Head of GTM Strategy & Operations, Enterprise
Scale AI
CA$275,200 - CA$336,700 / year
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Description
Head of Enterprise GTM Strategy & Operations
Reports to VP, Enterprise Sales · SF or NY
Reporting to the VP of Enterprise Sales, this role owns both halves of Scale AI’s enterprise revenue engine: the strategy that determines where we play and how we win, and the operating system - people, process, and systems - that makes that strategy executable, measurable, and repeatable.
On the strategy side, you set the analytical foundation for enterprise growth: segment and account prioritization, coverage and territory design, pricing and packaging inputs, and the diagnostic work that explains why the funnel behaves the way it does. On the operations side, you own the RevOps stack, forecasting, compensation design, sales enablement, and the operating cadences that convert strategy into predictable quarterly execution. The ideal candidate is equally comfortable building a segmentation model from a blank page and running a Monday morning pipeline review.
You will lead an established team, with the Head of Sales Enablement and the RevOps Manager as direct reports. Your first job is to raise the ceiling on what that team delivers: sharper analysis, tighter operating rhythm, and enablement that measurably shortens ramp and lifts win rates.
This is a senior, highly visible role partnering with Enterprise Sales leadership, Finance, Marketing, Product, and Solutions Engineering, with regular exposure to the executive team and board materials.
STRATEGY
- Define which segments, industries, and accounts Scale prioritizes, and build the analytical case behind those choices
- Build and maintain the market sizing, segmentation, and account-tiering models that drive coverage decisions and investment trade-offs
- Lead hypothesis-driven analyses of the enterprise funnel - win/loss patterns, conversion drivers, deal economics, coverage gaps - and translate findings into specific changes to how we sell
- Partner with Finance and Product on pricing, packaging, and deal-structure strategy for enterprise agreements
- Own the route-to-market point of view: direct vs. partner, land-and-expand mechanics, and where new capacity or capability is needed
- Build the strategic narrative and executive materials behind annual planning, board reporting, and major GTM investment decisions
- Serve as a strategic thought partner to Enterprise Sales leaders, bringing an independent, well-argued view on how accounts should be covered and engaged
OPERATIONS & ENABLEMENT
- Own and evolve the enterprise GTM operating model: account engagement strategy, funnel design, and sales execution standards
- Direct the RevOps systems stack (CRM, forecasting, reporting, planning tools) through the RevOps Manager, and hold the bar on data integrity and operational discipline
- Define and operationalize core GTM metrics across pipeline health, deal velocity, forecast accuracy, and rep productivity, with executive dashboards to match
- Run the sales operating cadence: pipeline reviews, forecast calls, QBRs, and performance reviews
- Set the enablement agenda with the Head of Sales Enablement - onboarding and ramp, ongoing skill development, and the playbooks and certification that turn GTM strategy into consistent field execution
- Tie enablement investment to outcomes, measuring impact on ramp time, win rate, and deal quality rather than activity or completion
- Partner with Sales Leadership and Finance on enterprise compensation plan design, quota governance, and attainment reporting
- Lead annual and quarterly planning, including territory design, capacity modeling, headcount planning, and quota setting
- Act as the connective tissue across Sales, Marketing, Finance, Product, and Solutions Engineering for enterprise GTM planning and execution
LEADERSHIP
- Lead, develop, and retain an established team spanning sales enablement and revenue operations
- Set clear priorities and standards for a team whose work is consumed by the entire enterprise sales organization
- Grow the function as the enterprise business scales, making the call on where added capacity creates the most leverage
WHAT WE'RE LOOKING FOR
- 8–12+ years spanning GTM strategy and revenue operations - for example, a foundation in strategy consulting, corporate strategy, or investing paired with in-house GTM Strategy, RevOps, or Sales Ops ownership at a high-growth company
- Experience managing and developing a team, including managing other managers or senior functional leads
- Proven ability to frame an ambiguous question, build the analytical approach, and drive to a defensible recommendation on incomplete data
- Quantitative depth across segmentation, market sizing, unit economics, and capacity and quota models, with the judgment to know which analysis will actually change a decision
- A track record of recommendations that were implemented and measured, not just presented
- Experience with complex, multi-stakeholder enterprise sales motions in high-growth B2B SaaS or platform companies
- Hands-on ownership of sales systems, forecasting, and enterprise compensation plans at scale
- Familiarity with what good sales enablement looks like, and a view on how to measure whether it is working
- Executive communication that holds up in front of a CRO, CFO, or board, and the ability to influence senior sales leaders without direct authority
- Strong command of the GTM stack (e.g., Salesforce, Clari, planning and reporting tools) and fluency in SQL or equivalent for independent analysis
- The range to operate at strategic altitude and in the details, and to move fluidly between the two
- Technical curiosity or experience alongside technical products; familiarity with AI, ML, or data platforms is a plus
Compensation packages at Scale for eligible roles include base salary, equity, and benefits. The range displayed on each job posting reflects the minimum and maximum target for new hire salaries for the position and may be inclusive of several career levels at Scale; it will be determined during the interview process based on work location and additional factors, including job-related skills, experience, qualifications, interview performance, and relevant education or training. Scale employees in eligible roles are also granted equity based compensation, subject to Board of Director approval. Your recruiter can share more about the specific salary range for your preferred location during the hiring process, and confirm whether the hired role will be eligible for equity grant. You'll also receive benefits including, but not limited to: comprehensive health, dental and vision coverage, retirement benefits, a learning and development stipend, and generous PTO. Additionally, this role may be eligible for additional benefits such as a commuter stipend.
PLEASE NOTE: Our policy requires a 90-day waiting period before reconsidering candidates for the same role. This allows us to ensure a fair and thorough evaluation of all applicants.
About Us:
At Scale, our mission is to develop reliable AI systems for the world's most important decisions. Our products provide the high-quality data and full-stack technologies that power the world's leading models, and help enterprises and governments build, deploy, and oversee AI applications that deliver real impact. We work closely with industry leaders like Meta, Ernst & Young, Mayo Clinic, Time Inc., the Government of Qatar, and U.S. government agencies including the Army and Air Force. We are expanding our team to accelerate the development of AI applications.
We believe that everyone should be able to bring their whole selves to work, which is why we are proud to be an inclusive and equal opportunity workplace. We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability status, gender identity or Veteran status.
We are committed to working with and providing reasonable accommodations to applicants with physical and mental disabilities. If you need assistance and/or a reasonable accommodation in the application or recruiting process due to a disability, please contact us at accommodations@scale.com. Please see the United States Department of Labor's Know Your Rights poster for additional information.
We comply with the United States Department of Labor's Pay Transparency provision.
PLEASE NOTE: We collect, retain and use personal data for our professional business purposes, including notifying you of job opportunities that may be of interest and sharing with our affiliates. We limit the personal data we collect to that which we believe is appropriate and necessary to manage applicants’ needs, provide our services, and comply with applicable laws. Any information we collect in connection with your application will be treated in accordance with our internal policies and programs designed to protect personal data. Please see our privacy policy for additional information.
Benefits
- vision insurance
- paid time off
- stock options
- professional development
About this role
Scale AI is building the data infrastructure for AI, and this role sits at the center of how the enterprise business scales. You'd own both the strategic thinking—which segments to pursue, how to price, why deals win or lose—and the operational machinery that turns strategy into predictable quarterly results. That means building segmentation and market-sizing models, running pipeline reviews and forecast calls, designing territories and compensation plans, and ensuring the RevOps stack and sales enablement actually move the needle on ramp time and win rates.
You'd report to the VP of Enterprise Sales and lead a team including the Head of Sales Enablement and RevOps Manager, with visibility across the executive team and board. The work is genuinely cross-functional—partnering with Finance on pricing, Product on packaging, Marketing on campaigns, and Solutions Engineering on deal structure. This isn't a role that stays in one lane; you need to be equally comfortable building a model from scratch and running a Monday morning review, and to influence senior leaders without direct authority.
The ideal candidate brings 8–12+ years mixing strategy (consulting, corporate strategy, or investing) with hands-on GTM or RevOps ownership at a high-growth B2B SaaS company. You should have shipped recommendations that were actually implemented and measured, deep quantitative chops in segmentation and unit economics, and real fluency with Salesforce, forecasting tools, and ideally SQL. Experience with complex enterprise sales motions, AI or data platforms, and a clear point of view on what good sales enablement looks like round out the profile. This is a senior, visible role for someone who can operate at both strategic altitude and in the details.
How this employer is doing
solid
- News: Recently Raised Funding
- News: Growing or Expanding
- H1B: Active Visa Sponsor
- Recently Raised Funding
In the news
Stuut Secures $52.5M Series B Led by Insight Partners to Scale AI Agents for Order-to-Cash, AI Insider
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Pay for this role
$275,200 to $336,700 per year
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