Enterprise Services Manager, Professional Services Sales

Stripe•Chicago, IL

About The Position

As an Enterprise Services Manager, you will be a quota-carrying services seller and strategic advisor for Stripe’s largest users. You will originate, shape, and close complex advisory, implementation, and transformation engagements. This role sits at the intersection of enterprise sales, solution strategy, and delivery. You will partner with Account Executives, Solutions Architects, Product, Engineering, implementation partners, and Stripe delivery teams to turn customer priorities into practical scopes, credible business cases, and executable paths to adoption. You will own the Professional Services sales cycle from account planning and discovery through solution shaping, proposal development, commercial negotiation, contract signature, and delivery handoff. You will help customers define not only what they want to build with Stripe, but also how they will achieve value from it.

Requirements

5+ years of experience selling Professional Services, consulting, implementation, managed services, or complex technology solutions to enterprise customers.
A track record of originating, shaping, and closing sizable services or transformation engagements.
Experience owning a services sales cycle from discovery through proposal, SOW development, negotiation, contract signature, and delivery handoff.
Experience leading executive-level discovery, workshops, assessments, or business-case conversations.
Ability to understand complex business and technical requirements and translate them into an executable services approach.
Experience partnering effectively with Account Executives, Solutions Architects, delivery teams, Product, Engineering, and external partners.
Strong commercial judgment across scope, pricing, assumptions, dependencies, risks, resourcing, and customer expectations.
Working knowledge of APIs, integrations, cloud-based platforms, data flows, and enterprise implementation considerations.
Ability to manage competing priorities, navigate ambiguity, and maintain a rigorous pipeline and forecast.

Nice To Haves

Experience in payments, fintech, financial infrastructure, billing, marketplaces, money movement, fraud, risk, or digital commerce.
Experience selling to senior product, engineering, finance, operations, security, or technology leaders.
Experience with enterprise integrations, cloud adoption, APIs, platform implementations, data modernization, or digital transformation programs.
Experience selling packaged, phased, outcome-oriented, or partner-delivered services.
Familiarity with AI-enabled software or automation, including practical implementation questions around data, security, governance, adoption, and measurable business value.
Experience in a high-growth technology company, cloud provider, enterprise SaaS company, consulting firm, or systems integrator.

Responsibilities

Own enterprise Professional Services opportunities
Own Professional Services bookings, pipeline creation, qualification, and forecasting across an assigned set of strategic enterprise accounts.
Partner with Account Executives and Solutions Architects on account plans that identify where Professional Services can accelerate adoption, reduce implementation risk, and unlock expansion.
Engage early in complex opportunities to shape the services strategy, customer value proposition, and path to implementation.
Build and maintain accurate forecasts, close plans, and stakeholder maps for complex, multi-party sales cycles.
Identify follow-on advisory, implementation, and transformation opportunities as customers expand their use of Stripe.
Lead discovery and shape practical solutions
Lead executive discovery sessions, assessments, and workshops with customer stakeholders across product, engineering, finance, operations, risk, security, and procurement.
Understand a customer’s business objectives, current environment, technical architecture, operating model, and implementation constraints.
Translate customer requirements into a practical services approach, including scope, assumptions, dependencies, milestones, risks, success measures, and an activation and realization plan.
Partner with Solutions Architecture, Product, Engineering, delivery teams, and external partners to validate feasibility and create solutions that are valuable to customers and deliverable by Stripe.
Advise senior customer leaders on business cases for digital transformation, platform adoption, operational efficiency, and new revenue opportunities.
Drive commercial execution
Create tailored proposals, pricing approaches, and Statements of Work for advisory, implementation, packaged, and phased transformation engagements.
Shape commercial models that balance customer outcomes, delivery confidence, scope clarity, and long-term Stripe adoption.
Lead negotiations with senior customer stakeholders, procurement, legal, and internal partners.
Manage scope, resourcing, dependencies, implementation risk, and customer expectations before work begins.
Apply strong commercial judgment to determine when a customer needs a focused assessment, a defined implementation package, a broader transformation roadmap, or partner-delivered support.
Connect sales to delivery and product strategy
Prepare delivery teams with clear customer context, business outcomes, decision history, risks, assumptions, and stakeholder expectations.
Maintain continuity from opportunity creation through customer kickoff and early delivery.
Partner with Customer Success, Delivery, and Support teams to help customers progress from signature to activation, adoption, and expansion.
Surface recurring enterprise customer needs and market insight to Product and Engineering teams to inform Stripe’s product strategy.
Contribute to repeatable sales plays, service offerings, tools, and best practices that improve how Stripe sells and delivers Professional Services.
AI and emerging technology
Discuss how AI-related initiatives affect data readiness, integrations, security, privacy, governance, adoption, and implementation sequencing.
Use AI-enabled tools responsibly to improve account research, solutioning, documentation, forecasting, and delivery visibility, while applying sound judgment and validating recommendations with the appropriate technical and delivery experts.