New

Global Head of Sales Performance and Operations

US - Boston; US - Remote

Shift delivers AI agents that transform insurers' most critical work. By combining deep industry expertise and unmatched data resources, Shift provides proven results that have earned the trust of hundreds of the world's leading insurers. Our insurance-grade AI is accurate, explainable, and secure—empowering human experts to move with unmatched speed, total confidence, and a renewed focus on the people they serve.

 

Our culture is built on innovation, trust, and a drive to transform the insurance industry through our SaaS platform. We come from more than 50 different countries and cultures and together we are creating the future of insurance.

Learn more at www.shift-technology.com

 

We are seeking a high-urgency, commercially minded Global Head of Sales Performance & Operations to drive greater discipline, consistency, and outcomes across our global sales organization.

This leader will serve as a critical operating partner to the CRO and Heads of Market, helping them run their businesses more effectively—from pipeline creation and opportunity progression through forecasting and close. The mandate is: bring rigor to how we sell, identify where execution is breaking down, and work alongside sales leadership to drive action and results.

Shift operates in a complex enterprise selling environment. Our AI-native platform serves sophisticated buyers in a highly regulated industry, with multi-stakeholder sales processes, 12+ month sales cycles, and opportunities ranging from $300K to several million dollars. Success requires more than reporting and traditional sales operations. The ideal candidate understands enterprise selling and combines commercial judgment, analytical rigor, operational discipline, and executive presence. They are equally comfortable challenging a forecast with a Head of Market, dissecting a strategic deal with an AE, identifying systemic pipeline issues, and translating those insights into action. 

This role is hybrid in Boston or fully remote in Eastern or Central US time zones, as you will manage a team in Paris and partner with a Global Sales team.

What Your Impact Looks Like

Execution Rigor & Pipeline Inspection

  • Drive high-frequency pipeline inspection rhythms, rigorously questioning stage qualification, deal momentum, and close-date accuracy across long sales cycles.
  • Implement and enforce standardized enterprise sales methodologies (e.g., Value Selling) to ensure rep-level accountability and eliminate deal slip.
  • Actively manage the Deal Desk, unblocking contract roadblocks, managing custom terms, and expediting legal, security, and procurement approvals to close deals faster.

Sales Accountability & Performance Management

  • Establish discipline, activity-based and milestone-based KPIs for reps to track deal velocity and risk exposure months before target close dates.
  • Lead the Sales Enablement team to create outcome driven programs aligned with business strategy and product development, ensuring reps quickly learn to navigate a long sales cycle and dynamic market.
  • Partner directly with Sales Leadership and Sales Enablement to identify underperforming territories or reps early, enforcing performance improvement plans and operational reset plans.
  • Own quota allocation, capacity planning, and territory design, ensuring rep coverage is directly tied to pipeline generation and immediate revenue capture.

Strategic Go-to-Market & Incentive Alignment

  • Architect incentive compensation and SPIFF structures that aggressively reward top-performer execution and support Shift's strategic objectives.
  • Continuously audit rep time allocation, removing administrative burden so Account Executives spend maximum time in active buyer conversations.
  • Translate revenue strategy into clear, executable weekly and monthly tactical mandates for field teams.

Tech Stack Execution & Process Enforcer

  • Enforce strict usage of our GTM tech stack (Salesforce), turning software from data repositories into active execution tools.
  • Streamline quote-to-cash workflows to eliminate sales friction and enforce strict compliance with pricing guidelines and discounting rules.
  • Deliver real-time, actionable execution dashboards to executive leadership, highlighting operational bottlenecks, conversion gaps, and rep productivity metrics.
  • Partner with Product, Finance, and Customer Success to ensure seamless post-sale operational transitions and retention visibility.

What You'll Need to Succeed

  • Experience: 8+ years in Sales Leadership, Sales/Revenue Operations in enterprise B2B SaaS with at least 3+ years managing global operational teams 
  • Execution Bias: Proven track record of operating as a proactive driver—not just a passive reporter of data—with an uncompromising standard for field execution and pipeline hygiene.
  • Enterprise Mastery: Deep experience driving execution across complex, long-cycle enterprise deals (12+ months, $300k+ to $5M+ ACV, multiple economic buyers).
  • Process & Framework Discipline: Expertise in implementing and enforcing structured enterprise sales frameworks (MEDDPICC, Force Management, or Challenger) down to the individual rep level.
  • Technical & Analytical Leadership: Advanced mastery of Salesforce architecture, revenue intelligence (Clari, Gong), and quantitative forecasting; able to translate metrics into swift operational shifts.
  • Help Others Grow and Succeed: Actively coach and mentor Shifters on your team and throughout the GTM organization, focusing on their development, giving candid, timely feedback, and inspiring the team by recognizing their individual impact. 

Preferred Qualifications

  • Prior experience executing inside a high-growth VC/PE-backed software company ($100M+ ARR scaling phase).
  • Prior experience as a seller, certification or deep implementation experience in formal enterprise sales frameworks.

The range listed is for base compensation.  Your actual base salary will vary based on factors including location and individual qualifications objectively assessed during the interview process. 

In addition to base salary, your total rewards package will include additional components such as incentive pay and benefits.  If you're interviewing for this role, speak with your Talent Acquisition Partner to learn more about the specific details for this position.

Base Salary Pay Range

$190,000 - $250,000 USD

To support our permanent, full time employees at every stage of their careers and lives, we provide a competitive total rewards and benefits package. Here are the global benefits we’d like to highlight:

  • Flexible remote and hybrid working options
  • Competitive Salary and a variable component tied to personal and company performance
  • Multiple Learning and Development opportunities, including Focus Fridays, a half-day each month to focus on learning and personal growth
  • Generous PTO and paid holidays
  • Mental health benefits 
  • 2 MAD Days per year (Make A Difference Days for paid volunteering)

Additional benefits may be offered by country, based on your eligibility - ask your recruiter for more information. Intern and Apprentice positions may receive some of these benefits - ask your recruiter for more details.

AI tools are used to help review applications for this role. Read our AI in Recruitment Notice for what the AI considers, how to request a human review, and our most recent bias audit.

At Shift we strive to be a diverse and inclusive workforce. We welcome applications from and hire people who will contribute to the diversity of our company, without regard to race, color, religion, marital status, age, national or ethnic origin, physical or mental disability, medical condition, pregnancy, genetic information, gender identity or expression, sexual orientation, or other non-merit criteria. Shift Technology is committed to providing reasonable accommodations for qualified individuals with disabilities in our application and employment process. Should you require accommodation, please email accommodation@shift-technology.com and we will work with you to meet your accessibility needs.

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Shift Technology does not accept unsolicited CVs from recruiters or employment agencies in response to the Shift Technology Careers page or a Shift Technology social media post. Any unsolicited CVs, including those submitted directly to hiring managers, are deemed to be the property of Shift Technology.

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We use Greenhouse’s AI-powered Talent Matching tool to compare your application against our job requirements. Read our AI in Recruitment Notice for what the AI considers, how to request a human review, and our most recent bias audit.

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