DevReady Podcast

Why Most Startups Fail - And What Adaptable Founders Do Differently | Ep 215 | DevReady Podcast

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 SaaS 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 SaaS 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.
#DevReadyPodcast #StartupStrategy #ProductMarketFit #AngelInvestor #WomenInTech #BuildInPublic #TechLeadership

Stop Avoiding It: Expert Tips for Handling Tough Conversations at Work | Ep 214 | DevReady Podcast

In this episode of the DevReady Podcast, host Anthony Sapountzis is joined by Mark McPherson, Leadership Communication Expert, Executive Coach, Speaker, and Author—for a deep dive into the art of handling difficult workplace conversations. Drawing on decades of experience coaching leaders and executives across Australia, Mark shares his practical frameworks for delivering feedback that is clear, constructive, and confident. Whether you're managing high-performing teams or navigating your first leadership role, Mark's insights offer actionable strategies to help you communicate with authority—without losing your humanity.
Mark begins by recounting the origin of his expertise: taking over a team where one toxic team member put his leadership to the test. Frustrated by the lack of useful, real-world advice available, he began developing his own methodologies focused on practical, immediate solutions rather than abstract theories. At the heart of his message is a simple but profound truth—avoiding tough conversations not only undermines team culture but also erodes a leader’s self-respect. For Mark, confident communication isn’t a “nice to have”; it’s a leadership essential.
Throughout the episode, Mark introduces his signature tool: personal conversation scripts. These scripts are designed to guide leaders through uncomfortable discussions using language that is assertive but tactful, clear but not combative. He explains how these scripts must be personalised to reflect each leader’s communication style, cultural context, and company environment. His advice? Focus on one issue at a time, be specific, and once you’ve made your point—zip it. Trying to address too many things at once only confuses the message and dilutes its impact.
Mark also highlights the importance of fact-based feedback. He warns against using vague or emotionally charged labels like “disrespectful” or “belligerent” and instead recommends sticking to observable behaviours. By referencing specific examples and tying them back to company policy—or even just common courtesy—leaders can reduce defensiveness and keep the conversation grounded. Consistency is another major theme: teams need to know the standards, and they need to see those standards applied evenly and fairly across the board.
In the final part of the conversation, Mark shares his FEA and FEAR frameworks—structured approaches that stand for Facts, Explain, Ask, and Request/Reward. These models give leaders a quick, repeatable format to address issues with calm authority. He walks through real-world examples, including how to handle something as seemingly simple (yet loaded) as a timesheet error. His closing message is one of balance: yes, some conversations are awkward, but with preparation, structure, and the right mindset, they can be delivered with both professionalism and empathy.
#LeadershipCommunication #ToughConversations #ExecutiveCoaching #PeopleManagement #FeedbackThatWorks #DevReadyPodcast #LeadershipDevelopment #AerionTechnologies

Secrets of a Serial Founder: How to Scale, Exit, and Buy Businesses That Last | Ep 213 | DevReady Podcast

In this episode of the DevReady Podcast, host Andrew Romeo is joined by Michael Bronfman, CCO & MD of baresop and a seasoned entrepreneur with a track record of scaling, exiting, and investing in high-growth businesses. From launching his first startup at just 18 to now being a shareholder in over a dozen ventures, Michael shares a candid account of the highs, lows, and pivotal lessons he's gathered along the way. With experience spanning tech, healthcare, SaaS, and consumer goods, Michael unpacks what it really takes to build and acquire successful businesses in today’s climate—and why long-term thinking, the right people, and strategic structuring matter more than ever.
Michael’s entrepreneurial journey began with a problem he encountered firsthand: struggling to get a haircut on his lunch break while working in sales at Telstra. That frustration sparked a beauty booking platform, which he later sold to Zomato—his first exit by the age of 22. His next major milestone was joining Openpay as its third employee, helping scale the buy-now-pay-later company to 250 staff and a listing on the ASX. This chapter of his journey offered a crash course in hypergrowth, hiring at scale, and the operational complexities that come with explosive expansion.
Throughout the conversation, Michael reflects on the value of patience, resilience, and learning through doing. He emphasises that real business success doesn’t come overnight and warns against the trap of chasing quick wins. Instead, he advocates for building relationships, surrounding yourself with complementary skills, and sticking with a venture long enough to see real results. He and Andrew highlight the importance of mindset over experience, noting that hunger and alignment are more valuable than credentials in early-stage ventures.
Michael also opens up about Openpay’s eventual liquidation—clarifying that it was due to investor issues rather than poor management. He shares how this experience, while challenging, strengthened his resolve and reinforced the importance of building sustainable, profitable ventures. It also prompted his transition into business acquisitions, where he began focusing on buying businesses with strong operations and recurring revenue, often backed by government funding. These characteristics, he explains, provide stability and long-term potential, even in unfamiliar industries.
Now a shareholder in around 14 businesses, Michael’s approach to acquisitions is strategic and structured. He’s moved away from the mindset of “100 companies by 40” and instead seeks quality over quantity, favouring calculated risk, strong leadership teams, and industries with long-term viability. He views his role as assembling a puzzle—bringing the right people into the right roles to unlock hidden potential. Deals, he notes, aren’t about the size of the business but the strength of the opportunity and how well the risk is managed.
Wrapping up, Michael reinforces his core principle: every acquisition must be a win–win. Whether it’s a well-performing business or one that needs operational tweaks, what matters most is ensuring all parties benefit and that relationships remain strong. Reputation, trust, and communication are everything in the acquisition space—and Michael makes it clear that ethical deal-making is just as important as financial success. This episode is a must-listen for anyone curious about startup exits, business acquisition strategy, or building a legacy through thoughtful entrepreneurship.
#StartupGrowth #BusinessAcquisition #Entrepreneurship #ScaleUpStrategy #RecurringRevenue #FounderInsights #DevReadyPodcast

Founders Beware: Charlie Ill Shares the ONE Mistake Killing Your Startup Success | Ep 212 | DevReady Podcast

In this episode of the DevReady Podcast, host Anthony Sapountzis speaks with Charlie Ill, CEO of Investible, exploring his intriguing journey from aerospace engineering into Venture Capital. Charlie reflects on his career transition, detailing how his early experiences in engineering and process improvement provided him with unique skills and perspectives beneficial to his role in Venture Capital, particularly regarding business restructuring and technological innovation.
Charlie delves into Singapore’s transformation into a leading global tech innovation hub. He discusses the strategic decisions made by Singapore's government, which focused on fostering deep-tech innovation through targeted incentives and a supportive environment. This has allowed Singapore to become a standout ecosystem for startups looking to rapidly scale their technological solutions and achieve international impact.
Strategic mentorship lies at the core of Investible’s philosophy. Charlie shares how Investible employs data-driven methodologies to carefully match startups with mentors possessing relevant experience and expertise. These tailored mentorships significantly address skill gaps, facilitate informed decision-making, and accelerate overall growth, positioning startups effectively for sustained success.
Charlie also discusses the importance of syndication among venture capital firms. He explains how collective VC involvement supports startups beyond mere funding, providing diverse perspectives, pooled resources, and more comprehensive support. This strategic collaboration ensures startups are equipped with broader insights and networks to navigate growth effectively.
Examining global startup ecosystems, Charlie highlights cultural and economic differences in Australia, Singapore, and the Middle East. He points out the significance of entrepreneurs understanding and addressing local market dynamics. Successful startups, Charlie emphasises, are those that tailor their products and strategies to align deeply with the needs and expectations of their cultural context.
Charlie stresses the essential traits of resilience and resourcefulness for startup success. He emphasises how limited resources can compel founders to creatively navigate challenges, resulting in innovative solutions. Charlie underscores that resilience, driven by necessity, often leads to more effective and efficient outcomes.
Lastly, Charlie discusses venture capital strategies during economic downturns. He believes these periods offer unique opportunities, emphasising the importance of disciplined execution, agility, and sustainability. He notes that while fewer startups may receive funding during such times, those that do often have stronger foundations, better adaptability, and higher potential for long-term success.
#VentureCapital #StartupInsights #Mentorship #DevReadyPodcast

The Digital Marketing Blueprint: Stephen's Proven SEO Strategies for Success | Ep 211 | DevReady Podcast

In this episode of the DevReady Podcast, host Anthony Sapountzis is joined by Stephen Kee, Head of Business Growth at SME Digital. Stephen shares his journey from financial mathematics to digital marketing, recounting his move from South Africa to Australia in 2011 and his entrepreneurial ventures. After building a successful Airbnb business that generated $1 million in turnover, the COVID-19 pandemic forced him to pivot. This led him to SEO and web design, where he now helps businesses optimise lead generation and conversion. Drawing on his mathematical background, he highlights the similarities between Airbnb’s algorithm-driven marketing and search engine optimisation, laying the foundation for his current role at SME Digital.
Stephen’s transition into digital marketing was shaped by his corporate experience and an intensive business course that equipped him with both technical web design skills and essential business knowledge. A pivotal moment in his journey was attending a bootcamp, where he realised the power of networking and the adage that "your network is your net worth." Initially developing a web agency to support his Airbnb business, he soon recognised a greater opportunity in helping service-based businesses enhance their online presence. He reflects on the evolving nature of SEO, particularly the growing influence of TikTok and AI-driven searches, emphasising the need for businesses to adapt to shifting digital trends.
Discussing marketing strategies, Stephen explains that while psychology plays a role, data and mathematics are equally crucial in ensuring success. He underscores the importance of a structured approach, using data-driven insights to refine marketing efforts. Anthony shares his experience with social media advertising, highlighting the necessity of experimentation to find the right approach for audience engagement. They discuss the challenge of balancing budget constraints with the time required to identify effective strategies, reinforcing the value of incremental progress. Stephen also outlines the key elements of SEO, stressing the importance of aligning content with search intent and leveraging over 2,300 ranking factors to improve visibility.
Client expectations play a critical role in digital marketing success, and Stephen highlights the importance of managing them effectively during onboarding and discovery calls. He explains that many clients base their keyword strategies on anecdotal advice rather than data, making it essential to guide them towards evidence-based decision-making. Comparing Google Ads to renting and SEO to property ownership, he demonstrates the long-term value of organic search rankings. He also advises businesses to calculate their customer acquisition costs to assess SEO viability, noting that ranking highly in both paid and organic search amplifies visibility. The discussion further explores how lifetime customer value shapes digital marketing strategies.
The episode concludes with a cautionary discussion on the risks associated with unregulated industries like software development and SEO. Stephen shares a case where a client lost $1.4 million due to poor supplier choices, highlighting the need for businesses to work with credible experts. Anthony draws parallels between software development and construction, stressing the importance of proper planning before execution to avoid costly mistakes. Stephen advocates for industry education, warning against misleading SEO metrics and urging businesses to prioritise tangible results over vanity metrics. The conversation serves as a valuable guide for businesses looking to navigate digital marketing with a strategic and data-driven mindset.
#DigitalMarketing #SEO #BusinessGrowth #MarketingStrategy #WebDesign #LeadGeneration #Entrepreneurship

Gareth Rydon on How SMBs Can Win Big with Human-Centric AI | Ep 210 | DevReady Podcast

In this episode of the DevReady Podcast, Anthony Sapountzis interviews, Gareth Rydon, Co-Founder of Friyay.ai, Australia’s first generative AI studio. A leader in human-centred AI design, Gareth returns to share fresh insights on how small and medium businesses can embrace AI as a strategic partner. Together, they unpack the latest developments in generative AI, discuss emerging tools and trends, and offer practical advice for business owners, developers, and innovators navigating the fast-moving AI landscape.
The conversation opens with Gareth reflecting on how the AI landscape has shifted dramatically, moving away from elaborate prompt engineering towards more intuitive, plug-and-play assistants embedded in business workflows. He and Anthony highlight the growing strength of reasoning models like GPT-4, which allow users to interact in a more natural, conversational manner. Gareth, known for his focus on human-first design, recommends a more collaborative approach—encouraging users to ask AI for clarification or even admit when it lacks information, in order to reduce hallucinations and improve reliability.
The two also share their hands-on experiences with Microsoft Copilot and Google Gemini, having recently made the switch from Microsoft 365 to Google Workspace. While Copilot fell short of expectations, Gemini impressed with its seamless integration and functionality, particularly within tools like Google Sheets. The discussion moves into the realm of coding, where tools like Claude in Cursor are enabling developers to rapidly prototype with minimal error—though both caution that a basic understanding of coding is still essential to get the most out of these tools.
As AI reshapes traditional development roles, Gareth points out a blurring of lines between business analysts, product managers, and developers. With the right approach, non-technical professionals can now build and launch real products. Tools like Bubble and other no-code platforms may soon become obsolete, as AI models like Claude 3.7 generate high-quality, scalable code with speed and precision. They touch on the rise of “vibe coding”—where AI assists in development based on natural language—and how this could even change the way startups secure funding, given that fewer resources are now needed to bring a concept to life.
In closing, Anthony and Gareth discuss the broader implications of AI in team collaboration, planning, and operations. From uploading wireframes to guide builds, to using AI tools as a ‘third person’ in strategic workshops, they illustrate how businesses can dramatically accelerate their planning cycles. Gareth also shares some favourite workflow hacks—like using AI to process meeting transcripts and draft planning documents. His parting advice is clear: don’t wait for the perfect time. Pick one tool, start small, and let curiosity guide you—because the best way to learn what AI can do for your business is simply to try.
#DevReadyPodcast #GenerativeAI #SmallBusinessGrowth #ClaudeAI #ChatGPT #AIForSMBs #TechLeadership

VC Secrets For 2025: Nicholas Ooi on AI, Founder Fit & Scaling Startups to Success | Ep 209 | DevReady Podcast

In this episode of the DevReady Podcast, host Andrew Romeo speaks with Nicholas Ooi, an investor at Investible, about his journey from corporate consulting to venture capital. Nicholas shares how his passion for technology and startups led him to make a career shift into the startup ecosystem, specifically during its rapid growth in Australia. Now, as part of Investible, Nicholas focuses on early-stage investments in the ANZ and Southeast Asia regions. Looking ahead to 2025, he is optimistic about improving market sentiment, especially for early-stage investments, and the growing role of AI in streamlining software development for founders.
Nicholas discusses the stages of investment that Investible focuses on, specifically Pre-Seed to Series A. These stages include companies that are either pre-revenue or just beginning to generate some revenue. He emphasises that Investible invests in a wide array of sectors, including AI-enabled software, deep tech, and hardware, with a strong emphasis on building defensible companies. One key insight Nicholas shares is the growing importance of vertical applications in AI startups, which are more effective than horizontal solutions. By targeting specific industries, vertical solutions allow companies to scale efficiently within their niche.
In addition to his thoughts on investment, Nicholas offers insights on the future of AI and its role in software products. He believes that all software companies will need to incorporate AI in the long term to remain competitive. However, he also stresses that successful companies must first focus on solving real customer problems before adopting AI. Nicholas acknowledges the challenges faced by Australian companies competing with US giants due to capital constraints but highlights emerging opportunities in adjacent sectors like semiconductor chip production and machine learning models.
Nicholas gives a look into his daily routine as a venture capital investor. His day typically involves three main tasks: meeting with early-stage startup founders, conducting due diligence on promising investment opportunities, and preparing materials for the investment committee to secure funding. He underscores the importance of ongoing support for portfolio companies post-investment, as helping them grow and succeed is a key part of his role. Nicholas also touches on the balance of screening, analysis, and strategic involvement that makes up the comprehensive nature of his work.
Another important discussion in the episode focuses on the evolving nature of software business models. Nicholas highlights the shift from traditional subscription-based models to usage-based models, such as API call-based pricing. He also shares the significance of "founder-market fit," explaining how successful founders often have a personal connection to the problems they are solving. Nicholas discusses how investors assess founders, looking for unique insights, technical expertise, and soft skills such as resilience and adaptability that are crucial for long-term success.
Lastly, Nicholas shares what sets Investible apart when working with founders seeking investment. He points to their strong presence in Southeast Asia, which offers businesses opportunities to expand into the region, and their angel syndicate model that provides hands-on, strategic value beyond financial backing. Nicholas also discusses the pressures of pursuing venture capital funding and encourages founders to carefully consider whether they truly want to scale their businesses under the expectations and long-term commitments that come with VC funding.
#VentureCapital #TechStartups #Entrepreneurship #StartupGrowth #Investing #BusinessFunding #DevReady

Dreamoro’s Klaus Bartosch Reveals the Startup Mistakes Costing You Millions | Ep 208 | DevReady Podcast

In this episode of the DevReady Podcast, host Anthony Sapountzis is joined by Klaus Bartosch, CEO of Dreamoro, to discuss the critical gaps in startup strategy and commercialisation. With over 35 years in IT and experience founding and exiting a listed health tech company, Klaus brings invaluable insights into the challenges facing entrepreneurs today. Having engaged with more than 450 founders in the past 18 months, he reveals a startling reality—only two had a well-thought-out strategy, while most confused go-to-market plans with a comprehensive business strategy. Klaus stresses the importance of strategic planning, capital allocation, and defining a clear target market early to increase the chances of successfully commercialising tech solutions.
A key challenge for many founders, particularly those in their early twenties, is their limited skill set beyond domain expertise. While they may understand their industry, they often struggle with areas like UX design, software architecture, commercialisation, and marketing. Klaus highlights how even experienced entrepreneurs make strategic mistakes and advocates for using the Playing to Win framework to define market positioning, customer focus, and growth strategies. A crucial factor in startup success is identifying the single most important metric that drives accelerated growth, as it shapes the overall business direction and informs key decision-making.
Understanding and leveraging key growth metrics is often overlooked by founders. Klaus discusses how many startups fail to correctly identify their actual customer base, drawing on examples like Xero’s strategy of turning accountants into their sales force. He emphasises the importance of co-designing solutions with end users to ensure real product-market fit, rather than relying on assumptions. Additionally, he challenges the conventional approach to Minimum Viable Products (MVPs), arguing that they must deliver tangible value beyond being a simple proof of concept. A true product-market fit is evident when demand grows organically without excessive marketing spend.
Klaus critiques the way marketing success is often measured, arguing that vanity metrics like clicks and likes are meaningless if they do not translate into revenue. He warns against marketing agencies that avoid accountability for business outcomes, stating that return on ad spend (ROAS) is the only metric that truly matters. He also highlights the need for founders to calculate customer acquisition cost (CAC) accurately, incorporating all related expenses such as sales, onboarding, and churn. Misleading figures that ignore early customer drop-off can create a false sense of success, and businesses must take a brutally honest approach to assessing and optimising acquisition costs.
Strategic focus is essential for early-stage startups, and Klaus warns against the temptation to pursue an overly broad market too soon. Referencing Playing to Win by A.G. Lafley and Roger L. Martin, he outlines five key steps: defining a winning aspiration, selecting where to play, determining how to win, identifying required capabilities, and establishing management systems to track success. One of the biggest pitfalls for founders is “chasing the money” by adapting their product for a single client at the expense of their broader vision. Short-term revenue wins that do not align with the company’s core strategy can lead to long-term failure, making it essential to resist distractions that could derail sustainable growth.
Finally, the conversation turns to the realities of entrepreneurship, including the pressures of setting ambitious goals and the misconceptions surrounding startup success. Klaus emphasises that simply setting high targets is not enough—founders must realistically assess the scale of the problem they aim to solve and establish practical milestones. Many entrepreneurs overestimate their market size, overlooking adoption curves and true market penetration challenges. He also addresses the impact of social media glamorising startup life, contrasting it with the stark reality of failure rates, which exceed 80-90%. Klaus critiques Australia’s "tall poppy syndrome," arguing that failure should be viewed as a learning experience rather than a reason to dismiss founders in future ventures.
#DevReadyPodcast #StartupGrowth #BusinessStrategy #Entrepreneurship #ScalingStartups #TechInnovation #Dreamoro

Kinde’s Security-First Approach: What Every Startup Needs to Know | Ep 207 | DevReady Podcast

In this episode of the DevReady Podcast, host Andrew Romeo sits down with Oliver Wolff, Product Manager at Kinde, to explore his journey from software engineer to product manager, and how his role has evolved in the startup environment. Oliver shares his transition from working at a large Australian logistics company to product management at Afterpay and Kinde. He highlights the dynamic nature of working in a startup, where responsibilities extend beyond product management to encompass sales, support, and marketing. Andrew and Oliver discuss the benefit of product managers being closely involved with sales to better understand customer needs, offering unique insights into the differences between working in a startup versus a scaling organisation.
Oliver dives into the core of successful product management, stressing the importance of focusing on the problem rather than the solution. He reflects on the ever-changing market conditions and technological advancements, noting that understanding the customer’s perspective—especially when selling to engineers—is crucial. He discusses how engineers value detailed, thoughtful information and need time to process it, leading to longer sales cycles. This deep customer engagement allows Oliver to gather valuable insights, which he uses to inform product decisions and keep the team aligned with user needs.
The conversation shifts towards Kinde’s approach to authentication. Oliver and Andrew agree that businesses should avoid building authentication systems from scratch, instead opting for solutions like Kinde’s plug-and-play service, which integrates easily with platforms such as Google and Microsoft. Oliver highlights that, unless authentication is a core part of the product’s value proposition, businesses should focus their engineering efforts on what makes them unique, leaving the complexities of security and authentication to specialists like Kinde. This approach saves valuable resources and ensures products remain secure and compliant.
Oliver further explores Kinde's security-first approach, noting how the company embedded security into its DNA from the beginning by hiring a security engineer as its first team member. While managing security concerns, Kinde balances user experience by ensuring customers remain confident in the platform’s security while also making it easy to use. Oliver explains how Kinde continuously adapts to emerging security challenges and meets increasing demands for transparency from engineers. He also discusses Kinde’s upcoming features, including tiered pricing models and expanded functionalities like user management and billing, designed to streamline workflows for startups.
Lastly, Oliver shares his vision for Kinde and how the platform aims to simplify the complexities of user management, feature flags, and subscription billing. As Kinde rolls out its new pricing models and enhances its offerings, it helps startups manage their systems more effectively, allowing engineers to focus on building value-driven features. Oliver explains how Kinde’s feature flags enable better product testing and controlled rollouts, while the platform’s no-lock-in policy fosters trust with users. Reflecting on his passion for product management, Oliver reveals how customer feedback and seeing real value delivered to users motivates him every day, ensuring Kinde’s solutions are always aligned with the customer’s needs.
#PasswordlessAuthentication #CyberSecurity #UserExperience #TechInnovation #DigitalIdentity #SoftwareDevelopment #DevReadyPodcast

How Top 1% Tech Sellers Are Made – Secrets Revealed by Jameel Rehman | Ep 206 | DevReady Podcast

In this episode of the DevReady Podcast, host Anthony Sapountzis speaks with Jameel Rehman, Founder of Tech Sales Academy, about the challenges in tech sales education. Jameel, a former top 1% account executive at Cisco and Telstra Enterprise, transitioned into coaching after recognising a significant gap in structured sales training. He discusses the importance of organisation, problem-solving, and genuine customer relationships in achieving top sales performance. Rather than simply selling products to hit KPIs, Jameel believes great salespeople act as trusted advisors, solving business problems with integrity and a service-first mindset. His success in high-stakes enterprise sales has been driven by a structured and ethical approach, which he now shares through his academy.
Jameel’s journey into tech sales was unexpected. While working at a gym, he discovered a natural talent for selling memberships and supplements, which led him to a role in Telstra’s retail division. He quickly became a top seller but faced challenges when transitioning from B2C to B2B due to the complexity of enterprise technology sales. However, his entrepreneurial mindset allowed him to adapt, treating sales like running his own business rather than simply being an employee. This perspective made his transition into entrepreneurship seamless, as he was already accustomed to managing high-value clients and solving complex problems. The conversation takes a humorous turn as both speakers reminisce about their early jobs at Coles, sharing stories about working in produce and dairy.
Recognising a lack of formal training in tech sales, Jameel founded Tech Sales Academy to help individuals develop structured sales skills. Despite achieving top performance globally, he realised that many professionals were left to figure things out independently, without proper frameworks or guidance. After being made redundant, he saw an opportunity to build a practical and structured learning system for sales professionals. Rather than targeting enterprises, he focuses on individual development, ensuring that those who are genuinely motivated receive meaningful training to advance their careers in tech sales.
Jameel’s passion for coaching stems from his own experience as a gifted child who struggled with traditional education systems. His approach combines technical skill development with personal transformation, appealing to those who feel lost within outdated societal structures. He likens his coaching to software installation, helping individuals "download" the mindset and knowledge required for success in tech sales, much like Neo learning kung fu in The Matrix. His mission is to empower sales professionals with both the confidence and the structured processes necessary to thrive in the industry.
While tech sales shares many similarities with traditional B2B sales, it requires a strong understanding of technology solutions and their impact on customer problems. Success hinges on core sales principles—identifying ideal customers, crafting strong value propositions, and effectively navigating sales cycles. Engaging both technical and financial stakeholders often lengthens the process, making it crucial to identify high-leverage decision-makers. Jameel also highlights the importance of structured hiring for startup founders looking to transition from founder-led sales to a dedicated sales team. Finding the right "Frontier AE"—someone with a strong sales structure, a hunter mentality, and a willingness to work within startup constraints—can be the difference between stagnation and growth. Ultimately, in today’s market, building a product is easier than selling it, making sales expertise a key differentiator for startup success.
#TechSales #DevReadyPodcast #SalesAcademy #CustomerRelationships #B2B #BusinessGrowth #SalesTips