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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RS Strategic Advisory

Helping DTC founders build their B2B playbook.

Coach + Sales Strategist

〰️ Sell Better Show • How to book more meetings with cold email
https://bit.ly/3yJkis3
〰️ Sell Better Show • How to run multi-stakeholder demos that win more deals
http://bit.ly/3wgYEtH
〰 Sales Showdown: Trick or Treat Edition with Pandadoc
http://bit.ly/45UE0vC
〰️ Sell Better Show • Boosting Sales With Expert Discovery Call Strategies
https://bit.ly/3SVUAHT
〰️ Scott Ingram's Sales Success Podcast • Curiosity, Persistence & 100% Ownership
https://top1fm.com/rachel-shi
〰️ The Millennial Sales Podcast • Tactical Ways To Use Video in Sales
https://bit.ly/3jhcguG
〰️ Vidyard • Blog • Social Selling: How to Connect, Engage & Sell on LinkedIn
www.vidyard.com/blog/social-selling-best-practices
〰️ SalesLabs • Podcast • Everything you need to know about using video for sales
https://bit.ly/48vcVjX
〰️ Vidyard • Blog • The Ultimate Guide to Virtual Selling
www.vidyard.com/blog/ultimate-guide-virtual-selling
〰️ K2 Sales Podcast • Podcast • Unlock the power of video
www.buzzsprout.com/1566959/7459972
〰️ SalesRight (FastSpring) • Blog • Q4 Pricing Strategies from Sales Experts
www.fastspring.com/blog/q4-pricing-strategies
〰️ Adobe • Blog • How video supercharges virtual selling
www.blog.adobe.com/en/publish/2021/03/26/how-video-supercharges-virtual-selling.html
〰️ Sandler Training • Podcast • How to succeed with video selling
www.sandler.com/blog/how-to-succeed-at-video-selling-podcast

Talks:

〰️ Sep 2022 • The State of Employee Advocacy, Speaker, Influitive
〰️ July 2021 • Newcomers in Tech Sales, Speaker, Scale Without Borders
〰️ April 2020 • Pride 2020: Designing For All: Why Accessibility Matters, Moderator, General Assembly ✕ Venture Out
〰️ Feb 2020 • Barriers & Lived Experiences, Moderator, Juno College
〰️ June 2019 • Pride Talks 2019: Celebrating LGBTQ+ Leaders, Panelist, #movethedial
〰️ Nov 2018 • Advocacy in Tech Panel, Moderator, Shopify ✕ Venture Out
〰️ Oct 2018 • Modern Leaders: Managing At Scale, Moderator, Wealthsimple ✕ Women and Color

Speaker & Writer

Ultimate Nutrition

Sales

KINEON INC.

Go To Market Leader Society

Creating distinctive experiences for senior GTM executives and VC/PEs.

GTM Sponsorships

metadata.io

• Top 10% performer 2022, 2023
• Outbound self-sourced 60% of closed won deals. $60-100K average deal size, 3-6 month sales cycle, selling to VP Marketing, Digital, Growth
• Built prospecting playbooks for Social Selling and Video Selling implemented by broader team
• Mentored 2 junior AEs
• 15+ net new logos: Bytedance (TikTok), RingCentral, Wrike, Docebo, Rockwell Automation and more

Strategic Account Executive

Journey

Advisor

Entrepreneur First

1 in 80 out of 10,000 applicants accepted to join EF's global talent investor and startup incubator. Backed by Reid Hoffman, Greylock Partners, Founders Fund, Mosaic Ventures and Lakestar.

My co-founder and I built DealDesk, a peer-learning platform for the future of work which solved the problem of fragmented knowledge in remote-first organizations. Raised $100K in pre-seed funding and secured 6 pilot customers. Wound down the biz due to personal circumstances. To date one of the best learning experiences I've had in my career.

Founder-in-Residence

Vidyard

Went all in on partnerships after building out eA's partner program leading to 80% of my leads going from Outbound to Partner-sourced. Vidyard had made the strategic decision to double down on the Sales ICP on the tailwinds of the pandemic. Hired to build a services moat to make Vidyard the go-to video platform for sellers. Created and launched Vidyard's Sales Trainer Partner Program from 0-1 6 months. Leadership role (player/coach).

Left after landing an opportunity to start my own venture.

• Acquired and activated 63 channel partnerships, ranging from solo consultants and influencers to enterprise training corporations
• Cross-functional role influencing all levels across Sales, Marketing, CX, Product & SLT
• Built case for additional headcount, recruiting, onboarding and managing Partner Manager to support activation and growth of channel
• Sourced, established and managed 3 of largest channel partnerships (Sandler Training, Corporate Visions, RAIN Group)
• Helped implement best in class tech-stack to scale processes (Crossbeam, Partnerstack)
• Drove thoughtleadership on video selling in the B2B sales community. Led to invitations to podcasts, premium features on Enterprise Sales Forum, the Adobe blog, private training sessions, 40+ virtual workshops and webinars on video selling, gaining exposure to 80,000+ salespeople
• Owned the Adobe book of business representing $1.6MM in pipeline and $1.3MM in closed revenue

Senior Manager, Strategic Partnerships

eSSENTIAL Accessibility

1 of first 2 SaaS AEs hired to transition company from unknown professional services firm of 15 to a SaaS model, leading to their $16MM Series A fundraise 8 months later and 4 years later a merger with their top competitor LevelAccess. Learned complex, multi-departmental enterprise sales, closing net new seed deals in a niche industry with F500 companies like Sephora, Whole Foods and Nike. Targeting GCs, CMOs, CTOs and CPOs. This role catapulted my growth.

• #1 AE out of 6 in 2019, 104% to annual quota
• Outbound prospecting and leading complex enterprise sales cycles with C-Level and Senior Executives in Fortune 500 (Product, Digital, Marketing, HR, Legal)
• Spearheaded eA's first Partner Program, individually sourcing, signing, enabling and managing 7 net new strategic channel partnerships, resulting in $200K+ ARR closed revenue and >$30M ARR in TAM with zero Marketing budget. Key partners included PixelMedia, mobileLIVE, One Rockwell, Avantia
• Evaluated and implemented tech stack to improve sales process: Outreach, Vidyard, Discover.org, ZoomInfo, LinkedIn Sales Navigator
• Promoted company at global conferences like Collision and #a11yTO to drive leads
• 20+ net new logos: Sephora, Whole Foods Market, Georgia-Pacific, Coty, Nike, Classpass, DevaCurl, Tatcha, Deckers Brands, LUSH Cosmetics, Toronto Star, The Honest Company, Talkspace, Bowlero, Hint, ResMed, Amplitude.

Venture Out

Led Canada's first and largest tech D&I nonprofit organization, cultivating a community of Toronto's best startups and tech talent.

• Led Sponsorships & Marketing teams of 18+ volunteers
• Recruited and built 2020 team through values-based framework
• Built network of 45+ start ups, corporations and non-profit community partners in Toronto tech community
• Led creative direction of Venture Out 2020 rebrand
• Owned Shopify x Venture Out 2018 event attended by 150+
• Built & grew relationships with strategic sponsors (Shopify, MaRS Discovery District, Wealthsimple, Loopio, Uberflip, Limelight, Security Compass, TWG & many more) developing high impact programming for 2018, 2019 and 2020 conferences attended by 630+

Formerly: Content & Programming Associate (Nov 2017-Mar 2019)

Co-Chair

• GTM consultant for early stage founders. Currently open to Sr AE roles.
• Based in London, lived in Toronto and Costa Rica, originally from Melbourne.
• 8+ years in enterprise b2b sales experienced in startups to F500.
• Creating courses for AEs on how to gain a competitive edge. Author of Win At Your Price with pclub.io. Building yourdreamjob.carrd.co.
• Drawing strange things at rachelshi.substack.com.
• A fan of excellence in every arena.

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Rachel Shi

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