Head of Sales (San Jose)

About Our Company

WeBox is the leading intelligent marketplace delivering personalized group orders.

WeBox is driven by three core principles: customer obsession over competitor focus, a commitment to operational excellence, and a passion for growth.

Our Mission

Deliver Happiness

Our Vision

By 2032, we will achieve $1 billion in revenue by leveraging technology to become a leading provider of intelligent and sustainable solutions for group orders.

Job Description

We are seeking an experienced Head of Sales to oversee and lead our Sales Development Representatives (SDRs) across all WeBox hubs. This role is responsible for driving outbound performance, standardizing sales development processes, and ensuring fast, consistent execution across locations.

The ideal candidate is a hands‑on sales leader who believes in getting the job done right away, operates with a results‑driven mindset, and leads with transparency. You have strong people‑management skills and experience scaling SDR teams in a multi‑hub or multi‑region environment, while effectively leveraging decision‑making, control, influence, and teamwork to drive measurable outcomes.

Key Responsibilities

• Lead, manage, and coach SDR teams across multiple WeBox hubs
• Own outbound pipeline generation and ensure SDR targets are met or exceeded
• Set clear performance expectations, KPIs, and activity metrics for SDRs
• Develop and standardize outbound processes, scripts, and best practices across hubs
• Partner closely with Sales, Customer Success, Operations to align on lead strategy and messaging
• Conduct regular performance reviews, coaching sessions, and training
• Hire, onboard, and ramp new SDRs as the team scales
• Monitor pipeline quality and ensure smooth handoff from SDRs to Customer Success
• Use data and reporting to identify performance gaps and drive continuous improvement
• Travel occasionally between hubs to support team alignment and execution

Leadership Expectations

Decision‑Making Power (Get the Job Done Right Away)

• Make timely, decisive, and results‑driven decisions regarding SDR strategy, priorities, and resource allocation
• Proactively identify issues and act quickly to implement solutions that improve performance and execution

Control Power (Results‑Driven Execution)

• Establish and enforce clear standards, processes, and accountability across all hubs
• Ensure consistent execution of sales development workflows, metrics, and reporting

Influence Power (Transparency‑Led Leadership)

• Motivate and inspire SDRs through transparent communication, coaching, and real‑time feedback
• Build trust by clearly sharing expectations, performance results, and the “why” behind decisions
• Influence cross‑functional partners to align on goals, messaging, and execution

Synergy (Teamwork Power)

• Foster strong collaboration across SDRs, Customer Success, Operations, and Business Development teams
• Build a culture of shared ownership, urgency, and collective success across hubs

Requirements

• 3+ years of experience managing sales or SDR teams
• Proven experience leading SDRs or outbound sales teams
• Strong understanding of B2B sales development, prospecting, and pipeline generation
• Experience managing teams across multiple locations or regions is a strong plus
• Excellent coaching, communication, and leadership skills
• Data‑driven approach with experience using CRM and sales tools
• Ability to thrive in a fast‑paced, growing environment

Preferred Qualifications

• Experience at start up or high‑growth company
• Experience working closely with Customer Success or post‑sales teams
• Prior experience in logistics, operations, or technology‑enabled services is a plus

Equal Opportunity Employer:

WeBox is an equal‑opportunity employer committed to hiring based on merit, competence, performance, and business needs. We do not discriminate based on race, color, religion, marital status, age, national origin, ancestry, physical or mental disability, medical condition, pregnancy, genetic information, gender, sexual orientation, gender identity or expression, veteran status, or any other status protected under federal, state, or local law.

Note:

• This position offers a competitive salary plus commissions, along with great benefits, PTO, and a 401K match.
• This job description offers a general overview and may not encompass all responsibilities, tasks, or skills required. Additional duties may be assigned to meet the company's evolving needs.

If you meet the requirements and are interested in this position, please submit your application.