AI Deployment Strategist

Wintermeyer Ventures; San Francisco (CA); On-site; USD 150,000 - 200,000; Full time

Job summary

Wintermeyer Ventures seeks a customer deployment lead to guide AI-enabled fintech implementations from discovery through adoption. You will align with operators and executives, ensuring measurable business outcomes and strong stakeholder engagement.

You will partner with product and engineering to translate customer feedback into improvements, troubleshoot issues in the field, and develop deep product expertise to apply AI to workflows.

Qualifications

• 2–5 years in management consulting or a customer-facing tech role.
• Experience owning customer-facing projects end-to-end.
• Strong analytical and problem-solving skills with Excel-based analysis.
• Confident client-facing communication with executives.
• Familiarity with modern AI tools and applying AI to business challenges.
• Ability to work independently in a fast-paced environment.
• Authorized to work in the United States without visa sponsorship.

Responsibilities

• Lead end-to-end AI deployments from discovery to adoption.
• Advise customer stakeholders across levels, from operators to sponsors.
• Partner with product/engineering to relay feedback for improvements.
• Troubleshoot field issues and document edge cases with engineering.
• Build product expertise and help apply AI to workflows.

Skills

Management consulting

Customer-facing

Attention to detail

Executive stakeholder comms

AI familiarity

Independent worker

Finance / fintech

Tools

Excel

Job description

About the Role

Join the customer deployment team at a Series A fintech company using AI to improve enterprise finance operations. You will guide customers from initial discovery through go-live and adoption, helping turn technical capabilities into measurable business outcomes.

What You'll Do

• Lead end-to-end AI deployments, including discovery, workflow mapping, configuration, launch, and adoption.
• Advise customer stakeholders, from frontline operators to executive sponsors.
• Partner with product and engineering teams to share customer feedback and inform product improvements.
• Troubleshoot issues in the field, document edge cases, and coordinate resolutions with engineering.
• Build deep product expertise and help customers apply AI to their workflows.

What We're Looking For

• Two to five years of experience in management consulting or a customer-facing role at a technology company, including at least two years at a leading consulting firm or equivalent experience.
• Experience owning customer-facing projects or implementations from start to finish.
• Strong analytical and problem-solving skills, attention to detail, and comfort with Excel-based analysis.
• Confident client-facing communication and presentation skills, including experience with executive stakeholders.
• Familiarity with modern AI tools and a genuine interest in applying AI to business challenges.
• Ability to work independently in a fast-paced, ambiguous environment and explain technical concepts to non-technical audiences.
• Experience in financial services, fintech, finance operations, or technology strategy and operations is valuable.
• Must be authorized to work in the United States without visa sponsorship.

Compensation & Benefits

Base salary: $150,000 to $200,000 annually. Visa sponsorship is not available.

Location

On-site in San Francisco, with five days per week in the office. Candidates based in New York may also be considered, with three to four days per week in the office.