GTM-focused SaaS Advisor and Board Member

I am a go-to-market-focused technology executive and board member with over 20 years experience leading SaaS companies.  

I have led product, marketing, sales, and customer success, and twice I have run companies as CEO.  Along the way I have served formally on 4 boards of directors (including one public company), 7 advisory boards and 3 non-profit boards.

As part of these roles, I have helped to:

* Sell 5 companies (to Oracle, Amazon, Aurea, Maritz, and NonProfitEZ)
* Secure over $100M in equity financing (series Seed, A, B, C)
* Acquire and integrate 5 companies
* Manage small and large quotas (up to $300M)
* Launch dozens of products
* Get two products to profitability on a pure PLG / self-serve basis
* Grow multiple companies at 50%+ growth rates
* Restructure / downsize multiple companies
* Hire hundreds of people
* Create over $1B of shareholder value

I am now 100% focused on teaching, writing, investing and advising.  

As the Executive Chairman of Winning by Design, I work with leadership teams to optimize go-to-market strategies, product development, and customer success.  As an active board member and advisor, I focus on product development and corporate strategy.  As a professor at BYU's Marriott School of Business I teach Product-led Growth, B2B Sales & Marketing, and Career Strategy.

I recently published my first book with Stanford University Press:  FREEMIUM, available from all book retailers.

I am proud to serve as a formal advisor to Mercato Partners, Pledge, Terrett, and ProAI, and an informal advisor to other entrepreneurs and business leaders changing the world.

My mission is to empower the next generation of software leaders and entrepreneurs to create value for their customers and for society.

Dave Boyce

It's almost 2026. Time to make a choice about how you kick off your year with your team:

▶️ "AI pilots are failing and sucking up a lot of time. We are sticking to the basics.  AI cannot replace what we do.  If you can use AI to help you in your individual job, great, but we are not going 'all in' on AI in 2026."

▶️ "The AI train is moving fast. The only thing worse than missing a train is missing a fast train--it's hard to catch up.  Based on our inititial AI pilots, here is what we are doing in 2026.  We will be the most AI-powered GTM team in our industry."

At Winning by Design we have chosen path B.  We spent all year launching AI pilots and agents.  Not all of them worked, but some of them now define how we work day to day. SiftHub is all in. Salesforce is all in. SAP is all in. Google, Meta, and Microsoft--all in. Also Winning by Design's certified partners:  SalesHood, Momentum.io, Fathom, Grain, Una Software, Vasco, Attention, PeopleAI-- all in.

Time to gut check.  What have you done, and what are you doing in AI GTM?  Are you ready to get on stage in January and launch your year with a clear AI strategy?

XOXO,

-db

25% of adults have a hole in their heart. 

It’s called a Patent Foramen Ovale (PFO), and it occurs when a baby’s heart fails to completely close the opening in the atrial septum as the heart starts to beat independently. 

This week I had my PFO surgically closed. 

The doctors wanted to close it to prevent any future deoxygenated blood clots from passing through the hole and on to the brain (vs going first to the lungs, which tend to do a better job breaking up clots). 

The surgeon inserted a titanium mesh septal occluder, all done arthroscopically (entered through the groin). 

I’ve attached two videos here:

1) an animation of the procedure
2) a video of my device, now in place 

CAN YOU BELIEVE THAT?

It’s amazing to me what humans are able to innovate with precision science. Whenever I engage with innovation like this (or AI or robotics or pharmaceuticals), I realize how much room we have in GTM to tighten up our game. 

200 years ago, we didn’t understand the human body like we do now, and we practiced bloodletting via leeches. We amputated, we blistered, we lobotomized. 

But when you know better, you do better. Medicine has come a LONG way… so have engineering, manufacturing, space exploration…. 

Next up: GTM. We still have a surprising amount of “winging it” in GTM. But there are underlying principles of compounding and system-led growth that can help us do better. 

Today I’m grateful for modern medicine. And tomorrow I’ll continue working with Winning by Design  on modernizing GTM. 

Let’s go!!!

XOXO

-db

https://lnkd.in/g72_jZhB

AI-Native companies run on PLG Rails.

We see the breakout success of some select AI-native companies (Cursor, Replit, Lovable, Mistral, OpenAI...) and assume there must be something special about their GTM.

Yes, they are in a hot space with wind at their backs.

But no, they are not using agents to sell to you.  It's just #PLG.  And if you dive deeper, you can see how and why.  

I wrote about this in the October issue of GROWTH, and I've now published that article to my Substack (linked below). You can get a free digital subscription to GROWTH by following the link at the end of the article.

XOXO,

-db

Winning by Design

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

Just watched a CEO spend $200K on a revenue operations hire that didn't work out

Great experience. Perfect credentials. Amazing interview.

Lasted 6 months.

Here's what he missed in the evaluation:
He asked about their EXPERIENCE with tools. 
He should have asked about their RESULTS with systems.

"What CRMs have you worked with?" 
vs 
"Show me a specific process you built that measurably improved forecast accuracy."

"How do you approach data hygiene?" 
vs 
"Walk me through the last time you cleaned up a messy pipeline and what the impact was."

"What's your philosophy on sales enablement?" 
vs 
"Give me an example of enablement you created that directly improved close rates."

Tool experience is table stakes. System results are what matter.

Anyone can learn Salesforce. Not everyone can design processes that actually drive revenue.

The person he should have hired had half the credentials but could show exactly how their work increased quota attainment by 23% at their last company.

Stop asking about what they know. Start asking about what they've improved. Everything else is just resume padding.

Building revenue operations that actually drives results requires the right expertise. See what we're doing at Skaled to help companies get this function right without the expensive trial and error

—
♻️ 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

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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Sales manager asked me the question that every CEO should be asking

"How do I know if my reps are actually getting better or just getting lucky?"

Most sales leaders track results, not progress 
They see someone hit quota and assume they're improving 
They see someone miss and assume they're struggling

But results don't tell you about skill development.

A rep can close 3 big deals in a month because of perfect timing and market conditions.

Another rep can improve their discovery process, objection handling, and demo skills but still miss quota because their territory got reassigned

The best sales managers track leading indicators of improvement: 
👉 Are they asking better questions in discovery?
 👉 Are they identifying budget and timeline earlier?
 👉 Are they bringing technical people to demos when needed?
 👉 Are they following up with value instead of "checking in"?

These behaviors predict future results better than last quarter's numbers.

Your top performer might be coasting on natural talent.

Your bottom performer might be building skills that'll make them a superstar next year.

If you only look at the scoreboard, you're missing the game.

—
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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

You asked for it and here it is: the TACTICAL day in the life of the AI powered seller

Exactly what can a rep do right now with AI? What should they do manually because it’s better?

Let me give you one of the first places to completely re-work their day today…follow up.

An AI-powered seller can generate three perfect emails in sub-five minutes that are better than 99% of what is going out today.

This is the new world…you just finished two discovery calls and start dreading the follow up email. The AI powered rep, instead of spending 45 minutes rewriting notes and sending generic recaps, uploads the transcript and says:

“Write me three versions. One for the CFO, one for the COO, one for Ops.”

RepGPT spits out all three in 90 seconds. You tweak, send, and move on.

That’s the difference between working harder and working smarter.

✅ Side note: I see A LOT of generic AI tools doing email recaps but they aren’t as tailored as they need to be and feel like a check box. Not personalized to each person which is what is required in 2026 to stand out

The best sellers in 2025 aren’t using AI to save time. They’re using it to buy time for better conversations.

New episode of AI Powered Seller is LIVE now. Check out the link in the comments. 

I break down how top reps use assistants like RepGPT and Meet Journey to crush their day before lunch.

How much of your day could you automate right now if you actually mapped it out?

RevOps has changed more in the last 18 months than in the previous decade.

Five years ago, “RevOps” meant dashboards and CRM hygiene. Let’s be honest….for many companies this where we still are.

Now it is the operating system for the entire GTM engine sales, marketing, and CS unified under one motion.

In 2025, 75% of the fastest-growing companies adopted RevOps models to eliminate silos and accelerate revenue alignment.

The adopted it but I only see about 15-20% of companies actually living it
Why? Two simple reasons:

1️⃣ They can’t keep up with changes in tech because they have too much noise on their plate. They are constantly forced to go on to the next thing vs optimizing what they have.

2️⃣ Companies keep staffing jacks of all trades and expecting them to be an expert at all 10K plus revtech tools. They buy a tool they have never implemented or implemented once and maybe get 30% of the potential. It’s a losing battle and only getting worse.

And the rise of fractional RevOps leaders is rewriting the hiring playbook.

→ Speed to value in weeks, not quarters
→ Strategic execution without full-time headcount
→ Immediate impact on forecasting, funnel velocity, and process leaks

The companies moving fastest aren’t adding more people..they are adding precision.

How long before your org structure catches up to how revenue really gets built today?

Open article: How to Hire a Fractional RevOps Leader: Your Step‑by‑Step Guide by skaled.com

How to Hire a Fractional RevOps Leader: Your Step‑by‑Step Guide

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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The Battle

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