Head of Sales – Custom Software & AI

SIDESTREAM

. Take responsibility for the entire new-business pipeline, from lead generation and qualification through proposal development to closing .

Posted 10/9/2026full-timeRemote • GermanyLeadWebsite

Core Competencies

Role fit

Core Competencies

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Demonstrates expertise in B2B Software Sales and Consultative Selling, with a strong ability to lead teams, manage customer relationships, and develop compelling business proposals. Proficient in navigating complex negotiations and collaborating with technical experts to drive results.

Highest-signal resume keywords

B2B Software SalesConsultative SellingTeam LeadershipCRM SystemsFluent German

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills

Proposal DevelopmentLead GenerationCustomer Relationship ManagementNegotiationBusiness Case Development

Soft Skills

Effective CommunicationPrioritizationDelegationConstructive FeedbackIndependence

Tools & Technologies

Digital Collaboration ToolsAI Applications

Industry Keywords

Complex B2B ProjectsIT ServicesMid-Sized CompaniesSales Pipeline Management

About the role

Key responsibilities & impact

Take responsibility for the entire new-business pipeline, from lead generation and qualification through proposal development to closing
Conduct customer conversations, understand business challenges, engage relevant decision-makers, and negotiate proposals
Travel to customer meetings for pitches, workshops, and important decisions
Lead two FTEs in Marketing and Sales, set priorities, allocate responsibilities, provide feedback, and further develop team capabilities
Manage customer relationships directly, including personal selling and closing
Develop compelling proposals together with the founding team and project leads
Coordinate commercial responsibility for the solution, effort, and feasibility together with technical experts
Identify upsell potential among existing customers and develop follow-on business
Manage the pipeline, next steps, and forecast
Identify stalled deals, make decisions, and improve collaboration within the team and with Adrelin

Requirements

What you’ll need

Have personally sold and closed complex B2B software projects or IT services that require consultative selling
Practical experience leading a small team, developing employees, and taking responsibility for results
Ability to set priorities, delegate, and conduct difficult conversations clearly and constructively
Strong commercial and technical understanding, with the ability to translate customer challenges into a compelling business case
Ability to collaborate effectively with technical experts
Demonstrated independence and accountability for decisions and results
Confident communication with managing directors and functional leaders in mid-sized companies
Residence in Germany
Willingness to travel regularly for customer meetings
Fluent German at a professional negotiating level
Confident communication in English
Experience with CRM systems and digital collaboration tools
Practical use of AI in day-to-day work

Benefits

Comp & perks

Entrepreneurial responsibility and direct collaboration with the founders
Collaboration with the Ardelin Group and its expertise in software, data, cloud, and AI
Remote work anywhere in Germany or work from the Cologne office
Attractive base salary and strong performance-based compensation
Opportunity to earn a total annual compensation well into six figures when targets are achieved
Regular team events
Modern working culture focused on AI, automation, clear responsibilities, quarterly goals, and EOS exchange