Head of Customer Outcomes - Strategy & Operations

ThoughtSpot; Chicago (IL); On-site; USD 180,000 - 240,000; Full time

Job summary

ThoughtSpot is seeking a Head of Customer Outcomes Strategy & Operations to realign post-sales around measurable outcomes. You will lead planning, operating rhythms, and cross-functional initiatives to improve GRR and NRR.

This role blends strategy, hands-on program management, and executive communication. You will drive annual planning, coverage models, and AI-enabled workflows for post-sales, partnering with Finance, HR, Product, and Enablement to design and implement scalable solutions.

Qualifications

• 8+ years across CS operations, RevOps, strategy and operations, management consulting, or chief of staff roles in B2B SaaS.
• Proven at scaling Customer Success and Professional Services functions in high-growth environments, including coverage models and capacity planning.
• A program leader who has run multi-quarter, cross-functional programs with many stakeholders and no direct authority.

Responsibilities

• Lead annual and long-range planning for post-sales.
• Own segmentation, coverage, and engagement models across Enterprise, Commercial, and Scaled.
• Run high-stakes analyses and initiatives for the VP, including retention and renewal questions.

Skills

CS operations

RevOps

Strategy

Program leadership

Job description

Head of Customer Outcomes - Strategy & Operations

ThoughtSpot is a Data & AI platform that helps companies turn data into enterprise advantage. We're Gartner MQ leaders with more than 1,000 customers globally and offices in Mountain View, Chicago, London, Bangalore, Sydney, and Tokyo.

The Role We’re realigning post-sales around outcomes. Our Customer Outcomes model ties every team to GRR and NRR, and it runs on new roles, new programs, and AI agents. The Head of Customer Outcomes Strategy & Operations is the VP's right hand in making that model work. The role is part strategist, part operator, and part program leader.

You’ll shape where the organization is going, run the operating rhythm that keeps it on course, and drive the cross-functional initiatives that get us there. You’ll be in every planning cycle, business review, and leadership decision. You won’t be supporting from a distance; you’ll help make the call. This is the right role for someone who thinks in frameworks, builds in sprints, and measures everything.

What You'll Do

Lead annual and long-range planning for post-sales. Own the targets, investment priorities, and headcount and capacity models, built in partnership with Finance and RevOps.

Own how we cover customers. Lead the annual review of segmentation, coverage, and engagement models across Enterprise, Commercial, and Scaled. Partner with Finance and HR on comp plan design.

Run the strategic projects. Scope and lead high-stakes analyses and initiatives for the VP. Examples include retention and churn deep dives, new program design, organization design, and questions that shape renewal and expansion.

Operating Cadence & Leadership Support

Run the operating rhythm. Own the weekly leadership meeting, monthly business reviews, QBRs, and offsites. That includes agendas, pre-reads, decisions, and follow-through.

Be the VP's leverage. Prepare executive and board materials, draft org-wide communications, and triage what needs leadership attention. Represent the VP in cross-functional forums when needed.

Keep leadership ahead of problems. Surface risks, capacity gaps, and process breakdowns before they become leadership problems, and bring a point of view on what to do about them.

Program Management

Run the transformation portfolio. Own the roadmap, milestones, owners, and status for org-wide initiatives. These include rolling out new roles, launching programs, and systems changes.

Drive cross-functional execution. Lead programs that span Sales, Product, Marketing, Finance, and Enablement, and keep them on time and accountable.

Own the AI and automation roadmap for post-sales. Prioritize, launch, and drive adoption of the agents and tools that power renewal, expansion, account health, and leadership workflows. Measure whether they actually save time and change outcomes.

Playbooks & Operational Excellence

Own the post-sales playbook. Define what good looks like at each lifecycle stage, from onboarding and adoption through health intervention, renewal, and expansion. Specify triggers, actions, escalation paths, and success criteria for each segment.

Launch playbooks. Work with post-sales leadership to embed them into team routines, 1:1s, and account reviews. Partner with Enablement on training and certification, and iterate quickly where playbooks break down or get bypassed.

Insights & Reporting

Own the story behind the numbers. Partner with RevOps on reporting for renewal coverage, health, time-to-value, utilization, and productivity. Translate it into what's happening, why it matters, and what the team should do.

Bring the customer into company decisions. Connect post-sales insight to GTM planning, product prioritization, and executive and board reporting.

How You'll Be Measured

Progress against GRR and NRR targets and the annual operating plan

• On-time delivery of priority initiatives


• Quality of the operating cadence: decisions made, owned, and followed through


• Playbook adoption and its impact on renewal, expansion, health, and time-to-value


• Measurable productivity gains from automation and AI agents


• Accuracy of forecasts and capacity plans

What You Bring

Strategy and operations depth. You have 8+ years across CS operations, RevOps, strategy and operations, management consulting, or chief of staff roles in B2B SaaS.

Proven at scaling post-sales. You've helped build and scale Customer Success and Professional Services functions in high-growth environments, including their coverage models, capacity plans, and operating rhythms.

A program leader. You've run multi-quarter, cross-functional programs with many stakeholders and no direct authority, and delivered them.

Executive presence. Senior leaders trust you, and you're comfortable in the room with the executive team. You write crisp narratives and can turn a messy problem into a clear decision.

Fluent in data and SaaS metrics. You have a deep understanding of NRR, GRR, churn, expansion, and lifecycle management. You're comfortable building models and working hands-on with data.

An AI-forward builder. You've built or deployed agents, automation, or apps that improve post-sales workflows, and you measure whether they work.

Comfortable in ambiguity. You create structure in fast-moving environments, and you know when a framework helps and when it slows the team down.

Discreet and trusted. You handle sensitive information on people, comp, and org design with sound judgment.

In-Office at ThoughtSpot

Spotters are expected in-office 3+ days per week to be part of the energy of their local team. Momentum compounds when we're in the room together with faster decisions, sharper problem-solving, and the kind of peer learning that doesn't happen over a screen. Being in-office is our default way of working, with flexibility available where it's genuinely needed.

About ThoughtSpot

The world’s most innovative companies turn to ThoughtSpot’s AI-Powered Analytics to put data in the hands of everyone, from the C-suite to the frontline. With simple, natural language search and AI, anyone can ask questions, discover insights, and act with confidence. Unlike legacy tools that sacrifice performance for complexity, ThoughtSpot is intuitively designed for every business user while being built to handle the most complex, large-scale data, wherever it resides. This unique combination of speed and simplicity is why enterprise leaders trust ThoughtSpot to transform decision-making into a truly data-driven culture.

At ThoughtSpot, we’re a curious, data-driven bunch. We believe the world works better when everyone has access to facts. That’s why we build products that make asking and answering data questions as natural as having a conversation.

Mandatory and Required Skills for All ThoughtSpot Roles

Spotters are expected to demonstrate AI literacy and workflow integration to include to ability to:

• Comfortably and confidently integrate artificial intelligence into their daily workflow to increase productivity and quality.


• Hands-on experience to leverage AI tools (industry-leading LLMs) to increase productivity, automate routine tasks, and improve work quality.


• Speak to the experience of using