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

The year was 2000.

➡️ I had never sold a company.
➡️ Never sat on a board.
➡️ Never sold a 7-figure deal (or 6, or 5)
➡️ I had raised funding and started two companies, both of which folded.

We lived in Boston--an expensive place, far away from family.  We had two kids (pictured), so I joined a company that could pay me a salary (ProfitLogic (Acquired by Oracle), and we buckled down.

25 years, 6 kids, 8 houses, 3 cities, and 7 exits later, and we are still doing it--life, career, faith, family, fun... 

Here's to those on the front end of the journey.  I see you. You are squinting, trying to see your successful future. The current circumstances seem impossible, and the road ahead is fuzzy. You will do it! Buckle down, work hard, take some calculated risks, pick yourself back up, put yourself back in the game, and you will do it! 

Don't do it for the rewards (they will come), do it for the journey. Do it for the adventure. Do it for the chance to make an impact. Care for the people in your life, keep your head up and eyes forward, and be grateful for the opportunities you have.

XOXO,

-db

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

Kearney

Bringing extensive experience in management, digital and technology strategy to aid clients in achieving digital and operational transformation goals. Focusing on crafting, implementing, and supervising effective digital, technology, and operational resilience strategies. Additionally, supporting clients in software procurement and negotiations to ensure optimal commercial terms and risk mitigation.

Director

Advised large and medium-sized companies on IT and digital strategy, focusing on redesigning operating models and optimising application architecture. Supported fintech companies in identifying regional opportunities and collaborated with independent consulting teams to deliver actionable strategic guidelines, target operating model roadmaps, and enterprise architecture aligned with digital agendas. 
Occasial contribution of expert content to IBS Intelligence for coverage of technology vendors across the financial technology sector

Enterprise design and IT expert 

GEN-I, d.o.o.

Member of The Supervisory Board

SID banka

Responsible for devising, executing and delivering the information and technology strategy at the Slovenian Export and Development Bank. We focused on updating application and ICT architectures and building a strong IT governance framework in line with DORA requirements to enhance the bank's technological resilience and operational effectiveness. 
Also responsible for executive management of treasury front office operations.

Executive Director Information Technology - CIO

NLB d.d.

Advising the management board on topics of IT strategy, with particular focus on the consolidation of the core banking system.

Advisor to the management board

Leading the Enterprise Architecture and Business Analysis teams, I lead a team that has been a key link between business and IT in the strategy design and execution. We initiated a large-scale technology transformation, overhauling both the application and infrastructure architecture to align with organisational goals. 
My role encompassed driving the development and execution of the IT strategy, integrating changes across multiple dimensions of the operating model to ensure alignment with business strategy.We established a robust demand management process and significantly enhanced requirements management, service design, and solution architecture practices. Managing a team of 25–70 professionals, I successfully delivered several large-scale initiatives and hundreds of smaller improvements, collectively contributing over €10 million in annual revenue.

General Manager - Chief Enterprise Architect

Responsible for demand management, business analysis, PMO, application development lifecycle, and priority management.

Deputy General Manager

Stretegic coordination and expert roles at bank transformation projects, focusing on strategy development, revamping business model for retail segment (small enterprises and private individuals) and introduction of SFE principles with supporting tools.

Advisor to the Management Board

HYPO Alpe-Adria-Bank International AG

•	Designed a sales support tool for effective portfolio steering, campaign management and activity tracking used in the international banking group with 8 large regional subsidiaries.
•	Coordinating product development process for corporate banking products, managing and enhancing product portfolio and product catalogue.
•	Contributing to development and implementation of Sales and service concept (main focus on performance and activity management).
•	Alignment and quality control of strategic policies aiming at restructuring and the operational enhancements of the troubled banking group.
•	Expert roles in the process optimization projects, resulting in the 20-30% efficiency increase.
•	Cooperating with implementation of base platform for Business intelligence and reporting tools.
•	Part of the implementation team for European Comission behavioral measures compliance reporting.

Senior Expert Product Management

•	Heading the development and maintenance of business infrastructure on 17 regional power markets. 
•	Establishing or maintaining relationship with several regional exchanges and brokerage houses. 
•	Coordination of organization and optimization of business process for energy trading as well as business process coordination of all units and subsidiaries within international power trading group.
•	Project management and user specification for IT development in support of energy trading activities.
•	Knowledge management coordination.

Head of Business development

Kranjska investicijska družba, d.o.o.

•	Responsible for liquidity management, controlling, accounting, MIS and tax related issues at Real Estate Investment Company. 
•	Finalized two feasibility studies of large real estate projects. 
•	Performed the real estate revaluation of all companies assets for reconciliation of financials.

CFO, CIO

BAWAG banka, d.d.

•	Project manager for second implementation of core banking system Flexcube with customization for adopting new local currency. The project was finished within time and scope goals, with 75% of the budget.
•	Managing and operational involvement with reporting project (business intelligence) for all controlling requirements of the bank.
•	Consultancy services on Flexcube projects at Index bank (Credit Agricole) in Kiev, Ukraine (requirement scope and initial project preparation), GE Money, Budapest  (vendor selection), BAWAG PSK, Prague (Project team workshops). Collaboration with Unisys and PMI International.
•	Member of IT and security forum at Slovenian banking association, Steering committee member for projects in Bawag PSK subsidiaries group 
•	Vendor coordination and negotiation.
•	Business development and organization of business processes in the bank.

Head of Development and IT

•	Business process setup implementation and workflow management for a green field banking operation.
•	Project manager for the initial implementation of core banking system Flexcube (complete solution for booking of banking business, specially loans and deposits, letters of credits, journal entries…)
•	Product manager for development of core banking products, with initiation of product based reporting.

Project Manager

Raiffeisen bank

Customer acquisition
Managing banking relationship with small and medium sized companies. 
Performing initial debt restructuring for distressed companies.

Client Relationship Manager

Kapital publications

Editor of world markets with business magazine Kapital 
Journalist
Project manager for establishing Golf Slovenia, the first national golf magazine in Slovenia, and it’s executive editor.

Executive and Contributing editor

With a background and experience in business, technology, and psychology, I help organisations navigate strategy and orchestrate change management to support growth. A senior professional in banking, IT, and consulting with over 20 years of expertise in IT management, strategy, digital transformation and technology procurement. 

Proven leadership in managing large-scale IT projects and streamlining processes to improve efficiency and performance, backed by a strong track record and as well as valuable lessons learned.

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Dave Boyce

Mitja Ucakar

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