Jake Dunlap

Skaled Consulting

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:
LinkedIn / Splunk / SEMRush / Microsoft 

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

Chief Executive Officer

Stage 2 Capital

Nowait Inc

This was one of the most amazing opportunities I have had to change the way that restaurants think about engaging with guests and managing throughout at the same time. 

How do you provide a world class experience for guests and ensure that your internal team can manage the flow of guests on your busiest days/nights?  This is what we helped 1000s of restaurants accomplish everyday. 

I built out, managed and led the process for how NoWait engaged with and deployed its software and service to the largest restaurant groups in the United States and Canada including Brinker (Chili’s), Applebee’s, BWW, Cheddars, On the Border and 1000s of other leading restaurants to transform the way they treat and manage their guest experience at the front of the house.

Vice President of Sales (acquired by Yelp)

Chartbeat

Partnered with the leading publishers (ESPN, New York Times, Wall Street Journal and 100s of others) and the largest websites in the world to better understand their audience in real-time. 

Developed and managed the growth, development and execution of product outreach, sales and account-management strategies to ensure Chartbeat met the need of our partners at the strategic and tactical levels. 

Over the course of the year and early 2013, we transformed the organization from a one-person function to four departments comprised of sales development, account executives, Chartcorps (service) and customer success to specialize in solving the needs of the largest websites in the world. 

In 2012, we grew annual bookings by more than 300% year-over-year and nearly doubled monthly recurring revenue during the first nine months

Head of Sales & Customer Success

Glassdoor

10 years after Glassdoor launched we sold to Recruit (owner of Indeed) for 1.2 billion dollars.  

My piece of this amazing journey was two fold:

1. Change the way that employers think about how they interact with their current employees, interviewees and attract the top new hires. 

2. Build a sales, success, service and operations organization that could consult and service the largest companies in the world on how to find and retain their most valuable asset - their people. 

From 2010-2012, I spearheaded the day-to-day operations of all sales, operations and account management, expanding the department from 0 to 40 employees in less than 18 months. 

We grew to $1 million MRR in less than 18 months and developed sales and operations training program as well as client-services workflow.

Had the amazing opportunity to work hands with Rich Barton, Bill Gurley and some of the other titans of Silicon Valley directly while reporting to the CEO and board of directors

Vice President of Sales, Success, and Sales Operations

Careerbuilder.com

•	Managed 15-member team responsible for providing industry- and regional-recruiting guidance on best practices for utilizing services to develop advertising campaigns for mid-sized businesses
•	Identified organizational goals and aligned them with team’s core competencies
•	Consulted with organizations’ multi-level leaders to better understand their needs and correlated best ways for meeting them
•	Worked with executives nationwide to develop various industry-specific, human-capital strategies
•	Developed corporate strategies for Fortune 500 organizations that directly impacted revenue generation and cost control through human resources
•	Initiated relationships and managed day-to-day consulting of Fortune 100 organizations

Senior Sales Manager - Pacific Northwest

National Accounts Manager

Arizona Coyotes

I was the top Premium Sales person until I made the mistake of telling my boss to F**k off 🤷‍♂️

Senior Account Manager

Tampa Bay Devil Rays

Hired and managed inside sales team 
Responsible for group, season and premium-season ticket sales

Account Manager - Corporate Accounts

My deep passion for the science and art of sales has fueled my journey over the past 11 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. 

For those who demand excellence and are looking to accelerate growth in today’s competitive landscape, I invite you to explore how Skaled can partner with you to achieve unparalleled success.

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)
	• VP of Sales at NoWait (acquired by Yelp - March 2017)

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

As of November 20th, I’ve ran over 320 sales calls this year

I had our Strategic Deal Navigator Assistant analyze where I messed up and lost deals

Here are 5 lines, or versions of them, that kill momentum immediately

I have said every single one and lost deals because of it

When I started as an AE, I thought demos were about impressing people

So I'd over explain, show too much, talk way too fast (still do that at times)

Now I treat every conversation like a consultation, not a performance

I still make plenty of mistakes for sure so hopefully these are good reminders

Here are 5 lines you should cut immediately and what to say instead:

1️⃣ "Let me tell you about where we can help"…before understanding what they need.

Say this instead "You mentioned reducing churn, so let's start there."

2️⃣ "This is something I see real value in, and it’s going to be really helpful"

Why it's bad…You don't know that. Focus on value, not your opinion

Say this instead "Our customers in fintech use this to cut onboarding time by 40%. Could that help your team too?"

3️⃣ "You can automate everything with just a few clicks"

Why it's bad…Vague. Sounds like a pitch, not a solution.

Say this instead "This automation saved a similar team 6+ hours per week. Let me show you how."

4️⃣ "Do you have any questions?"

Why it's bad… It puts all the pressure on them. Often leads to silence and usually a “no…pretty self explanatory”

Say this instead "How does this compare to how you're handling it today?"

5️⃣ "Let me know what you think"

Why it's bad… Passive. No next step.

Say this instead "If this solves what we discussed, would it make sense to explore pricing next week with your team?"

With all of this 👆 you’ll get
More engaged prospects, clearer business value, and higher conversion to next steps

Alright…your turn. What’s a line you’ve used (or heard) that kills momentum instantly? Drop it in the comments

👉 Check out your personal Strategic Deal Navigator at Journey AI (link in comments) 

—
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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

It’s that time of year…let’s completely deflate 80% of the sales organization in 2026 time of year!

Most quota methodologies are probably destroying team morale

Many sales leaders set quotas using last year's results plus a growth factor.

"We did $50M last year, so we need $68M this year. Divide by number of reps." 

This approach assumes all territories and reps are identical.

They're not.

Some territories have higher market potential. Some have been farmed longer. 

Some have a better concentration of our ICP

Some reps inherit hot accounts. Others get burned territories.

Setting uniform quotas across different situations creates instant unfairness.

High-potential territories get easy quotas. Challenging territories get impossible ones.

The reps who need the most support get the most pressure.

Better quota methodology considers: 
Market potential ➡️ What's the addressable market size for each territory? 
Account maturity ➡️ How long have these accounts been worked? 
Historical performance ➡️ What's the realistic baseline for this specific territory?
Pipeline health ➡️ What's already in motion for next year? 
Investment level ➡️ How much marketing/SDR support does each territory get?

The goal isn't equal quotas. It's the right quota based on the territory.

Fair means each rep has a realistic path to success based on their specific situation.

When quotas feel achievable, reps stretch for them. When quotas feel impossible, reps give up before they start.

We just started implementing BoogieBoard for this exact reason for clients. 

Excited to see the potential results!

I finally wrote it all down. What ACTUALLY does a day in the life of a top seller look like today with AI?

What are they still doing manual because it’s better?

What have the automated completely?

Here is the playbook..enjoy 👇

If you could compress what used to take 3 hours of prep, follow-up, and CRM cleanup into 15 minutes with AI…would you still do it the old way?

Your morning used to look like this:
→ Dig through tabs to prep for meetings
→ Re-type the same follow-up emails
→ Copy notes into Salesforce just to “check the box” for your leader…who probably never looks at it and asks you about it on slack instead

Now it looks like this:
→ AI Assistant auto-generates call briefs and talking points
→ Your meeting notes are summarized instantly
→ Follow-ups and CRM updates are done before your next call

That’s not a fantasy it’s already happening.

AI Assistants are cutting 11–12 hours of admin work a week for sellers who use them right.

And those reps? They’re not just “working faster.”

They’re finally spending time where it matters talking to buyers.

Would you still pay sellers to “pay their dues,” or would you pay them to sell? 💥

👉 Read the full article to see what an AI-powered seller’s day actually looks like.

Open article: A Day in the Life of an AI-Powered SaaS Seller in 2026 by skaled.com

A Day in the Life of an AI-Powered SaaS Seller in 2026

GenAI isn’t a “tool.”

It’s the internet moment happening inside your company, and most teams are treating it like a browser plugin

Leaders keep saying, “We turned it on… why didn’t anything change?”

Because nothing changes if people don’t change behavior. GenAI only works when workflows, expectations, and habits get rewritten, not when teams try to bolt it onto 2018 processes

Ryan Cahill nailed it on the pod: most companies are “more efficiently wrong.” 

They deploy AI, skip the behavior change, and wonder why the ROI never shows up.

Here’s the real shift:
→ GenAI isn’t making old tasks faster
→ It’s forcing you to rethink why those tasks existed in the first place

The internet didn’t upgrade fax machines. It eliminated them. Same idea here.

New episode with Ryan Cahill drops TOMORROW with two tactical behavior changes leaders can make this week to get real impact from GenAI.

What is the one behavior your team needs to change for GenAI to actually work?

I’ve talked to at least 10 PE backed companies this month and the universal truth is the AI hire they are thinking about will actually slow them down and cost them an entire year of innovation

Promoting someone into an AI role they can’t grow into fast enough creates negative ROI

Hiring someone from the outside who built a few customgpts is like hiring a top performing rep who built their own reports in SFDC as your RevOps hire

AI is evolving weekly

But your “AI person” is stuck fighting fires from systems built in 2017

So companies say:
“AI is moving too fast.”

No…your staffing plan is just for solving problems in 2016 not 2026

The real cost of inaction isn’t failing to adopt AI

It’s hiring someone who can’t keep up while they’re building

What that creates:
👉Workflows that launch already outdated
👉Models that never improve because no one has time to retrain them
👉A GTM engine that’s miles behind competitors who built with specialists, not stretched operators

AI GTM Engineers aren’t a luxury.

They’re the difference between scaling AI and creating an expensive science project.

If your AI lead is doing admin work 70% of the week, you’re not just behind, you are building outdated assistants before they even launch

If your team had an AI GTM Engineer today, which part of your GTM motion would you automate first?

Open article: The Rise of the AI GTM Engineer in 2026 by skaled.com

Everyone keeps calling this an AI bubble

So why are the smartest investors buying even more AI instead of pulling back?

SoftBank just sold billions in Nvidia stock and moved deeper into AI

Not into chips. Into the intelligence layer.

If this was a real bubble, insiders would be exiting quietly.

Instead they’re rotating capital into the parts of AI they believe will dominate long term

The mistake people make is treating AI like one giant category

It isn’t.

Infrastructure is crowded.

Apps are noisy.

Platforms and data are where the power consolidates

So the question isn’t “Is AI a bubble?”

The question is “Which part is overpriced and which part is still early?”

Most people betting on an AI crash are assuming everything will collapse at once

History rarely works that way

Are we in a hype cycle or the start of the biggest tech shift since the internet?

Where do you stand: bubble or breakout?
👇 Comment your take down below

—
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HubSpot

Enterprise Account Executive - Growth Specialist

Outreach

FY2025 Highlights:
• Ranked #2 out of 23 in the Strategic & Enterprise Leaderboard with most meetings & pipeline generated in H1

Trusted advisor to Global GTM Leaders in organizations with 100,000+ employees. We research the science behind effective sales strategies to eliminate the guesswork for your specific revenue tech stack.

Sr. Enterprise Account Executive - New Logos

FY2024 Highlights:
•H2 quota attainment: 134%
•Ranked #1 out of 23 Strategic & Enterprise AEs on the Pipeline Generation Leaderboard (1489% attainment)
•Maintained 100% Renewal Rate for existing customers 
•Sourced and closed a strategic multi-year $437,000 Net New Logo opportunity within 4 months of starting

Helping organizations in the North America market unleash their maximum potential through Outreach's Sales Execution Platform to create and close more pipeline, with robust forecasting capabilities. 

Outreach is the Sales Engagement pioneer and according to Forrester, Gartner and Pavilion, also the Sales Revenue & Intelligence leader with 6,000+ customers such as Zoom, Nvidia, DocuSign, Cisco and Adobe.

Enterprise Account Executive - New Logos & Renewals

MongoDB

FY2023 Highlights: 
•159% quota attainment. Excellence Club FY2023
•Managed #1 ranked team out of 18 Sales teams
•Promoted 9 reps
•Generated over $13.1m in Qualified Pipeline
•Recipient of the "Manager of the Quarter" award 
•Sourced, Hired, Trained and Coached a total of 17 reps during my tenure

Q1: 204% 
Q2: 151% 
Q3: 142% 
Q4: 137%

Sales Director

FY2022 Highlights:
•2,881% Professional Services quota attainment. Excellence Club FY2022
•148% New Annual Contract Value quota attainment
•Ranked #1 out of 23 Enterprise Account Executives in my segment
•Sourced & closed multi-year Enterprise Net New Logo opportunities such as Warner Media 
•Maintained a 100% commitment renewal rate with 40+ expansion deals
•Recipient of the "Think Big, Go Far" award for embodying one of MongoDB's core values

Q1: 101% (ramping quarter)
Q2: 172% (with 1,980% Professional Services quota attainment)
Q3: 127% (with 1,133% Professional Services quota attainment)
Q4: 192% (with 5,530% Professional Services quota attainment)

Enterprise Account Executive

FY2021 Highlights:
•2,579% Quota attainment. Excellence Club FY2021
•Ranked #1 out of 24 Product-Led Account Executives 
•Achieved the highest call volume in MongoDB worldwide (averaged 7 discovery meetings per day)

Q1: 200% (first quarter, 2 months instead of the usual 3)
Q2: 828% (#1 out of 24 Cloud Account Executives worldwide, first 3-month quarter)
Q3: 1,546% (#1 out of 24 Cloud Account Executives worldwide, #2 rep did 334%, #3 rep did 264%)

Product Led Account Executive

Loveshare

Technology startup, multi-award-winning mobile app and customer experience platform that assists 20,000+ users with keeping the spark alive in their relationships through couples-specific activities from local enterprises
• Trained and managed a team of 9 sales and marketing specialists with monthly performance reviews for 3+ years
• Negotiated with C-level decision makers to create and manage 250 strategic collaborations with local enterprises
• Wrote creative copy for 400+ unique Social Media advertisements and optimized their marketing budget
• Attained a $110,000 investment from SkyRocket Development to grow the Loveshare Platform
• Won $35,000 in equity-free funding through the Parallel18 (350 applied, 40 selected) and Startup.pr (125 applied, 10 selected) entrepreneurship competitions. Completed Georgia Tech’s Enterprise Innovation Institute’s I-Corps program

Founder & Sales Director

Xerox

• Supervised IT sales performance of 6 enterprise solution specialists, ensuring their annual sales quota of $2,160,000
• Worked directly with the VP of Sales to provide industry-specific strategies and tactics to Enterprise Account Executives

Enterprise Sales Director

• Prepared presentations and sold specialized IT infrastructure solutions and hardware to strategic enterprise accounts
• Highlights: Closed a $600,000 opportunity with a dealership network in under 3 months that other peers had not been able to in a 3-year period. Generated an average of $400k in revenue per quarter
• Completed Xerox sales and technical training programs in New York and California

• Developed the Lead Generation Department from the ground up, creating sales opportunities by identifying and acquiring new databases with business contact information. Qualified leads and provided support to the Sales Representatives
• Managed relationships with existing Xerox customers with the Salesforce Customer Relationship Management tool
• Trained and supervised 3 new Enterprise Sales Representatives

Enterprise Sales Representative

Microsoft

• Worked directly with the Chief Marketing Officer while researching and managing strategic collaborations between Microsoft, Solution Providers, and the most impactful professional associations in Puerto Rico
• Independently acquired and delivered contact information to Microsoft from 60,000 businesses in Puerto Rico and the Dominican Republic to generate new sales opportunities through channel partners

Marketing Specialist

Saatchi & Saatchi

Student internship at the multinational advertising and public relations firm with annual revenue of $40 million.
• Conceptualized, planned and managed 3 events for Toyota, Lexus, and Scion with budgets upwards of $200,000
• Wrote creative copy used on presentations, events, and websites for Dewar’s, Mead Johnson and Toyota

Experiential Marketing Coordinator

Passionate Enterprise Sales Professional with a track record of helping companies drive sustainable growth through scalable sales strategies. I partner with organizations to uncover what drives their success, eliminate inefficiencies, and optimize the customer journey—ensuring every rep performs at their highest level, consistently.

With experience across Enterprise, Mid-Market, and SMB accounts, I bring a deep understanding of diverse business needs and how to align sales and marketing efforts for maximum impact. My approach empowers teams to deliver world-class results by leveraging data-driven insights and cutting-edge technology.

I’m also the former Founder and Sales Director of Loveshare, a multi-award-winning mobile app that helped over 20,000 couples create meaningful, memorable experiences.

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