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

Inscaler

Boutique Fractional Sales Leadership agency for early-stage startups <5M ARR.

We help founders with limited sales experience sell more and better through up-to-date and tailored B2B revenue processes that scale and grow sustainably.

How It Works ⭐

➡︎ Get in touch with us via our website or Linkedin.
➡︎ We will send you a Sales Assessment to fill out.
➡︎ We will run a discovery call of 30 minutes together where we try to understand if we are a fit.
➡︎ Send and discuss the proposal.
➡︎ Kick off.

Start today!

Founder

Pavilion

Executive Member

ShippyPro

Advisor to CEO and co-founder on sales strategy and GTM.
I moved to Full-time later in October

VP of Sales

BOOM

Responsible for Sales GTM, globally. I lead >15 strong reps who are responsible to grow Boom. 

Results:

• Growing revenue by multiple X each year
• Started and led the transition from marketplace to SaaS leading to multiple X growth in MRR YoY 
• Grew headcount from 0 to 15 reps
• Developed a complete outbound sales strategy, and built Sales Dev, Customer Success, and Sales Ops organizations.
• Worked extensively with Marketing to align on inbound
• Worked hand by hand with Head of Product and Co-founders on the product roadmap.
• Evaluated, purchased, and implemented a full sales stack with tools including Salesforce, Outreach, Lusha, Gong, Sales Navigator, Aircall.

Head Of Global Sales

Cloudbeds

Cloudbeds is a #remotefirst travel industry startup that works to make the world a more welcome place. 

Main responsibilities:

• I'm responsible for new biz acquisition in Europe managing a team of +15 talented AEs; 
• Hiring, coaching, and performance management; 
• Working closely with marketing to ensure enough and quality level of leads;
• Working closely with sales ops and leaderships to increase win rate, conversion rate and improve sales excellence;

Results:

• Grew team from 7 to 15 people
• 150K ACV monthly revenue on avg 
• Went from last performing region worldwide to 1st in 4 months
• Doubled win rate conversion

Regional Sales Manager | Europe

Rebrandly

Rebrandly is the industry-leading link management platform to brand, track and share short URLs using a custom domain name.

Reporting to CEO & Founder, I built and scaled the global sales organization, managing an incredible and talented team of account executives, account managers and SDRs. Main market US.

Main responsibilities:

• Built from the ground - up a B2B sales organisation;
• Hiring, Coaching and Mentoring a team of AEs, AMs and SDRs;
• Acquired tools like CRM, video conferencing, prospecting and implemented playbooks;
• Work closely with the Marketing team on lead generation and inbound strategy;
• Developed and created outbound sales strategies;
• Worked with CEO on growth & strategic goals;

Achievements:

• Successfully built inside Sales Org from scratch
• YoY MRR growth 8X
• YoY ASP growth  10X
• YoY Headcount growth 4X
• FY Churn rate existing business <5%

Head of Sales | Global

LinkedIn

Promoted in the role:

• Reporting to Senior Management on forecast and attainment of team
• Conducting Interviews
• Onboarding of new hires
• Lead internal project on selected business priorities

Senior Relationship Manager - Sales Solutions

I was fortunate enough to be the 1st Italian Relationship Manager hired in the LSS business.

I invest the majority of my time on:

• Managing a Mid-Market book of accounts within Italy and EMEA; I'm responsible for renewal and upselling. (ratio of 60/40).
• I was Enterprise Relationship Manager ad interim for the FY16 managing Key and strategic accounts;
• I run and lead training +300 people on LinkedIn Sales Solutions in order to have higher engagement and better ROI;
• Mentoring and coaching new hires within the team;

Relationship Manager - Sales Solutions

FaxBox

Europe’s fax and SMS Cloud solutions startup, Firstway  provides organisations high quality, value-added communication services. (recently acquired by J2 Global Inc.).

In my role, I was the first international Sales Lead to open the markets outside of France (core market).

Main responsibilities:

• Lead, train and coaching a multilingual team of Sales Reps;
• Identify, prospect, negotiate and implement commercial agreements with strategic partners;
• Working with the Marketing department in order to implement successful marketing campaigns;
• Providing coaching and feedback to the team;
• Training groups up to +100 on IT topics

Manager, Channel and Direct Sales Italy, Spain & Benelux

Ryanair - Europe's Favourite Airline

This was my first job experience in Ireland. 

Ryanair is Europe’s biggest low fares airline and 1st airline in Italy.

In my role, as Sales & Marketing Manager for Italy, Greece & Croatia, I was responsible for sales & marketing activities across the markets.

The job had a 360 degrees scope, from sales to marketing, communication and media. I was basically acting as a 'country manager' for the sales & marketing activities of Ryanair in those markets. 

Main tasks & responsibilities:

• Leading & coaching a team of Sales Executives;
• New business development with tourist boards & relevant Government departments;
• Dealing with almost 40 airports;
• Planning marketing and strategic activities;
• Reviewing and issuing press releases;
• Dealing with media across the markets through 1-2-1’ interview or PR’s activities;

Manager, Sales & Marketing Italy, Greece and Croatia

Cisalpina Tours / Uniglobe Travel

Worked as Account Executive at Cisalpina Tours one of the biggest travel management companies in Italy. I was selling business travel services to small and medium companies in south of Italy.

After 2,5 years I went to Uniglobe Travel in Roma, doing the same thing and selling business travel services to large organisations in Italy.

Account Executive

Build and Scale your 1st Sales Team with me 🪄 | Build your Own Fractional Business with the Fractional School 📕 | Follow me on Instagram @matteopapaluca

If you don't know how to build your first sales playbook, team and processes, you are on the right profile.

Matteo Papaluca ⚡️

Last Friday evening I caught up with a founder I worked with last year.

It was late - one of those chats that starts casual and turns into a working session.

He said:

“𝘐’𝘮 𝘱𝘭𝘢𝘯𝘯𝘪𝘯𝘨 𝘧𝘰𝘳 𝟤𝟢𝟤𝟨 — 𝘵𝘦𝘢𝘮, 𝘦𝘹𝘱𝘦𝘯𝘴𝘦𝘴, 𝘨𝘰𝘢𝘭𝘴. 𝘊𝘢𝘯 𝘐 𝘳𝘶𝘯 𝘴𝘰𝘮𝘦 𝘯𝘶𝘮𝘣𝘦𝘳𝘴 𝘣𝘺 𝘺𝘰𝘶?”

We spent 45 minutes sketching ideas and planning for 2026.

What I reminded him was simple: 𝗲𝗮𝗿𝗹𝘆-𝘀𝘁𝗮𝗴𝗲 𝘀𝗮𝗹𝗲𝘀 𝗽𝗹𝗮𝗻𝗻𝗶𝗻𝗴 𝗶𝘀 𝗮 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁 𝘀𝗽𝗼𝗿𝘁.

If you’re still below 2–3M ARR, you don’t need complex models.

Here’s how I approach it 👇

𝗦𝘁𝗮𝗿𝘁 𝗯𝗼𝘁𝘁𝗼𝗺-𝘂𝗽.

→ 𝘏𝘰𝘸 𝘮𝘢𝘯𝘺 𝘱𝘦𝘰𝘱𝘭𝘦 𝘥𝘰 𝘺𝘰𝘶 𝘩𝘢𝘷𝘦?
→ 𝘞𝘩𝘢𝘵 𝘤𝘢𝘯 𝘦𝘢𝘤𝘩 𝘳𝘦𝘢𝘭𝘪𝘴𝘵𝘪𝘤𝘢𝘭𝘭𝘺 𝘥𝘦𝘭𝘪𝘷𝘦𝘳?
→ 𝘈𝘯𝘥 𝘩𝘰𝘸 𝘥𝘰𝘦𝘴 𝘵𝘩𝘢𝘵 𝘳𝘰𝘭𝘭 𝘶𝘱 𝘵𝘰 𝘵𝘩𝘦 𝘤𝘰𝘮𝘱𝘢𝘯𝘺 𝘵𝘢𝘳𝘨𝘦𝘵?

3 AEs × 500K targets = 1.5M.
But early-stage teams rarely hit 100%.
Assume two out of three perform - now you’re closer to 1M. (ouch!)

Then layer in your 𝗮𝘀𝘀𝘂𝗺𝗽𝘁𝗶𝗼𝗻𝘀 🧑‍🔬
↳ ACV, win rate, and demo volume per AE

Now it's time for 𝗲𝘅𝗶𝘀𝘁𝗶𝗻𝗴 𝗯𝘂𝘀𝗶𝗻𝗲𝘀𝘀 🧮
↳ Baseline revenue and churn

Ultimately - total cost vs. revenue goal (aim for a 𝟯–𝟱𝘅 𝗿𝗮𝘁𝗶𝗼)

If your win rate is 33%, each AE needs 30 demos/month.
At 20%, that number explodes. Can they handle it? 
Probably not.

Go back to point 1.

Planning isn’t a fantasy exercise. It’s a human one.

Hiring 3 reps and expecting them to hit full quota by month six - without onboarding or enablement - is wishful thinking.

So, as you plan for 2026:

↳ Anchor your targets in reality.
↳ Respect ramp and readiness for your team.
↳Don’t over engineer - iterate.

And if you’re heading into 2026 without a Head of Sales yet... you know where to find me. 👀

Matteo Papaluca

Your Sales Co-Pilot | Founder at Inscaler.com

My first job as a sales leader was at an early-stage startup.

It paid more than 30% less than my previous role - with almost no benefits.

I was leaving Linkedin glory for a 20-people startup. In 2018.

On a personal level wasn't easier either.
We’d just had our first baby. My wife thought I was crazy. 

But those years were transformational.

I learned more about building teams, hiring, and selling than any MBA or big-company gig could teach.

Inscaler was born there.

If you’re an ambitious sales person dreaming of leadership - don’t chase the biggest pay-check.

Don't chase security. Don't chase the shiny offices.

Chase the steepest learning curve.

Chase the grind.

The money will catch up. 

The experience never leaves.

3 biggest mistakes I see from early-stage founders

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The Battle

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Likes

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