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

Kasey Devine

IRS has your runway. Take it back.

PEO shopping is broken — and it’s broken on purpose.

For over a decade, I worked inside HR, payroll, benefits, and PEOs at companies like ADP and TriNet. I saw the same pattern repeat itself: small and mid-sized businesses forced into opaque, slow, and biased buying processes, often evaluating only a fraction of the market before making one of the most consequential financial decisions they’ll face.

That experience led me to build Entravia.

Entravia is the infrastructure layer for PEO shopping. We help small businesses, CFOs, brokers, and advisors securely collect data once, compare multiple PEO options at the same time, and make informed decisions without vendor bias, spreadsheet chaos, or endless follow-ups.

Our platform standardizes and normalizes PEO data across hundreds of vendors using automation, bots, and AI-driven document processing — reducing shopping timelines from months to days while improving accuracy, security, and outcomes. It’s always free for employers and aligns incentives by partnering with ethical brokers, advisors, and PEOs rather than competing against them.

Before founding Entravia, I spent my career advising and selling into small and mid-market companies navigating payroll, benefits, HR compliance, and multi-state complexity. I’ve worked directly with founders, CEOs, CFOs, heads of finance, fractional CFOs, insurance brokers, and PEO brokers — and I’ve seen firsthand how misaligned incentives quietly cost businesses time, money, and leverage.

Entravia is built for one simple outcome: give employers and their advisors clarity, speed, and control in a system that has historically profited from confusion.

If you are:
• A founder or CEO tired of renewal shock
• A CFO or head of finance supporting growing companies
• A broker, advisor, or PEO who wants better tools, not more admin work

You are exactly who we built this for.

Vice President of Sales

We're Not Your Typical PEO...

As a care operator, your needs are different than other companies. That’s why we only provide HR solutions to facilities offering home care, skilled nursing, senior housing, assisted living, disability services, and long-term care. You can have the peace of mind that when you call, you will receive a solution specific to you.

Care is All We Do:
We hire people from the senior and disability care industries. Everything we do is built for the care industry.

Medium to Enterprise:
Unlike other PEOs, our model is built to handle large care operations with 50-10,000 employees.
	
Care-Specific Services:
Since we are built for you, our services are custom-designed to help drive better HR outcomes for care providers.
	
Tech for Care Providers:
Our technology is built to ensure scheduling, time and attendance, reporting, and functionality meets our clients' needs.

Kasey Devine, MBA

1) Entravia is in the same place
2) I slipped shaving and all my facial hair is now gone

#letsdothis

John Taylor Logan Geoffrion

Helping Brokers & PEOs Fix Pipeline Leaks with Technology & Connection | Founder & CEO, Entravia

No alternative text description for this image

This post is meant to help anyone in my network who is hurting and needs a job. 

I’ve seen an uptick in really talented people who are looking for a new home and I’m going to do two things to stand with you here:

1) As Founder & CEO of Entravia I am publicly committing to not hire anyone outside of the U.S. unless I have literally exhausted all other options to collaborate with a neighbor in need here. I think it’s sick that we are increasingly okay with exploiting people in other countries because we don’t want to pay fair wages and provide dignified employment to our neighbors. If we want to have the rewards of entrepreneurship, we must not shirk our responsibility to our communities that enabled that opportunity in the first place. *Conscious* capitalism…Not grow at ALL costs. 

2) Please like and re-share this as widely as possible. Comment for reach. Comment if you’re looking for a role and what PERFECT would look like because dang it you deserve that. We’re not actively hiring at Entravia but I do have my eyes open for the right collaboration opportunities as we continue to grow, and I also have the ear of execs in th PEO and HCM industry. I’ll do anything I can to help you and I know there are people here who share that commitment.   

3) I can’t believe I need to write this, but I’m not targeting any specific company in any way here. If you feel like I am, look in the mirror on your conviction. I’m just trying to help and empathize…human-to-human. 

Saint Joseph the Worker, pray for us.

Our company is 3 months old and Logan Geoffrion received a phishing attempt impersonating me. 

WE MADE IT Y’ALL 😂🥳🎉

Thank you everyone for coming out! We’re proud to be a part of the PEO Brokers Collective and to see the community here in the Cities, too!

There’s something powerful about getting people in the same room who care about similar work.

Monday night in Minneapolis we got a group of PEO brokers, PEO reps, and HR professionals together in the North Loop.

Pretty informal. Just good conversations, meeting new people, and hearing different stories about how everyone ended up working in and around the PEO and small business world.

Thanks to Entravia for underwriting this fun event!  Really enjoyed the chance to connect with people across the industry. Looking forward to doing more of these.

taplio

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Jake Dunlap

Kasey Devine, MBA

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taplio

The Battle

Jake Dunlap

Kasey Devine, MBA

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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