Head of Enterprise Sales

The Role & Your Mission

We are seeking a seasoned Head of Enterprise Sales to sharpen and scale our go-to-market (GTM) sales strategy, and drive predictable revenue attainment. This role will oversee a team of 3-6 Account Executives, ensuring disciplined pipeline management, high win rates, and scalable processes. Reporting to the CEO, the Head of Enterprise Sales will play a critical role in accelerating Weave’s growth by building a high-performance sales culture, refining our enterprise selling motion, and partnering cross-functionally to align GTM execution with customer and market needs.

What You'll Own

Sales Team Execution

• Set territory sales goals, pipeline targets, and incentive structures aligned with new business growth objectives.
• Establish and drive a strategic, account-based sales motion
• Drive predictable revenue through accurate forecasting and disciplined pipeline management.
• Collaborate cross-functionally with Customer Success, Marketing, and Product to ensure GTM alignment and consistent value messaging.
• Lead by example on high-value enterprise deals and support the team in complex negotiations.

Team Building & Management

• Recruit, train, and develop a high-performing enterprise SaaS sales team.
• Coach new hires to ramp rapidly and support the ongoing training and development of the sales team.
• Establish week-over-week accountability for deal progression.
• Refine and scale the existing sales process; build a playbook for repeatability that anchors around optimized pipeline coverage, forecast accuracy, sales cycle length (velocity), win rate and quota attainment.
• Lead weekly pipeline reviews and quarterly business reviews, keeping performance-driven culture front and center.

Operational Oversight

• Optimize CRM usage (HubSpot) to ensure pipeline visibility, KPI tracking, and data integrity.
• Establish sales dashboards for internal use and leadership reporting.
• Monitor industry and competitive trends to inform pricing strategy and customer engagement models.
• Ensure compliance with procurement, contracting, and data security requirements in enterprise deals.

What You’ll Bring

• 10+ years of SaaS sales experience with at least 5+ years in a sales leadership role.
• Demonstrated success managing enterprise sales teams selling into pharma is required.
• Proven track record of exceeding quarterly and annual bookings/revenue goals.
• Strong leadership and coaching ability with excellent communication skills.
• Skilled in pipeline management, forecasting, and effective system use (e.g., CRM).
• Ability to engage with C-level executives and influence strategic decision-making.
• Bachelor's degree in Life Sciences, Business or a related field is required, advanced degree is preferred.
• Experience with SaaS or document management solutions is required.
• Documented sales management/leadership experience with teams managing business pipelines from identification to contract signing.
• Up to 50% travel for prospect/customer meetings, tradeshows and events.

What We Offer

🎯 The opportunity to work at a modern, cutting-edge healthcare technology company devoted to meaningful positive impact on human life. Collaboration, velocity, and customer obsession are our baseline, demonstrations of craftsmanship and ROI are celebrated.

🏆 Competitive salary ($250,000 - $300,000) with performance-based incentives (OTE $400,000 to $500,000) plus equity.

🧬 Comprehensive health, dental and vision insurance.

🏝️ Take care of you and yours: generous PTO, parental leave, OneMedical, TalkSpace, Teladoc.

🚀 Career development opportunities within a company entering a growth phase.

🌎 This position is based in San Francisco or Boston with flexibility to occasionally work remote.