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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Aptude Inc. (Acquired 2022 by New Era Technology) 

Industry: IT Services and IT Consulting
Specialties: Digital Transformations, Professional Services, Managed Services 

At the helm of a technology-agnostic practice, led a global team of solution consultants, project managers, and engineers, specializing in Smartsheet engagements. Spearheaded process improvements and policy development to ensure projects were delivered on-time, within budget, and with high customer satisfaction. Managed a P&L, overseeing financial performance and driving profitability through effective contract negotiations and SOW developments. Accountable for capacity management and resource utilization with oversight, leadership, and subject matter expertise for strategic projects, while also driving pre-sales and post-sales initiatives and interfacing with the sales and marketing department to support business growth initiatives.

Director of Professional Services

CORTAC Group (Acquired 2022 by MI-GSO | PCUBED) 

Industry: Management Consulting Services
Specialties: Delivery of strategic project leadership and PMO services 

Dynamic Senior Consultant specializing in fractional leadership and strategic initiatives, contracted through CORTAC Group - a premier management consulting firm with a track record of partnering with industry leaders.   Leading transformative efforts across a spectrum of roles, including engagement management, program/project management, and implementation consulting. While engaged in diverse projects, my primary dedication has been directed towards partnering with Smartsheet to drive transformative efforts. This targeted focus ensures the delivery of tailored solutions and strategic outcomes, contributing to the success of both Smartsheet and our esteemed clients.

Sr. Consultant – Transformational Leadership & Strategic Initiatives

EMS Software (Acquired 2018 by Accruent)

Industry: Software 
Specialties: Meeting & Room Scheduling, Event Scheduling, Hoteling, Classroom Scheduling

EMS Software offers an industry-leading event management platform designed to simplify the process of event planning and conference management. Whether approving conference room requests, booking large-scale hybrid events, or communicating with service providers, our event booking software simplifies the process each step of the way. Led comprehensive project management initiatives including managing the end-to-end project lifecycle, from solution consulting to system configuration, utilizing an agile approach with iterative sprints and demos. Provided extensive training and documentation development.

Sr. Implementation Consultant & Project Manager

PGi (Acquired 2015 by Siris Capital Group LLC)

Industry: IT Services and IT Consulting
Specialties: Virtual Events, Webcasts, Webinars, and Video Conferencing

As a Senior Global Success Manager at PGi, played a pivotal role in ensuring client success and satisfaction with advanced broadcasting and webcasting solutions. Acted as a dedicated customer advocate, proactively engaging clients to advise on potential issues, recommend policy enhancements, and highlight new product functionality and learning opportunities. Developed and executed long-term account plans to drive user adoption, expand value, and foster lasting relationships. Provided mentorship and guidance to clients, leveraging in-depth product knowledge to help them achieve their business objectives using PGi's solution suite. Conducted thorough quality and product usage checks, analyzed customer data, and facilitated webinars and workshops to educate clients on best practices. Acted as a point of escalation for both internal and external stakeholders, ensuring critical issues were addressed promptly and effectively. Built strong partnerships at senior levels and mediated between clients and the organization to drive mutual success and growth.

• Strategic Partnership Building: Collaborated with internal stakeholders to ensure a seamless client experience, sharing client insights to inform product development, and contributing to the creation of new offerings that directly addressed market demands.

• Upsell and Cross-Sell Opportunities: Proactively identified opportunities to expand service offerings within existing client accounts, presenting value propositions that directly addressed their evolving needs and contributed to revenue growth.

• Exceeded 100% revenue attainment, $25M in revenue in 2014.

Sr. Global Success Manager

PGi (Acquired 2015 by Siris Capital Group LLC) 

Industry: IT Services and IT Consulting
Specialties: Virtual Events, Webcasts, Webinars, and Video Conferencing

Leveraged data analytics to extract actionable insights and support informed decision-making. Proficient in collecting and analyzing data from diverse sources, specializes in designing and generating reports and interactive dashboards using tools like Excel, Tableau, and Power BI. Adept in defining performance metrics, conducting trend analysis, ensuring data accuracy, and collaborate closely with stakeholders to understand reporting needs and deliver comprehensive reports that drive operational improvements.

• Dashboard Development: Designed and developed interactive dashboards using tools like Tableau or Power BI, visualizing data trends, patterns, and KPIs to facilitate data-driven decision-making.

• Root Cause Analysis: Conducted root cause analyses to identify factors impacting business performance, presenting recommendations to address issues and capitalize on opportunities for improvement.

• Business Intelligence Reporting: Produced comprehensive and user-friendly reports for stakeholders, highlighting key performance metrics, trends, and actionable insights that facilitated informed decision-making.

• Data Governance and Security: Ensured compliance with data governance policies and security protocols, maintaining data integrity and confidentiality while adhering to industry regulations such as GDPR or HIPAA.

Sr. Global Data Analyst

Service Delivery | PMP® | Client-Centric | Operational Excellence | Cross-Functional Leader | Strategic 

🌟 CAREER PROFILE:

With two decades of immersion in the SaaS enterprise landscape, I have navigated diverse industries including Technology, Government, FinTech, Education, Construction, Manufacturing, and Healthcare. My journey spans engagements with Fortune 500 corporations, medium-sized enterprises, and startups alike, shaping a career dedicated to a leadership style centered on accountability, innovation, results-driven strategies, and operational excellence. I have consistently exceeded performance benchmarks, achieving an average team utilization rate of 90% and driving projects to completion with a 97% customer satisfaction rate. Through strategic leadership and cross-functional collaboration, I have driven operational efficiency, strategic vision, and dynamic leadership necessary to ensure the alignment of Professional Services operations with broader organizational objectives. My experience and skills enable me to engage effectively with internal and external stakeholders, rallying support for Professional Services objectives and enhancing stakeholder engagement. With a strong background in project management, service delivery, and customer advocacy within the realm of SaaS enterprises, I am well-equipped to lead teams, manage complex projects, and navigate challenges in a dynamic environment.

In addition to my industry-spanning experience, I bring a toolkit of competencies including Customer Experience Transformation, Strategic Partnership Development, Implementation, Digital Transformation, Program/Project Management, Cross-Functional Leadership, Matrix Leadership, Stakeholder Management, Operational Excellence, Change Management, Process Optimization, Customer Centricity, Risk Management, Data Analytics, Customer Engagement, Consulting

👥 Looking for:

Roles that require client-centric leadership, operational finesse, and transformative advancement. My expertise is an invaluable asset for industries seeking growth through customer-centric strategies.

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Jake Dunlap

Sandokan Stage, MBA, MSc., PMP®, ITIL

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The Battle

Jake Dunlap

Sandokan Stage, MBA, MSc., PMP®, ITIL

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Likes

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