# Toptal — VP, AI Services

- Generated: 2026-09-10 03:32 AM EDT
- Original/canonical posting: https://www.linkedin.com/jobs/view/vp-ai-services-at-toptal-4428863224
- User-provided LinkedIn posting: https://www.linkedin.com/jobs/view/4428863224/
- Alert email subject: Vice President, Engineering and AI Innovations at Five9
- Canonical-identity note: The supplied LinkedIn job ID currently resolves to Toptal's VP, AI Services posting, not the Five9 role named in the email subject. The live canonical posting was treated as authoritative.
- Posting time: LinkedIn displayed “1 day ago” at capture; exact timestamp was not exposed
- Applicants: Over 200 applicants
- Work model/location: Remote — United States; the role-specific JD explicitly states, “This is a remote position.”
- Compensation: Base salary amount not disclosed; quarterly discretionary bonus and monthly commissions based on revenue generated from engagements sold
- Travel: Not disclosed
- Positioning track: Executive leader
- Fit outcome: FAIL — 47% weighted evidence coverage, with multiple hard gaps and an applicant-count hard stop

## Direct-match strengths

- Built an AI/ML consulting practice as VP of AI/ML at NorthBay Solutions, including a reusable Data Lake Accelerator offering and leadership of an offshore delivery team.
- Built and led AI engineering teams, including 11 direct-report engineers at Intelligent DataWorks and an 18-person offshore delivery organization at NorthBay Solutions.
- Advised more than 200 AWS enterprise customers on AI/ML, data, cloud adoption, and production architectures; strong C-suite and executive communication evidence.
- Hands-on production GenAI experience with OpenAI APIs, AWS Bedrock, Anthropic Claude, RAG, AI agents, evaluation, workflow automation, and multi-tenant SaaS architecture.
- Direct experience defining AI product strategy, pricing, customer discovery, technical roadmaps, delivery standards, and measurable automation outcomes.

## Hard or material gaps

- Applicant-count hard stop: LinkedIn displays “Over 200 applicants,” exceeding Keith's standing ceiling of 90.
- Required hands-on ServiceNow delivery expertise is unsupported. The JD specifically requires architect- or delivery-leadership experience with ServiceNow ITSM Pro, ITOM, Virtual Agent, or Now Assist.
- Required deep, applied ITIL v4 knowledge is unsupported; no ITIL framework or ITIL certification evidence appears in the source career materials.
- The role requires 10+ years of IT services experience and at least five years of senior leadership within an MSP, systems integrator, or IT consulting firm. Keith has strong client-facing AWS and NorthBay experience, but the source record does not establish the exact required duration and setting.
- Required P&L accountability for practice revenue, margin, and utilization is unsupported. Keith has budget ownership, company-level financial modeling, pricing, and commercialization experience, but not documented practice P&L ownership against revenue, margin, and utilization targets.
- The mandate is materially centered on pricing, packaging, go-to-market execution, selling engagements, expansion opportunities, commissions, and practice revenue growth; this conflicts with Keith's preference to prioritize AI development rather than GTM-centered roles.

## Evidence map

Scoring: 3 = direct/recent/outcome-backed; 2 = direct but older or less measurable; 1 = adjacent/transferable; 0 = unsupported. Weight 3 = essential, 2 = important, 1 = preferred.

1. **10+ years in IT services, including 5+ years senior leadership in an MSP/SI/consulting firm** (weight 3, evidence 1/3) — AWS customer advisory and NorthBay MSP leadership are relevant, but the documented experience does not establish the required duration and organizational setting.
2. **Build or scale an AI/ITSM practice in an MSP or professional-services organization** (weight 3, evidence 3/3) — Direct evidence from building NorthBay's AI/ML consulting practice and reusable Data Lake Accelerator offering.
3. **Hands-on ServiceNow architecture/delivery leadership** (weight 3, evidence 0/3) — No source-supported ServiceNow, ITSM Pro, ITOM, Virtual Agent, or Now Assist experience.
4. **Deep applied ITIL v4 expertise** (weight 3, evidence 0/3) — No source-supported ITIL framework or certification experience.
5. **Apply AI/automation/ML within ITSM or IT Operations for enterprise clients** (weight 3, evidence 1/3) — Strong enterprise AI and workflow automation evidence, but not within source-supported ITSM or ServiceNow delivery.
6. **C-suite advisory, maturity discovery, business cases, and executive relationships** (weight 2, evidence 3/3) — Direct evidence advising 200+ AWS customers and enterprise leaders, plus executive product and consulting roles.
7. **P&L ownership for practice revenue, margin, and utilization** (weight 3, evidence 1/3) — Adjacent budget, pricing, financial-modeling, and commercialization evidence; required operating P&L metrics are not documented.
8. **Recruit and lead AI architects, ServiceNow practitioners, and ITSM consultants** (weight 2, evidence 2/3) — Strong AI/engineering recruiting and leadership evidence, but not the required ServiceNow/ITSM disciplines.
9. **Pricing, packaging, GTM, and revenue growth for AI services** (weight 2, evidence 2/3) — Direct pricing, commercialization, customer discovery, and consulting-offer evidence, but limited documented services-revenue ownership and a preference conflict with GTM-centered work.
10. **Enterprise LLMs, GenAI APIs, AWS Bedrock, and multi-tenant solution architecture** (weight 1, evidence 3/3) — Direct, recent, production-backed evidence.

Weighted result: 35 earned points out of 75 possible = **47%**.

## Fit-gate decision

**FAIL.** The central mandate is not general AI leadership: it is a ServiceNow- and ITIL-centered MSP practice with explicit P&L, sales, and revenue-growth accountability. The required ServiceNow and ITIL qualifications are unsupported and material to day-one execution. The posting also exceeds Keith's applicant-count ceiling. No resume, cover letter, or LinkedIn connection note was generated.

## Full normalized job description

### About Toptal

Toptal is a global network of top talent in business, design, and technology that enables companies to scale their teams on demand. It reports more than $200 million in annual revenue and describes itself as the world's largest fully remote workforce, with team members based around the globe.

### Job summary

Toptal describes the hiring organization as a managed service provider focused on AI-driven IT service transformation. The Vice President of AI Services is the executive owner of the design, delivery, and scaling of AI-powered ITSM solutions for clients. The role sits at the intersection of artificial intelligence, ITIL best practices, and ServiceNow and is central to the organization's growth strategy.

The VP will build and lead the AI Services practice, partner with client executives to understand ITSM challenges, translate those needs into repeatable AI-enabled service offerings, and develop the methodologies, tooling, and talent needed for delivery at scale. The position reports directly to the CEO of Services and carries P&L accountability for the practice.

This is a remote position. Applicants must be authorized to work in the United States at the time of hire. Resumes and communication must be submitted in English.

### Responsibilities

#### AI Services practice leadership

- Own the vision, strategy, and P&L for the AI Services practice and establish it as a differentiated, revenue-generating offering within the MSP portfolio.
- Develop repeatable service offerings and delivery frameworks that apply AI to ITIL processes, including Incident Management, Problem Management, Change Enablement, Service Request, and Knowledge Management.
- Define pricing models, packaging, and go-to-market strategy for AI-enabled ITSM services with Sales and Marketing.
- Build playbooks, accelerators, and preconfigured ServiceNow AI assets that reduce client time-to-value.

#### Client engagement and advisory

- Serve as an executive-level AI advisor to key clients and engage C-suite and IT leaders on maturity, opportunities, and AI-driven ITSM roadmaps.
- Lead discovery workshops and maturity assessments for current ITSM and AI capabilities.
- Present business cases and ROI models for AI investments, including MTTR reduction, ticket deflection, and cost avoidance.
- Maintain executive relationships across a portfolio of accounts, support client satisfaction, and identify expansion opportunities.

#### ServiceNow AI delivery

- Oversee architecture and delivery of ServiceNow AI solutions, including Now Assist, Virtual Agent, Predictive Intelligence, ITOM AIOps, NLU, and generative-AI integrations.
- Govern ServiceNow integrations with external AI platforms such as Azure OpenAI, AWS Bedrock, and Anthropic.
- Establish delivery standards and quality-assurance processes across client engagements.
- Drive measurable adoption of AI-powered ServiceNow capabilities.

#### ITIL and process excellence

- Apply deep ITIL v4 expertise so AI improves service-management processes without creating risk or technical debt.
- Champion shift-left service through AI-driven self-service, knowledge deflection, and automated resolution.
- Establish KPIs, SLAs, and OLAs for AI-enhanced ITSM processes.

#### Team building and talent development

- Recruit, develop, and lead AI architects, ServiceNow practitioners, and ITSM consultants.
- Establish career paths and capability-building programs across the broader services organization.
- Foster innovation and continuous improvement and encourage adoption of emerging AI capabilities.
- Lead by example while exercising discretion and independent judgment.

#### Partnerships and ecosystem

- Manage and deepen the ServiceNow partnership, including ISV/reseller programs and co-sell opportunities.
- Evaluate complementary AI and AIOps vendors.
- Represent the company at industry events, conferences, and ServiceNow communities.

### Expected outcomes

- First week: onboard, meet colleagues, learn Toptal's history, culture, vision, industry position, and operating model.
- First month: understand the client portfolio and internal capabilities; build relationships with key clients and the ServiceNow partner team.
- First three months: define the AI Services roadmap and initial offerings; identify, scope, and land the first client AI-ITSM engagement.
- First six months: finalize repeatable delivery playbooks and document client outcomes such as ticket deflection and MTTR improvements for business development.
- First year: grow and operate a profitable AI Services practice, continue growing the revenue line, and establish the practice as a differentiator in the MSP market.

### Required qualifications

- Bachelor's degree.
- 10+ years of IT services experience, including at least five years in a senior leadership role within an MSP, systems integrator, or IT consulting firm.
- Proven record building or scaling an ITSM- or AI-focused practice within an MSP or professional-services organization.
- Hands-on ServiceNow expertise at architect or delivery-leadership level across ITSM Pro, ITOM, Virtual Agent, or Now Assist.
- Deep applied ITIL v4 knowledge; ITIL Managing Professional or Strategic Leader certification is strongly preferred.
- Experience applying AI, automation, or ML within ITSM or IT Operations for enterprise clients.
- C-suite influence, investment-case presentation, and executive-relationship management.
- P&L management with accountability for practice revenue, margin, and utilization.
- Outstanding written and verbal communication skills.
- Ability to operate in a fast-paced, rapidly growing company with varied challenges, deadlines, and contacts.
- Strong individual-contributor capability in addition to leadership.

### Preferred qualifications

- ServiceNow Certified Implementation Specialist (CIS-ITSM) or higher ServiceNow partner certification.
- Familiarity with LLMs, enterprise generative-AI APIs, OpenAI, Azure OpenAI, Anthropic, and prompt engineering.
- Experience with AIOps platforms such as Moogsoft, BigPanda, and Dynatrace and their ServiceNow integrations.
- Multi-tenant or multi-client MSP solution architecture.
- MBA or advanced degree in Computer Science, Information Systems, or a related field.
- Active presence in the ServiceNow partner ecosystem or ITSM community.

### Essential functions

- Attend scheduled virtual meetings on camera reliably.
- Work independently with minimal supervision.
- Use required digital collaboration tools.
- Prioritize and self-manage workflows and deadlines.

### Employment and compensation

Full-time, exempt. The role receives a base salary and is eligible for a quarterly discretionary bonus based on assigned objectives and monthly commissions based on revenue generated from engagements sold. Individual pay depends on work location, skills, experience, and education or training. The posting does not disclose a numerical salary range. Applications are accepted on an ongoing basis. U.S. benefits include 401(k), medical, dental, vision, life insurance, short- and long-term disability, spending and savings accounts, telehealth, employee assistance, and flexible paid time off.

## Artifact metadata

- Resume: Not generated — FAIL outcome
- Cover letter: Not generated — FAIL outcome
- LinkedIn connection note: Not generated — prohibited for FAIL outcomes
- Archived JD capture: https://files.keithsteward.com/Toptal/Toptal_VP_AI_Services_4428863224_JD_capture.md
- Google Drive used: No
- Validation: JD identity, work model, location, applicant count, fit calculation, hard-gap reasoning, and capture content validated; public-link validation pending publication