From Product Validation to $100M ARR: The Critical Decisions That Make or Break SaaS - EP 99 | Dave Boyce

In this episode, I talk with Dave Boyce, the Chief Strategy
Officer at Winning by Design, about the critical decisions that
make or break SaaS companies' journeys from product validation to
scalable growth.




What to expect:


Why investors no longer fund multiple attempts at finding
product-market fit and what this means for founders

Dave's counterintuitive approach to measuring product-market
fit: "If 70% of new users hit first impact before running out of
attention span, you can start scaling"

The danger of hiring experienced revenue leaders too early
and why curious problem-solvers outperform decorated executives
at this stage

How to build a revenue architecture with proper
instrumentation before attempting to scale

Take an inside look at how HubSpot, MongoDB and Unity
successfully launched new growth initiatives by creating
dedicated "pods" outside their core structure






My highlights:


Dave's brilliant framework: "You need three things - mindset,
talent, and time. It will take 18 months to iterate into a new
business that works"

His candid perspective on why founders struggle to know when
to pivot: "You're simultaneously convincing investors, employees
and yourself that you're onto something"

The tactical blueprint for building your first commercial
team: Hire director-level sales leaders and heads of demand
generation, not CMOs

Why a CEO should insist that all go-to-market leaders get
certified in revenue architecture: "I don't want to waste time
translating between silos"






About the guest: 


Dave Boyce brings a wealth of experience from both enterprise
(Oracle) and high-growth SaaS environments. As Chief Strategy
Officer at Winning by Design, he's helped countless companies
build scalable revenue architectures. His upcoming book,
"Freemium" (August 2025) explores how
companies can successfully implement product-led growth
strategies. Dave's unique perspective bridges traditional
enterprise sales and modern PLG approaches, making him the
perfect guide for founders navigating the growth journey.





Who should listen to this episode:


Founders who've achieved initial traction but are unsure if
they genuinely have product-market fit

CEOs building their first commercial team beyond founder-led
sales

Established companies ($10M-100M ARR) looking to rediscover
growth through new verticals or products

Anyone responsible for aligning product, marketing, sales and
customer success






The success formula? 


Don't scale until you've confirmed product-market fit through
usage data, build a unified commercial language with proper
instrumentation, hire curious problem-solvers at the director
level, and give them time to iterate toward success.


P.S. Highly recommend. Pre-order Dave's book,
"Freemium" (gets published in August 2025)





Song by StockTune


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