This bachelor thesis deals with empowering frontline service employees for cross-selling success, discussing training, knowledge, and support in business-to-business settings within the Sales and Sales Management field. The primary aim of this research is to explore the training pieces and expertise required to cross-sell as frontline service employees successfully, as well as to recognize the barriers that would prevent it, plus understand what a company can do to support successful implementation and what influence it has on motivation to cross-sell within their service teams. All these points have become increasingly relevant due to the widely growing importance of cross-selling as a strategic revenue driver for companies across different industries. The study employs a qualitative research methodology. Semi-structured interviews with seven frontline service employees and managers helped understand their experiences and perceptions regarding training, organizational barriers, and company support mechanisms. Thematic analysis was employed to interpret the data, supported by a comprehensive literature review. The research found that the best training method recognized is on-the-job learning, going hand in hand with mentorship by senior technicians or managers. Next, product-specific and technical knowledge emerged as a fundamental prerequisite for effective cross-selling among frontline service employees. Furthermore, soft skills and sales communication training for learning proactivity, trust building, empathetic listening, and need-based questioning are also beneficial for successful crossselling. As it is about B2B technical settings, the training should be regular, preferably in-person, hands-on, to gain quality experience. Lastly, informal knowledge sharing and peer learning are significant in cross-selling among frontline service employees. The factors contributing to the failure of cross-selling implementation among frontline service employees are incentives because they serve as a forefront motivation for them to engage in crossselling. Furthermore, a strong presence of role conflict and identity tension add to the lack of motivation - frontline service employees prioritize their main tasks over sales ones. There are also customer dynamics and external factors, such as lack of technical understanding from the customer decision maker, time constraints, prioritizing service tasks, economic downturns or low production demand, and market competition. The research concluded that explicit organizational sales objectives, incorporated into the job descriptions of frontline service employees, are essential for facilitating cross-selling engagement. Also, if they do not want to engage in cross-selling, there should be support from colleagues and management present to close the sale. Clear communication, transparency, and responsiveness in the company emerge as a vital catalyst to facilitate cross-selling among frontline service employees. Recommendations 1. Firstly, cross-selling should be formally integrated into the service role to eliminate the perception of being optional or extra. Companies can achieve this through job descriptions, onboarding, or performance reviews. 2. Companies should adopt balanced incentive structures that reward sales results of both frontline sales and service teams. It can be through performance-based bonuses, nonmonetary recognition, and promotion paths for successful cross-sellers. 3. Soft skills are essential for frontline service employees to cross-sell successfully; therefore, incorporating these types of training should be a priority for B2B companies. 4. Companies should encourage informal learning and peer exchange, as many frontline service employees learn well through collaborative reflection and shared field experiences. 5. Managerial support and involvement are vital for cross-selling; therefore, managers must provide real-time guidance, support, and encouragement to their frontline service team. 6. Companies should also provide tools to help frontline service employees recognize highpotential selling scenarios, as research has shown that they tend to misjudge when to initiate cross-selling. 7. Rather than imposing targets, companies should give frontline service employees flexibility in how and when they cross-sell. 8. Finally, cross-selling should be reframed as an extension of service excellence rather than additional sales activity, reinforcing that recommending relevant and additional solutions is part of delivering high-quality service. The thesis demonstrates that empowering frontline service employees for cross-selling success in B2B settings requires shifting from rigid, exclusively technical learning to dynamic, informal, and experience-driven one. Support from peers and managers, mentorship, and ongoing on-the-job training can all help to improve cross-selling. Even though there are many barriers, such as a lack of incentives or unclear job role definitions, there is a potential to align training initiatives with real-time situations to ensure open communication and nourish a collaborative work culture. Companies that provide such environments are more likely to achieve service-sales ambidexterity.