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Salary: USD 190,000 - 250,000 / annual
Shift Technology is seeking a Global Head of Sales Performance and Operations to drive discipline, consistency, and measurable outcomes across the global sales organization. This is a VP-level role reporting to the CRO, serving as a critical operating partner to the CRO and Heads of Market.
Shift delivers AI agents that transform insurers' most critical work. The company operates in a complex enterprise selling environment with sophisticated buyers, highly regulated industry dynamics, multi-stakeholder sales processes, 12+ month sales cycles, and deal sizes ranging from $300K to several million dollars.
Key Responsibilities:
Execution Rigor & Pipeline Inspection: Drive high-frequency pipeline inspection rhythms, rigorously questioning stage qualification, deal momentum, and close-date accuracy. Implement and enforce standardized enterprise sales methodologies (e.g., Value Selling) to ensure rep-level accountability. Actively manage the Deal Desk, unblocking contract roadblocks, managing custom terms, and expediting legal, security, and procurement approvals.
Sales Accountability & Performance Management: Establish discipline through activity-based and milestone-based KPIs for reps to track deal velocity and risk exposure. Lead the Sales Enablement team to create outcome-driven programs aligned with business strategy and product development. Partner with Sales Leadership to identify underperforming territories or reps early and enforce performance improvement plans. Own quota allocation, capacity planning, and territory design.
Strategic Go-to-Market & Incentive Alignment: Architect incentive compensation and SPIFF structures that reward top-performer execution and support strategic objectives. Continuously audit rep time allocation to maximize Account Executive engagement in buyer conversations. Translate revenue strategy into clear, executable weekly and monthly tactical mandates.
Tech Stack Execution & Process Enforcement: Enforce strict usage of the GTM tech stack (Salesforce), turning software into active execution tools. Streamline quote-to-cash workflows and enforce compliance with pricing guidelines. Deliver real-time, actionable execution dashboards to executive leadership. Partner with Product, Finance, and Customer Success on post-sale transitions and retention visibility.
The role is hybrid in Boston or fully remote in Eastern or Central US time zones, with responsibility for managing a team in Paris and partnering with a global sales team.
Requirements:
- 8+ years in Sales Leadership or Sales/Revenue Operations in enterprise B2B SaaS
- At least 3+ years managing global operational teams
- Proven track record as a proactive driver—not just a passive reporter of data—with uncompromising standards for field execution and pipeline hygiene
- Deep experience driving execution across complex, long-cycle enterprise deals (12+ months, $300K+ to $5M+ ACV, multiple economic buyers)
- Expertise in implementing and enforcing structured enterprise sales frameworks (MEDDPICC, Force Management, or Challenger) down to the individual rep level
- Advanced mastery of Salesforce architecture, revenue intelligence tools (Clari, Gong), and quantitative forecasting
- Ability to translate metrics into swift operational shifts
- Strong coaching and mentoring capabilities; ability to give candid, timely feedback and inspire team recognition
Preferred Qualifications:
- Prior experience executing inside a high-growth VC/PE-backed software company ($100M+ ARR scaling phase)
- Prior experience as a seller or certification/deep implementation experience in formal enterprise sales frameworks
