** Please note that this opportunity is located in New York, NY, and requires this hire to work from our office 4 days a week. **

 
The Head of Business Transformation (AI) is a high-visibility, cross-functional leadership role responsible for driving the company's internal AI program from strategy through execution. Acting as the operational owner of AI at the business, you will partner with functional leaders to identify where AI creates the highest leverage across revenue growth and margin improvement, design and launch pilots with functional owners, and hold the organization accountable to real business outcomes — not just tool deployments. You will translate the rapidly evolving AI landscape into a prioritized, sequenced roadmap that leadership can align behind and the business can actually execute.

This role is designed for a seasoned cross-functional operator with real authority to change workflows and systems — not just advise on them. You will be trusted and respected across GTM, Customer Success, Finance, and Operations, with the C-suite mandate to move fast, make hard prioritization calls, and drive adoption through functions that have competing priorities. Reporting directly to the SVP of Business Operations, you will own the internal AI transformation roadmap and be accountable for the business impact it generates.

We are looking for an operator who understands the business deeply, is technically dangerous enough to evaluate and direct AI solutions, and has the change management skills and organizational credibility to get programs live and make them stick.

As Head of Business Transformation (AI), you can expect to:

• Own the internal AI transformation roadmap: Build and maintain the company's portfolio of AI initiatives — defining the prioritization framework, sequencing the work, and ensuring executive alignment at every stage. You work with functional leaders to decide what gets resourced and what gets deprioritized.
• Partner with functional owners to identify and launch AI use cases: Embedded with GTM, Customer Success, Finance, and Operations, you will work with functional owners to surface the highest-impact opportunities for AI to drive revenue growth or margin improvement, design the pilots, and manage them from hypothesis through adoption. You are not handing off to someone else to implement — you are in the room until it works.
• Drive adoption and change management: Getting an AI tool live is the easy part. Getting an organization to change how it works is the job. You will work with functional owners to design the change management approach for each initiative — the rollout plan, the training model, the accountability structure, and the feedback loop that separates tools that stick from tools that get abandoned after week three.
• Build the operating model for AI at the company: Establish the governance structure, vendor evaluation framework, and decision rights that determine how AI initiatives are approved, funded, and measured. Build the intake process so that good ideas from anywhere in the company have a path to evaluation and execution.
• Measure and report business impact: Every initiative has a hypothesis and a measurement plan before it launches. You will own the ROI framework — working with the data team to define what success looks like, track it rigorously, and report it to the executive team in a way that builds confidence in the program and informs future prioritization.
• Manage vendors and the AI tool landscape: Evaluate, select, and manage AI vendors across the GTM and operational stack — from outbound and enrichment tools (e.g. Clay) to conversation intelligence (Gong) to workflow automation. You know the landscape, have opinions about it, and can direct vendors rather than being directed by them.
• Influence systems, data, and process: You understand how data flows across the business — across Salesforce, our data warehouse, CS tools, and financial systems — and you use that understanding to evaluate what AI solutions are technically feasible, what data gaps need to be closed before a use case can go live, and how existing workflows need to change to support AI-powered processes.
• Build organizational AI fluency: Not through generic training sessions, but by embedding AI thinking into how functional teams plan, prioritize, and operate. The measure of success is not how many people attended an AI workshop — it is how many workflows have been permanently changed.

To thrive in this role you should have/you must:

• 6+ years in a cross-functional operator role — Business Operations, Revenue Operations, Chief of Staff, Strategy & Operations, or a comparable function at a SaaS company. You have held a role where you had to change how other people's functions worked, without those people reporting to you.
• Demonstrated track record of rolling out AI initiatives that produced measurable business outcomes. Not a pilot that got shelved, not a tool that got purchased but not adopted — a program that changed how a team worked and you can point to the before and after. You should be able to describe at least two or three examples in detail: what the initiative was, how you designed and launched it, what resistance you encountered, how you drove adoption, and what the result was.
• Technical fluency without being a pure technologist. You understand how LLMs work at a conceptual level, how AI agents and workflow automation function, what APIs do, and how data needs to be structured for AI to use it effectively. You can evaluate a vendor's technical claims critically, brief an engineer on what you need built, and identify when a proposed AI solution is technically infeasible given the company's data infrastructure — all without needing to write the code yourself.
• Deep familiarity with the modern GTM and AI tool landscape. You have hands-on experience with tools like Clay, Gong, Outreach or Salesloft, ZoomInfo, and AI-powered workflow automation platforms. You know which tools are genuinely differentiated and which are overhyped, and you have opinions about where the category is heading.
• Organizational credibility and executive presence. You have operated at a level where VPs and C-suite leaders trusted you to tell them what to deprioritize. You can walk into a room with the CRO, CMO, and CFO and hold your own — challenging their assumptions with data, making a clear recommendation, and getting alignment on a difficult tradeoff. You have done this before and you are comfortable doing it again.
• Ruthless prioritization. The AI landscape generates more ideas than any organization can execute. You know how to say no, how to build a framework that feels principled rather than arbitrary, and how to keep the portfolio focused on the initiatives that will actually move the needle on revenue or margin rather than the ones that are interesting to work on.
• Change management skills that have been tested. You have managed a change program where the initial reaction from the function was resistance — and you got through it. You know how to build coalitions, how to make change feel inevitable rather than imposed, and how to identify and work through the real blockers (which are almost always human, not technical).
• Understanding of business data and systems. You are fluent enough in how GTM and financial data is structured — across a CRM, a data warehouse, CS tools, and financial systems — to evaluate technical feasibility, identify data gaps that need to be closed before a use case can go live, and have a credible conversation with a data or engineering team about what it will take to support an AI initiative.

Strongly Preferred:

• Experience with GTM functions – Some of the highest-impact AI opportunities at this stage are in Sales, Marketing, and CS — e.g. outbound automation, conversation intelligence, customer health, proactive churn intervention. Candidates who have lived inside these functions or been deeply embedded in them as operators will have a meaningful advantage.
• Experience with AI tools in production at a SaaS company — not just pilots. You have deployed tools like Clay for outbound enrichment and sequencing, Gong for conversation intelligence and coaching, AI-powered CS platforms, or workflow automation built on LLM APIs, and you have managed the full lifecycle including adoption, iteration, and measurement.
• Familiarity with AI agent frameworks and workflow automation platforms — tools like Workato, n8n, or Claude-powered workflows. You do not need to build these yourself, but you need to understand how they work and be able to direct a technical resource who does.
• Experience managing or evaluating AI vendor contracts and relationships — understands how to structure a pilot agreement, what evaluation criteria matter, and how to avoid getting locked into tools that underdeliver.
• Background that spans more than one business function — operators who have touched GTM teams, Product and Finance are significantly more effective in this role than those who have lived in a single function.

What VTS Values & How We Show It

• Strive for Excellence - We know your potential is unlimited. Take advantage of our executive coaches and our training and career development programs available to all employees! 
• Be Customer Obsessed - We’re employee obsessed too! VTS offers competitive compensation, comprehensive health benefits (including dental and vision), pre-tax commuter benefits, and a 401(k) plan. Not to mention the fun stuff - quarterly happy hours, wellness events, clubs, and team lunches! 
• Be Curious - Benefit from a culture that promotes new learning. VTS offers an education stipend to all employees! 
• Move as One - We work in an open floor plan to promote cross-functional collaboration. 
• Take Ownership - Be an owner of the company you’re building with our equity packages. 
• Appreciate the Difference - VTS embraces and celebrates diversity. We understand the importance of a strong work-life balance. We offer a flexible PTO policy, generous family leave program, and more!

** Please note that this opportunity is located in New York, NY, and requires this hire to work from our office 4 days a week. **

The Head of Data & Analytics is a high-visibility, foundational role responsible for establishing the company's single source of truth for data across all functions. Acting as the analytical backbone of the business, you will ensure every critical metric is defined, governed, and reportable from one place — giving leadership the data clarity they need to make fast, confident decisions. You will translate raw data across a modern SaaS stack into a trustworthy, scalable intelligence layer that the entire organization can rely on.

This role is designed for a seasoned data leader who excels at building from scratch — someone who can architect a data platform, establish governance standards, and be a genuine strategic partner to senior leaders – not just delivering data, but shaping decisions. You will connect data to business context, identify what matters, and provide clear, prescriptive recommendations. Reporting directly to the SVP of Business Operations, you will own the data infrastructure that underpins our next phase of growth.

This role is intentionally hands-on to start. You will personally build and shape the foundation of our data platform while partnering closely with leaders across the business. As we scale, you will have the opportunity to evolve into a player-coach, building and leading a small but high-impact data team.

In the first 6-12 months, you will:

• Establish a clear, trusted definition of core company metrics across GTM, Product, Finance, and Customer Success
• Reduce reliance on manual reporting by automating high-impact workflows
• Build a scalable data model that connects our core systems into a coherent source of truth
• Enable leadership to access and trust data without needing constant ad hoc support

What you can expect as the Head of Data & Analytics:

• Build the single source of truth: Audit, rationalize, and own the company's data model end to end — from raw sources through transformation to consumption. Every key metric will have one definition, one owner, and one place to find it.
• Identify the highest-impact manual reporting workflows across functions and automate them: Today, much of our reporting lives across spreadsheets and manual workflows, with no single owner of data. One of your first priorities will be to bring structure, consistency, and trust to this environment, and build a self-serve analytics layer that increases data trust and reduces ad hoc requests across the company.
• Own executive and board-level reporting: Build and maintain the metrics layer that leadership, the board, and ultimately investors rely on — each defined, documented, and reportable from a single governed layer.
• Mature the dbt layer: Partner with engineering team to audit existing dbt models, close gaps, and establish transformation standards that will scale the platform. You won't be coding alone, but you need to be fluent enough to review, direct, and govern the work.
• Establish metric governance: Define the operating model for how metrics are created, changed, and communicated — including a cross-functional process for resolving metric disputes and maintaining a company-wide data dictionary that becomes the authoritative reference.
• Build a scalable, auditable data foundation: Ensure our data is structured, documented, and fully traceable from source systems to reported metrics. Establish clear data lineage, metric definitions, and governance so leadership can rely on data with confidence as reporting needs become more complex.
• Act as a strategic partner to senior leadership: Show up to QBRs, pipeline reviews, and planning cycles with a clear point of view on what the data means and what the business should do next. Be the person who changes decisions — not by reporting the data, but by interpreting it and making actionable recommendations.
• Cross-functional data leadership: Partner with all functions to ensure their data needs are captured, while also challenging assumptions, refining questions, and guiding teams toward the metrics and analyses that drive better decisions. 
• Drive insight and action, not just visibility: Go beyond building dashboards to proactively identify trends, risks, and opportunities across the business. Translate data into clear recommendations and influence leaders on what actions to take — even when it challenges existing assumptions or priorities.

To thrive in this role you have: 

• 7-10+ years in analytics, analytics engineering, or a senior BI role with hands-on data modeling experience, including experience owning or significantly shaping a company’s data model or analytics infrastructure
• Experience building and governing a BI layer (e.g., Looker, Tableau): you know what good looks like, what breaks at scale, and how to make a BI tool something people actually use. 
• Experience working with modern data warehouses (e.g., Snowflake, BigQuery, Redshift):  Warehouse management, schema design, cost monitoring — you understand the platform and can make architectural decisions on it.
• dbt fluency: You can read, write, review, and govern dbt models. You understand staging, intermediate, and mart layer design, and you have strong opinions about what belongs where and why.
• Strong SQL: Window functions, CTEs, and performance optimization are comfortable ground. You write modeling SQL, not just analytical SQL.
• Broad business fluency and SaaS literacy: You understand the operational levers of a SaaS P&L - ARR, NRR, churn, CAC, LTV, product velocity, product adoption, as well as financial levers, such as unit economics, financial performance ratios, financial analysis. 
• Track record of strategic partnership: You have been in rooms with senior leaders and said things that changed decisions — not because you were asked, but because the data told you something important. You elevate data from reporting to a strategic asset that shapes how the company operates and makes decisions.
• Comfort operating without formal authority: You can direct an analytics engineer you don't manage, get a VP to prioritize data quality, and get Finance to adopt a metric definition they initially resisted.
• Strong prioritization instincts: You focus on the highest-impact problems and avoid over-engineering, balancing speed with long-term scalability.

• Experience building from scratch: You have built a data function, a data layer, or a centralized reporting infrastructure at a company that previously had none. You know how to sequence the work and how to manage stakeholder expectations during the build phase.
• Salesforce data model familiarity: You understand how CRM objects map to business concepts and how to extract Salesforce data reliably into a warehouse environment.
• Product analytics experience: You have worked with Mixpanel or a comparable tool and know how to join event-level product data with CRM and financial data to create a complete picture of customer behavior.
• C-suite and investor exposure: You know what executives and investors ask for and what breaks under that scrutiny.
• CS analytics background: Experience with customer health scoring, adoption reporting, proactive value engineering, or churn prediction data models, is a meaningful plus.
• Background in FP&A, investment banking, or management consulting before moving into data — brings structured analytical thinking and executive communication skills.

What VTS Values & How We Show It

• Strive for Excellence - We know your potential is unlimited. Take advantage of our executive coaches and our training and career development programs available to all employees! 
• Be Customer Obsessed - We’re employee obsessed too! VTS offers competitive compensation, comprehensive health benefits (including dental and vision), pre-tax commuter benefits, and a 401(k) plan. Not to mention the fun stuff - quarterly happy hours, wellness events, clubs, and team lunches! 
• Be Curious - Benefit from a culture that promotes new learning. VTS offers an education stipend to all employees! 
• Move as One - We work in an open floor plan to promote cross-functional collaboration. 
• Take Ownership - Be an owner of the company you’re building with our equity packages. 
• Appreciate the Difference - VTS embraces and celebrates diversity. We understand the importance of a strong work-life balance. We offer a flexible PTO policy, generous family leave program, and more!