest ROI automation targets.
3. AI agents are better at browser automation than you'd expect.
4. The bottleneck is rarely the AI.

We're entering a whole new era where the competitive advantage isn't knowing how to use AI, but it's knowing how to wire AI into your actual workflows.

If you're a seller or sales leader doing repetitive pre or post-session work every week you're sitting on hours of reclaimed time (houuuurs)




P.S. I’ve been coaching AEs in my community on how to leverage AI in sales. Feb and March coaching slots are sold out, but if you’re interested in joining HMU, we have a waitlist.

See this woman to the left?

If you're in SaaS sales, you might not recognize her.

Her name is Erica Feidner

She's known as the Piano Matchmaker

And every serious salesperson should study her.

Inc. called her one of the top 10 salespeople of all time.

She was Steinway & Sons's top salesperson for a decade & sold over $40M in pianos.

Here are 5 things she does that puts her in another league:

1. REDEFINE YOUR ROLE:
Erica refers to herself as a "piano matchmaker" rather than a salesperson.

Her: "My passion in life is to pair people to pianos in a way that reflects their lifestyle and their personality."

That means YOUR solution may not be the right fit for your prospect (and that's okay)

It took me years to realize not every interested prospect is a fit.

Instead of being a salesperson, be a [solution] matchmaker.


2. PRIORITIZE CLIENT EXPERIENCE OVER THE SALE:
The best salespeople know that buyers don't want to be sold, they want to be helped.

They know that if a prospect feels good with you early on, you're closer to making a deal.

Erica: "What I try to bring to the floor is a wonderful experience for clients and finding exactly the right piano that is in line with their needs and financial comfort zone."

If your prospect's highest priority is price, consider showing them a range of your rates first.

Every sales call should be customized.


3. DON'T RUSH TO MAKE THE SALE:
If the perfect piano isn't available, Erica tells clients to wait until she finds the right one, even at the risk of them purchasing elsewhere.

Her: "If I feel that the piano isn't perfect, I'll tell them to go home and I'll call them when I find the right one."

But, this is exactly how she builds trust and credibility.

I closed a Series D company last year to do onsite sales training for their AEs.

I told the head of sales I'd rather we slow down just to make sure I'm the right fit.

We spent an extra 2 days doing more due diligence.

I earned his trust and closed the deal.


4. READ THE ROOM:
Use conversational cues and body language to understand what the client's sentiment is.

Erica: "I listen to the tone of their voice, the speed of their voice, eye contact or not."

This is why turning on webcam first on Zooms is table stakes.

Example: If your prospect raises their eyebrows in surprise during your sales demo, that's an indicator that they're impressed.

"Sam, seems like this is striking a chord with you?"


5. ADAPT BY PERSONA:
Customize your communication style to fit the client's background and preferences.

Erica: "For instance, engineers might need detailed technical information, while musicians might prioritize sound quality. Once I figured that out, I can speak in a language that they understand best."

For example: In my experience, meet with your prospect before a demo to understand who's showing up and what they care about.

I used to make the mistake of winging it and showing up half prepared.

Half prepared = not prepared.

I review 30+ calls a week for the reps I coach. This is the single most expensive habit I see (it's not discovery).

I was reviewing a call last week where the rep did everything right.

Really solid discovery and demo. 

Then he showed pricing.

Prospect said: "Hmm, that's a bit more than we expected."

And the rep, without missing a beat, said: "Yeah, so we actually have some Q4 pricing incentives right now. If you move forward by end of month, I can probably get you a better rate."

Nobody asked for a discount.

The prospect hadn't said they couldn't afford it.

Hadn't even finished their thought.

The rep just gave it away.

Here's what happens when you do that:

1. You tell the buyer the price was never real. 
2. And you train them to expect a deal every single time you show a number. 

So now every future conversation with that buyer starts with them waiting for you to cave.

I call this flinching.

Most reps don't even realize they're doing it. 

They hear "that's more than expected" and their brain skips to "I'm about to lose this deal."

So they reach for the only tool they think will save it.

The problem: "that's more than we expected" means completely different things depending on who's saying it and why. 

Each version needs a different response.

If you flinch before figuring out which one you're dealing with, you give away money for nothing.

Stop treating every pricing pushback the same. 

Start diagnosing before you respond.

I'm breaking down the full framework in Monday's newsletter. The diagnosis, the talk tracks, all of it (including a cheatsheet you can use).

Read it here tomorrow along with 6.6K+ sellers: demotoclose.com/newsletter


P.S.  It's my birthday today. Instead of cake, I'm giving you a newsletter that'll save you thousands in commission.

I'm consulting for a company that raised over $120M, and we've built AI agents based on my sales methodology to audit thousands of sales calls at scale and score them automatically.

The results are automatically fed into:

a) Slack - real time notifications
b) Salesforce - to generate report on trends

We’re using this to coach reps on high leverage strategies.

It took us about 1.5 months to get to v1 (and still tweaking it)

But the takeaway from implementing this is:
1. What is a high frequency task
2. That is low complexity
3. But is manual and guzzles time,
4. That you can chop up into smaller mini tasks?

Build an AI agent around that and tinker.

Then do it again, and tinker.

You won’t learn about how to be an AI native by reading about it all day.

This is where I built my confidence in sales.

Wearing a suit and door knocking during in Miami (in summer...it's hot).

The cheapest homes in this neighborhood are $10M-$15M.

2 years prior I had quit my first sales job because I was scared.

That notebook you see me holding was a list of all the homeowners that told us to F off.

I had to make sure we never knocked on their homes again.

I never closed a single deal that year in that neighborhood.

But I walked away with a sales MBA

The one thing that can compensate for lack of sales skill is confidence.

And after 1 year of door knocking and cold calling I was confident as hell.

That’s how I eventually found myself in tech sales and teaching others how to be confident and sell better.

First as an early stage AE.

Then as a 2X VP of sales.

Here are 14 (of the many) rules that will never be dead in sales that I've learned:

1. Always show up even if you're not in the mood

2. Don't move onto another skill until you've improved the current one

3. You'll sell more when asking questions vs talking/pitching

4. Always have a compelling reason for the prospect to listen/show up

5. A few bad experiences and screw ups doesn't mean YOU are a screw up

6. You'll always learn more when you fail vs succeed

7. Betting on yourself is the best seed you can plant

8. Surround yourself with people who you look up to

9. Affirmations are cheesy until you do it consistently

10. Community is underrated, never do it alone.

11. Expect the work to be harder/longer than what you anticipated 

12. There is always a trade-off, always.

13. How you say things is sometimes more important than what you say.

14. Building a brand makes sales so much easier

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