Mid-Market Sales Leader

The Role
This role leads the North America MidMarket team and is accountable for new logo acquisition and expansion revenue across the segment. The expectations are high: a team that generates its own pipeline, deals that are qualified with discipline, forecasts that hold, and Account Executives who improve every quarter.

This is not an oversight role. The leader in this seat works alongside their team, sets the standard for outbound execution, and uses data to drive performance. It is built for a first-line leader who has already delivered results and wants to operate at the pace and scale of a fast-growing company.

Responsibilities
Deal leadership
Engage directly in the team's most important opportunities: discovery, executive alignment, mutual close plans, pricing and commercial structure, procurement, and security review.
Set the standard for value-based selling: quantifying the customer's business pain, building the business case, and tying Bitwarden to measurable risk reduction and operational outcomes.
Diagnose and unblock stalled deals, and use them to raise the skill level of the entire team.
Outbound pipeline generation
Build and mature a repeatable cold outbound motion with AEs and partnered SDRs: territory and account prioritization, ICP and persona targeting, multi-threaded sequencing, and messaging that resonates with IT, security, and finance buyers.
Set activity and pipeline-generation standards, inspect them weekly, and hold every AE accountable for self-sourced pipeline.
Align with Marketing and Sales Development on programs that produce qualified pipeline at a predictable rate.
MEDDPICC and value-based execution
Run MEDDPICC as the team's operating system across qualification, deal reviews, forecast calls, and win/loss analysis, with value-based selling defining how the team earns and proves each element.
Inspect every material opportunity for quantified Metrics, a validated Economic Buyer, a tested Champion, clear Decision Criteria and Process, a mapped Paper Process, and an honest read on Competition.
Deliver an accurate weekly forecast built on deal evidence and maintain CRM data the business can rely on.
Data-driven coaching
Own the team's KPIs (pipeline generation, coverage, stage conversion, win rate, cycle length, average deal size, and activity-to-outcome ratios) and act on what they show.
Identify where each AE is losing ground (pipeline creation, qualification, progression, or close) and build targeted coaching plans to close the gap.
Run a disciplined operating cadence: weekly 1:1s, pipeline and deal reviews, forecast calls, and call reviews.
Team building
Recruit, hire, onboard, and ramp high-caliber Account Executives, and develop them toward promotion.
Build a culture of accountability, competitiveness, and continuous improvement.
Work across Sales Operations, Solutions Engineering, Customer Success, Channel, and Marketing to deliver revenue as one team.

Requirements
3–5 years of first-line sales leadership, ideally leading AEs selling security SaaS (identity, access, credential, endpoint, or adjacent categories).
A proven, documented track record of quota attainment as a leader, and as an individual contributor before that.
Deep working fluency in MEDDPICC and value-based selling, applied together to qualify, inspect, forecast, and coach.
A track record of building and maturing a cold outbound pipeline, with the ability to explain exactly how it was done and what it produced.
Strong analytical skills, including fluency with Salesforce reporting, dashboards, and spreadsheets, and a record of using KPIs to direct coaching and improve AE performance.
A hands-on approach to leadership, with direct, regular involvement in live deals.
Strong intellect, a fast learning curve, and the drive to perform in a high-growth environment with demanding targets.
Experience selling to IT, security, and executive buyers in organizations of roughly250–2,500 employees.