Head of Sales Development

Stripe

Confirmed live 9 days ago High trust

Quick summary

Work type
On-site
Location
Chicago, IL
Salary
$333,000–$499,600 / yr
Posted
44 days ago
Freshness
Confirmed live 9 days ago

Market check

Salary context

Above market

How this pay compares to similar roles

Similar $224k
This role $416k
$129k most similar roles pay here $539k

This role pays more than 98% of similar roles. Most pay $174,600–$273,186 — the shaded band above. At the midpoint, this role pays about $416k versus about $224k for comparable roles.

Based on 240 similar postings.

Employer

About Stripe

Stripe is a financial infrastructure platform for internet businesses, providing payment processing, billing, fraud prevention, and banking-as-a-service APIs to businesses of all sizes globally. Industry: Payments Infrastructure & Financial Technology

Stripe currently has 173 open roles on FindRole.

Listed pay typically runs $190,400–$285,600 across 171 roles with salary data.

Most-posted roles

View all roles at Stripe

At a glance

TL;DR · Head of Sales Development

The Head of Sales Development, AMER leads a multi-layered organization responsible for generating approximately 60% of the company's sales pipeline through hybrid inbound and outbound motions. This leader manages managers to oversee SDR teams across startup, digital native, commercial, and enterprise segments. Key responsibilities include designing an AI-first operating model that utilizes automation and agentic outreach systems while maintaining high standards for human discovery, qualification, and seller handoffs. The role involves setting segmentation strategies, managing multi-touch outreach via email, LinkedIn, video, and phone, and partnering with Marketing and Sales Development Systems to align pipeline targets. The ideal candidate possesses over 10 years of experience in sales leadership or revenue operations, demonstrating expertise in data-driven performance management, talent development, and cross-functional collaboration to solve complex problems regarding lead routing and conversion within the financial infrastructure space.

What you'll do

  • Lead the AMER Sales Development organization by managing managers to drive inbound and outbound sales pipelines.
  • Design segmentation and coverage strategies across startup, digital native, commercial, and enterprise accounts.
  • Develop and execute multi-touch outbound strategies using email, LinkedIn, video, and phone outreach.
  • Redesign sales development workflows and operating models to integrate AI-driven automation and agentic tools.
  • Partner with Marketing and Sales leadership to align pipeline targets, lead routing, and go-to-market priorities.
  • Coach and develop managers to improve their people management skills and pipeline strategy capabilities.
  • Analyze funnel and capacity data to manage the organization against opportunity counts and revenue goals.
  • Build a talent pipeline by developing SDRs and internal candidates into future commercial leaders.

What we're looking for

  • You must have 10+ years of relevant commercial leadership experience in Sales, Sales Development, Revenue Operations, or Enablement.
  • You must have proven manager-of-managers experience to develop leaders and build a leadership bench at scale.
  • You must have deep experience in both inbound and outbound sales-development motions including qualification, routing, and conversion.
  • You must be able to design AI-first operating models that integrate automation while maintaining quality and human judgment.
  • You must have a proven track record of improving qualified pipeline, SQOs, and revenue impact rather than just activity volume.
  • You must possess strong data fluency to analyze funnel and capacity metrics to diagnose problems and drive execution.
  • You must be able to influence cross-functional partners in Marketing, Sales, Growth, and Operations to align on shared goals.
  • Preferred experience includes MEDDIC-style qualification, AI-assisted sourcing workflows, and developing internal talent into leadership roles.

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