In this episode of the DevReady Podcast, Andrew Romeo is joined by Dannielle K. Pearson—an award-winning strategist, keynote speaker, and former U.S. military intelligence officer—whose diverse career has spanned global consultancy, enterprise strategy, and tech innovation. Dannielle shares her journey from high-stakes defence work to shaping scale-ups and SaaSThe term SaaS stands for Software as a Service. SaaS is an evolution of an application that runs on the... companies, bringing a rare blend of analytical rigour and commercial acumen to every conversation. Now based in Australia, Dannielle draws from her experiences at Deloitte, Salesforce, and Procore to empower founders and teams to think more critically, act more strategically, and adapt to fast-changing markets. Whether you’re building a product, seeking funding, or shaping a go-to-market plan, this episode is packed with practical insights and refreshing truths.
Dannielle begins by unpacking how her formative years in the U.S. Air Force intelligence community instilled her with core competencies that remain central to her work today—critical thinking, accountability, and situational awareness. Transitioning into the corporate world through Deloitte and then Salesforce, she applied these skills to enterprise strategy, eventually leading the development of vertical market roadmaps for one of the world’s most recognised SaaSThe term SaaS stands for Software as a Service. SaaS is an evolution of an application that runs on the... platforms. Her unique ability to blend big-picture strategy with practical execution took her to Procore, where she played a key role in market expansion during its pre-IPO phase. At each stage, her approach to strategy has remained rooted in data, clarity, and adaptability.
Sharing an inside look at her time at Procore, Dannielle recounts the company’s unconventional founding story, including how the CEO famously worked for $1 a year and recruited talent from local coffee shops. She speaks candidly about the missteps many U.S.-based tech companies make when expanding into international markets—particularly Australia—and how strategic localisation is often the missing piece. Her role at Procore saw her leading efforts across APAC, prioritising markets, and tailoring strategy to ensure effective market entry, with a sharp focus on product-market fit and executional timing.
When it comes to early-stage product development, Dannielle challenges conventional wisdom. She explains why too much upfront market research can stall momentum and argues for a more agile approach: build something, put it in front of real users, and be willing to adapt. She illustrates this with a compelling example of a startup that unintentionally built a rostering tool, only to discover—through live feedback—that it solved a major problem in the hotel industry. Dannielle urges founders to embrace adaptability, avoid perfectionism, and understand that real validation comes through customer engagement, not desktop research.
Drawing from her work with Startmate and her experience reviewing hundreds of pitch decks, Dannielle outlines the three types of founders she sees most often: the hype-chasers, the emotionally attached builders, and the adaptable, market-driven entrepreneurs. She encourages founders to fall into the third category—those willing to listen, evolve, and say no when needed. Investors, she notes, don’t fund ideas—they fund people. A founder’s mindset, adaptability, and ability to execute consistently outweigh flashy slides and inflated market claims.
Rounding out the conversation, Dannielle and Andrew discuss the psychology behind startup funding, busting the myth of the “TAM slide” and underscoring the importance of understanding your obtainable market. They reflect on how different business models—consulting-led, low-cost/high-volume, enterprise SaaS—require distinct funding paths. From client-funded MVPs to early wins through strategic partnerships, they explore how founders can build sustainably and profitably. Most importantly, Dannielle leaves listeners with three takeaways: adaptability is everything, don’t rely on total addressable market metrics alone, and know what to say no to.
Topics Covered
- Dannielle’s transition from military intelligence to tech and strategy
- Core skills developed in the U.S. Air Force: critical thinking and situational awareness
- Leading vertical strategy and go-to-market planning at Salesforce
- Market entry challenges and localisation at Procore
- Data-informed strategy and establishing a baseline
- Agile execution and testing in-market vs. over-researching
- Founder mindset types and the value of adaptability
- Why investors prioritise people over pitch decks
- The limitations of TAM slides and the importance of obtainable markets
- When to bootstrapThe term bootstrap is used in development when describing the initial part of any development or a quick way to... vs. raise capital and how client funding can support product development
Important Time Stamps
- From Military Intel to Tech Strategy: Dannielle’s Wild Career Pivot (0:07 – 4:24)
- $1 Salary to $34 Billion: The Grit Behind Procore’s Rise (4:25 – 6:20)
- Why Too Much Market Research Might Kill Your Startup (6:21 – 10:40)
- The 3 Types of Founders—Which One Are You? (10:41 – 14:56)
- Forget the TAM Slide—Show Me Your First 10 Customers (14:57 – 23:00)
- % of a Huge Market? Not Impressive—Here’s Why (23:01 – 28:06)
- Funding, Focus, and FOMO: How to Stay on Track as a Founder (28:07 – 37:26)
