Freelance Management Development Program Jobs in Chicago, IL

Stripe is a financial infrastructure platform for businesses. Millions of companies - from the world’s largest enterprises to the most ambitious startups - use Stripe to accept payments, grow their revenue, and accelerate new business opportunities. Our mission is to increase the GDP of the internet, and we have a staggering amount of work ahead. That means you have an unprecedented opportunity to put the global economy within everyone's reach while doing the most important work of your career.

The Global Sales Enablement Team is responsible for partnering with cross-functional teams to equip our sales organizations with the skills, tools, and knowledge they need to perform at their best. We are currently leading one of the most significant transformations in Stripe's Sales history — reshaping how Sales Development operates through the adoption of AI-powered tooling and redesigning the SDR's role in driving pipeline quality. This transformation spans multiple geographies, sales motions, and hundreds of sellers. The stakes are high, the pace is fast, and the change management challenge is real.

As a Sales Development Change Management Specialist, you will owner the strategy and execution of our global change management and communications program for the Sales Development transformation. You sit at the intersection of strategy, content, and field engagement — responsible for ensuring that complex, high-priority initiatives are adopted at pace and land durably in the field. This is not a support role. You own the change narrative, the communication strategy, and the measurement of adoption. You'll partner with senior program leadership, subject matter experts, and regional enablement leads to drive consistent, high-impact transformation across a global sales organization.

• Own the end-to-end change management program — from preparing the organization for change through launch, adoption, reinforcement, and measurement
• Develop and execute a global communications strategy that ensures sellers understand what is changing, why it matters, and what it means for them — sequenced to land with impact and without creating unnecessary noise
• Write and distribute seller-facing communications, executive briefings, and stakeholder updates; own the core program narrative throughout the transformation lifecycle
• Distill complex program initiatives into clear, compelling, sales-ready content — translating what engineers and product teams build into what sellers and managers need to hear
• Build and maintain a strategic communications plan in partnership with cross-functional teams, including Product, Engineering, and SD Operations
• Create and manage a structured feedback loop with the field — capturing seller sentiment, surfacing blockers, and using adoption data to iterate on the change approach
• Partner with subject matter experts and regional enablement leads to ensure change initiatives are contextualized for each market and sales motion
• Advise program leadership on the pacing and sequencing of change, balancing urgency with the organization's capacity to absorb it
• Build strong relationships with key stakeholders and senior leaders to ensure change and communications strategies remain aligned to program goals and business performance targets
• Track and report on adoption metrics against defined program success criteria

We're looking for someone who meets the minimum requirements to be considered for the role. If you meet these requirements, you are encouraged to apply. The preferred qualifications are a bonus, not a requirement.

• 10+ years of experience in change management, organizational transformation, strategic communications, program management, or a closely related discipline
• Experience navigating and implementing complex change programs within Sales Development organizations
• Exceptional written and verbal communication skills — the ability to distill complex, technical concepts into clear, seller-ready, action-oriented content
• Proven ability to develop and execute multi-channel communications strategies for large, globally distributed audiences
• Strong cross-functional partnership and influencing skills — including the ability to work effectively with executive-level stakeholders and subject matter experts without direct authority
• A data-driven mindset with experience using adoption metrics, field feedback, and performance data to measure, iterate, and improve
• Experience supporting go-to-market or sales organizations through significant workflow, tooling, or operating model changes
• High threshold for ambiguity — you build structure and clarity in environments that don't yet have it

• ProSci certification or equivalent change management credential
• Experience supporting the adoption of AI-powered or emerging technology tooling within a sales or GTM organization
• Background in building and scaling sales communications programs in a global SaaS or fintech environment
• Familiarity with Salesforce and sales productivity tooling ecosystems