Head of Sales Development, AMER (Chicago)

Who we are About StripeStripe 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.About the teamSales Development is a customer-facing team that connects prospective customers with Stripe. The AMER Sales Development org generates roughly 60% of Stripe's overall sales pipeline through a hybrid inbound and outbound motion, using a multi-touch, multi-method strategy that includes personalized email, LinkedIn outreach, video prospecting, and phone calls. The team covers every market segment, from startups to enterprise, and partners closely with Sales, Marketing, and Sales Development Systems to keep pipeline generation aligned with go-to-market priorities.What you’ll doThe role is an operator-builder and change leader: redesigning AMER Sales Development for an AI-first future while raising the bar for human discovery, qualification, user engagement, pipeline progression, and seller handoffs. The leader will partner with AMER Sales, Marketing, Operations, and Sales Development Systems to turn automation capacity into higher-value commercial work and a healthier pipeline.The Head of AMER Sales Development leads the Core AMER Sales Development team across inbound and outbound motions. This leader directly manages managers and owns qualified pipeline, SQOs, ONR contribution, and talent progression into the wider Sales organization.ResponsibilitiesLead the AMER Sales Development org through a team of sales development managers, who in turn manage the SDRs driving roughly 60% of Stripe's overall sales pipelineSet segmentation and coverage strategy across startups, digital natives, commercial, and enterprise accounts, and direct how managers structure their teams to pursue the right leads and accounts for quality and volumeOwn outbound strategy for AMER, including target markets, account and contact prioritization, and multi-touch outreach across email, LinkedIn, video, and phone, and translate that strategy into direction for your managersPartner with AMER sales leadership, Marketing, and Sales Development Systems to align pipeline targets, lead routing, and tooling (including agentic outreach and account intelligence systems) with go-to-market prioritiesDevelop and coach sales development managers directly, building their people management and pipeline strategy skills, and build bench strength and succession plans across the AMER SDR orgManage the org against opportunity count and cumulative revenue generation, reviewing manager-level performance and reallocating coverage or adjusting strategy where the data points to itRepresent Sales Development in AMER sales leadership planning, bringing an operator's view of pipeline health, capacity, and org productivityWho you areYou have 10+ years of relevant commercial leadership experience in Sales, Sales Development, Revenue Operations, Enablement, lead qualification, or a related function.You have led leaders at scale and can demonstrate how you have developed managers, built a leadership bench, and delivered ambitious outcomes through a multi-layer organisation.You have deep experience across inbound and outbound sales-development motions, including qualification, routing, handoff, conversion, pipeline quality, and commercial performance management.You are AI-first in your approach to operating-model design: you can apply automation and agents pragmatically while protecting user experience, quality, and sound human judgment.You have a record of improving qualified pipeline, SQOs, conversion, progression, and revenue impact—not activity volume alone.You are highly analytical and can use funnel, capacity, and outcome data to diagnose problems, make trade-offs, and drive execution.You have strong cross-functional influence and know how to work with Sales, Marketing, Growth, Operations, and systems teams to create shared plans and accountability.You are comfortable leading through ambiguity, taking informed risks, and driving necessary change with clarity, urgency, and care for people.You communicate clearly, operate with high integrity, and take ownership for outcomes.Minimum requirementsLeader of leaders: proven manager-of-managers leadership, including manager development, organizational design, and accountability through layers.AI-first operating leadership: ability to redesign roles, workflows, and capacity around agents and automation while protecting user experience, quality, and sound human judgment.Full-funnel ownership: a record of improving qualified pipeline, SQOs, conversion, progression, and revenue outcomes—not activity volume alone.Commercial partnership: credibility with Sales and Marketing leaders, including source-mix planning, shared funnel accountability, and seller-handoff design.Operating rigor: strong data fluency, consistent management systems, weekly performance reviews, and the ability to separate scalable standards from appropriate experimentation.Talent builder: demonstrated ability to develop managers, SDR and internal candidates into future commercial leaders.Stakeholder management: ability to navigate complex cross-functional relationships, build consensus with Sales and Marketing leadership, and maintain alignment across competing priorities.Preferred qualificationsExperience leading AI-assisted sourcing or SDR-in-the-loop workflows.Experience with MEDDIC-style qualification, pipeline defibrillation, aging-pipeline recovery, or later-funnel commercial support.Experience developing internal AE talent into people leaders or Sales Development managers.Deep familiarity with AMER segment design, field-sales coverage, vendor operations, or commercial-systems partnerships.Why this role mattersAMER Sales Development is entering a period of meaningful change. AI-assisted sourcing can free capacity for stronger user conversations, better qualification, and deeper progression support—but only if the operating model, manager expectations, and partner relationships evolve with it. This leader will set that direction, build the organisation to execute it, and create a stronger commercial engine and talent pipeline for Stripe.