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) 

—
♻️ Repost & Follow for more insights

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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Sprout Social, Inc.

I champion AI-driven innovation across the company, co-chairing our AI enablement taskforce and leading initiatives to integrate artificial intelligence for an enhanced user experience, improved operational efficiency, and new capabilities. 

My role also involves developing and implementing comprehensive AI governance frameworks, covering responsible AI principles, data privacy, and ethical review processes. I lead, mentor, and grow a dedicated team of business systems engineers, fostering a culture of innovation, continuous improvement, and agile project delivery. Additionally, I provide strategic business case analyses, feasibility studies, and ROI projections to guide executive decision-making on technology investments and process improvements, acting as a crucial liaison between technical and non-technical teams.

Director, Business Systems Operations

-Acted as a second-line leader, providing strategic oversight and mentorship to first-line managers and their teams.
-Spearheaded cross-functional coordination to develop and enhance sales processes, ensuring efficient and effective sales operations.
-Led a program management team focused on the orchestration and successful execution of high-value business initiatives.
-Oversaw vendor management, administration, and strategic planning for the Sales and Success technology stack.
-Directed the strategy for technology investments, ensuring optimal deployment and alignment with business goals.
-Managed go-to-market operations, including the design and optimization of sales territories to maximize market coverage.
-Guided new go-to-market (GTM) initiatives, playing a pivotal role in achieving the company's revenue targets.

Sr. Director Sales Strategy

In this role, I partnered across Sales, Marketing, and Operations to build and refine processes, successfully unlocking new revenue streams through efficiency gains and strategic channel partnerships. I led internal sales tool procurement, management, and integration. A major project was leading the systems integration workstream following the acquisition of 'Simply Measured.' This complex undertaking involved successfully migrating critical data and processes within 12 months, decommissioning redundant systems and improving data accuracy. I also lead our Channel Sales efforts, launching our affiliate partners, sales partnerships and directed new channel development and managed existing channel relationships to expand our market reach.

Director, Sales Strategy

Managed a diverse group of sales leaders across SMB, Mid-Market, Agency, Sales Development, Business Development, Enterprise, and Growth Sales Segments, collectively achieving 114% to target in 2018. I also led the sales integration efforts during the acquisition of Simply Measured, successfully aligning processes and maximizing sales of our combined product suites.

Head of Sales - Sprout Social Seattle

Managed a team of 9 Account Executives. By creating and implementing new sales processes, the team's rate per sale increased by 23% within six months. I also developed new outbound lead generation methodologies tailored for the SMB market.

SMB Sales Manager

Sales Assembly

Featured Thought Leader

Partnership Leaders

Member

Groupon

Managed a team of 23 business development representatives, consistently achieving 140% to our monthly target while overseeing a $900K+ gross profit target. I developed and implemented novel techniques and strategies that significantly increased revenue within a new vertical. My analytical work, which involved studying sales data for over 900 representatives, led to the development of more targeted interviewing questions and strategies that demonstrably improved employee retention and satisfaction.

Divisional Sales Manager - Leisure and Activities

Managed and trained over 27 new sales representatives. Through data-driven coaching and strategic reporting, I led teams to achieve consistent growth in both client acquisition and profit goals. I also overhauled and standardized the reporting and data-driven management strategy for the department.

OnBoarding Sales Manager

Consistently met and exceeded contract and gross profit goals on a quarterly basis. Developed and implemented incentive-driven marketing plans for small businesses.

Account Representative

DePaul Young Life College

-	Founded Young Life DePaul in the spring of 2011 and grew the organization to over 100+ students, becoming the largest student ministry on campus.
-	Provided and planned events for 100+ students on a weekly basis with sponsors from a wide range of companies including Monster and Adobe.
-	Provided marketing strategy and design work for the organization, including PR campaigns to community members and print, web and guerrilla marketing campaigns to advertise the group’s presence.
-	Managed community relations and support in order to acquire fundraising and leadership support.
-	Trained students in leadership and sent teams into at-risk areas within Chicago to assist with youth outreach.

College Director

Fox Associates

-	Directed a team of 7 project managers in the completion of major business projects, while maintaining project timelines to ensure all goals were met.
-	Created and instituted new training and office procedures to create uniformity company-wide.
-	Authored decks and assisted in customer presentations which secured two new business clients.
-	Drove the introduction of new technologies and marketing platforms to better serve our clients and to improve the image of the company.
-	Developed new processes and new business strategies while contributing to the growth the business.
-	Provided strategic support to a national sales force.
-	Assisted in the strategic analysis and monetization of digital assets in the publishing industry.
-	Worked in teams to assist sales persons and to improve systems within the company.

Director of Project Management

A results-driven and forward-thinking leader with over 10 years of experience in architecting enterprise-wide strategic initiatives, optimizing business systems, and spearheading digital transformation. Proven ability to operate as a trusted advisor, shaping strategic direction and influencing senior executives to resolve complex structural and technological debt. Deep expertise in strategically leveraging AI and automation to significantly enhance internal operational efficiency, streamline processes, and drive measurable organizational impact. Adept at building and leading high-performing teams to deliver systemic, high-leverage change. Passionate about applying enterprise-scale problem-solving skills and a bias for execution to deliver transformative outcomes.

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