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Head of Sales Development, AMER

Job in Chicago, Cook County, Illinois, 60601, USA
Listing for: Stripe
Full Time position
Listed on 2026-08-09
Job specializations:
  • Sales
    Business Development, Sales Development Rep/SDR
Salary/Wage Range or Industry Benchmark: 333000 USD Yearly USD 333000.00 YEAR
Job Description & How to Apply Below

Head Of Sales Development, AMER

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.

Sales 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, Linked In 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.

The 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.

  • Lead 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 pipeline
  • Set 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 volume
  • Own outbound strategy for AMER, including target markets, account and contact prioritization, and multi-touch outreach across email, Linked In, video, and phone, and translate that strategy into direction for your managers
  • Partner 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 priorities
  • Develop 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 org
  • Manage the org against opportunity count and cumulative revenue generation, reviewing manager-level performance and reallocating coverage or adjusting strategy where the data points to it
  • Represent Sales Development in AMER sales leadership planning, bringing an operator's view of pipeline health, capacity, and org productivity

We're looking for someone who meets the minimum requirements to be considered for this role.

  • Leader 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.
  • Experience 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.

The annual US base salary range for this role is $333,000 - $499,600. For sales roles, the range provided is the role's On Target Earnings ("OTE") range, meaning that the range includes both the sales commissions/sales bonuses target and annual base salary for the role. This salary…

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