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 👇

Jarrod Best-Mitchell

$100MUSD+ in Client Revenue Generated | Helping Individuals Stand Out on LinkedIn | Sales Trainer | Sales Coach | LinkedIn Trainer | LinkedIn Profile Optimization | Social Selling Trainer | Keynote Speaker

Whether you’re a business looking to empower your Sales team or an individual wanting to take your LinkedIn game to the next level, I've been able to make an impact across the Caribbean using my unique combination of Sales and LinkedIn experience. 

OH - I'm also known for my obsession with the colour yellow. You'll see it in ALLLLLLL of my content. 

To learn more about what I do Reach out via LinkedIn visit www.jarrodbestmitchell.com to schedule a consultation and learn how I can help you achieve your goals.


SALES |LINKEDIN | YELLOW

Ambassador

There are 100 Sales AI tools that focus on salespeople.

Humantic AI is the only one that focuses on buyers.

It is a Buyer Intelligence platform for revenue teams.

Top revenue teams use Humantic's Personality AI to identify early adopters, help their BDRs personalize outreach and enable their AEs with vital customer insights for every deal.

I'm not a fan of the re-introductions posts but just in the last 7 days I've had over 100 new followers and over 2,500 for 2025. So here it goes. 

Most persons think I'm a marketer. (I'm just good a making myself known) 

I'm a Sales Trainer. A LinkedIn Strategist. And I'm OBSESSED with the colour Yellow. 

Most persons call me "The Yellow Guy" 

Over the past five years companies across the Caribbean have called on me when sales performance has plateaued and they need modern sales strategies to help sales teams sell to today's buyers. 

I’ve trained sales teams in banking, insurance, telecoms, manufacturing, FMCG, energy, retail, and professional services.

Across Trinidad, Jamaica, Barbados, Guyana, Cayman, Turks and Caicos, and The Bahamas, The Lesser and Greater Antilles. 

I’ve been fortunate to work with companies like Republic Bank, Guardian General, Sagicor T&T - Barbados - Eastern Caribbean, BTC, Guardian Life T&T - Jamaica, Scotiabank, Unilever, Digicel, ANSA Bank, and several regional institutions.

How most companies find me is through this amazing platform...LinkedIn. 

I post Sales & LinkedIn content daily with a sprinkle of motivation here and there. I'm recognised as an expert on the platform and have helped over 350 persons in 2025 alone understand and better use the platform. 

So if your need is for Sales, here's how I can help;
- Sales Strategy
- Sales Training 
- Sales Talks
- Sales Coaching
- Sales Content

My strategies is focused on the buyer and has helped the 60+ companies I've worked with generate over 100MUSD in revenue. 

If LinkedIn is where you need guidance;
- LinkedIn Profile Optimization for Job Seekers
- LinkedIn Strategy for Companies and C-Level Execs
- LinkedIn Content that converts. 

Clients hire me because my content has educated them on their problem and they want context for their exact situation. 

They sense my passion to help them solve their problem and they get to learn about why I'm obsessed about Yellow. 

If you've been engaging with my content - THANK YOU!

Don't hesitate to DM me to ask questions or give feedback on content that has helped you. 

For 2026 my goal is to help more persons gain visibility in order to achieve their goals. DM if you'd like to be visible in 2026. 

P.S. The Yellow thing started since I was five years. old it just got worse as I made my own money and worser when I became an entrepreneur.

Sales Trainer | LinkedIn Trainer | LinkedIn Profile Optimization using AI | Social Selling Trainer | Keynote Speaker

If you're looking for a great book on Leadership written from a Caribbean perspective...let me introduce you to Johnathan Johannes

I've been connected with him since 2017 and seeing his content all throughout 2024/5. 

In particular about leadership and then following the journey as he launched his book - The Exception Code. 

Of course I had to grab a copy and then when he said he would be in Trinidad briefly I had to take the opportunity to get it signed.

Johnathan, Thank you for the amazing words written and taking the time to chat. 

And the advice as I also write my book....priceless. I feel alot calmer. 

And I have no doubt that your book will win an award at the upcoming Bocas Lit Fest. 

You can grab a copy here - https://lnkd.in/e_wJm6_Y 

Y.O. 💛

Two first year insurance advisors say hi to me at a coffee shop. Guess what happened next? 

A full masterclass on sales. 
- The importance of content
- Sales strategies
- Revised call scripts (because my gosh
...those scripts they had were awful) 
- Understanding their numbers.
- The mindset needed to be in insurance sales. 

And of course I made them both do a video and post it to their WhatsApp and social media platforms. 

About 20mins total.

Their quota is attainable once the effort is given. 

Great meeting you Omadarah and Shauna!

Saying allow me to reintroduce myself makes some persons cringe. So here's an alternative. 

Share the lessons you learnt in 2025 that youll be taking into 2026.

Successes
Failures
Advice

Pick one, a combo or use all three. 

Y.O. 💛

The best advice I got in 2025 came from a CRO of a tech firm. 

They're not hiring more sales reps. They're making sure the current team is optimized.

She planned on spending $30KUSD in tech to help her team versus hiring more reps which would cost about $150KUSD. That's the easiest math ever.

AI, automation and better processes. No more increasing headcount. 

So for every sales leader in the Caribbean that's my advice to you as well. 

Optimize your team before you increase their sizes. 

The average sales rep globally spends about 50% on administrative and manual tasks. 

I think for the Caribbean that figure is higher. 

Think about the impact if you helped your team get more selling time? 

Would you really need to increase your headcount? 

And yes, if you're reading this and not in sales you know this is applicable to your department as well. 

Optimization > Headcount

This advice might be obvious but most persons do the opposite. 

Most sellers on LinkedIn create pitch content. 

Its about them. 

Their services.

How great they are. 

All the generic words you can think of. 

But content that gets leads is designed with your buyer in mind. 

It thinks about the buyer's process. 

All the questions they ask. 

All the apprehensions they have. 

The content answers it. 

So when they reach to you they’re ready to buy. 

They understand your value. 

They don't feel like they've been sold to rather than they were educated. 

So if you want your content to get more leads...stop selling. 

Think about your buyer's journey and create the content for them. 

Y.O.💛

If you have to ask someone what their priorities are you're already behind. 

Experts frame the conversation and immediately position themselves as someone that can be trusted. 

This is a mistake I see all the time in sales. 

They come in and think asking about their priorities will get the prospect to open up. 

What gets a prospect to open up is context. 

I lead with three things. 

1. An overview of their industry. 
2. The impacts currently being experienced.
3. End with an assimption.

That framing creates the trust that allows the customer to share what's happening and they naturally share the priorities. 

But leading with that question (priorities) can position you as more of an order taker versus an expert.  

Which one do you want to be seen as?

I think in this AI world it's important to let your connections know that the person they connected with is a human. 

That's why I still love sending personalized video DMs. 

No pitches. 
Just a message of thanks. 
I ask why they decided to connect.

If you sent the connect request then you video should be saying why you connected. 

And that approach has allowed me to build genuine connections here in LinkedIn. 

Not a fan of video? Send a voicenote. Voice or Video should always be the forst message. 

Especially if you're a job seeker or providing services this is an excellent strategy for 2026. 

On average I get a 30% response rate and a 40% on those for my services. 

And that's after sending over 8,000 of them. 

It says 6,500 because I had to deleted some to make space. 

Interesting fact: I've gotten less than 50 video responses back. Most replies are text. Which is ok, I'm thankful for the reply, for acknowledging the video. 

But they work. DMs work. And you should be using them...daily. 

Who here has sent a video to their new connections? 

Y.O.💛

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The Battle

Jake Dunlap

Jarrod Best-Mitchell

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

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Performance ScoreJake Dunlap's LinkedIn Performance