Head of Sales Development

Stripe

Confirmed live 10 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 10 days ago

Market check

Salary context

Above market

How this pay compares to similar roles

Similar $224k
This role $416k
$128k most similar roles pay here $539k

This role pays more than 98% of similar roles. Most pay $174,450–$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 and enterprise segments, focusing on high-value commercial work rather than just activity volume. Key responsibilities include designing an AI-first operating model that utilizes automation and agentic outreach systems while maintaining human judgment in discovery and qualification. The role requires coordinating with Marketing and Sales Development Systems to align lead routing and tooling with go-to-market priorities. Candidates must possess over 10 years of experience in sales leadership, revenue operations, or enablement. They will utilize data fluency to manage pipeline health, coach managers on strategy, and oversee multi-touch outreach across email, LinkedIn, video, and phone platforms.

What you'll do

  • Lead the AMER Sales Development organization by managing a team of managers to drive inbound and outbound sales pipelines.
  • Design segmentation and coverage strategies across startup, digital native, commercial, and enterprise account segments.
  • Develop and execute multi-touch outbound strategies using email, LinkedIn, video, and phone outreach.
  • Redesign the operating model to integrate AI-first automation while maintaining high standards for human discovery and qualification.
  • Partner with Sales, Marketing, and Systems teams to align pipeline targets, lead routing, and tooling with go-to-market goals.
  • Coach and develop sales development managers to build leadership bench strength and succession plans.
  • Analyze funnel and capacity data to manage the organization against opportunity counts and revenue generation targets.
  • Represent the Sales Development function in leadership planning to provide insights on pipeline health and organizational productivity.

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 across a multi-layer organization.
  • 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 high 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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