Mid-Market Sales Leader

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead the MidMarket team in North America, focusing on acquiring new logos and driving expansion revenue.

• Directly engage in significant opportunities, which include discovery sessions, executive alignment, mutual closing strategies, pricing discussions, procurement processes, and security reviews.

• Establish a benchmark for value-based selling, linking Bitwarden to quantifiable risk reduction and operational results.

• Identify and resolve obstacles in stalled deals.

• Develop and enhance repeatable cold outreach strategies alongside Account Executives and partnered Sales Development Representatives (SDRs).

• Set standards for activity and pipeline generation, holding Account Executives responsible for their self-sourced pipeline.

• Collaborate with Marketing and Sales Development on qualified pipeline initiatives.

• Implement MEDDPICC across qualification processes, deal evaluations, forecast discussions, and win/loss assessments.

• Examine key opportunities for metrics, identifying the economic buyer, champion, decision criteria and process, documentation processes, and competition.

• Provide precise weekly forecasts and maintain dependable CRM data.

• Own and monitor team KPIs to enhance performance.

• Identify performance shortcomings and create targeted coaching strategies.

• Conduct weekly one-on-ones, pipeline and deal reviews, forecast discussions, and call assessments.

• Recruit, hire, onboard, train, and develop Account Executives.

• Foster a culture of accountability, competition, and continuous improvement.

• Work in collaboration with Sales Operations, Solutions Engineering, Customer Success, Channel, and Marketing teams.

⛳️ Requirements

• 3–5 years of experience in first-line sales leadership, preferably leading Account Executives selling security SaaS (identity, access, credential, endpoint, or related fields).

• A proven, documented history of meeting quotas both as a leader and individual contributor.

• In-depth working knowledge of MEDDPICC and value-based selling methodologies.

• A successful track record in developing and enhancing a cold outbound pipeline.

• Strong analytical capabilities, including proficiency with Salesforce reporting, dashboards, and spreadsheets.

• Proven experience in utilizing KPIs to guide coaching and improve Account Executive performance.

• A hands-on leadership style with direct, frequent involvement in live deals.

• Strong intellect, quick learning ability, and a drive to excel in a high-growth environment with challenging targets.

• Experience selling to IT, security, and executive buyers within organizations with approximately 250–2,500 employees.

🏝️ Benefits

• A sense of purpose by contributing to a more secure internet experience.

• The opportunity to become an expert in the security and open-source software markets.

• Professional development and growth opportunities.

• Opportunity to develop expertise in demand generation and product-led growth.

• Remote work with a motivated and supportive global team.

• Uncapped variable compensation.