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 👇

Amir Reiter

RevOps Marketplace CEO | Pioneering remote hiring solutions in LATAM | Empowering companies to hire skilled talent at competitive costs l 4.9⭐️on G2

I built CloudTask because hiring sales talent is broken.

US companies post jobs and get hundreds of unvetted applicants. 

They pay recruiters placement fees regardless of outcome. 

They try offshore and get overnight shifts and communication gaps. 

I knew there had to be a better way.

Most of our clients come to us because:

- They need sales talent who can ramp in weeks, not months
- They want to see verified skills and results before the first call
- They are tired of paying fees for hires that do not work out
- They need US timezone coverage without domestic costs

CloudTask is the managed marketplace for SaaS skilled remote professionals in Latin America. 

Post a role, receive curated matches within 48 hours, interview as many candidates as needed, and pay only when the right hire is made. 

Every profile shows verified experience with tools like HubSpot, Salesforce, Outreach, Gong, Zendesk, and Intercom.

- Since 2016, we have completed over 2,000 placements. 
- 85% of hires stay past 90 days. 
- Average tenure is 24 months. 

If you sell software and need SDRs, BDRs, Account Executives, or CSMs who work US business hours natively, post a role and meet qualified candidates this week.

Vision: Every business is a lifestyle business.

Mission: Help 10,000 businesses transition to the right cloud software, which means their teams will get work done better, faster, and cheaper so they have more opportunities to enjoy the fruits of their labor.

- Set company strategies and direction.
- Model and guide the company culture, values, and behavior for maximum efficiency and healthy growth. 
- Build and lead our fast-growing sales, support, and executive teams. 
- Hone and optimize our product and service offerings. 
- Oversee and manage team building, brand management, investor relations, and overall corporate development.

Big watch out for anyone running LATAM teams, especially Colombia.

If you hired Colombian talent on fixed USD-equivalent pay in early 2025, many of them are effectively earning materially less today due to -17.2% currency swings while still absorbing local inflation around 5%. 

So their paycheck just went down 22.3%

That delta is real money in daily life.

Here’s the risk most US leaders miss: culturally, strong performers rarely raise this directly. 

They do not complain. 
They quietly start looking.

We’re seeing a spike in top-rated, already-employed talent landing new roles through our marketplace. 

Not because they were unhappy. 
Because their purchasing power dropped and they needed to correct it.

If you don’t proactively have this conversation, your best people will solve it for you by leaving.

Question for operators: are you checking real purchasing power, or just assuming retention equals satisfaction?

Founder & CEO | I help SaaS companies hire LATAM sales talent through a managed marketplace. If you want SDRs, BDRs, or CSMs who work US hours, post on CloudTask and get curated matches in 48 hours.

The Hidden Deal Killer Nobody Budgets For

You spend thousands on SDR training, CRMs, and lead lists.

Then you let a $30 headset ruin the call in the first three seconds.

That’s not a skills problem. That’s negligence.

Here’s the reality of outbound.

You don’t control when a prospect answers.

Your SDR might be in a Bogotá apartment, a Medellín coworking space, or a shared home in the Caribbean. A dog barks. 

A motorcycle passes. Someone laughs in the background.

- The prospect hears chaos.
- They don’t think “remote.”
 - They think “unprofessional.”
  -They hang up.

Deal over.

What Background Noise Actually Costs You

Noise doesn’t just sound bad. It kills outcomes.

• You lose the first impression window. Credibility is decided in seconds.
 • Key words get lost. Your intro becomes noise.
 • Qualified prospects disengage without explanation.
 • SDR confidence drops. Performance drops with it.

This compounds quietly. Most teams never diagnose it.

Why This Matters More for Remote SDR Teams

Hiring SDRs in Latin America is a strategic advantage. Better talent density. Better economics. Better retention when done right.

But remote work requires real infrastructure.

A $2,000/month SDR with a $30 headset will underperform a $2,000/month SDR with a $150 headset every time.

Not sometimes. Every time.

What Actually Matters in a Headset

Not the brand. Not the marketing.

One thing matters:
A noise-canceling microphone, not just noise-canceling speakers.

If the mic doesn’t filter background sound, nothing else matters.
The Math Most Leaders Ignore

If background noise kills just 5 percent of your connected calls:

 • 2 lost conversations per week
 • 100+ lost conversations per year
 • At a 10 percent close rate and $5K deal size
 • That’s ~$50K in lost pipeline

A professional headset pays for itself in days.

The Bottom Line
A headset is not a perk.

It’s revenue infrastructure.

If you’re hiring remote SDRs and not standardizing audio quality, you’re bleeding deals and blaming the wrong things.


Your SDR can’t control when a prospect answers.

You can control whether the prospect hears professionalism or chaos.
Choose wisely.

Amir Reiter ☁️

CEO of an AI-Powered GTM / RevOps Marketplace | Hire Remote Talent, Agencies, and Software Quickly and Easily | $5.4M in SaaS Revenue

Most CROs do not come from HR.

That is exactly why this one will win.

For years, the market treated LATAM leaders as “people operators.”
Good at hiring.
Good at culture.
Not trusted with revenue.

That belief is outdated.

Dave Menjura built his reputation as the #1 bilingual HR leader in LATAM by doing the hard work most companies avoid.

He did not optimize perks.
He engineered retention.
He learned why teams fail after 30 days, not 3 years.

That perspective is now his edge as he steps into a CRO role.

Most CROs learn revenue first and people later.
David learned people first, then revenue.

That matters.

Because revenue does not break from lack of activity.
It breaks from bad hiring.
It breaks from churn.
It breaks when teams look good on paper and collapse under pressure.

We see this every week at CloudTask.
The fastest growing revenue teams in LATAM are not led by closers.
They are led by operators who understand behavior, incentives, and accountability.

David is not becoming a CRO by title.
He is becoming one by operating like one.

Owning the full revenue engine.
Focusing on outcomes, not activity.
Building Dream 100 strategies.
Training weekly.
Protecting time like a weapon.

This is not a career pivot.
It is a market correction.

LATAM does not need more recruiters.
It needs revenue leaders who understand humans first and systems second.

That is where the next generation of CROs will come from.

If you still think revenue leadership only comes from sales backgrounds, you are already behind.

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The Battle

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