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

Jeremy Ramos

Are you an innovative thinker eager to achieve a breakthrough, either for your team or for yourself?
Do you possess a deep passion for transforming your ideas and vision into reality? 
If you're ready to embark on a new journey, let's connect.

With over 20 years of experience, I am an entrepreneur and a leader in technology product development, known for my results-oriented approach. I have a proven track record of building and guiding product teams to deliver high-value outcomes. My expertise lies in fostering innovative thinking and disciplined execution within dynamic, fast-paced environments.

I value:
- Collaborating as a team to surpass expectations.
- Cultivating a love for your work and maintaining harmony with your surroundings.
- Approaching challenges with courage and executing tasks with discipline.
- Valuing diversity, embracing creativity, and fostering a fun environment.
- Communicating effectively to build trust across all levels.
- Consistently generating results that add net value to society.
- Committing to continual growth and learning every day.

I thrive when working alongside business leaders, entrepreneurs, and aspiring entrepreneurs who are not only motivated themselves but also inspire those around them. 

If this resonates with you, I'd be delighted to have a conversation.

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The Battle

Dave Boyce

Jeremy Ramos

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