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

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.

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