Creating Magic in Startup Sales

Insights in Startup Sales from Chalom Malka, Co-founder & CEO @ Siit

In this thought-provoking episode of Tech Salescraft, James Hounslow sits down with Chalom Malka, Co-founder and CEO of Siit, to discuss the extraordinary journey of building a company from the ground up. With his unique background in Startup Sales, tech sales and leadership roles at Aircall, Chalom provides invaluable insights into navigating the challenges of entrepreneurship, leveraging sales expertise, and finding structure in the chaos of early-stage startups. This episode is a must-listen for aspiring founders, sales professionals, and anyone looking to succeed in the ever-evolving world of tech startups.

From Sales Expertise to Startup Leadership

Chalom Malka’s career is a blueprint for aspiring tech sales professionals who dream of making the leap to leadership. His story begins with a foundation in corporate finance, but he quickly realised that his passion lay elsewhere. Joining Aircall as the second sales employee, he dove headfirst into the unpredictable world of startups. The early days were a whirlwind of challenges, where Chalom had to navigate the lack of formal processes and rely on his ability to organise and execute.

Reflecting on his time at Aircall, Chalom shares how he thrived in the chaos, finding opportunities to grow both personally and professionally. Over the course of six years, he climbed the ranks to become Director of Sales for the Southern European market, witnessing the company’s evolution into a unicorn. These experiences shaped his approach to leadership, teaching him the importance of balancing short-term goals with long-term vision—a skill that has proven indispensable in his role as a founder. Chalom emphasises that his experience at Aircall was not just about selling products but about building a system that could sustain growth and innovation. These lessons have deeply influenced his approach to Siit, where he aims to replicate and refine this model of success.

Identifying and Solving Pain Points

The transition from Aircall to Siit was driven by Chalom’s deep understanding of organisational inefficiencies. While Aircall’s external-facing teams excelled at customer service, internal processes often lagged behind. Chalom recounts a moment of clarity when he realised that employees frequently faced barriers to accessing basic resources and support. This pain point became the foundation for Siit, a conversational, AI-powered internal service desk designed to streamline communication between employees and support teams like IT, HR, finance, and legal.

Siit’s innovative approach prioritises user-friendly solutions, enabling employees to type requests in natural language and receive prompt assistance. This seamless integration of AI and internal services has positioned Siit as a game-changer for SMBs and mid-market companies. By addressing inefficiencies that often go unnoticed, Siit is transforming how businesses operate, helping them save time and resources while improving employee satisfaction. Chalom’s journey underscores the value of firsthand experience in identifying market gaps and translating them into actionable solutions, a lesson that resonates deeply with tech sales recruiters and aspiring founders alike.

The Role of Sales in Startup Startups

One of the most compelling themes of the episode is the critical role that sales expertise plays in the success of early-stage startups. Chalom’s background in tech sales equipped him with a unique perspective on building and scaling businesses. He describes how the skills he honed at Aircall, including consultative selling and pipeline management, became instrumental in Siit’s early growth. Sales, Chalom notes, is not merely about closing deals but about building relationships and understanding customer pain points—skills that are directly transferable to every aspect of running a startup.

Chalom shares a fascinating anecdote about the first months at Siit, where he approached fundraising as a sales process. Using a CRM to track VC relationships, manage follow-ups, and close deals, he applied the same principles that had driven his success in tech sales. This systematic approach enabled Siit to secure $5 million in funding from top-tier investors like Stage One and Venture. In a challenging economic climate, Chalom’s ability to execute and deliver results proved to be a decisive factor in Siit’s success. He explains that the discipline required in tech sales translates seamlessly into the high-pressure world of entrepreneurship, where every decision can have a ripple effect on the future of the business

Building Teams and Cultivating Talent in Startup

Hiring the right people is often cited as one of the most significant challenges for startups, and Chalom’s experience at Aircall offered him valuable insights into this process. He explains how early-stage hiring decisions should prioritise mindset and adaptability over specific skill sets. At Aircall, he focused on bringing in entrepreneurial individuals who could thrive in a fast-paced, unstructured environment. These lessons carried over to Siit, where Chalom has worked to build a team capable of driving innovation and executing the company’s vision.

For tech sales recruiters, Chalom’s approach serves as a reminder of the importance of matching talent with company culture. By focusing on resilience, curiosity, and a willingness to learn, recruiters can identify candidates who will excel in high-growth environments. Chalom elaborates on the importance of fostering an environment where employees feel empowered to take risks and contribute ideas. This philosophy aligns with North Starr’s mission to connect top talent with transformative opportunities in tech sales and SaaS startups, ensuring that both businesses and employees thrive in the dynamic tech industry.

Embracing Chaos and Finding Structure

A recurring theme in Chalom’s journey is the ability to embrace chaos and transform it into structure. He recalls his early days at Aircall, where there were no predefined processes or playbooks. Instead, he relied on his organisational skills to prioritise tasks, build workflows, and create scalable systems. This mindset proved invaluable during Siit’s formative years, where the team faced significant challenges in aligning their vision and executing their strategy. Chalom explains that the ability to create order from disorder is not just a skill but a mindset, one that he believes is essential for success in both tech sales and entrepreneurship.

Chalom’s story highlights the importance of resilience and adaptability in overcoming obstacles. His ability to remain focused on the bigger picture, even during periods of uncertainty, offers a powerful lesson for tech sales professionals navigating their own career paths. He encourages aspiring founders to view chaos not as a hurdle but as an opportunity to innovate and grow. This mindset, Chalom believes, is what separates successful leaders from those who struggle to adapt.

Securing Funding and Scaling for Growth

Siit’s recent $5 million funding round marks a significant milestone in its journey. Chalom attributes this achievement to the company’s strong focus on execution and its commitment to solving meaningful problems. He explains that investors were particularly impressed by Siit’s ability to demonstrate traction and scalability, even in a competitive market. Chalom highlights the importance of clarity and communication in fundraising, noting that the ability to articulate a compelling vision is as critical as the product itself.

The funding will enable Siit to double down on AI innovation and expand its go-to-market strategy. Chalom envisions a future where Siit becomes a global leader in internal service management, providing solutions that empower employees and streamline operations. This vision aligns with the broader trends in tech sales and SaaS recruitment, where innovation and customer-centric solutions are driving industry growth. He underscores the importance of staying ahead of the curve, adapting to market demands, and continuously iterating on the product to maintain a competitive edge.

Advice for Aspiring Entrepreneurs

As the episode draws to a close, Chalom offers valuable advice for aspiring entrepreneurs. He emphasises the importance of resilience, particularly during the early stages of building a business. Challenges and setbacks are inevitable, but they also present opportunities for growth and learning. By staying focused on solving real problems and trusting in the process, founders can navigate the uncertainties of entrepreneurship and build lasting success. Chalom encourages founders to seek out mentors, network with industry professionals, and never shy away from asking for help when needed.

Chalom’s insights are particularly relevant for tech sales professionals considering a transition to leadership roles. Whether it’s launching a startup or scaling an existing business, the ability to adapt, execute, and lead with purpose is critical to achieving long-term success. He advises aspiring leaders to focus on building strong relationships and maintaining a customer-first approach, as these are the cornerstones of any successful business.

Conclusion

This episode of Tech Salescraft is a masterclass in leveraging tech sales experience for entrepreneurial success. Chalom Malka’s journey from sales leader to startup founder exemplifies the transformative power of resilience, adaptability, and execution. For North Starr, a tech sales recruitment business, Chalom’s story reinforces the importance of connecting top talent with innovative opportunities in SaaS, FinTech, and technology sales. His insights serve as a roadmap for anyone looking to build a thriving career in the tech industry, whether as a sales professional or a visionary entrepreneur.

Listen to the full episode to gain deeper insights into Chalom Malka’s inspiring story and discover actionable lessons for your career in tech sales or entrepreneurship.

This podcast episode directly aligns with North Starr’s mission as a tech sales recruitment business by showcasing the transformative role of sales expertise in entrepreneurial success. Chalom Malka’s journey from sales professional to startup founder highlights the essential skills North Starr values, such as adaptability, execution, and a customer-first approach. His insights into building resilient teams, navigating high-pressure environments, and leveraging sales processes for startup growth provide a masterclass for aspiring leaders. By connecting these themes with North Starr’s commitment to matching top talent with high-growth opportunities, this episode serves as both an inspiration and a guide for those aiming to thrive in the dynamic world of tech sales.