Head of Sales
$100kTrajectory Recruiting
Location: Remote / Hybrid
Position Type: Full-Time (Executive / Growth Track)
About the Company
Founded in 2012, we are an established technology partner and technical services firm that works in highly regulated environments like financial services or healthcare where security, compliance, governance matters but serve all SMB and large enterprises that are looking to drive Data and AI transformation initiatives.
We architect and deliver modular, secure, and scalable AI solutions, enterprise data platforms, business process automation (BPA), and strategic consulting. Our model bridges the gap for firms wanting to leverage enterprise-grade technology without the burden of building massive, in-house IT teams. By utilizing reusable accelerators and industry-specific modules, we allow our clients to move faster with less risk, keeping compliance and data governance at the core of every deployment.
About the Role
We are entering a foundational growth phase and are seeking an entrepreneurial, sophisticated Head of Sales to design, execute, and scale our commercial engine.
This is a true player-coach opportunity for an elite individual contributor ready to transition into structural leadership. Initially, you will operate as the primary driver of new business, validating the sales playbook and securing foundational enterprise logos. As you establish a repeatable revenue model, you will have the autonomy and resources to recruit, build, and lead a high-performing sales organization around your framework.
You will report directly to the CEO, serving as a strategic partner in shaping our market positioning and commercial trajectory.
Core Responsibilities
- Go-to-Market Execution: Take full ownership of the end-to-end sales lifecycle, from targeted outbound prospecting and pipeline generation to enterprise-level contract negotiation and closure.
- Playbook Development: Document and institutionalize a repeatable, scalable sales methodology tailored to our advanced AI, data, and automation offerings.
- Enterprise Acquisition: Identify, target, and secure complex new logos across mid-market and enterprise segments, navigating multi-stakeholder procurement processes.
- Executive Alignment: Establish deep credibility and trusted advisor status with VP, C-suite, and technical decision-makers within the finance, healthcare, and other verticals.
- Organizational Scaling: Define the hiring roadmap, key performance indicators (KPIs), and training infrastructure to transition the role from solo execution to organizational leadership.
Candidate Profile
The ideal candidate possesses a rare blend of tactical execution and strategic vision. You have a deep understanding of complex technical sales and thrive in high-autonomy environments where the infrastructure must be built rather than inherited.
Required Experience:
- Tenure: 10+ years of quantified success in B2B technology sales, specifically within IT professional services, technical consulting, or complex engineering solutions.
- Outbound DNA: A proven track record of generating net-new enterprise pipelines from scratch without reliance on inbound marketing or warm inbound leads.
- Deal Complexity: Demonstrated ability to manage long, consultative sales cycles and consistently close complex, multi-stakeholder deals ($100k+ ACV) at the executive level.
- Technical Domain Expertise: Strong familiarity selling solutions rooted in modern data architectures, cloud ecosystems, AI/ML deployment, predictive analytics, or blended technical delivery models.
What We Offer
- Direct Impact: A seat at the table with executive leadership to influence company strategy and product-market fit.
- Uncapped Career Architecture: A direct, performance-based pathway to build and lead a dedicated sales team.
- Competitive Compensation: A comprehensive package including a strong base salary, an aggressive commission structure, and meaningful equity to align with long-term enterprise value creation.
If you're interested in bringing your AI and sales prowess to a company where you can make a substantial impact, apply now!
Vacancy posted 1 day ago
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