[Hiring] Senior Manager, Direct Sales @JumpCloud

Role Description

The Senior Manager, Direct Sales leads JumpCloud's Commercial Direct Sales team (5–7 Account Executives) responsible for acquiring new logos and expanding market footprint within organizations of 100 to 1,000 employees. As JumpCloud scales, this leader solves the critical business need for a structured, high-velocity outbound pipeline generation engine that drives predictable Annual Recurring Revenue (ARR). By embedding daily AI-driven sales workflows, rigorous MEDDPICC qualification, and data-backed Gong coaching cadences, you will lead a proven team of high performers through organizational transitions into their next phase of growth.

Reporting directly to the VP of Global Sales, you will turn strategic growth priorities into consistent quarterly execution, driving new customer acquisition and market leadership.

Qualifications

• Proven track record of managing and leading quota-carrying B2B SaaS direct sales teams to consistent target achievement.
• Demonstrated success in designing and executing outbound hunting motions, pipeline generation playbooks, and territory build-outs.
• Mastery of structured sales qualification frameworks (MEDDPICC) and conversational intelligence deal inspection.
• Proven leadership in sales coaching—diagnosing performance gaps, coaching both underperformers and top performers, and driving accountability with empathy.
• Experience integrating channel, reseller, and ecosystem partners into active direct sales cycles.

Requirements

• Commercial B2B SaaS sales segment (100–1,000 employees) and understanding of IT, DevOps, and Security buyer personas.
• Identity and Access Management (IAM), cloud directory services, or cybersecurity infrastructure software.
• Experience managing sales motions or expanding territories in Latin America (LATAM) is a plus.

Benefits

• Comprehensive benefits package, including several medical plans to choose from.
• High deductible HSA plan with employer contribution.
• Two dental plans and vision insurance.
• Flexible spending account (FSA) and employee assistance program (EAP).
• Short- and long-term disability and life insurance.
• 401k savings plan with match.
• Flexible paid time off policy.

Major Performance Objectives

• Deliver 100%+ of Team Quota Attainment: Achieve the team roll-up revenue target by coaching and managing 5–7 Account Executives to consistently hit and exceed individual quarterly quotas within the first 6–12 months.
• Establish a Predictable Outbound Pipeline Motion: Design and scale a repeatable outbound hunting framework that increases rep-generated outbound pipeline by at least 35% within the first 6 months, mitigating reliance on inbound channels.
• Operationalize Daily AI Prospecting Adoption: Embed daily generative and predictive AI workflows across the entire sales team within 90 days, demonstrating measurable gains in outbound sequencing velocity, account research depth, and conversion speed.
• Institute Structured MEDDPICC & Gong Coaching Frameworks: Standardize weekly deal inspection and call reviews using MEDDPICC criteria and Gong conversational intelligence, achieving quarterly forecast accuracy within ±5% and improving late-stage deal conversion rates within 6 months.
• Scale Channel & Partner-Sourced Pipeline: Collaborate with Alliances and Channel Partners to integrate partner co-selling motions into commercial territory plans, generating at least 20% of new commercial pipeline via partner channels within the first 12 months.

Critical Subtasks

• Evaluate current territory distribution, pipeline coverage ratios, and historical conversion metrics across the commercial direct sales segment.
• Develop, test, and roll out standardized outbound sales plays, messaging sequences, and multi-touch cadences utilizing Outreach and LinkedIn Sales Navigator.
• Integrate daily AI tools into standard rep workflows to streamline target account research, craft personalized outreach, and surface deal risk early.
• Implement weekly structured 1:1 coaching and deal review sessions utilizing Gong call recordings and MEDDPICC frameworks to upskill reps and remove pipeline blockers.
• Manage and deliver precise weekly, monthly, and quarterly ARR forecasts in Salesforce, maintaining continuous alignment with executive sales leadership.
• Partner cross-functionally with Channel/Alliances, Sales Enablement, and Product Marketing to align territory co-selling, campaign execution, and competitive positioning.
• Mentor, retain, and recruit high-performing sales talent, maintaining high team morale, accountability, and professional growth during structural and organizational shifts.