Why Starting Over Is the Best Move You’ll Make

Ardon Wesly, Director of Sales at The Journey Platform

Resilience, Adaptability, and Sales Leadership

In the latest episode of Tech Salescraft, host James Hounslow engages in a fascinating conversation with Ardon Wesly, Director of Sales at The Journey Platform. Ardon’s career is a testament to the power of resilience, adaptability, and strategic thinking. From the high-pressure world of founding a startup in Israel’s “Startup Nation” to mastering the intricacies of tech sales and outbound strategies, his journey is one of growth and determination.

This episode explores the highs and lows of entrepreneurship, the shift into structured sales roles, and the unique challenges of selling to CEOs. It’s packed with actionable insights for anyone in tech sales, SaaS recruitment, or startup leadership.

Starting Out in the “Startup Nation”

Ardon began his career in Maastricht, a picturesque Dutch city, but it was his move to Tel Aviv, Israel, that defined his professional trajectory. Dubbed the “Startup Nation,” Israel is a hub of innovation and entrepreneurship, and it was here that Ardon transitioned from a background in hospitality to the world of technology.

Inspired by the entrepreneurial culture, he launched his own tech startup, combining AI technology with concierge services for hotels. This venture aimed to revolutionise hospitality by introducing one of the first AI-powered chatbots long before generative AI became mainstream.

However, starting a company in a highly competitive and fast-paced environment like Tel Aviv came with its challenges. Ardon candidly shares his struggles with raising initial capital, building a technical team, and learning leadership skills on the go. With limited experience in sales or marketing, he had to rely on mentorship and startup accelerators to guide him through the complexities of running a business.

Although the startup closed after three years due to funding difficulties and product-market fit issues, Ardon views this period as an invaluable learning experience. He explains how the challenges he faced shaped his resilience, provided hands-on operational knowledge, and prepared him for his future in tech sales.

The Mental and Emotional Toll of Entrepreneurship

One of the standout moments in this episode is Ardon’s openness about the emotional impact of founding a startup. Borrowing money from family and friends, managing the expectations of stakeholders, and living in Tel Aviv—one of the most expensive cities in the world—all took a significant toll on his mental health.

Ardon describes how therapy became a crucial part of his journey, helping him regain balance and perspective after the closure of his business. He emphasises that therapy isn’t just for overcoming challenges but is also a valuable tool for personal growth and development.

His advocacy for mental health resonates with anyone in high-pressure roles, whether in tech sales, SaaS recruitment, or entrepreneurship. Ardon’s experience serves as a reminder that prioritising mental well-being is a key factor in achieving long-term success.

Pivoting to Tech Sales

After closing his startup, Ardon recognised the need to fill gaps in his skillset, particularly in structured sales. This led him to join monday.com, a leading SaaS company, as an Account Executive. Despite being a step down in seniority, this role allowed him to immerse himself in the fundamentals of tech sales.

At monday.com, Ardon mastered essential sales techniques, from lead qualification and relationship building to executing effective sales cycles. The structured environment provided him with the training and mentorship he needed to thrive. His ability to adapt quickly and embrace a learner’s mindset helped him excel, becoming one of the company’s top performers.

This period in his career highlights the importance of humility and the willingness to start from scratch. By focusing on learning and growth, Ardon laid the foundation for his transition into leadership roles.

Selling to CEOs: A High-Stakes Challenge

Today, Ardon serves as the Director of Sales at The Journey Platform, an innovative startup based in Tel Aviv. The Journey Platform offers a unique “McKinsey in a box” solution, combining personalised strategic advising with AI-powered tools to help CEOs achieve their goals.

Selling to CEOs is one of the most challenging aspects of Ardon’s role. CEOs are often time-constrained, sceptical, and difficult to engage. However, Ardon thrives in this high-stakes environment, using his interpersonal skills and strategic thinking to build trust and demonstrate value.

The Journey Platform’s model focuses on empowering CEOs with actionable insights, helping them identify bottlenecks, prioritise tasks, and delegate responsibilities effectively. Ardon’s ability to craft tailored messaging and refine sales processes has been instrumental in positioning The Journey Platform as a valuable partner for small and medium-sized businesses.

Mastering Outbound Sales

One of the biggest shifts for Ardon at The Journey Platform has been the transition from inbound to outbound sales. At monday.com, he benefited from a steady stream of high-quality inbound leads, supported by the company’s substantial marketing investments. In contrast, The Journey Platform requires a hands-on approach to prospecting and engagement.

Ardon has embraced the challenges of outbound sales, developing expertise in email outreach, LinkedIn messaging, and cold calling. He collaborates with external lead generation partners, tests different strategies, and continuously refines the sales process to optimise results.

His experience underscores the importance of adaptability in tech sales. By mastering both inbound and outbound techniques, Ardon has equipped himself with a versatile skillset that enables him to succeed in diverse sales environments.

Leadership Through Example

As a sales leader, Ardon adopts a hands-on approach to mentoring his team. His philosophy of “leading by example” stems from his experiences at monday.com, where he informally took on mentorship roles despite being an individual contributor.

At The Journey Platform, Ardon combines individual contributions with strategic leadership. He plays a key role in shaping the company’s direction, from refining sales messaging to exploring new go-to-market strategies. His ability to inspire and empower his team has been a driving force behind The Journey Platform’s growth.

The Evolving Role of Sales Leadership

In the fast-paced world of tech sales, the role of a sales leader extends far beyond managing quotas and forecasting revenue. Ardon Wesly’s story illustrates how modern sales leadership requires a blend of strategic thinking, emotional intelligence, and adaptability. At The Journey Platform, his role as Director of Sales involves not just achieving targets but also shaping the company’s go-to-market strategies and mentoring the next generation of sales professionals.

Ardon’s ability to pivot from a startup founder to a sales leader highlights the critical importance of continuous learning and growth. His willingness to embrace change and take on new challenges has allowed him to thrive in dynamic environments. For companies like North Starr, which specialise in connecting businesses with top tech sales talent, Ardon’s journey exemplifies the type of candidate that is in high demand: someone who brings resilience, creativity, and a proactive approach to problem-solving.

As technology and customer expectations evolve, so too does the skillset required to succeed in tech sales. Ardon’s experiences underscore the importance of cultivating a mindset that embraces innovation and focuses on long-term success. For aspiring sales professionals, his story is both a roadmap and an inspiration.

The Future of The Journey Platform

Looking ahead, The Journey Platform has ambitious plans for 2025. The company aims to scale its sales team, double its annual recurring revenue, and advance its AI solutions to move beyond the MVP stage. Ardon is at the forefront of these efforts, leveraging his expertise to drive innovation and growth.

He discusses the importance of staying agile in a rapidly changing market. Whether it’s refining messaging, experimenting with new sales channels, or adapting to shifting buyer behaviours, Ardon’s focus on continuous improvement positions The Journey Platform for success.

A Blueprint for Success

Ardon Wesly’s career is a testament to the power of resilience, adaptability, and continuous learning. From navigating the highs and lows of entrepreneurship to excelling in tech sales and leadership, his journey offers invaluable lessons for anyone in the industry.

This episode of Tech Salescraft is a must-listen for tech sales professionals, SaaS recruiters, and entrepreneurs alike. Whether you’re looking to build a career in technology sales or seeking inspiration to overcome challenges, Ardon’s story provides a blueprint for success.

This episode of Tech Salescraft aligns closely with North Starr’s mission as a leading tech sales recruitment business. Ardon Wesly’s journey—from navigating the challenges of founding a startup to excelling in sales leadership—reflects the dynamic career paths we help shape at North Starr. His insights into building resilience, mastering outbound sales, and connecting with CEOs underscore the essential skills we seek in top tech sales talent. As experts in technology sales recruitment, North Starr specialises in matching businesses with professionals who not only bring technical expertise but also the adaptability and determination to thrive in competitive environments. Ardon’s story encapsulates the qualities that define exceptional candidates in today’s fast-paced tech sales landscape, making this episode a must-listen for both aspiring professionals and hiring manag

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