Head of Sales Development, AMER

EngineersOfAI; Chicago, Northern (IL, KY); Hybrid; USD 180,000 - 320,000; Full time

Job summary

Stripe is seeking a Head of AMER Sales Development to redesign the AMER Sales Development function for an AI-first future, elevating how we discover, qualify, engage, and move leads through the pipeline. This 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

Qualifications

• 10+ years of leadership in sales or revenue operations.
• Experience leading managers and building leadership bench.
• Deep experience with inbound and outbound sales development.
• AI-first approach to operating models with balance of UX.
• Proven track record improving pipeline and revenue impact.
• Highly analytical with data-driven decision making.
• Strong cross-functional collaboration.

Responsibilities

• Lead the AMER Sales Development org through managers who supervise SDRs.
• Set segmentation and coverage strategy across startups to enterprise.
• Own outbound strategy for AMER including multi-touch outreach.
• Partner with AMER sales, Marketing, and Systems to align pipelines and tooling.
• Develop and coach sales development managers and build succession plans.
• Manage org performance and adjust strategy based on data.
• Represent Sales Development in AMER leadership planning.

Skills

Sales leadership

Revenue operations

Enablement

Lead qualification

Inbound & outbound sales

AI-first mindset

Analytical

Cross-functional leadership

Tools

CRM systems

Automation tools

Account intelligence systems

Job description

Who we are

About Stripe

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.

About the team

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, 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 do

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.

Responsibilities

• 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, LinkedIn, 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

Who you are

• You 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